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29513

Sigma-Aldrich

(S)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine]

≥97%, optical purity ee: ≥99%

Synonym(s):

(S)-[6,6′-Dimethoxy(1,1′-biphenyl)-2,2′-diyl]bis{bis[3,5-bis(1,1-dimethylethyl)-4-methoxyphenyl]phosphine}, (S)-3,5-t-Bu-4-MeO-MeOBIPHEP, SL-A109-2

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About This Item

Empirical Formula (Hill Notation):
C74H104O6P2
CAS Number:
910134-30-4
Molecular Weight:
1151.56
MDL number:
MFCD09265029
UNSPSC Code:
12352112
PubChem Substance ID:
329753360
NACRES:
NA.22

Assay

≥97%

optical purity

ee: ≥99%

functional group

phosphine

SMILES string

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

InChI

1S/C74H104O6P2/c1-67(2,3)49-37-45(38-50(63(49)77-27)68(4,5)6)81(46-39-51(69(7,8)9)64(78-28)52(40-46)70(10,11)12)59-35-31-33-57(75-25)61(59)62-58(76-26)34-32-36-60(62)82(47-41-53(71(13,14)15)65(79-29)54(42-47)72(16,17)18)48-43-55(73(19,20)21)66(80-30)56(44-48)74(22,23)24/h31-44H,1-30H3

InChI key

JSSIQFXOSWLAGA-UHFFFAOYSA-N

General description

sold in collaboration with Solvias AG

Application

Atropisomeric MeOBIPHEP ligands
(S)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine] can be used:
  • As a ligand in the rhodium-catalyzed asymmetric (3+2) annulation reactions of ketimines and alkynes.
  • As a chiral catalyst in one of the key synthetic steps for the preparation of the fragrances canthoxal and p-isobutyl-alpha-methylhydrocinnamaldehyde.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

13 - Non 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

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Certificates of Analysis (COA)

Lot/Batch Number
BCBH9927V
BCBT3684
BCBD9203V
1316951

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A practical, enantioselective synthesis of the fragrances Canthoxal and Silvial, and evaluation of their olfactory activity
Beghetto V, et al.
Synthesis, 47(02), 272-288 (2015)
Metal-Catalyzed Annulations through Activation and Cleavage of C- H Bonds
Gul'ias M and Mascarenas J
Angewandte Chemie (International ed. in English), 55(37), 11000-11019 (2016)

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