{"product_id":"r-binap-cas-76189-55-4","title":"(R)-BINAP | CAS 76189-55-4 | ≥99%","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;\"\u003e76189-55-4\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;\"\u003e616-304-7\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;\"\u003eMFCD00010805\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=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8\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\/C44H32P2\/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38\/h1-32H\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;\"\u003eMUALRAIOVNYAIW-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;\"\u003e634876\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;\"\u003eC44H32P2\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;\"\u003e622.67 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;\"\u003e239-242 °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;\"\u003eInsoluble in water, soluble in common organic solvents\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≥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;\"\u003ePhysical Form\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eWhite to off-white 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;\"\u003e2931.49\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\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(R)-BINAP\u003c\/strong\u003e ((R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) is a C₂-symmetric atropisomeric diphosphine and a landmark chiral ligand in asymmetric catalysis. Its chirality is axial rather than centred on a stereogenic atom: restricted rotation about the 1,1'-binaphthyl bond locks the two naphthyl units into a fixed, twisted arrangement, and on chelation to a metal the two diphenylphosphino groups define a rigid C₂-symmetric chiral pocket. (R)-BINAP is the antipode of (S)-BINAP — identical in constitution but opposite in axial sense — providing the opposite-handed catalyst environment, so the two enantiomers are commonly selected as a matched pair when either product configuration is required under a given catalyst system.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eStructure and stereochemical basis\u003c\/strong\u003e\u003c\/p\u003e\n\u003cp\u003eThe axial chirality of BINAP is configurationally robust: computed enantiomerisation barriers exceed 200 kJ·mol⁻¹, with a calculated racemisation temperature near 490 °C, so the resolved atropisomers are configurationally stable under ordinary laboratory handling and catalytic-use conditions. On binding a metal through both phosphorus atoms, the two diphenylphosphino groups project their P-phenyl rings into a C₂-symmetric array of alternating steric quadrants around the metal centre. Because the ligand is C₂-symmetric, its two phosphorus donors are equivalent, reducing the number of competing diastereomeric substrate-binding arrangements; this quadrant-controlled steric environment is a major structural basis for BINAP's high enantioselectivity and underlies its standing as a privileged chiral ligand.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eRuthenium-catalysed asymmetric hydrogenation\u003c\/strong\u003e\u003c\/p\u003e\n\u003cp\u003eRu–BINAP complexes are central to Noyori asymmetric hydrogenation chemistry. They reduce β-keto esters to β-hydroxy esters in high enantiomeric excess and, through dynamic kinetic resolution of configurationally labile α-substituted β-keto esters, can set two stereocentres in a single operation. The scope extends to β-functionalised ketones, allylic and homoallylic alcohols — the chemoselective hydrogenation of geraniol to citronellol is a well-documented example — and to enamides and α-(acylamino)acrylates used to prepare enantioenriched amine and amino-acid derivatives, including tetrahydroisoquinoline alkaloid frameworks. Paired with a 1,2-diamine, BINAP\/diamine–Ru systems hydrogenate simple and functionalised ketones chemoselectively in the presence of olefins; in optimised systems, turnover numbers above 100,000 have been reported.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eRhodium-catalysed asymmetric transformations\u003c\/strong\u003e\u003c\/p\u003e\n\u003cp\u003eRh–BINAP catalyses the enantioselective isomerisation of allylic amines to enamines; the diethylgeranylamine-to-citronellal-enamine transformation is the key asymmetric step in an industrial route to (−)-menthol, reported with high enantioselectivity and turnover numbers above 400,000. Rh–BINAP systems also feature in the asymmetric hydrogenation of enamides and in Hayashi–Miyaura-type asymmetric 1,4-addition of aryl- and alkenylboronic acids to enones and other α,β-unsaturated carbonyl compounds.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003ePalladium-catalysed asymmetric catalysis\u003c\/strong\u003e\u003c\/p\u003e\n\u003cp\u003ePd–BINAP systems mediate asymmetric allylic substitution and amination through chiral η³-allylpalladium intermediates; the allylation of unsymmetrical 1,3-diketones to chiral 2,2-dialkyl-1,3-diketones is a representative example. They are also prominent in asymmetric Heck chemistry, including intramolecular cyclisations where alkene carbopalladation forms C–C bonds and can establish tertiary or all-carbon quaternary stereocentres. Pd–BINAP was likewise among the first-generation catalyst systems for Buchwald–Hartwig C–N coupling, joining aryl halides and triflates with amines.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eGold and broader asymmetric catalysis\u003c\/strong\u003e\u003c\/p\u003e\n\u003cp\u003eBeyond the group 8–10 metals, binuclear gold(I)–BINAP complexes are among the most-studied catalysts for enantioselective π-acid transformations, including cycloisomerisations of 1,n-enynes, cyclopropanations, and alkene hydrofunctionalisations. More broadly, BINAP is a parent scaffold for a family of axially chiral diphosphines — including tolyl- and xylyl-substituted variants tuned for steric bulk and electronic donation — and a reference ligand for assembling well-defined chiral metal complexes in mechanistic, structural, and asymmetric-induction studies. Its rigid C₂-symmetric pocket and broad metal compatibility make it a common reference ligand in catalyst screening for chiral alcohol, amine, and carbonyl-derived building blocks, typically deployed alongside (S)-BINAP when both senses of enantioselectivity are required.\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":"1.0 g","offer_id":53847139189073,"sku":"NOR-76189554-1g","price":34.9,"currency_code":"EUR","in_stock":true},{"title":"2.0 g","offer_id":53847139221841,"sku":"NOR-76189554-2g","price":49.9,"currency_code":"EUR","in_stock":true},{"title":"5.0 g","offer_id":53847139254609,"sku":"NOR-76189554-5g","price":74.2,"currency_code":"EUR","in_stock":true},{"title":"10 g","offer_id":53847139287377,"sku":"NOR-76189554-10g","price":129.2,"currency_code":"EUR","in_stock":true},{"title":"25 g","offer_id":53847139320145,"sku":"NOR-76189554-25g","price":229.9,"currency_code":"EUR","in_stock":true},{"title":"50 g","offer_id":53847139352913,"sku":"NOR-76189554-50g","price":398.2,"currency_code":"EUR","in_stock":true},{"title":"100 g","offer_id":53847139385681,"sku":"NOR-76189554-100g","price":540.0,"currency_code":"EUR","in_stock":true}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/0954\/6357\/1793\/files\/NorrChemica__R_-BINAP_v2.png?v=1782872620","url":"https:\/\/www.norrchemica.com\/products\/r-binap-cas-76189-55-4","provider":"NorrChemica","version":"1.0","type":"link"}