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Sigma-Aldrich

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

greener alternative

≥97%, optical purity ee: ≥99%

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Synonym(s):
(R)-(+)-2,2′-Bis(diphenylphosphino)-6,6′-dimethoxy-1,1′-biphenyl, (R)-(+)-MeO-BIPHEP, SL-A101-1
Empirical Formula (Hill Notation):
C38H32O2P2
CAS Number:
133545-16-1
Molecular Weight:
582.61
Beilstein:
4790083
MDL number:
MFCD03095430
PubChem Substance ID:
24857757
NACRES:
NA.22

Assay

≥97%

optical purity

ee: ≥99%

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

greener alternative category

Aligned

SMILES string

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

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

InChI key

KRJVQCZJJSUHHO-UHFFFAOYSA-N

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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 ß-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 Code

11 - 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

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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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