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29525

Sigma-Aldrich

(S)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine]

≥97%, optical purity ee: ≥99%

Synonym(s):

(S)-2,2′-Bis[bis(3,5-di-tert-butyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl, (S)-3,5-t-Bu-MeOBIPHEP, SL-A121-2

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About This Item

Empirical Formula (Hill Notation):
C70H96O2P2
Molecular Weight:
1031.46
MDL number:
MFCD09753001
UNSPSC Code:
12352112
PubChem Substance ID:
329753372
NACRES:
NA.22

Assay

≥97%

optical purity

ee: ≥99%

SMILES string

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

InChI

1S/C70H96O2P2/c1-63(2,3)45-33-46(64(4,5)6)38-53(37-45)73(54-39-47(65(7,8)9)34-48(40-54)66(10,11)12)59-31-27-29-57(71-25)61(59)62-58(72-26)30-28-32-60(62)74(55-41-49(67(13,14)15)35-50(42-55)68(16,17)18)56-43-51(69(19,20)21)36-52(44-56)70(22,23)24/h27-44H,1-26H3

InChI key

PBYRAYONARLAQJ-UHFFFAOYSA-N

General description

sold in collaboration with Solvias AG

Application

Atropisomeric MeOBIPHEP ligands
(S)-3,5-t-Bu-MeOBIPHEP can be used as a ligand in the stereoselective preparation of allenoates via palladium-catalyzed asymmetric carbonylation of propargylic carbonates. It can also be used in the C-C coupling reactions.

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBV7317
BCBT3106
BCBH4012V
BCBF0001V
1348355

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Enantioselective Homogeneous Catalysis and the ?3, 5-Dialkyl Meta-Effect?. MeO- BIPHEP Complexes Related to Heck, Allylic Alkylation, and Hydrogenation Chemistry
Trabesinger G, et al.
Journal of the American Chemical Society, 119(27), 6315-6323 (1997)
A room-temperature catalytic asymmetric synthesis of allenes with ECNU-Phos
Wang Y, et al.
Journal of the American Chemical Society, 135(31), 11517-11520 (2013)

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.

Chromatograms

application for HPLC

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