29516

Sigma-Aldrich

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bisbis(3,5-dimethylphenyl)phosphine

≥97% (CHN), optical purity ee: ≥99%

Synonym(s):
SL-A120-1, (R)-2,2′-Bisbis(3,5-dimethyl)phosphino-6,6′-dimethoxy-1,1′-biphenyl, (R)-3,5-Xyl-MeOBIPHEP
Empirical Formula (Hill Notation):
C46H48O2P2
CAS Number:
Molecular Weight:
694.82
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

≥97% (CHN)

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

Related Categories

Application

(R)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bisbis(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

1, 5 g in glass bottle
100, 500 mg in glass bottle
Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

sold in collaboration with Solvias AG

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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)
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)
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)
Articles
Solvias® Ligand Portfolio for Enantioselective Hydrogenation
Read More
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.
Read More

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