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494011

Sigma-Aldrich

(4-Bromophenylethynyl)trimethylsilane

98%

Synonym(s):

(p-Bromophenyl)ethynyl)trimethylsilane, 1-(p-Bromophenyl)-2-trimethylsilylacetylene, 1-Bromo-4-(2-trimethylsilylethynyl)benzene, 1-Bromo-4-(trimethylsilylethynyl)benzene, 1-Bromo-4-[2-(trimethylsilyl)ethynyl]benzene, 2-(p-Bromophenyl)-1-trimethylsilylacetylene, 4-(Trimethylsilylethynyl)phenyl bromide, [(4-Bromophenyl)ethynyl]trimethylsilane, [1-(4-Bromophenyl)-2-trimethylsilyl]acetylene, [2-(4-Bromophenyl)ethynyl]trimethylsilane

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About This Item

Linear Formula:
BrC6H4C≡CSi(CH3)3
CAS Number:
Molecular Weight:
253.21
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

Quality Level

Assay

98%

mp

61-63 °C (lit.)

SMILES string

C[Si](C)(C)C#Cc1ccc(Br)cc1

InChI

1S/C11H13BrSi/c1-13(2,3)9-8-10-4-6-11(12)7-5-10/h4-7H,1-3H3

InChI key

RNMSGCJGNJYDNS-UHFFFAOYSA-N

Related Categories

General description

(4-Bromophenylethynyl)trimethylsilane can be synthesized by the palladium catalyzed reaction between 4-bromo-1-iodobenzene and trimethylsilylacetylene. It undergoes Buchwald-Hartwig coupling with para-substituted diphenylamines.

Application

(4-Bromophenylethynyl)trimethylsilane may be used to synthesize:
  • 1-bromo-4-ethynylbenzene
  • 4-(4-bromophenyl)-3-butyn-2-one
  • 4-ethynyl-4′-tert-butylbiphenyl
  • 1,4-bis[2-(4-bromophenyl)ethynyl]-2,5-dihexylbenzene

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Probing surface-adlayer conjugation on organic-modified Si (111) surfaces with microscopy, scattering, spectroscopy, and density functional theory.
Kellar JA, et al.
The Journal of Physical Chemistry C, 113(7), 2919-2927 (2009)
Experimental and computational probes of the space in a self-assembled capsule.
Ajami D, et al.
Proceedings of the National Academy of Sciences of the USA, 103(24), 8934-8936 (2006)
Synthesis and Solid-State Investigations of Oligo-Phenylene-Ethynylene Structures with Halide End-Groups.
Jenny NM, et al.
European Journal of Organic Chemistry, 2012(14), 2738-2747 (2012)
Tunable, strongly-donating perylene photosensitizers for dye-sensitized solar cells.
Mathew S and Imahori H.
Journal of Materials Chemistry, 21(20), 7166-7174 (2011)
Enantioselective synthesis of both enantiomers of various propargylic alcohols by use of two oxidoreductases.
Schubert T, et al.
European Journal of Organic Chemistry, 2001(22), 4181-4187 (2001)

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