Skip to Content
Merck
All Photos(1)

Key Documents

29516

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

Sign Into View Organizational & Contract Pricing


About This Item

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

Assay

≥97% (31P-NMR)

optical purity

ee: ≥99%

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

(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

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’.

Already Own This Product?

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

Visit the Document Library

Aldrich Chemfiles, 5(4), 4-4 null
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)
Recent Advances in the Synthesis of Indanes and Indenes.
Gabriele B, et al.
Chemistry?A European Journal (2016)
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)
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)

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