{"product_id":"copper-i-thiophene-2-carboxylate-cutc-cas-68986-76-5","title":"Copper(I) Thiophene-2-carboxylate (CuTC) | CAS 68986-76-5 | ≥98%","description":"\u003cdiv style=\"margin-bottom: 28px;\"\u003e\n\u003cdiv style=\"background: #002147; padding: 10px 20px; margin-bottom: 0;\"\u003e\u003ch3 style=\"margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; font-size: 0.70em; font-weight: bold; letter-spacing: 0.12em; text-transform: uppercase; color: #fff;\"\u003eTechnical Specifications\u003c\/h3\u003e\u003c\/div\u003e\n\u003ctable style=\"width: 100%; border-collapse: collapse; font-size: 0.95em; border: 1px solid #e4e8f0; border-top: none; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif;\"\u003e\u003ctbody\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eCAS Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e68986-76-5\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eEC \/ EINECS Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e633-277-7\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eMDL Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eMFCD02183524\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eSMILES\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0; word-break: break-all;\"\u003eC1=CSC(=C1)C(=O)[O-].[Cu+]\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eInChI\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0; word-break: break-all;\"\u003eInChI=1S\/C5H4O2S.Cu\/c6-5(7)4-2-1-3-8-4;\/h1-3H,(H,6,7);\/q;+1\/p-1\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eInChIKey\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0; word-break: break-all;\"\u003eSFJMFSWCBVEHBA-UHFFFAOYSA-M\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003ePubChem CID\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e11194830\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eMolecular Formula\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eC₅H₃CuO₂S\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eMolecular Weight\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e190.69 g\/mol\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003ePurity\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e≥98%\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003ePhysical Form\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eOrange to brown to dark red powder or crystals\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eHS Code\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e2934.99\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eShelf Life\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eRetest period: 36 months from date of manufacture\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eStorage Conditions\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333;\"\u003eKeep container tightly closed in a dry, cool and well-ventilated place. Store under an inert atmosphere. Protect from light.\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003c\/tbody\u003e\u003c\/table\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"margin-bottom: 28px;\"\u003e\n\u003cdiv style=\"background: #002147; padding: 10px 20px; margin-bottom: 0;\"\u003e\u003ch3 style=\"margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; font-size: 0.70em; font-weight: bold; letter-spacing: 0.12em; text-transform: uppercase; color: #fff;\"\u003eProduct Description \u0026amp; Scientific Applications\u003c\/h3\u003e\u003c\/div\u003e\n\u003cdiv style=\"padding: 16px 20px; border: 1px solid #e4e8f0; border-top: none; font-family: Georgia, 'Times New Roman', serif; font-size: 0.95em; line-height: 1.65; color: #333;\"\u003e\u003cdiv\u003e\n\u003cp\u003e\u003cstrong\u003eCopper(I) thiophene-2-carboxylate (CuTC)\u003c\/strong\u003e is a copper(I) carboxylate: the copper(I) salt of thiophene-2-carboxylic acid. It is also known as Liebeskind's reagent. It is used both as a copper(I) mediator in palladium-catalysed cross-couplings and as a copper catalyst in its own right.