Skip to Content
Merck
All Photos(1)

Documents

Safety Information

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

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

About This Item

Linear Formula:
BrC6H4C≡CSi(CH3)3
CAS Number:
16116-78-2
Molecular Weight:
253.21
MDL number:
MFCD01863556
UNSPSC Code:
12352100
PubChem Substance ID:
24872871
NACRES:
NA.22

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

494011-25G:
494011-5G:
494011-VAR:
494011-BULK:

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

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)
Tunable, strongly-donating perylene photosensitizers for dye-sensitized solar cells.
Mathew S and Imahori H.
Journal of Materials Chemistry, 21(20), 7166-7174 (2011)
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)
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)

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