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)-3,5-t-Bu-4-MeO-MeOBIPHEP, SL-A109-2, (S)-[6,6′-Dimethoxy(1,1′-biphenyl)-2,2′-diyl]bis{bis[3,5-bis(1,1-dimethylethyl)-4-methoxyphenyl]phosphine}
Empirical Formula (Hill Notation):
C74H104O6P2
CAS Number:
Molecular Weight:
1151.56
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥97%

optical purity

ee: ≥99%

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

Related Categories

General description

sold in collaboration with Solvias AG

Application

(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

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

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
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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