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eLiebeskind–Srogl coupling.\u003c\/strong\u003e In the Liebeskind–Srogl reaction, thioesters couple with boronic acids to give ketones under neutral conditions. A review describes this desulfitative coupling as catalytic in palladium(0) and stoichiometric in copper(I), and as applicable to a range of organosulfur compounds and organometallic nucleophiles. A 2023 study of the reaction describes the role of the copper(I) cofactor as twofold: it activates the C(O)–S bond towards oxidative addition, and it facilitates transmetallation from boron to palladium. Another study demonstrated that the Liebeskind–Srogl protocol is orthogonal in selectivity to Suzuki–Miyaura and Stille couplings, in a modular synthesis of functionalised pyrimidinones.\u003c\/p\u003e\n\u003cp\u003eWith CuTC as the mediator, π-deficient heteroaromatic thioethers undergo palladium-catalysed cross-coupling with boronic acids. In one study, thioalkynes coupled with boronic acids under palladium catalysis in the presence of CuTC or copper(I) 3-methylsalicylate, under mild, non-basic conditions, giving functionalised alkynes; the authors present the reaction as complementary to the Sonogashira protocol. Another study made nitriles from boronic acids and benzyl thiocyanate under palladium catalysis with CuTC. The authors present this reaction as a cyanide-free alternative to the classic cyanation of aryl halides with cyanide sources. A bis(arylthio)cyclobutenedione coupled with both organostannanes and (hetero)arylboronic acids using catalytic palladium and stoichiometric CuTC, giving symmetrically disubstituted cyclobutenediones.\u003c\/p\u003e\n\u003cdiv style=\"margin:8px 0 18px 0;\"\u003e\n\u003cdiv style=\"display:flex;flex-wrap:wrap;align-items:center;justify-content:flex-start;gap:2px;\"\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"170px\" height=\"80px\" viewbox=\"0 0 170 80\"\u003e\u003cpath d=\"M 106,64 L 106,55\"\u003e\u003c\/path\u003e\u003cpath d=\"M 110,46 L 119,41\"\u003e\u003c\/path\u003e\u003cpath d=\"M 102,46 L 90,39\"\u003e\u003c\/path\u003e\u003cpath d=\"M 90,39 L 90,20\"\u003e\u003c\/path\u003e\u003cpath d=\"M 90,20 L 73,10\"\u003e\u003c\/path\u003e\u003cpath d=\"M 87,21 L 73,13\"\u003e\u003c\/path\u003e\u003cpath 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y=\"64\" font-size=\"11\"\u003eN\u003c\/text\u003e\u003ctext x=\"65\" y=\"43\" font-size=\"11\"\u003eS\u003c\/text\u003e\u003c\/g\u003e\u003c\/svg\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"display:flex;flex-direction:column;align-items:center;justify-content:center;min-width:90px;max-width:130px;padding:0 4px;text-align:center;font-size:12px;line-height:1.3;\"\u003e\n\u003cdiv\u003ePd (cat.), CuTC\u003c\/div\u003e\n\u003cdiv style=\"font-size:30px;line-height:1;\"\u003e→\u003c\/div\u003e\n\u003cdiv\u003e\u003c\/div\u003e\n\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"170px\" height=\"70px\" viewbox=\"0 0 170 70\"\u003e\u003cpath d=\"M 124,56 L 111,49\"\u003e\u003c\/path\u003e\u003cpath d=\"M 122,59 L 109,51\"\u003e\u003c\/path\u003e\u003cpath d=\"M 126,54 L 112,46\"\u003e\u003c\/path\u003e\u003cpath d=\"M 111,49 L 94,39\"\u003e\u003c\/path\u003e\u003cpath d=\"M 94,39 L 94,19\"\u003e\u003c\/path\u003e\u003cpath d=\"M 94,19 L 76,9\"\u003e\u003c\/path\u003e\u003cpath d=\"M 91,21 L 76,12\"\u003e\u003c\/path\u003e\u003cpath d=\"M 76,9 L 59,19\"\u003e\u003c\/path\u003e\u003cpath d=\"M 59,19 L 46,11\"\u003e\u003c\/path\u003e\u003cpath d=\"M 59,19 L 