{"product_id":"products-2-hydroxyphenylboronic-acid-cas-89466-08-0","title":"(2-Hydroxyphenyl)boronic Acid | CAS 89466-08-0 | ≥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;\"\u003e89466-08-0\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;\"\u003e677-277-5\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;\"\u003eMDL Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eMFCD01074581\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;\"\u003eB(C1=CC=CC=C1O)(O)O\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\/C6H7BO3\/c8-6-4-2-1-3-5(6)7(9)10\/h1-4,8-10H\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;\"\u003eYDMRDHQUQIVWBE-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;\"\u003e2773454\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;\"\u003eC₆H₇BO₃\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;\"\u003e137.93 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;\"\u003e178–182 °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;\"\u003eSoluble in methanol, ethanol, DMSO, DMF, chloroform, dichloromethane, and THF.\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%. May contain varying amounts of the corresponding boronic acid anhydrides\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;\"\u003eWhite to pale yellow crystalline powder\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;\"\u003e2931.90\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;\"\u003eCountry of Origin\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eFinland\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 in a cool, dry place in a tightly sealed container. Refrigeration recommended.\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\u003e(2-Hydroxyphenyl)boronic acid\u003c\/strong\u003e (2-boronophenol) is a phenylboronic acid bearing a phenolic hydroxyl ortho to boron. The boron is a handle for carbon–carbon coupling, the phenol for carbon–oxygen bond formation. It forms cyclic esters reversibly with 1,2- and 1,3-diols and binds anions, the position of both equilibria set by its acidity.\u003c\/p\u003e\n\u003cp\u003eMay contain small amounts of the cyclic anhydride (2-hydroxyphenyl)boroxine. Under the aqueous, basic coupling conditions the two forms re-equilibrate, and the effect on yield is minor.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eSuzuki–Miyaura coupling.\u003c\/strong\u003e Under a suitable palladium\/ligand system it couples with aryl and heteroaryl halides to 2-hydroxybiaryls, the ortho phenol carried through unprotected.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eOxygen heterocycles.\u003c\/strong\u003e Suzuki coupling with a 1,2-dihaloarene, followed by copper(I) thiophene-2-carboxylate cyclisation, converts the reagent into dibenzofurans and benzofuro-fused heterocycles such as benzofuropyridines. The boron forms the biaryl bond, and the phenol closes onto the retained halide as an intramolecular carbon–oxygen bond. These ring systems serve as OLED emitters and host materials and as bioactive cores.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eAxially chiral biaryls.\u003c\/strong\u003e As its boronate ester it couples atroposelectively with ortho-substituted aryl bromides. A resolved sulfonated SPhos ligand (sSPhos) builds axially chiral 2,2′-biphenols in high enantioselectivity, 92% ee in a representative case. The related sRuPhos ligand extends the method to 2-amino-2′-hydroxybiphenyls in up to 99% ee. A hydrogen bond from the phenol to the ligand sulfonate organises the transition state and sets the axis. These biaryl diols are standard chiral ligands and recurring motifs in medicinal chemistry.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eLabile carbon–boron bond.\u003c\/strong\u003e The ortho hydroxyl labilises the carbon–boron bond, so the free acid protodeboronates readily and is commonly stored and used as its MIDA boronate. The same lability is a tool: installed on a phenol, the boronic acid blocks the ortho position or directs meta functionalisation, then leaves by thermal protodeboronation in DMSO.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eFurther Reading.\u003c\/strong\u003e For boronic acids, boronic esters, protodeboronation, boroxine content, and Suzuki–Miyaura reagent selection, see NorrChemica's Lab Journal guide: \u003ca href=\"https:\/\/www.norrchemica.com\/blogs\/lab-journal\/boron-reagent-selection-suzuki-miyaura-coupling\"\u003eChoosing Your Boron Source for Suzuki–Miyaura Coupling\u003c\/a\u003e.\u003c\/p\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\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":53674883285329,"sku":"NOR-89466080-5g","price":37.2,"currency_code":"EUR","in_stock":true},{"title":"10 g","offer_id":53674883383633,"sku":"NOR-89466080-10g","price":57.2,"currency_code":"EUR","in_stock":true},{"title":"25 g","offer_id":53674883416401,"sku":"NOR-89466080-25g","price":98.2,"currency_code":"EUR","in_stock":true},{"title":"50 g","offer_id":54227266928977,"sku":"NOR-89466080-50g","price":184.2,"currency_code":"EUR","in_stock":true},{"title":"100 g","offer_id":54227266961745,"sku":"NOR-89466080-100g","price":349.2,"currency_code":"EUR","in_stock":true},{"title":"250 g","offer_id":54227266994513,"sku":"NOR-89466080-250g","price":749.2,"currency_code":"EUR","in_stock":true}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/0954\/6357\/1793\/files\/NorrChemica__2-Hydroxyphenyl_boronicAcid.png?v=1782777926","url":"https:\/\/www.norrchemica.com\/products\/products-2-hydroxyphenylboronic-acid-cas-89466-08-0","provider":"NorrChemica","version":"1.0","type":"link"}