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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:
185990-03-8
Molecular Weight:
262.23
MDL number:
MFCD05664111
UNSPSC Code:
12352103
PubChem Substance ID:
24885765
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

Related Categories

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

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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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)
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)
Kang-Sang Lee et al.
Journal of the American Chemical Society, 132(9), 2898-2900 (2010-02-13)
An efficient Cu-catalyzed protocol for enantioselective addition of a dimethylphenylsilanyl group to a wide range of cyclic and acyclic unsaturated ketones, esters, acrylonitriles, and alpha,beta,gamma,delta-dienones is disclosed. Reactions are performed in the presence of 1-2 mol % of commercially available
Yun-He Xu et al.
Chemical communications (Cambridge, England), 50(54), 7195-7197 (2014-05-29)
An efficient and general copper(I)-catalyzed method for the synthesis of multi-substituted vinylsilanes is reported. Multi-substituted allenes with electron-withdrawing groups and propiolate derivatives reacted well with (dimethylphenylsilyl)boronic acid pinacol ester to afford silyl-substituted butenoate derivatives and β-silyl-substituted acrylate derivatives, respectively. The
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