1365531-75-4

Basic information

• Product Name: (R)-2,2'-Bis(diphenylphosphino)-4,4',6,6'-tetraMethoxybiphenyl, 97+%
• Synonyms: (R)-2,2'-Bis(diphenylphosphino)-4,4',6,6'-tetraMethoxybiphenyl, 97+%;(R)-2,2'-Bis(diphenylphosphino)-4,4',6,6'-tetraMethoxybiphenyl, Min. 97% (R)-Ph-Garphos;(R)-2,2'-Bis(diphenylphosphino)-4,4',6,6'-tetramethoxy)-1,1'-biphenyl;(R)-2,2'-Bis(diphenylphosphino)-4,4',6,6'-tetramethoxy)-1,1'-biphenyl, min. 97% (R)-Ph-Garphos(TM)
• CAS NO: 1365531-75-4
• Molecular Formula: C40H36O4P2
• Molecular Weight: 642.658962
• Product Categories: Garphos Series;Chiral Phosphine
• Mol File: 1365531-75-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 708.1±60.0 °C(Predicted)
• Appearance: white/crystal
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive: air sensitive
• CAS DataBase Reference: (R)-2,2'-Bis(diphenylphosphino)-4,4',6,6'-tetraMethoxybiphenyl, 97+%(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2,2'-Bis(diphenylphosphino)-4,4',6,6'-tetraMethoxybiphenyl, 97+%(1365531-75-4)
• EPA Substance Registry System: (R)-2,2'-Bis(diphenylphosphino)-4,4',6,6'-tetraMethoxybiphenyl, 97+%(1365531-75-4)

Safety Data

• Hazardous Substances Data: 1365531-75-4(Hazardous Substances Data)

Usage

Reaction

Chiral ligand used in the preparation of hydrogenation catalysts with exceptionally high activity and selectivity.

Upstream product

• 1071069-49-2 (R,S)-(4,4′,6,6′-tetramethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine oxide) 
• 1365320-10-0 (2-bromo-3,5-dimethoxyphenyl)diphenylphosphine oxide 
• 1365320-08-6 (3,5-dimethoxyphenyl)diphenylphosphine oxide 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 1079-66-9 chloro-diphenylphosphine 
• 100-58-3 phenylmagnesium bromide 

Relevant articles and documents

Biaryl diphosphine ligands and their ruthenium complexes: Preparation and use for catalytic hydrogenation of ketones

Procedures for the preparation of the nucleophilic diphosphine ligands (R)-(4,4′,6,6′-tetramethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine) ((R)-Ph-Garphos, 2a) and (S)-(4,4′,6,6′-tetramethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine) ((S)-Ph-Garphos, 2b) were described. The ligands were used to prepare the ruthenium(II) Ph-Garphos complexes, chloro(p-cymene)(R)-(4,4′,6,6′-tetraamethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine)ruthenium(II) chloride ([RuCl(p-cymene)(R)-Ph-Garphos]Cl (3)) and chloro(p-cymene)(S)-(4,4′,6,6′-tetraamethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine)ruthenium(II) chloride ([RuCl(p-cymene)(S)-Ph-Garphos]Cl (4)). In the presence of the chiral diamine co-ligands (1R,2R)-1,2-diphenylethane-1,2-diamine (R,R-DPEN) and (1S,2S)-1,2-diphenylethane-1,2-diamine (S,S-DPEN), complexes 3 and 4 were found to be catalyst precursors for the enantioselective reduction of aryl ketones under mild conditions (room temperature and 3–4 atm of H2). The chiral alcohols were isolated in moderate to good yields and with enantioselectivities of up to 93percent. The ruthenium complexes chloro(p-cymene)(R)-(4,4′,6,6′-tetramethoxybiphenyl-2,2′-diyl)bis(bis(3,5-dimethylphenyl)-phosphine)ruthenium(II) chloride ([RuCl(p-cymene)(R)-Xyl-Garphos]Cl (5)) and chloro(p-cymene)(S)-(4,4′,6,6′-tetramethoxybiphenyl-2,2′-diyl)bis(bis(3,5-dimethylphenyl)-phosphine)ruthenium(II) chloride ([RuCl(p-cymene)(S)-Xyl-Garphos]Cl (6)) were also prepared and used as catalyst precursors for the hydrogenation of aryl ketones in the presence of (R,R)-DPEN and (S,S)-DPEN. Significant improvements in the enantioselectivities of the alcohols (up to 98percent ee.) were afforded. A combination of 6 and (S,S)-DPEN afforded (R)-1-(3-methoxyphenyl)ethanol in 89percent yield and with 95percent ee which was shown to be a suitable precursor for the preparation of (S)-rivastigmine.