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29510

Sigma-Aldrich

(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:
Molecular Weight:
582.61
Beilstein:
4790083
MDL number:
UNSPSC Code:
12352112
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥97%

optical purity

ee: ≥99%

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

greener alternative category

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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