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693065

Sigma-Aldrich

(R)-BINAP

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

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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Related Categories

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

693065-VAR:
693065-500MG:
693065-100MG:
693065-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Asymmetric Allylation of Unsymmetrical 1, 3-Diketones Using a BINAP- Palladium Catalyst.
Kuwano R, et al.
Organic Letters, 5(12), 2177-2179 (2003)
Centenary lecture. Chemical multiplication of chirality: science and applications
Noyori, Ryoji
Chemical Society Reviews, 18, 187-208 (1989)
Asymmetric Hydrogenation of 3?Oxo Carboxylates Using Binap?Ruthenium Complexes:(R)?(?)?Methyl 3?Hydroxybutanoate
Kitamura, Masato, et al.
Organic Syntheses, 1-1 (1993)
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)
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)
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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