871707-40-3

Basic information

• Product Name: 2-bromo-6-(dicyclohexylphosphino)-2'-(diphenylphosphino)-6'-methoxy-1,1'-biphenyl
• Synonyms: 2-bromo-6-(dicyclohexylphosphino)-2'-(diphenylphosphino)-6'-methoxy-1,1'-biphenyl
• CAS NO: 871707-40-3
• Molecular Weight: 643.583
• Mol File: 871707-40-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-bromo-6-(dicyclohexylphosphino)-2'-(diphenylphosphino)-6'-methoxy-1,1'-biphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-6-(dicyclohexylphosphino)-2'-(diphenylphosphino)-6'-methoxy-1,1'-biphenyl(871707-40-3)
• EPA Substance Registry System: 2-bromo-6-(dicyclohexylphosphino)-2'-(diphenylphosphino)-6'-methoxy-1,1'-biphenyl(871707-40-3)

Safety Data

• Hazardous Substances Data: 871707-40-3(Hazardous Substances Data)

Upstream product

• 911297-81-9 2,6,6'-tribromo-1,1'-biphenyl-2-ol 
• 871707-39-0 2-bromo-6-(dicyclohexylphosphino)-2'-iodo-6'-methoxy-1,1'-biphenyl 
• 1079-66-9 chloro-diphenylphosphine 
• 97038-96-5 2,2’,6,6’-tetrabromobiphenyl 
• 871707-38-9 2-bromo-2',6-diiodo-6'-methoxy-1,1'-biphenyl 
• 871707-37-8 2,6,6'-tribromo-2'-methoxy-1,1'-biphenyl 

Relevant articles and documents

First modular synthesis of dissymmetric biaryldiphosphine ligands allowing tunable steric and electronic effects

The first modular synthesis of a family of C1-symmetric diphosphine ligands is presented. Their synthesis is based on unprecedented highly regioselective halogen/metal interconversions on a common polybrominated biaryl precursor. This methodology allows the functionalization of the ortho- and ortho'-positions of the biaryl core. Diphosphine ligands carrying only one substituent at the 6-position and the two phosphine substituents at the 2- and 2′-position become easily accessible. The two phosphine substituents may be identical (as in compounds 2 and 3) or different (as in compounds 1 and 4). All diphosphines were prepared on gram scale, and the enantiopure ligands were obtained by chromatography of the racemate on a chiral HPLC column. The asymmetric hydrogenation of β-keto esters, acetamidocinnamates and dimethyl itaconate revealed good to excellent asymmetric inductions of up to 99 % ee, and are often close to those of the well-known C2-symmetric MeO-BIPHEP.

Process for the preparation of asymmetrically substituted biaryldiphosphines

Provided is a process for the preparation of asymmetrically substituted biaryldiphosphine ligands of the formula wherein R1 is C1-6-alkyl or C3-10-cycloalkyl optionally being substituted with one or more halogen atoms, and R2 and R3 are independently selected from the group consisting of aryl, C5-10-cycloalkyl and C1-6-alkyl, wherein each aryl moiety is optionally substituted with one or more substituents selected from the group consisting of halogen atoms, nitro, amino, C1-6-alkyl, C1-6-alkoxy and di-C1-6-alkylamino groups, and each C1-6-alkyl, C1-6-alkoxy, di-C1-6-alkylamino and C5-10-cycloalkyl group in R2 and R3 optionally being substituted with one or more halogen atoms, from 2,2',6,6'-tetrabromobiphenyl by a sequence of halogen-metal exchanges and subsequent reactions.