{"product_id":"tosmic-cas-36635-61-7","title":"TosMIC | CAS 36635-61-7 | ≥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: 700; letter-spacing: 0.12em; text-transform: uppercase; color: #fff;\"\u003eTechnical Specifications\u003c\/h3\u003e\n\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;\"\u003e36635-61-7\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;\"\u003eEC \/ EINECS Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e253-140-1\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;\"\u003eMDL Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eMFCD00000005\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;\"\u003eCC1=CC=C(C=C1)S(=O)(=O)C[N+]#[C-]\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\/C9H9NO2S\/c1-8-3-5-9(6-4-8)13(11,12)7-10-2\/h3-6H,7H2,1H3\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;\"\u003eCFOAUYCPAUGDFF-UHFFFAOYSA-N\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;\"\u003e161915\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;\"\u003eC₉H₉NO₂S\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;\"\u003e195.24 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;\"\u003eMelting Point\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e109-113 °C\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;\"\u003eSolubility\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eSlightly soluble in water; soluble in common organic solvents (THF, dichloromethane, chloroform, DMSO, 1,2-dimethoxyethane, ethyl acetate, benzene); slightly soluble in methanol, ethanol and diethyl ether.\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;\"\u003eSolid\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;\"\u003e2930.90\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; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eStorage Conditions\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eStore refrigerated (2–8 °C) under inert gas (N₂ or Ar) in a tightly sealed container, protected from moisture and light\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003c\/tbody\u003e\u003c\/table\u003e\n\u003c\/div\u003e\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: 700; letter-spacing: 0.12em; text-transform: uppercase; color: #fff;\"\u003eProduct Description \u0026amp; Scientific Applications\u003c\/h3\u003e\n\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\n\u003cp\u003e\u003cstrong\u003eTosMIC\u003c\/strong\u003e (p-toluenesulfonylmethyl isocyanide; (p-tolylsulfonyl)methyl isocyanide), the van Leusen reagent, is a densely functionalised isocyanide and one of the most versatile isocyanide reagents in synthesis. It delivers a C–N–C unit in azole ring synthesis and a single carbon in the homologation of carbonyl compounds to nitriles.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eReactivity basis.\u003c\/strong\u003e Its behaviour follows from three groups on one short framework: a strongly acidic methylene (pKa ≈ 14), flanked by the sulfonyl and isocyanide groups, that bases from potassium carbonate to n-butyllithium deprotonate; the p-toluenesulfonyl (tosyl) group, which departs as a sulfinate; and the isocyanide carbon, incorporated as the new ring or nitrile carbon.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eHandling.\u003c\/strong\u003e Unusually for an isocyanide, TosMIC is an odourless, bench-stable white solid.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eApplications and Reactions\u003c\/strong\u003e\u003c\/p\u003e\n\u003cul\u003e\n\u003cli\u003e\n\u003cstrong\u003eOxazoles — van Leusen oxazole synthesis:\u003c\/strong\u003e deprotonated TosMIC adds to an aldehyde; cyclisation and elimination of toluenesulfinic acid deliver a 5-substituted oxazole. Under milder base the 4,5-dihydrooxazole (oxazoline) intermediate can be isolated.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003eImidazoles — van Leusen imidazole synthesis:\u003c\/strong\u003e with an aldimine — or with an aldehyde and a primary amine forming the imine in situ (three-component) — TosMIC undergoes base-induced [3+2] cycloaddition to 1,5-disubstituted and 1,4,5-trisubstituted imidazoles.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003ePyrroles — van Leusen pyrrole synthesis:\u003c\/strong\u003e TosMIC reacts with electron-deficient alkenes (Michael acceptors bearing ester, ketone, nitro, cyano or aryl groups) by [3+2] cycloaddition to give substituted pyrroles.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003eThiazoles:\u003c\/strong\u003e under phase-transfer conditions TosMIC reacts with carbon disulfide, giving a thiazole salt that is converted to the thiazole.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003e1,2,4-Triazoles:\u003c\/strong\u003e TosMIC condenses with aryldiazonium salts to give 1,2,4-triazoles.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003eCarbonyls to nitriles — reductive cyanation:\u003c\/strong\u003e with potassium tert-butoxide in a non-protic solvent (DME, DMSO), TosMIC converts ketones directly into the one-carbon-homologated nitriles, without an α-hydroxy (cyanohydrin) intermediate; the same reductive cyanation extends to aldehydes. The reaction spans a broad range of substrates.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003eConnective C1 reagent:\u003c\/strong\u003e as a formaldehyde equivalent of reversed polarity, the acidic methylene is mono- or dialkylated and the isocyanide then hydrolysed, coupling alkyl halides through a carbonyl carbon to give aldehydes and symmetrical or unsymmetrical ketones — an umpolung of formaldehyde.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003eCatalytic asymmetric addition:\u003c\/strong\u003e a dimethylzinc-mediated catalytic, enantio- and diastereoselective addition of TosMIC to ketones gives enantioenriched oxazolines.\u003c\/li\u003e\n\u003c\/ul\u003e\n\u003c\/div\u003e\n\u003c\/div\u003e\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: 700; letter-spacing: 0.12em; text-transform: uppercase; color: #fff;\"\u003eShipping Destinations\u003c\/h3\u003e\n\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\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 only: Priority delivery, 2–5 business days. Classified as dangerous goods — shipping restrictions apply outside the EU\/UK.\u003c\/li\u003e\u003c\/ul\u003e\u003c\/div\u003e\n\u003c\/div\u003e","brand":"NorrChemica™","offers":[{"title":"5 g","offer_id":53867985469777,"sku":"NOR-36635617-5g","price":47.2,"currency_code":"EUR","in_stock":true},{"title":"10 g","offer_id":53867985502545,"sku":"NOR-36635617-10g","price":74.2,"currency_code":"EUR","in_stock":true},{"title":"25 g","offer_id":53867985535313,"sku":"NOR-36635617-25g","price":98.2,"currency_code":"EUR","in_stock":true},{"title":"50 g","offer_id":54195447529809,"sku":"NOR-36635617-50g","price":149.2,"currency_code":"EUR","in_stock":true},{"title":"100 g","offer_id":54195447562577,"sku":"NOR-36635617-100g","price":199.2,"currency_code":"EUR","in_stock":true},{"title":"250 g","offer_id":54195447595345,"sku":"NOR-36635617-250g","price":429.2,"currency_code":"EUR","in_stock":true}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/0954\/6357\/1793\/files\/NorrChemica_TosMIC_v2.png?v=1782881121","url":"https:\/\/www.norrchemica.com\/products\/tosmic-cas-36635-61-7","provider":"NorrChemica","version":"1.0","type":"link"}