59,39\"\u003e\u003c\/path\u003e\u003cpath d=\"M 62,21 L 62,37\"\u003e\u003c\/path\u003e\u003cpath d=\"M 59,39 L 76,49\"\u003e\u003c\/path\u003e\u003cpath d=\"M 76,49 L 94,39\"\u003e\u003c\/path\u003e\u003cpath d=\"M 76,45 L 91,37\"\u003e\u003c\/path\u003e\u003cpath d=\"M 112,49 L 111,49 L 110,48\"\u003e\u003c\/path\u003e\u003cpath d=\"M 94,20 L 94,19 L 93,18\"\u003e\u003c\/path\u003e\u003cpath d=\"M 77,10 L 76,9 L 76,10\"\u003e\u003c\/path\u003e\u003cpath d=\"M 59,38 L 59,39 L 60,39\"\u003e\u003c\/path\u003e\u003cpath d=\"M 76,48 L 76,49 L 77,48\"\u003e\u003c\/path\u003e\u003cg style=\"font-family:sans-serif;fill:#000;stroke:none\"\u003e\u003ctext x=\"125\" y=\"64\" font-size=\"11\"\u003eN\u003c\/text\u003e\u003ctext x=\"39\" y=\"15\" font-size=\"11\"\u003eR\u003c\/text\u003e\u003c\/g\u003e\u003c\/svg\u003e\u003c\/div\u003e\n\u003c\/div\u003e\n\u003cp style=\"font-size:12px;margin:4px 0 0 0;\"\u003e\u003cem\u003eCyanation of arylboronic acids with benzyl thiocyanate under palladium catalysis with CuTC, as reported in one study. The position of R is drawn for illustration only; other reagents and conditions are not shown.\u003c\/em\u003e\u003c\/p\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"margin:8px 0 18px 0;\"\u003e\n\u003cdiv style=\"display:flex;flex-wrap:wrap;align-items:center;justify-content:flex-start;gap:2px;\"\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"150px\" height=\"50px\" viewbox=\"0 0 150 50\"\u003e\u003cpath d=\"M 43,36 L 54,29\"\u003e\u003c\/path\u003e\u003cpath d=\"M 54,29 L 73,18\"\u003e\u003c\/path\u003e\u003cpath d=\"M 52,26 L 71,16\"\u003e\u003c\/path\u003e\u003cpath d=\"M 55,32 L 74,21\"\u003e\u003c\/path\u003e\u003cpath d=\"M 73,18 L 88,10\"\u003e\u003c\/path\u003e\u003cpath d=\"M 96,10 L 107,16\"\u003e\u003c\/path\u003e\u003cpath d=\"M 53,30 L 54,29 L 55,29\"\u003e\u003c\/path\u003e\u003cpath d=\"M 72,19 L 73,18 L 74,18\"\u003e\u003c\/path\u003e\u003cg style=\"font-family:sans-serif;fill:#000;stroke:none\"\u003e\u003ctext x=\"32\" y=\"46\" font-size=\"11\"\u003eR\u003c\/text\u003e\u003ctext x=\"39\" y=\"42\" font-size=\"7\"\u003e1\u003c\/text\u003e\u003ctext x=\"89\" y=\"13\" font-size=\"11\"\u003eS\u003c\/text\u003e\u003ctext x=\"108\" y=\"24\" font-size=\"11\"\u003eR\u003c\/text\u003e\u003ctext x=\"115\" y=\"20\" font-size=\"7\"\u003e2\u003c\/text\u003e\u003c\/g\u003e\u003c\/svg\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;font-size:20px;padding:0 4px;\"\u003e\u003cspan\u003e+\u003c\/span\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;font-size:15px;padding:0 4px;\"\u003e\u003cspan\u003eArB(OH)\u003csub\u003e2\u003c\/sub\u003e\u003c\/span\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"display:flex;flex-direction:column;align-items:center;justify-content:center;min-width:90px;max-width:130px;padding:0 4px;text-align:center;font-size:12px;line-height:1.3;\"\u003e\n\u003cdiv\u003ePd (cat.), CuTC\u003c\/div\u003e\n\u003cdiv style=\"font-size:30px;line-height:1;\"\u003e→\u003c\/div\u003e\n\u003cdiv\u003eno base\u003c\/div\u003e\n\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"130px\" height=\"50px\" viewbox=\"0 0 130 50\"\u003e\u003cpath d=\"M 26,25 L 47,25\"\u003e\u003c\/path\u003e\u003cpath d=\"M 47,25 L 78,25\"\u003e\u003c\/path\u003e\u003cpath d=\"M 47,20 L 78,20\"\u003e\u003c\/path\u003e\u003cpath d=\"M 47,29 L 78,29\"\u003e\u003c\/path\u003e\u003cpath d=\"M 78,25 L 104,25\"\u003e\u003c\/path\u003e\u003cpath d=\"M 46,25 L 47,25 L 49,25\"\u003e\u003c\/path\u003e\u003cpath d=\"M 76,25 L 78,25 L 79,25\"\u003e\u003c\/path\u003e\u003cg style=\"font-family:sans-serif;fill:#000;stroke:none\"\u003e\u003ctext x=\"13\" y=\"31\" font-size=\"12\"\u003eR\u003c\/text\u003e\u003ctext x=\"21\" y=\"26\" font-size=\"7\"\u003e1\u003c\/text\u003e\u003ctext x=\"105\" y=\"31\" font-size=\"12\"\u003eA\u003c\/text\u003e\u003ctext x=\"113\" y=\"31\" font-size=\"12\"\u003er\u003c\/text\u003e\u003c\/g\u003e\u003c\/svg\u003e\u003c\/div\u003e\n\u003c\/div\u003e\n\u003cp style=\"font-size:12px;margin:4px 0 0 0;\"\u003e\u003cem\u003eCoupling of thioalkynes with boronic acids under palladium catalysis with CuTC and without base, as reported in one study. An arylboronic acid is drawn for illustration; conditions are not shown.