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29513

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

Name: (<I>S</I>)-(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis[bis(3,5-di-<I>tert</I>-butyl-4-methoxyphenyl)phosphine]
Brand: ALDRICH

≥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%

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.

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’.

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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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