{"product_id":"tris2-methoxyphenylphosphine-cas-4731-65-1-97","title":"Tris(2-methoxyphenyl)phosphine | CAS 4731-65-1 | ≥97%","description":"\u003cdiv style=\"margin-bottom: 28px;\"\u003e\n\u003cdiv style=\"background: #002147; padding: 10px 20px; margin-bottom: 0;\"\u003e\n\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\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\n\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;\"\u003e4731-65-1\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;\"\u003eEC \/ EINECS Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e225-235-8\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;\"\u003eMFCD00014892\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;\"\u003eCOC1=CC=CC=C1P(C2=CC=CC=C2OC)C3=CC=CC=C3OC\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\/C21H21O3P\/c1-22-16-10-4-7-13-19(16)25(20-14-8-5-11-17(20)23-2)21-15-9-6-12-18(21)24-3\/h4-15H,1-3H3\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;\"\u003eIIOSDXGZLBPOHD-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;\"\u003e78464\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;\"\u003eC₂₁H₂₁O₃P\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;\"\u003e352.4 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;\"\u003e198–204 °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≥97%\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 almost white powder to crystal\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;\"\u003eKeep container tightly closed. Store at room temperature; a cool, dark place below 15 °C is recommended.\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;\"\u003eSDS \/ CoA\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333;\"\u003e\u003ca href=\"https:\/\/cdn.shopify.com\/s\/files\/1\/0954\/6357\/1793\/files\/Tris_2-methoxyphenyl_phosphine_EU_MSDS_1.0.pdf?v=1788025839\" rel=\"noopener noreferrer\" style=\"color: #002147; text-decoration: underline; font-weight: 500;\" target=\"_blank\"\u003eDownload PDF\u003c\/a\u003e\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003c\/tbody\u003e\n\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\n\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\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\u003eTris(2-methoxyphenyl)phosphine\u003c\/strong\u003e (tri-\u003cem\u003eo\u003c\/em\u003e-anisylphosphine, P(\u003cem\u003eo\u003c\/em\u003e-anisyl)₃) is a monodentate, electron-rich triarylphosphine ligand for palladium. Electron density at phosphorus rises with the number of methoxy groups on the phenyl rings, and one group on every ring is the optimum. Further substitution only adds steric hindrance, which impedes substrate coordination and lowers catalyst activity.\u003c\/p\u003e\n\u003cp\u003eIt is the most widely used ligand for direct arylation, and increasing its loading per palladium centre does not improve catalytic activity. It is also the reference ligand against which new \u003cem\u003eortho\u003c\/em\u003e-substituted phosphines are benchmarked in polymerisation. It is readily available from anisole and relatively air-stable.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eApplications and Reactions\u003c\/strong\u003e\u003c\/p\u003e\n\u003cul\u003e\n\u003cli\u003e\n\u003cstrong\u003eDirect arylation polymerisation:\u003c\/strong\u003e It is paired with a palladium dibenzylideneacetone source, pivalic acid and caesium carbonate in toluene. Density functional theory attributes its effect to suppression of head-to-head and tail-to-tail linkages, which raises the regioregularity of the polymer produced.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003eDirect C–H heteroarylation:\u003c\/strong\u003e With the Herrmann palladacycle it gives conjugated copolymers at high molecular weight. On small molecules the same system arylates heteroaryl bromides, with potassium carbonate as base and pivalic acid as proton shuttle. A palladium acetate variant of the same coupling runs with caesium carbonate and caesium pivalate.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003eHindered Suzuki biaryls:\u003c\/strong\u003e With palladium acetate it couples aryl bromides with arylboronic acids and is chosen where the biaryl is congested: with \u003cem\u003eortho\u003c\/em\u003e-methyl aryl halides it raised the isolated yield from 64-69% to 96%.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003eButadiene telomerization:\u003c\/strong\u003e In palladium-catalysed telomerization of glycerol with 1,3-butadiene it gave the maximum activity of the phosphines screened, reaching a comparable yield in 0.5 instead of 5 h. The same pairing telomerizes 1,3-butadiene with carbon dioxide to an unsaturated δ-lactone, with significantly increased yields.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003eCoupling at hindered carbons:\u003c\/strong\u003e It couples organocopper(I) reagents under palladium acetate, joining a 9-triptycenylcopper(I) complex where the boronate ester and zinc analogues gave none.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003eCarborane functionalisation:\u003c\/strong\u003e A palladium catalyst supported by this ligand is the optimal system for building densely functionalised icosahedral carboranes.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003eDocumented limits:\u003c\/strong\u003e In Buchwald-Hartwig amination with palladium acetate it gives only moderate to good conversion, in the same range as triphenylphosphine under the same ligand screen. In direct heteroarylation it may prevent homocoupling between the electron-poor comonomer units, but homocoupling at other positions and backbone defects can still arise.\u003c\/li\u003e\n\u003c\/ul\u003e\n\u003cp\u003e\u003cstrong\u003eFurther Reading\u003c\/strong\u003e\u003c\/p\u003e\n\u003cp\u003ePractical guidance on choosing a phosphine ligand for palladium- and nickel-catalysed cross-coupling in NorrChemica's Lab Journal: \u003ca href=\"https:\/\/www.norrchemica.com\/blogs\/lab-journal\/choosing-a-phosphine-ligand-for-cross-coupling-a-practical-guide\"\u003ePhosphine Ligands for Cross-Coupling\u003c\/a\u003e.\u003c\/p\u003e\n\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\n\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\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\n\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, 3–5 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\n\u003c\/div\u003e\n\u003c\/div\u003e","brand":"NorrChemica™","offers":[{"title":"500 mg","offer_id":54728381202769,"sku":"NOR-4731651-500mg","price":29.2,"currency_code":"EUR","in_stock":true},{"title":"1.0 g","offer_id":54728381235537,"sku":"NOR-4731651-1g","price":37.2,"currency_code":"EUR","in_stock":true},{"title":"2.0 g","offer_id":54728381268305,"sku":"NOR-4731651-2g","price":45.2,"currency_code":"EUR","in_stock":true},{"title":"5.0 g","offer_id":54728381301073,"sku":"NOR-4731651-5g","price":57.2,"currency_code":"EUR","in_stock":true},{"title":"10 g","offer_id":54728381333841,"sku":"NOR-4731651-10g","price":74.2,"currency_code":"EUR","in_stock":true},{"title":"25 g","offer_id":54728381366609,"sku":"NOR-4731651-25g","price":119.2,"currency_code":"EUR","in_stock":true},{"title":"50 g","offer_id":54728381399377,"sku":"NOR-4731651-50g","price":198.2,"currency_code":"EUR","in_stock":true},{"title":"100 g","offer_id":54728381432145,"sku":"NOR-4731651-100g","price":329.2,"currency_code":"EUR","in_stock":true},{"title":"250 g","offer_id":54728381464913,"sku":"NOR-4731651-250g","price":798.2,"currency_code":"EUR","in_stock":true}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/0954\/6357\/1793\/files\/NorrChemica_TMPP_v2.png?v=1788022385","url":"https:\/\/www.norrchemica.com\/products\/tris2-methoxyphenylphosphine-cas-4731-65-1-97","provider":"NorrChemica","version":"1.0","type":"link"}