Description

(6,6′-Dimethoxy-2,2′-biphenyldiyl)bis[bis(3,5-dimethylphenyl)phosphine] (CAS No. 362634-22-8) is a highly specialized organophosphorus compound with the molecular formula C₄₆H₄₈O₂P₂. This biphenyl-based phosphine ligand features methoxy and dimethylphenyl substituents, offering steric and electronic tuning for transition metal catalysis. Its rigid biphenyl backbone and electron-rich phosphine centers make it ideal for asymmetric synthesis, cross-coupling reactions, and other metal-mediated transformations. The compound is supplied as a high-purity solid, rigorously characterized by ¹H/³¹P NMR, HPLC, and elemental analysis. Store under inert atmosphere at -20°C to maintain stability.

Properties

• CAS Number: 362634-22-8
• Complexity: 864
• IUPAC Name: [2-[2-bis(3,5-dimethylphenyl)phosphanyl-6-methoxy-phenyl]-3-methoxy-phenyl]-bis(3,5-dimethylphenyl)phosphane
• InChI: InChI=1S/C46H48O2P2/c1-29-17-30(2)22-37(21-29)49(38-23-31(3)18-32(4)24-38)43-15-11-13-41(47-9)45(43)46-42(48-10)14-12-16-44(46)50(39-25-33(5)19-34(6)26-39)40-27-35(7)20-36(8)28-40/h11-28H,1-10H3
• InChI Key: IMUHNRWTDUVXOU-UHFFFAOYSA-N
• Exact Mass: 694.31295476
• Molecular Formula: C46H48O2P2
• Molecular Weight: 694.8
• SMILES: CC1=CC(=CC(=C1)P(C2=CC=CC(=C2C3=C(C=CC=C3P(C4=CC(=CC(=C4)C)C)C5=CC(=CC(=C5)C)C)OC)OC)C6=CC(=CC(=C6)C)C)C
• Topological: 18.5
• Monoisotopic Mass: 694.31295476
• Synonyms: 362634-22-8, (6,6′-Dimethoxy-2,2′-biphenyldiyl)bis(bis(3,5-dimethylphenyl)phosphine), (6,6′-Dimethoxy-2,2′-biphenyldiyl)bis[bis(3,5-dimethylphenyl)phosphine], 811-686-3, 811-687-9, 394248-45-4, (S)-(-)-2,2′-Bis[di(3,5-xylyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl, (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-dimethylphenyl)phosphine], MFCD09753009, (R)-(+)-2,2′-Bis[di(3,5-xylyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl, [2-[2-bis(3,5-dimethylphenyl)phosphanyl-6-methoxyphenyl]-3-methoxyphenyl]-bis(3,5-dimethylphenyl)phosphane, (S)-(-)-2,2′-Bis[di(3,5-xylyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl,min.97%, (R)-(6,6′-Dimethoxybiphenyl-2,2-‘-diyl)bis[bis(3,5-dimethylphenyl)phosphine], (S)-(6,6′-DIMETHOXYBIPHENYL-2,2′-DIYL)BIS[BIS(3,5-DIMETHYLPHENYL)PHOSPHINE], 3,5-xyl-meo-biphep, AGN-PC-004SVW, SCHEMBL1224437, DTXSID00459317, IMUHNRWTDUVXOU-UHFFFAOYSA-N, (R)-(6,6 inverted exclamation marka-Dimethoxybiphenyl-2,2 inverted exclamation marka-diyl)bis[bis(3,5-dimethylphenyl)phosphine], SY066941, SY075188, E76889, E76890, (R)-(6,6?-Dimethoxybiphenyl-2,2?-diyl)bis[bis(3,5-dimethylphenyl)phosphine], (S)-(-)-2,2”-Bis[di(3,5-xylyl)phosphino]-6,6”-dimethoxy-1,1”-biphenyl, (R)-(+)-2,2 inverted exclamation mark -Bis[di(3,5-xylyl)phosphino]-6,6 inverted exclamation mark -dimethoxy-1,1 inverted exclamation mark -biphenyl, (R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-dimethylphenyl)phosphine], >=97% (CHN), optical purity ee: >=99%, (S)-(6,6 inverted exclamation mark -Dimethoxy-[1,1 inverted exclamation mark -biphenyl]-2,2 inverted exclamation mark -diyl)bis[bis(3,5-dimethylphenyl)phosphine], (S)-(6,6′-Dimethoxybiphenyl-2,2’-diyl)bis[bis(3,5-dimethylphenyl)phosphine], >=97%, optical purity ee: >=99%

Application

This sterically demanding bisphosphine ligand is particularly valuable in asymmetric hydrogenation and C-C bond-forming reactions, where its electron-donating methoxy groups and bulky 3,5-dimethylphenyl substituents promote high enantioselectivity. It has shown excellent performance in rhodium- and ruthenium-catalyzed reductions of unsaturated substrates. Researchers also employ it in Suzuki-Miyaura and Heck couplings where traditional ligands fail due to steric constraints.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

If you are interested or have any questions, please contact us at support@atomfair.com

Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.