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(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

MDL number:

MFCD00010805

UNSPSC Code:

12352005

PubChem Substance ID:

329761559

NACRES:

NA.22

form

crystals

Quality Level

100

optical activity

[α]20/D +222°, c = 0.5% in benzene

mp

239-241 °C (lit.)

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

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Chiral Catalysts & Ligands

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Application

Takasago Ligands and Complexes for Asymmetric Reactions

(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.

Legal Information

Sold in collaboration with Takasago for research purposes only.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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

Kitamura, Masato, et al.

Organic Syntheses, 1-1 (1993)

Centenary lecture. Chemical multiplication of chirality: science and applications

Noyori, Ryoji

Chemical Society Reviews, 18, 187-208 (1989)

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)

Asymmetric Allylation of Unsymmetrical 1, 3-Diketones Using a BINAP- Palladium Catalyst.

Kuwano R, et al.

Organic Letters, 5(12), 2177-2179 (2003)

View All Related Papers

Articles

BINAP/SEGPHOS® Ligands and Complexes

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

Takasago Ligands

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

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