\u003c\/em\u003e\u003c\/p\u003e\n\u003c\/div\u003e\n\u003cp\u003e\u003cstrong\u003eBase-free coupling of iodides with boronic acids.\u003c\/strong\u003e CuTC also mediates a palladium-catalysed coupling of aryl and alkenyl iodides with boronic acids that runs without a base. The authors present it as an alternative to the Suzuki coupling and expect it to be particularly useful for substrates with base-sensitive or thermally sensitive groups.\u003c\/p\u003e\n\u003cdiv style=\"margin:8px 0 18px 0;\"\u003e\n\u003cdiv style=\"display:flex;flex-wrap:wrap;align-items:center;justify-content:flex-start;gap:2px;\"\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"150px\" height=\"70px\" viewbox=\"0 0 150 70\"\u003e\u003cpath d=\"M 112,56 L 96,46\"\u003e\u003c\/path\u003e\u003cpath d=\"M 96,46 L 96,23\"\u003e\u003c\/path\u003e\u003cpath d=\"M 96,23 L 75,11\"\u003e\u003c\/path\u003e\u003cpath d=\"M 92,25 L 75,15\"\u003e\u003c\/path\u003e\u003cpath d=\"M 75,11 L 54,23\"\u003e\u003c\/path\u003e\u003cpath d=\"M 54,23 L 38,13\"\u003e\u003c\/path\u003e\u003cpath d=\"M 54,23 L 54,46\"\u003e\u003c\/path\u003e\u003cpath d=\"M 58,25 L 58,44\"\u003e\u003c\/path\u003e\u003cpath d=\"M 54,46 L 75,58\"\u003e\u003c\/path\u003e\u003cpath d=\"M 75,58 L 96,46\"\u003e\u003c\/path\u003e\u003cpath d=\"M 75,54 L 92,44\"\u003e\u003c\/path\u003e\u003cpath d=\"M 96,24 L 96,23 L 94,22\"\u003e\u003c\/path\u003e\u003cpath d=\"M 76,12 L 75,11 L 74,12\"\u003e\u003c\/path\u003e\u003cpath d=\"M 54,45 L 54,46 L 56,47\"\u003e\u003c\/path\u003e\u003cpath d=\"M 74,58 L 75,58 L 76,58\"\u003e\u003c\/path\u003e\u003cg style=\"font-family:sans-serif;fill:#000;stroke:none\"\u003e\u003ctext x=\"113\" y=\"64\" font-size=\"11\"\u003eI\u003c\/text\u003e\u003ctext x=\"31\" y=\"16\" font-size=\"11\"\u003eR\u003c\/text\u003e\u003ctext x=\"38\" y=\"12\" font-size=\"7\"\u003e1\u003c\/text\u003e\u003c\/g\u003e\u003c\/svg\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;font-size:20px;padding:0 4px;\"\u003e\u003cspan\u003e+\u003c\/span\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"170px\" height=\"80px\" viewbox=\"0 0 170 80\"\u003e\u003cpath d=\"M 106,64 L 106,55\"\u003e\u003c\/path\u003e\u003cpath d=\"M 110,47 L 119,42\"\u003e\u003c\/path\u003e\u003cpath d=\"M 102,47 L 90,40\"\u003e\u003c\/path\u003e\u003cpath d=\"M 90,40 L 90,21\"\u003e\u003c\/path\u003e\u003cpath d=\"M 90,21 L 73,11\"\u003e\u003c\/path\u003e\u003cpath d=\"M 87,22 L 73,14\"\u003e\u003c\/path\u003e\u003cpath d=\"M 73,11 L 57,21\"\u003e\u003c\/path\u003e\u003cpath d=\"M 57,21 L 44,13\"\u003e\u003c\/path\u003e\u003cpath d=\"M 57,21 L 57,40\"\u003e\u003c\/path\u003e\u003cpath d=\"M 60,22 L 60,38\"\u003e\u003c\/path\u003e\u003cpath d=\"M 57,40 L 73,49\"\u003e\u003c\/path\u003e\u003cpath d=\"M 73,49 L 90,40\"\u003e\u003c\/path\u003e\u003cpath d=\"M 73,46 L 87,38\"\u003e\u003c\/path\u003e\u003cpath d=\"M 90,22 L 90,21 L 89,20\"\u003e\u003c\/path\u003e\u003cpath d=\"M 74,12 L 73,11 L 72,12\"\u003e\u003c\/path\u003e\u003cpath d=\"M 57,39 L 57,40 L 58,40\"\u003e\u003c\/path\u003e\u003cpath d=\"M 72,49 L 73,49 L 74,49\"\u003e\u003c\/path\u003e\u003cg style=\"font-family:sans-serif;fill:#000;stroke:none\"\u003e\u003ctext x=\"103\" y=\"74\" font-size=\"11\"\u003eO\u003c\/text\u003e\u003ctext