71042-54-1

Basic information

• Product Name: (2S,3S)-(+)-2,3-BIS(DIPHENYLPHOSPHINO)-BICYCLO[2.2.1]HEPT-5-ENE
• Synonyms: (2S,3S)-(+)-2,3-BIS(DIPHENYLPHOSPHINO)-BICYCLO[2.2.1]HEPT-5-ENE;(S,S)-NORPHOS;(2S,3S)-(+)-2,3-Bis(diphenylphosphino)-bicylo[2.2.1]hept-5-ene;(2S,3S)-(+)-2,3-Bis(diphenylphosphino)-bicyclo[2.2.1]hept-5-ene,min.95%(S,S)-NORPHOS;(2S,3S)-(+)-2,3-BIS(DIPHENYLPHOSPHINO)-BICYCLO[2.2.1]HEPT-5-ENE (S,S)-NORPHOS, (C 1,CHCL3);(1S,4R)-5α,6β-Bis(diphenylphosphino)bicyclo[2.2.1]hepta-2-ene;[[1R,4S,(+)]-Bicyclo[2.2.1]hept-5-ene-2α,3β-diyl]bis(diphenylphosphine);[[1R,4S,(+)]-Bicyclo[2.2.1]hepta-5-ene-2α,3β-diyl]bis(diphenylphosphine)
• CAS NO: 71042-54-1
• Molecular Formula: C₃₁H₂₈P₂
• Molecular Weight: 462.5
• Product Categories: organophosphine ligand;Chiral Phosphine;NORPhos Series
• Mol File: 71042-54-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 120 °C
• Boiling Point: 577.0±50.0 °C(Predicted)
• Appearance: white/crystal
• Sensitive: air sensitive
• CAS DataBase Reference: (2S,3S)-(+)-2,3-BIS(DIPHENYLPHOSPHINO)-BICYCLO[2.2.1]HEPT-5-ENE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-(+)-2,3-BIS(DIPHENYLPHOSPHINO)-BICYCLO[2.2.1]HEPT-5-ENE(71042-54-1)
• EPA Substance Registry System: (2S,3S)-(+)-2,3-BIS(DIPHENYLPHOSPHINO)-BICYCLO[2.2.1]HEPT-5-ENE(71042-54-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• TSCA: No
• Hazardous Substances Data: 71042-54-1(Hazardous Substances Data)

Usage

Reaction

Ligand used in the enantioselective rhodium catalyzed hydrogenation of α–dehydroaminoesters and enamides. Ligand used in the enantioselective rhodium catalyzed hydroboration of cyclopropenes. Ligand used in the asymmetric rhodium catalyzed cleavage of racemic 1,3-oxazolidines.

Chemical Properties

White crystalline powder

InChI:InChI=1/C31H28P2/c1-5-13-26(14-6-1)32(27-15-7-2-8-16-27)30-24-21-22-25(23-24)31(30)33(28-17-9-3-10-18-28)29-19-11-4-12-20-29/h1-22,24-25,30-31H,23H2/t24?,25?,30-,31-/m0/s1

Upstream product

• 71075-23-5 (2S,3S)-bicyclo(2.2.1)hept-5-ene-2,3-diyl-bis(diphenylphosphine oxide) 

Relevant articles and documents

Synthesis of (R,R)- and (S,S)-Norphos

Oxidation of (E)-1,2-bis(diphenylphosphanyl)ethene with hydrogen peroxide gave (E)-1,2-bis(diphenylphosphoryl)ethene. Diels-Alder reaction of (E)-1,2-bis(diphenylphosphoryl)ethene with cyclopentadiene yielded 2,3-bis(diphenylphosphoryl)bicyclo[2.2.1]hept-5-ene (NorphosO). rac-NorphosO was resolved with O,O-dibenzoyltartaric acid. (R,R)- and (S,S)-NorphosO were reduced with trichlorosilane to give 2,3-bis(diphenylphosphanyl)bicyclo[2.2.1] hept-5-ene [(R,R)- and (S,S)-Norphos]. Georg Thieme Verlag Stuttgart.