Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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.)

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

Looking for similar products? Visit Product Comparison Guide

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCV8732
MKCS0258
MKCS8203
MKCN7718
MKCL6606

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service