x=\"110\" y=\"74\" font-size=\"11\"\u003eH\u003c\/text\u003e\u003ctext x=\"103\" y=\"55\" font-size=\"11\"\u003eB\u003c\/text\u003e\u003ctext x=\"119\" y=\"45\" font-size=\"11\"\u003eO\u003c\/text\u003e\u003ctext x=\"127\" y=\"45\" font-size=\"11\"\u003eH\u003c\/text\u003e\u003ctext x=\"37\" y=\"17\" font-size=\"11\"\u003eR\u003c\/text\u003e\u003ctext x=\"45\" y=\"12\" font-size=\"7\"\u003e2\u003c\/text\u003e\u003c\/g\u003e\u003c\/svg\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"display:flex;flex-direction:column;align-items:center;justify-content:center;min-width:90px;max-width:130px;padding:0 4px;text-align:center;font-size:12px;line-height:1.3;\"\u003e\n\u003cdiv\u003ePd (cat.), CuTC\u003c\/div\u003e\n\u003cdiv style=\"font-size:30px;line-height:1;\"\u003e→\u003c\/div\u003e\n\u003cdiv\u003eno base\u003c\/div\u003e\n\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"240px\" height=\"95px\" viewbox=\"0 0 240 95\"\u003e\u003cpath d=\"M 173,79 L 160,72\"\u003e\u003c\/path\u003e\u003cpath d=\"M 160,72 L 160,52\"\u003e\u003c\/path\u003e\u003cpath d=\"M 160,52 L 143,42\"\u003e\u003c\/path\u003e\u003cpath d=\"M 157,54 L 143,46\"\u003e\u003c\/path\u003e\u003cpath d=\"M 143,42 L 126,52\"\u003e\u003c\/path\u003e\u003cpath d=\"M 126,52 L 126,72\"\u003e\u003c\/path\u003e\u003cpath d=\"M 129,54 L 129,70\"\u003e\u003c\/path\u003e\u003cpath d=\"M 126,72 L 143,82\"\u003e\u003c\/path\u003e\u003cpath d=\"M 126,52 L 109,42\"\u003e\u003c\/path\u003e\u003cpath d=\"M 109,42 L 109,23\"\u003e\u003c\/path\u003e\u003cpath d=\"M 109,23 L 92,13\"\u003e\u003c\/path\u003e\u003cpath d=\"M 106,24 L 92,16\"\u003e\u003c\/path\u003e\u003cpath d=\"M 92,13 L 75,23\"\u003e\u003c\/path\u003e\u003cpath d=\"M 75,23 L 62,15\"\u003e\u003c\/path\u003e\u003cpath d=\"M 75,23 L 75,42\"\u003e\u003c\/path\u003e\u003cpath d=\"M 78,24 L 78,40\"\u003e\u003c\/path\u003e\u003cpath d=\"M 75,42 L 92,52\"\u003e\u003c\/path\u003e\u003cpath d=\"M 143,82 L 160,72\"\u003e\u003c\/path\u003e\u003cpath d=\"M 143,78 L 157,70\"\u003e\u003c\/path\u003e\u003cpath d=\"M 92,52 L 109,42\"\u003e\u003c\/path\u003e\u003cpath d=\"M 92,49 L 106,40\"\u003e\u003c\/path\u003e\u003cpath d=\"M 160,53 L 160,52 L 160,52\"\u003e\u003c\/path\u003e\u003cpath d=\"M 144,43 L 143,42 L 142,43\"\u003e\u003c\/path\u003e\u003cpath d=\"M 126,71 L 126,72 L 127,72\"\u003e\u003c\/path\u003e\u003cpath d=\"M 142,81 L 143,82 L 144,81\"\u003e\u003c\/path\u003e\u003cpath d=\"M 109,24 L 109,23 L 108,22\"\u003e\u003c\/path\u003e\u003cpath d=\"M 93,13 L 92,13 L 92,13\"\u003e\u003c\/path\u003e\u003cpath d=\"M 75,41 L 75,42 L 76,43\"\u003e\u003c\/path\u003e\u003cpath d=\"M 92,52 L 92,52 L 93,52\"\u003e\u003c\/path\u003e\u003cg style=\"font-family:sans-serif;fill:#000;stroke:none\"\u003e\u003ctext x=\"174\" y=\"87\" font-size=\"11\"\u003eR\u003c\/text\u003e\u003ctext x=\"182\" y=\"83\" font-size=\"7\"\u003e1\u003c\/text\u003e\u003ctext x=\"55\" y=\"18\" font-size=\"11\"\u003eR\u003c\/text\u003e\u003ctext x=\"63\" y=\"14\" font-size=\"7\"\u003e2\u003c\/text\u003e\u003c\/g\u003e\u003c\/svg\u003e\u003c\/div\u003e\n\u003c\/div\u003e\n\u003cp style=\"font-size:12px;margin:4px 0 0 0;\"\u003e\u003cem\u003eBase-free coupling of aryl iodides with arylboronic acids under palladium catalysis with CuTC, as reported in one study; alkenyl iodides also reacted. The positions of R¹ and R² are drawn for illustration only; conditions are not shown.\u003c\/em\u003e\u003c\/p\u003e\n\u003c\/div\u003e\n\u003cp\u003e\u003cstrong\u003eCouplings with organostannanes.