295817
(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene
97%
Synonym(s):
(R)-(+)-(1,1′-Binaphthalene-2,2′-diyl)bis(diphenylphosphine), (R)-(+)-BINAP
About This Item
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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
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General description
(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions.
Application
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_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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