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683434

Sigma-Aldrich

(Dimethylphenylsilyl)boronic acid pinacol ester

95%

Synonym(s):

2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, B-(dimethylphenylsilyl)pinacolborane

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About This Item

Empirical Formula (Hill Notation):
C14H23BO2Si
CAS Number:
Molecular Weight:
262.23
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Assay

95%

form

liquid

refractive index

n20/D 1.4946

density

0.962 g/mL at 25 °C

SMILES string

CC1(C)OB(OC1(C)C)[Si](C)(C)c2ccccc2

InChI

1S/C14H23BO2Si/c1-13(2)14(3,4)17-15(16-13)18(5,6)12-10-8-7-9-11-12/h7-11H,1-6H3

InChI key

ARMSAQNLTKGMGM-UHFFFAOYSA-N

Application

(Dimethylphenylsilyl)boronic acid pinacol ester (Suginome′s reagent) can be used as a reagent:
  • For the selective addition of dimethylphenylsilanyl group to cyclic and acyclic unsaturated ketones, esters, acrylonitriles using a copper catalyst.
  • In the synthesis of (Z)-4-boryl-1-silyl-2-alkene derivatives by stereoselective addition of silicon-boron bond to acyclic 1,3-dienes in presence of Ni catalyst.
  • In the preparation of silyl-substituted butenoate and β-silyl-substituted acrylate derivatives from allenes and propiolate derivatives via hydrosilylation reactions using a copper catalyst.
  • In the palladium-catalyzed asymmetric silaboration of allenes and alkanes to offered corresponding β-borylallylsilanes and 2-boryl-1-silylalkanes respectively.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Enantioselective conjugate silyl additions to cyclic and acyclic unsaturated carbonyls catalyzed by Cu complexes of chiral N-heterocyclic carbenes.
Lee K S and Hoveyda A H
Journal of the American Chemical Society, 132(9), 2898-2900 (2010)
Geminal Difunctionalization of Alkenylidene?Type Carbenoids by Using Interelement Compounds.
Hata T, et al.
Angewandte Chemie (International Edition in English), 40(4), 790-792 (2001)
Stereoselective 1, 4-silaboration of 1, 3-dienes catalyzed by nickel complexes
Suginome M, et al.
Organic Letters, 1(10), 1567-1569 (1999)
Platinum?Catalyzed Regioselective Silaboration of Alkenes.
Suginome M, et al.
Angewandte Chemie (International Edition in English), 36(22), 2516-2518 (1997)
Palladium-catalyzed asymmetric silaboration of allenes.
Ohmura T, et al.
Journal of the American Chemical Society, 128(42), 13682-13683 (2006)

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