\u003c\/strong\u003e In one Stille–Migita protocol, catalytic Pd(PPh₃)₄ combined with CuTC and tetrabutylammonium diphenylphosphinate allowed a series of demanding couplings; because the protocol is fluoride-free, \u003cem\u003eO\u003c\/em\u003e-silyl and \u003cem\u003eC\u003c\/em\u003e-silyl groups remained intact. Thiocarbamoyl-protected α-hydroxystannanes, racemic or enantioenriched, cross-coupled with alkenyl, aryl and heteroaryl iodides using CuTC, with retention of configuration at the stereocentres. A pH-neutral, CuTC-catalysed cross-coupling of amino acid thiol esters with chiral α-alkoxyalkylstannanes gave α-amino-α′-alkoxy ketones with complete retention of configuration at both stereocentres.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003e1-Sulfonyl-1,2,3-triazoles.\u003c\/strong\u003e In one study, CuTC catalysed the formation of 1-sulfonyl-1,2,3-triazoles from sulfonyl azides and copper(I) acetylides generated in situ, both under non-basic anhydrous conditions and in water. The authors found CuTC by screening sulfur ligands and sulfur-containing copper(I) complexes for selective formation of the triazole over an \u003cem\u003eN\u003c\/em\u003e-acyl sulfonamide by-product. They propose that CuTC stabilises the triazolyl–copper intermediate and so disfavours loss of nitrogen to a ketenimine. They also suggest that, in toluene, the carboxylate may deprotonate the alkyne; if the thiophene-2-carboxylic acid formed stays bound to copper, the final protonolysis would be intramolecular. Internal alkynes did not react, which the authors take as strong support for copper(I) acetylide intermediates. In another study, a 1-sulfonyl triazole made with CuTC from tosyl azide and phenylacetylene was converted, without isolation, into a 1-sulfonyl imidazole by rhodium(II)-catalysed reaction with benzonitrile. CuTC also catalysed the reaction of sulfamoyl azides with alkynes to 1-sulfamoyl-1,2,3-triazoles, which the authors describe as shelf-stable precursors of rhodium azavinyl carbenes.\u003c\/p\u003e\n\u003cdiv style=\"margin:8px 0 18px 0;\"\u003e\n\u003cdiv style=\"display:flex;flex-wrap:wrap;align-items:center;justify-content:flex-start;gap:2px;\"\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"170px\" height=\"80px\" viewbox=\"0 0 170 80\"\u003e\u003cpath d=\"M 34,26 L 52,36\"\u003e\u003c\/path\u003e\u003cpath d=\"M 50,45 L 41,60\"\u003e\u003c\/path\u003e\u003cpath d=\"M 54,47 L 46,62\"\u003e\u003c\/path\u003e\u003cpath d=\"M 61,35 L 70,20\"\u003e\u003c\/path\u003e\u003cpath d=\"M 57,33 L 66,18\"\u003e\u003c\/path\u003e\u003cpath d=\"M 61,42 L 79,52\"\u003e\u003c\/path\u003e\u003cpath d=\"M 87,50 L 105,39\"\u003e\u003c\/path\u003e\u003cpath d=\"M 89,54 L 107,44\"\u003e\u003c\/path\u003e\u003cpath d=\"M 117,32 L 132,24\"\u003e\u003c\/path\u003e\u003cpath d=\"M 120,36 L 134,28\"\u003e\u003c\/path\u003e\u003cg style=\"font-family:sans-serif;fill:#000;stroke:none\"\u003e\u003ctext x=\"26\" y=\"29\" font-size=\"12\"\u003eR\u003c\/text\u003e\u003ctext x=\"34\" y=\"24\" font-size=\"7\"\u003e1\u003c\/text\u003e\u003ctext x=\"53\" y=\"45\" font-size=\"12\"\u003eS\u003c\/text\u003e\u003ctext x=\"37\" y=\"72\" font-size=\"12\"\u003eO\u003c\/text\u003e\u003ctext x=\"68\" y=\"18\" font-size=\"12\"\u003eO\u003c\/text\u003e\u003ctext x=\"80\" y=\"60\" font-size=\"12\"\u003eN\u003c\/text\u003e\u003ctext x=\"107\" y=\"45\" font-size=\"12\"\u003eN\u003c\/text\u003e\u003ctext x=\"115\" y=\"40\" font-size=\"7\"\u003e+\u003c\/text\u003e\u003ctext x=\"134\" y=\"29\" font-size=\"12\"\u003eN\u003c\/text\u003e\u003ctext x=\"142\" y=\"24\" font-size=\"7\"\u003e-\u003c\/text\u003e\u003c\/g\u003e\u003c\/svg\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;font-size:20px;padding:0 4px;\"\u003e\u003cspan\u003e+\u003c\/span\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"100px\" height=\"40px\" viewbox=\"0 0 100 40\"\u003e\u003cpath d=\"M 24,20 L 52,20\"\u003e\u003c\/path\u003e\u003cpath d=\"M 52,20 L 90,20\"\u003e\u003c\/path\u003e\u003cpath d=\"M 52,14 L 