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Sigma-Aldrich

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-dimethylphenyl)phosphine]

≥97% (31P-NMR), optical purity ee: ≥99%

Synonym(s):

(R)-2,2′-Bis[bis(3,5-dimethyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl, (R)-3,5-Xyl-MeOBIPHEP, SL-A120-1

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About This Item

Empirical Formula (Hill Notation):
C46H48O2P2
CAS Number:
394248-45-4
Molecular Weight:
694.82
MDL number:
MFCD09753009
UNSPSC Code:
12352112
PubChem Substance ID:
329753364
NACRES:
NA.22

Assay

≥97% (31P-NMR)

optical purity

ee: ≥99%

functional group

phosphine

SMILES string

COc1cccc(P(c2cc(C)cc(C)c2)c3cc(C)cc(C)c3)c1-c4c(OC)cccc4P(c5cc(C)cc(C)c5)c6cc(C)cc(C)c6

InChI

1S/C46H48O2P2/c1-29-17-30(2)22-37(21-29)49(38-23-31(3)18-32(4)24-38)43-15-11-13-41(47-9)45(43)46-42(48-10)14-12-16-44(46)50(39-25-33(5)19-34(6)26-39)40-27-35(7)20-36(8)28-40/h11-28H,1-10H3

InChI key

IMUHNRWTDUVXOU-UHFFFAOYSA-N

Application

Atropisomeric MeOBIPHEP ligands
(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-dimethylphenyl)phosphine] can be used as a ligand:
  • In the synthesis of (S)-3-amino-4-methoxy-butan-1-ol, a key starting material for many pharmaceutical drugs.
  • In the synthesis of 3-substituted indanones through the reductive Heck reaction of chalcones with various amines.
  • In the palladium-catalyzed Tsuji-Trost cyclizations of aldehydes to yield vinylcyclopentane derivatives.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

sold in collaboration with Solvias AG

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ1969
BCCC6134
BCBR4265V
BCBM6960V
BCBL4965V

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Aldrich Chemfiles, 5(4), 4-4 null
Recent Advances in the Synthesis of Indanes and Indenes.
Gabriele B, et al.
Chemistry?A European Journal (2016)
Asymmetric Synthesis of (S)-3-Amino-4-methoxy-butan-1-ol by Way of Reductive Amination.
Mattei P, et al.
Organic Process Research & Development, 15(2), 353-359 (2011)
Synthesis of chiral 3-substituted indanones via an enantioselective reductive-Heck reaction
Minatti A, et al.
The Journal of Organic Chemistry, 72(24), 9253-9258 (2007)
Organocatalyzed Tsuji--Trost reaction: a new method for the closure of five-and six-membered rings
Vulovic B, et al.
Tetrahedron, 65(50), 10485-10494 (2009)

Articles

MeOBIPHEP

Solvias MeOBIPHEP Ligands: State-of-the-art atropisomeric MeOBIPHEP ligands, also referred to as MeO-BIPHEP, originally developed by Roche, have an extraordinarily broad performance profile for many synthetic applications due to their modular ligand design.

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