Skip to Content
Merck
All Photos(1)

Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Quality Level

100

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service