90,14\"\u003e\u003c\/path\u003e\u003cpath d=\"M 52,26 L 90,26\"\u003e\u003c\/path\u003e\u003cpath d=\"M 50,20 L 52,20 L 54,20\"\u003e\u003c\/path\u003e\u003cg style=\"font-family:sans-serif;fill:#000;stroke:none\"\u003e\u003ctext x=\"10\" y=\"26\" font-size=\"12\"\u003eR\u003c\/text\u003e\u003ctext x=\"19\" y=\"21\" font-size=\"7\"\u003e2\u003c\/text\u003e\u003c\/g\u003e\u003c\/svg\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"display:flex;flex-direction:column;align-items:center;justify-content:center;min-width:90px;max-width:130px;padding:0 4px;text-align:center;font-size:12px;line-height:1.3;\"\u003e\n\u003cdiv\u003eCuTC (cat.)\u003c\/div\u003e\n\u003cdiv style=\"font-size:30px;line-height:1;\"\u003e→\u003c\/div\u003e\n\u003cdiv\u003etoluene or water\u003c\/div\u003e\n\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"190px\" height=\"110px\" viewbox=\"0 0 190 110\"\u003e\u003cpath d=\"M 32,52 L 50,52\"\u003e\u003c\/path\u003e\u003cpath d=\"M 53,60 L 53,80\"\u003e\u003c\/path\u003e\u003cpath d=\"M 57,60 L 57,80\"\u003e\u003c\/path\u003e\u003cpath d=\"M 57,48 L 57,27\"\u003e\u003c\/path\u003e\u003cpath d=\"M 53,48 L 53,27\"\u003e\u003c\/path\u003e\u003cpath d=\"M 60,52 L 82,52\"\u003e\u003c\/path\u003e\u003cpath d=\"M 92,59 L 106,78\"\u003e\u003c\/path\u003e\u003cpath d=\"M 106,78 L 136,68\"\u003e\u003c\/path\u003e\u003cpath d=\"M 108,73 L 132,65\"\u003e\u003c\/path\u003e\u003cpath d=\"M 136,68 L 158,84\"\u003e\u003c\/path\u003e\u003cpath d=\"M 136,68 L 136,43\"\u003e\u003c\/path\u003e\u003cpath d=\"M 132,35 L 110,28\"\u003e\u003c\/path\u003e\u003cpath d=\"M 130,39 L 109,33\"\u003e\u003c\/path\u003e\u003cpath d=\"M 101,33 L 90,48\"\u003e\u003c\/path\u003e\u003cpath d=\"M 105,77 L 106,78 L 107,78\"\u003e\u003c\/path\u003e\u003cg style=\"font-family:sans-serif;fill:#000;stroke:none\"\u003e\u003ctext x=\"19\" y=\"58\" font-size=\"12\"\u003eR\u003c\/text\u003e\u003ctext x=\"28\" y=\"54\" font-size=\"7\"\u003e1\u003c\/text\u003e\u003ctext x=\"51\" y=\"58\" font-size=\"12\"\u003eS\u003c\/text\u003e\u003ctext x=\"51\" y=\"90\" font-size=\"12\"\u003eO\u003c\/text\u003e\u003ctext x=\"51\" y=\"26\" font-size=\"12\"\u003eO\u003c\/text\u003e\u003ctext x=\"84\" y=\"58\" font-size=\"12\"\u003eN\u003c\/text\u003e\u003ctext x=\"159\" y=\"93\" font-size=\"12\"\u003eR\u003c\/text\u003e\u003ctext x=\"167\" y=\"88\" font-size=\"7\"\u003e2\u003c\/text\u003e\u003ctext x=\"133\" y=\"42\" font-size=\"12\"\u003eN\u003c\/text\u003e\u003ctext x=\"102\" y=\"32\" font-size=\"12\"\u003eN\u003c\/text\u003e\u003c\/g\u003e\u003c\/svg\u003e\u003c\/div\u003e\n\u003c\/div\u003e\n\u003cp style=\"font-size:12px;margin:4px 0 0 0;\"\u003e\u003cem\u003eCuTC-catalysed synthesis of 1-sulfonyl-1,2,3-triazoles from sulfonyl azides and terminal alkynes, as reported in one study, with toluene or water as the solvent. Quantities and conditions are not shown.\u003c\/em\u003e\u003c\/p\u003e\n\u003c\/div\u003e\n\u003cp\u003e\u003cstrong\u003eOther uses in copper chemistry.\u003c\/strong\u003e One study coupled aryl iodides, mostly piperazine-substituted pyrimidines, pyridines and benzenes, with aryl thiols to diaryl sulfides using CuTC, which the authors describe as a soluble, non-basic catalyst; \u003cem\u003eortho\u003c\/em\u003e-substituted and heteroaryl partners also coupled. In another, catalytic CuTC converted propargylic halides and (trifluoromethyl)trimethylsilane into trifluoromethylated products with high selectivity. In a copper-catalysed trifluoromethylation of unactivated alkenes, CuTC was chosen for an epoxide-containing substrate as a catalyst of lower Lewis acidity, to avoid ring-opening of the epoxide by methanol.