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Merck
CN

29516

(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:
Molecular Weight:
694.82
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352112
MDL number:
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Quality Level

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

(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

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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Articles

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.


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)



Global Trade Item Number

SKUGTIN
29516-5G04061832622736
29516-1G04061826094761
29516-500MG04061832622729
29516-100MG04061832622712