(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

• Catalog No.: B23785
• CAS Number: 76189-55-4
• M. F.: C44H32P2
• M. W.: 622.672402
• Purity: 98%

SYNONYMS

• Title: (R)-(+)-2,2'-联(二苯基膦基)-1,1'-联萘
• IUPAC name: {1-[2-(diphenylphosphanyl)naphthalen-1-yl]naphthalen-2-yl}diphenylphosphane
• IUPAC Traditional name: binap
• Synonyms: (R)-(+)-BINAP

DATABASE IDS

• CAS Number: 76189-55-4
• MDL Number: MFCD00010805
• Merck Index: 141223
• Beilstein Number: 4914063

PROPERTIES

• Purity: 98%
• Melting Point: 239-241°C
• Optical Rotation: +230 (c=0.3 in toluene)
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• Storage Warning: Air Sensitive
• TSCA Listed: 否

REFERENCES

• Chiral chelating ligand which is the basis of a number of homogeneous catalysts which promote hydrogenation reactions with very high enantiomeric excesses. Rh complexes catalyze the asymmetric hydrogenation of ɑ-acylaminoacrylic acids: J. Am. Chem. Soc., 102, 7932 (1980), and the isomerization of allylamines to chiral enamines: J. Chem. Soc., Chem. Commun., 600 (1982); Synthesis, 665 (1991). Asymmetric hydrogenation of ?-keto esters is achieved with a Ru based catalyst: J. Org. Chem., 57, 6691 (1992). For preparation of a cycloocta-1,5-diene Rh complex and use in enantioselective hydrogenation reaction, see: Org. Synth. Coll., 8, 183 (1993). For a review of the use of Ru BINAP complexes in asymmetric hydrogenation, see: Acta Chem. Scand., 50, 380 (1996).
• Reviews: BINAP catalysis: Acc. Chem. Res., 23, 345 (1990); binaphthylic derivatives as chiral auxiliaries: Synthesis, 503 (1992); advances in biaryl-type biphosphne ligands: Tetrahedron, 61, 5405 (2005).