\u003c\/p\u003e\n\u003cp\u003eIn one study, CuTC catalysed the enantioselective S\u003csub\u003eN\u003c\/sub\u003e2′ allylic alkylation of difunctionalised allylic halides, such as 1,4-dihalo-2-butenes, with Grignard reagents; more substituted alkenes gave all-carbon quaternary stereocentres. With DMEDA as the ligand, CuTC served as the copper source for the \u003cem\u003eN\u003c\/em\u003e-allenylation of allylic sulfonamides with bromoallenes. Combined with FeCl₃, CuTC formed a bimetallic system that coupled aryl Grignard reagents with 1-arylvinyl halides to 1,1-diarylethylenes, and the system outperformed either metal used alone. An air-stable \u003cem\u003eN\u003c\/em\u003e-heterocyclic carbene–copper thiophene-2-carboxylate complex catalysed the stereoselective hydroboration of terminal alkynes with pinacolborane or HBdan, and hydroboranes activated it directly, without a base co-catalyst.\u003c\/p\u003e\n\u003c\/div\u003e\u003c\/div\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"margin-bottom: 28px;\"\u003e\n\u003cdiv style=\"background: #002147; padding: 10px 20px; margin-bottom: 0;\"\u003e\u003ch3 style=\"margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; font-size: 0.70em; font-weight: bold; letter-spacing: 0.12em; text-transform: uppercase; color: #fff;\"\u003eShipping Destinations\u003c\/h3\u003e\u003c\/div\u003e\n\u003cdiv style=\"border: 1px solid #e4e8f0; border-top: none; padding: 12px 16px; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; font-size: 0.95em;\"\u003e\u003cul style=\"margin: 0; padding: 0; list-style: none;\"\u003e\n\u003cli style=\"padding: 5px 0; border-bottom: 1px solid #f0f0f0;\"\u003e\n\u003cspan style=\"display: inline-block; width: 7px; height: 7px; background: #002147; border-radius: 50%; margin-right: 10px; vertical-align: middle;\"\u003e\u003c\/span\u003eEU \u0026amp; UK: Priority delivery, 2–5 business days.\u003c\/li\u003e\n\u003cli style=\"padding: 5px 0; border-bottom: 1px solid #f0f0f0;\"\u003e\n\u003cspan style=\"display: inline-block; width: 7px; height: 7px; background: #002147; border-radius: 50%; margin-right: 10px; vertical-align: middle;\"\u003e\u003c\/span\u003eUnited States (DDP): 3–7 business days, duties and taxes prepaid.\u003c\/li\u003e\n\u003cli style=\"padding: 5px 0; border-bottom: 1px solid #f0f0f0;\"\u003e\n\u003cspan style=\"display: inline-block; width: 7px; height: 7px; background: #002147; border-radius: 50%; margin-right: 10px; vertical-align: middle;\"\u003e\u003c\/span\u003eEFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.\u003c\/li\u003e\n\u003cli style=\"padding: 5px 0; border-bottom: 1px solid #f0f0f0;\"\u003e\n\u003cspan style=\"display: inline-block; width: 7px; height: 7px; background: #002147; border-radius: 50%; margin-right: 10px; vertical-align: middle;\"\u003e\u003c\/span\u003eWorldwide: 7–14 business days, selected locations.\u003c\/li\u003e\n\u003c\/ul\u003e\u003c\/div\u003e\n\u003c\/div\u003e","brand":"NorrChemica™","offers":[{"title":"5.0 g","offer_id":55166901420369,"sku":"NOR-68986765-5g","price":74.2,"currency_code":"EUR","in_stock":true},{"title":"10 g","offer_id":55166901453137,"sku":"NOR-68986765-10g","price":98.2,"currency_code":"EUR","in_stock":true},{"title":"25 g","offer_id":55166901485905,"sku":"NOR-68986765-25g","price":129.2,"currency_code":"EUR","in_stock":true},{"title":"100 g","offer_id":55166901518673,"sku":"NOR-68986765-100g","price":298.8,"currency_code":"EUR","in_stock":true},{"title":"500 g","offer_id":55166901551441,"sku":"NOR-68986765-500g","price":1195.0,"currency_code":"EUR","in_stock":true}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/0954\/6357\/1793\/files\/NorrChemica_Copper_I_Thiophene-2-carboxylate.png?v=1791061644","url":"https:\/\/www.norrchemica.com\/products\/copper-i-thiophene-2-carboxylate-cutc-cas-68986-76-5","provider":"NorrChemica","version":"1.0","type":"link"}