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About This Item
Linear Formula:
[(C6H5)2PC10H6-]2
CAS Number:
Molecular Weight:
622.67
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Quality Level
assay
97%
form
solid
optical activity
[α]19/D +233°, c = 0.3 in toluene
optical purity
ee: 99% (HPLC)
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
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.
(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions.
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.
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Articles
We present an article concerning BINAP/SEGPHOS® Ligands and Complexes.
Sci. Synth., 1, 113-264 (2002)
Journal of Organometallic Chemistry, 692, 550-550 (2007)
Tetrahedron, 50, 335-335 (1994)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 295817-1G | 04061826649039 |
| 295817-250MG | 04061833482223 |
| 295817-5G | 04061833546284 |