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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 Level

100

optical activity

[α]20/D +222°, c = 0.5% in benzene

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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Articles

Takasago Ligands

Hydrogenation, Asymmetric Catalysis, Binap, SEGPHOS®, Aldol reaction, Alkenylation, Arylation, Mannich reaction, Fluorination, Michael addition, Hydrosilylation, Cycloaddition, Takasago

BINAP/SEGPHOS® Ligands and Complexes

We present an article concerning BINAP/SEGPHOS® Ligands and Complexes.

Asymmetric Hydrogenation of 3?Oxo Carboxylates Using Binap?Ruthenium Complexes:(R)?(?)?Methyl 3?Hydroxybutanoate

Kitamura, Masato, et al.

Organic Syntheses, 1-1 (1993)

Synthesis and resolution of the biaryl-like diphosphine (S)-Me2-CATPHOS, preparation of a derived rhodium precatalyst and applications in asymmetric hydrogenation

Doherty, Simon, and Catherine H. Smyth

Nature Protocols, 7.10, 1884-1896 (2012)

RuHCl (diphosphine)(diamine): Catalyst Precursors for the Stereoselective Hydrogenation of Ketones and Imines1

Abdur-Rashid, Kamaluddin, Alan J. Lough, and Robert H. Morris

Organometallics, 20.6, 1047-1049 (2001)

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Global Trade Item Number

SKU	GTIN
693065-100MG	04061833550656
693065-500MG	04061832768847