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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

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

>230.0 °F - closed cup

Flash Point(C)

> 110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Nickel-catalyzed Hiyama-type decarboxylative coupling of propiolic acids and organosilanes
Edwin Raja GC, et al.
The Journal of Organic Chemistry, 81(12), 5244-5249 (2016)
Synthesis of azobenzene substituted tripod-shaped bi (p-phenylene) s. Adsorption on gold and CdS quantum-dots surfaces
Hierrezuelo J, et al.
Tetrahedron, 69(16), 3465-3474 (2013)
Tuning zinc oxide/organic energy level alignment using mixed triethoxysilane monolayers
Brenner TM, et al.
Journal of Material Chemistry C, 1(37), 5935-5943 (2013)
Palladium-Catalyzed Hiyama Cross-Couplings of Arylsilanes with 3-Iodoazetidine: Synthesis of 3-Arylazetidines
Liu Z, et al.
The Journal of Organic Chemistry, 84(19), 12358-12365 (2019)
Denmark, S. E.; Ober, M. H.
Aldrichimica Acta, 36, 75-75 (2003)

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