74974-14-4

Basic information

• Product Name: (R)-(+)-2,2'-BIS[(DIPHENYLPHOSPHINO)AMINO]-1,1'-BINAPHTHYL
• Synonyms: (R)-(+)-2,2'-BIS[(DIPHENYLPHOSPHINO)AMINO]-1,1'-BINAPHTHYL;R-2,2'-Bis-[(N-diphenylphosphino)-amino]-1,1'-binaphthyl;(R)-BinaMP;(R)-2,2'-Bis(diphenylphosphinoaMino)-1,1-binaphthyl (R)-BinaMP;(R)-2,2'-Bis-[(N,N'-diphenylphosphino)-amino]-1,1'-binaphthyl;N,N'-(1R)-[1,1'-binaphthalene]-2,2'-diylbis[P,P-diphenyl-Phosphinous amide
• CAS NO: 74974-14-4
• Molecular Formula: C₄₄H₃₄N₂P₂
• Molecular Weight: 652.701682
• Product Categories: Achiral Nitrogen;BINAM Series
• Mol File: 74974-14-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 151-156°C
• Appearance: /
• CAS DataBase Reference: (R)-(+)-2,2'-BIS[(DIPHENYLPHOSPHINO)AMINO]-1,1'-BINAPHTHYL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-2,2'-BIS[(DIPHENYLPHOSPHINO)AMINO]-1,1'-BINAPHTHYL(74974-14-4)
• EPA Substance Registry System: (R)-(+)-2,2'-BIS[(DIPHENYLPHOSPHINO)AMINO]-1,1'-BINAPHTHYL(74974-14-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 36/37/39-45
• WGK Germany: 3
• Hazardous Substances Data: 74974-14-4(Hazardous Substances Data)

Usage

General Description

(R)-(+)-2,2'-BIS[(DIPHENYLPHOSPHINO)AMINO]-1,1'-BINAPHTHYL, also known as BINAP, is a chiral diphosphine ligand commonly used in asymmetric synthesis and homogeneous catalysis. It consists of two biaryl rings connected by a central phosphorus atom with two bulky diphenylphosphino substituents. BINAP is widely used in metal-catalyzed reactions to control the stereochemistry of the products, making it an important tool in pharmaceutical, agrochemical, and material science research. Its unique structure and properties make it a valuable reagent for the synthesis of complex organic molecules with high enantiomeric purity.

Upstream product

• 18531-95-8 (S)-2,2'-diamino-1,1'-binaphthalene 
• 1079-66-9 chloro-diphenylphosphine 
• 18741-85-0 (R)-1,1'-binaphthyl-2,2'-diamine 
• 4488-22-6 1,1'-binaphthalene-2,2'-diamine 

Downstream Products

• 134532-03-9 2-amino-2’-hydroxy-1,1’-binaphthyl 
• 1174130-96-1 [Rh(COD)((R)-(+)-2,2'-bis(diphenylphosphinoamino)-1,1'-binaphthyl)]BF₄ 

Relevant articles and documents

Synthesis of Binam-P Derived C2-Symmetric bis-Iminophosphonamide Ligands. Molecular Structure of [(R)-Binam(Ph2PN(H)tBu)2]

The Staudinger reaction of organic azides tBuN3, 1-Ad-N3, and DippN3 (Dipp = 2,6-diisopropylphenyl) with (R)-N,N′-bis(diphenylphosphanyl)-2,2′-diamino-1,1′-binaphthyl [(R)-Binam-P], obtained by an optimized procedure from (R)-(+)-Binam, Ph2PCl, and Et3N in DCM, leads to preparation of a series of new C2-symmetric bis-iminophosphonamide ligands [(R)-Binam(Ph2PN(H)R)2] [R = tBu (1), Ad (2), and Dipp (3)]. The molecular structure of 1·2DMSO was confirmed by X-ray structure analysis.

Calcium catalyzed enantioselective intramolecular alkene hydroamination with chiralC2-symmetric bis-amide ligands

The chiral building block (R)-(+)-2,2′-diamino-1,1′-binaphthyl, (R)-BINAM, which is often used as backbone in privileged enantioselective catalysts, was converted to a series ofN-substituted proligandsR1-H2(R = CH2tBu, C(H

Application of phosphinous amide ligands in palladium complex-catalyzed asymmetric allylic alkylation: Influence of steric effects on enantioselectivity

Phosphinous amide ligands 1-4 derived from 2,2′-diamino-1,1′- binaphthyl (BINAM) and 2,2′-diamino-5,5′,6,6′,7,7′,8, 8′-octahydro-1,1′-binaphthyl (H8-BINAM) have been prepared and applied in palladium complex-catalyzed asymmetric allylic alkylat