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693065

(R)-BINAP

Name: (<I>R</I>)-BINAP
Brand: ALDRICH

Synonym(s):

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene, (R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl, (R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (R)-(+)-BINAP

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About This Item

Linear Formula:

[(C₆H₅)₂PC₁₀H₆-]₂

CAS Number:

76189-55-4

Molecular Weight:

622.67

NACRES:

NA.22

PubChem Substance ID:

329761559

UNSPSC Code:

12352005

MDL number:

MFCD00010805

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Properties

form

crystals

Quality Segment

100

optical activity

[α]20/D +222°, c = 0.5% in benzene

reaction suitability

reaction type: Asymmetric synthesis, reagent type: ligand
reaction type: Noyori Asymmetric Hydrogenation

mp

239-241 °C (lit.)

functional group

phosphine

SMILES string

c1ccc(cc1)P(c2ccccc2)c3ccc4ccccc4c3-c5c(ccc6ccccc56)P(c7ccccc7)c8ccccc8

InChI

1S/C44H32P2/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38/h1-32H

InChI key

MUALRAIOVNYAIW-UHFFFAOYSA-N

Description

Application

(R)-BINAP reacts with allylpalladium(II) chloride dimer to form a BINAP-palladium catalyst, which can catalyze the asymmetric allylation of 1,3-diketones to form chiral 2,2-dialkyl-1,3-diketones. It may also be used in the preparation of chirally stabilized rhodium nanoparticles, which can be used as a catalyst for the asymmetric hydroformylation of styrene and vinyl acetate.

Takasago Ligands and Complexes for Asymmetric Reactions

Legal Information

Sold in collaboration with Takasago for research purposes only.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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