Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

29524

Sigma-Aldrich

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

≥97%, optical purity ee: ≥99%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C70H96O2P2
CAS Number:
192138-05-9
Molecular Weight:
1031.46
MDL number:
MFCD09753001
UNSPSC Code:
12352112
PubChem Substance ID:
329753371
NACRES:
NA.22

Quality Level

100

Assay

≥97%

optical purity

ee: ≥99%

functional group

phosphine

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
(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] can be used as a ligand to prepare:
  • 1,2-Dihydropyridines through Rh-catalyzed cycloaddition of diynes to sulfonimines.
  • Enantiorich disubstituted γ-lactams via intramolecular allylic alkylation reaction using Pd catalyst.
  • A Ru-metal complex, which acts as a hydrogenation catalyst applicable in the synthesis of an organic building block (S)-3-fluoromethyl-γ-butyrolactone.

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCK5961
BCBT6863
BCCG2463
BCCC3116
BCBT2488

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

Development of a scalable synthesis of (S)-3-fluoromethyl-γ-butyrolactone, building block for Carmegliptin′s lactam moiety
Adam J-M, et al.
Organic Process Research & Development, 15(3), 515-526 (2011)
Highly enantioselective rhodium-catalyzed [2+2+2] cycloaddition of diynes to sulfonimines
Amatore M, et al.
Journal of the American Chemical Society, 135(12), 4576-4579 (2013)
Enantioselective γ-lactam synthesis via palladium-catalyzed intramolecular asymmetric allylic alkylation
Bantreil X, et al.
Synlett, 2009(09), 1441-1444 (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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service