MilliporeSigma
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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
Linear Formula:
[(C6H5)2PC10H6-]2
CAS Number:
Molecular Weight:
622.67
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

crystals

Quality Level

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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Application

(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.[1] 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.[2]

Packaging

100, 500 mg in amber glass bottle

Legal Information

Sold in collaboration with Takasago for research purposes only.

Storage Class Code

13 - Non 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

Certificate of Analysis

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Certificate of Origin

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