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(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene

ALDRICH/295817 - 97%

Synonym: (R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine); (R)-(+)-BINAP

CAS Number: 76189-55-4
Empirical Formula (Hill Notation): C44H32P2
Molecular Weight: 622.67
MDL Number: MFCD00010805
Linear Formula: [(C6H5)2PC10H6-]2
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-295817-1G 1 g
 $92.80
1/EA		 Add To Favorites
45-295817-5G 5 g
 $147.00
1/EA		 Add To Favorites
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: 295817-250MG.

 

assay 97%
form solid
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
mp 239-241 °C (lit.)
optical activity [α]19/D +233°, c = 0.3 in toluene
optical purity ee: 99% (HPLC)
SMILES string c1ccc(cc1)P(c2ccccc2)c3ccc4ccccc4c3-c5c(ccc6ccccc56)P(c7ccccc7)c8ccccc8
Application: Useful ligand for transition metal catalyzed asymmetric reactions, including hydrogenation and disilylation. 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones, β-keto esters, and α-amino ketones. They have also been used for asymmetric hydrogenation and hydroformylation of olefins, asymmetric Heck reactions, and asymmetric isomerizations of allyls.
Complex with Ag(I) used to catalyze an asymmetric aldol reaction between alkenyl trichloroacetates and aldehydes. Also used with Ag(I) to catalyze an enantioselective hetero-Diels-Alder reaction of azo compounds.
General description: (R)-(+)-BINAP is a chiral diphosphine ligand that exhibits high enantioselectivity and reactivity in various organic reactions.

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions.
Packaging: 1, 5 g in glass bottle
Packaging: 250 mg in glass insert
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity 97%
mp 239-241 °C (lit.)
UNSPSC 12352005

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