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597910

Sigma-Aldrich

(4-Chlorophenyl)triethoxysilane

97%

Synonym(s):

1-Chloro-4-triethoxysilylbenzene

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About This Item

Linear Formula:
ClC6H4Si(OC2H5)3
CAS Number:
Molecular Weight:
274.82
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

refractive index

n20/D 1.474 (lit.)

bp

82-84 °C/0.07 mmHg (lit.)

density

1.069 g/mL at 25 °C (lit.)

SMILES string

CCO[Si](OCC)(OCC)c1ccc(Cl)cc1

InChI

1S/C12H19ClO3Si/c1-4-14-17(15-5-2,16-6-3)12-9-7-11(13)8-10-12/h7-10H,4-6H2,1-3H3

InChI key

AFILDYMJSTXBAR-UHFFFAOYSA-N

Application

(4-Chlorophenyl)triethoxysilane can be used:
  • To facilitate the connection between dipolar mixed monolayers and zinc oxide in photovoltaic devices.
  • As a substrate in the Ni-catalyzed decarboxylative coupling with alkynyl carboxylic acids to yield substituted diarylalkynes.
  • As a substrate in the Hiyama cross-coupling reactions with 3-iodoazetidines to yield substituted 3-arylazetidines.
  • As an intermediate in the synthesis of tripod-shaped oligo(p-phenylene)s, which are used in the surface immobilization of gold and CdS quantum dots for sensor applications.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

> 110 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)


Certificates of Analysis (COA)

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Denmark, S. E.; Ober, M. H.
Aldrichimica Acta, 36, 75-75 (2003)

Articles

A viable alternative to the popular Stille and Suzuki coupling reactions mainly due to the formation of nontoxic byproducts and stability to many reaction conditions.

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