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683434

(Dimethylphenylsilyl)boronic acid pinacol ester

Name: (Dimethylphenylsilyl)boronic acid pinacol ester
Brand: ALDRICH

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

NACRES:

NA.22

PubChem Substance ID:

24885765

UNSPSC Code:

12352103

MDL number:

MFCD05664111

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Properties

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

Description

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

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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)

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)

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Global Trade Item Number

SKU	GTIN
683434-5G	04061838120656
683434-1G	04061838084934