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Merck
CN

29510

(R)-(+)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine)

greener alternative

≥97%, optical purity ee: ≥99%

Synonym(s):

(R)-(+)-2,2′-Bis(diphenylphosphino)-6,6′-dimethoxy-1,1′-biphenyl, (R)-(+)-MeO-BIPHEP, SL-A101-1

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About This Item

Empirical Formula (Hill Notation):
C38H32O2P2
CAS Number:
133545-16-1
Molecular Weight:
582.61
UNSPSC Code:
12352112
NACRES:
NA.22
PubChem Substance ID:
24857757
MDL number:
MFCD03095430
Beilstein/REAXYS Number:
4790083

Key Documents

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SMILES string

COc1cccc(P(c2ccccc2)c3ccccc3)c1-c4c(OC)cccc4P(c5ccccc5)c6ccccc6

InChI key

KRJVQCZJJSUHHO-UHFFFAOYSA-N

InChI

1S/C38H32O2P2/c1-39-33-25-15-27-35(41(29-17-7-3-8-18-29)30-19-9-4-10-20-30)37(33)38-34(40-2)26-16-28-36(38)42(31-21-11-5-12-22-31)32-23-13-6-14-24-32/h3-28H,1-2H3

assay

≥97%

optical purity

ee: ≥99%

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

functional group

phosphine

greener alternative category

Aligned

Quality Level

100

General description

We are committed to bringing you Greener Alternative Products, which adhere to one of the  four categories of Greener Alternatives. This product is a Biobased products, showing key improvements in Green Chemistry Principles “Less Hazardous Chemical Syntheses” and “Use of Renewable Feedstock”.
sold in collaboration with Solvias AG

Application

Atropisomeric MeOBIPHEP ligands

  • Hydrogenation of α- and β-functionalized ketones
  • Hydrogenation of heteroarenes
  • C–C coupling reactions
Atropisomeric diphosphine; the Rh(I) complex is employed for highly enantioselective asymmetric isomerization of allylamines to enamines; the Ru(II) complex hydrogenates β-keto esters in high enantioselectivity; the Pd(0) complex for cyclization of hydroxy allylic carbonates.
Ligand for ruthenium-catalyzed greener amine synthesis by enamine reduction with hydrogen gas.

Asymmetric Synthesis of (S)-3-Amino-4-methoxy-butan-1-ol by Way of Reductive Amination

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC7245
BCBK6750V
BCCH6415
BCCB2284
BCBT6487

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

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R. Schmid et al.
Pure and Applied Chemistry. Chimie Pure Et Appliquee, 68, 131-138 (1996)
V. Blandin et al.
European Journal of Organic Chemistry, 1787-1787 (1999)
B. Heiser et al.
Tetrahedron Asymmetry, 2, 51-51 (1991)
R. Schmid et al.
Helvetica Chimica Acta, 74, 370-370 (1991)
J.R. Labrosse et al.
Tetrahedron Asymmetry, 10, 1069-1069 (1999)

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