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

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

Uses

Used in Pharmaceutical Industry:
BINAP is utilized as a chiral ligand in the synthesis of pharmaceutical compounds, where its ability to control the stereochemistry of metal-catalyzed reactions is crucial for producing enantiomerically pure products. This ensures the desired biological activity and minimizes potential side effects associated with the less active or unwanted enantiomer.
Used in Agrochemical Industry:
In the agrochemical sector, BINAP serves as a key component in the development of chiral pesticides and agrochemicals. Its role in asymmetric synthesis allows for the production of enantiomerically pure active ingredients, which can exhibit higher efficacy and lower environmental impact compared to their racemic counterparts.
Used in Material Science Research:
BINAP is employed as a chiral ligand in the synthesis of advanced materials with specific optical, electronic, or mechanical properties. Its ability to control the stereochemistry of metal-catalyzed reactions is essential for the development of materials with tailored properties for various applications, such as optoelectronics, sensors, and nanotechnology.
Used in Asymmetric Synthesis:
BINAP is used as a chiral ligand in asymmetric synthesis processes to achieve high enantioselectivity and enantiomeric excess. This is particularly important in the preparation of enantiomerically pure compounds, which are often required for biological activity, pharmaceutical development, and other applications where stereochemistry plays a critical role.
Used in Homogeneous Catalysis:
BINAP functions as a chiral ligand in homogeneous catalysis, where it enhances the selectivity and efficiency of catalytic reactions. Its use in this context is instrumental in the production of enantiomerically pure compounds and the development of more sustainable and efficient synthetic processes.

Upstream product

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

Downstream Products

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

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.

Effects of π-Electron Systems on Optical Activity of Au11 Clusters Protected by Chiral Diphosphines

We systematically examined the effects of π-electron systems on the chiroptical activity of atomically precise gold clusters [Au11(DP)4L2]+, where DP and L represent chiral diphosphines and achiral anionic ligands, respectively. Reducing the distance between the π-electron systems of the chiral DP and the Au11 core enhanced the anisotropy factor of [Au11(DP)4L2]+ in the range of 300–450 nm while extension of the π-electron system of the achiral L did not. This tendency supports our previous proposal that the proximity of the chiral π-electron system to the gold core amplifies the optical activity.

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

Synthesis of chiral titanium-containing phosphinoamide ligands for enantioselective heterobimetallic catalysis

The synthesis of six chiral titanium-containing phosphinoamide ligands is discussed. These ligands assemble chiral heterobimetallic Pd–Ti complexes, enable enantioselective intramolecular allylic aminations with hindered amine nucleophiles and achieve sel

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

AXIALLY DISSYMMETRIC bis(AMINOPHOSPHINE)S DERIVED FROM 2,2 prime -DIAMINO-1,1 prime -BINAPHTHYL. SYNTHESIS AND APPLICATION TO RHODIUM(I)-CATALYZED ASYMMETRIC HYDROGENATIONS.

Axially dissymmetric bisphosphine ligands, (R)- and (S)-2,2 prime -bis(diphenylphosphinoamino)-1,1 prime -binaphthyl (BDPAB) and (R)-2,2 prime -bis left bracket N-(diphenylphosphino)methylamino right bracket -1,1 prime -binaphthyl (Me-BDPAB) were conveniently prepared from 2,2 prime -diamino-1,1 prime -binaphthyl. The rhodium(I)-catalyzed asymmetric hydrogenation of alpha -acylamidoacrylic acids and esters gave the corresponding amino acids of up to 95% optical purity. The sign of the centro-chirality of the product amino acids was always the same to that of axial chirality of the ligand in both cases of BDPAB and Me-BDPAB.

ASYMMETRIC HYDROGENATION OF α-ACYLAMINOACRYLIC ACIDS AND ESTERS WITH AXIALLY DISSYMMETRIC BISAMINOPHOSPHINE-RHODIUM COMPLEXES

From easily resolved 2,2'-diamino-1,1'-binaphthyl were prepared axially dissymmetric bisphosphine ligands, (R)- and (S)-2,2'-bis(diphenylphosphinamino)-1,1'-binaphthyl; the rhodium-catalyzed asymmetric hydrogenation of α-acylaminoacrylic acids and esters gave the corresponding amino acids of up to 95percent optical purity.