ChemicalBook > CAS DataBase List > (4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE

(4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE

Product Name
(4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE
CAS No.
16116-78-2
Chemical Name
(4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE
Synonyms
1-Bromo-4-[2-(trimethylsilyl)ethynyl]benzene;DK567;(4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE;(4-Bromophenyl)Trimethylsilylacetylene;(2-(4-bromophenyl)ethynyl)trimethylsilane;(4-BroMophenylethynyl)triMethylsilane 98%;(4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE, 9 8%;(4-Bromophenylethynyl)trimethylsilane;Benzene, 1-bromo-4-[2-(trimethylsilyl)ethynyl]-;((4-Bromophenyl)ethynyl)trimethylsilane - [B54598]
CBNumber
CB9131154
Molecular Formula
C11H13BrSi
Formula Weight
253.21
MOL File
16116-78-2.mol
More
Less

(4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE Property

Melting point:
61-63 °C(lit.)
Boiling point:
60-80°C/0.2mmHg
Density 
1,192 g/cm3
storage temp. 
2-8°C
form 
Powder
color 
White to yellow
Specific Gravity
1.192
Hydrolytic Sensitivity
1: no significant reaction with aqueous systems
InChI
InChI=1S/C11H13BrSi/c1-13(2,3)9-8-10-4-6-11(12)7-5-10/h4-7H,1-3H3
InChIKey
RNMSGCJGNJYDNS-UHFFFAOYSA-N
SMILES
C1(Br)=CC=C(C#C[Si](C)(C)C)C=C1
More
Less

Safety

Risk Statements 
36/37/38
Safety Statements 
26-36/37/39
WGK Germany 
3
TSCA 
No
HS Code 
2931.90.6000
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
494011
Product name
(4-Bromophenylethynyl)trimethylsilane
Purity
98%
Packaging
5g
Price
$80.64
Updated
2025/07/31
Sigma-Aldrich
Product number
494011
Product name
(4-Bromophenylethynyl)trimethylsilane
Purity
98%
Packaging
25g
Price
$200
Updated
2025/07/31
TCI Chemical
Product number
B6028
Product name
(4-Bromophenylethynyl)trimethylsilane
Packaging
1G
Price
$35
Updated
2025/07/31
TCI Chemical
Product number
B6028
Product name
(4-Bromophenylethynyl)trimethylsilane
Packaging
5G
Price
$137
Updated
2025/07/31
AK Scientific
Product number
8155AA
Product name
(4-Bromophenyl)ethynyl)trimethylsilane
Packaging
25g
Price
$321
Updated
2021/12/16
More
Less

(4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE Chemical Properties,Usage,Production

Uses

(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

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.

Synthesis

589-87-7

1066-54-2

16116-78-2

In a two-necked round-bottomed flask (RBF) equipped with a magnetic stirrer, triethylamine (TEA, 200 mL) was added and 1-bromo-4-iodobenzene (24.00 g, 84.83 mmol) was added at room temperature and protected by nitrogen. After stirring the mixture for 5 min, ethynyltrimethylsilane (13.19 mL, 93.31 mmol), dichlorobis(triphenylphosphine)palladium(II) (Pd(PPh3)2Cl2, 2.98 g, 4.24 mmol), and cuprous iodide (CuI, 1.62 g, 8.48 mmol) were added sequentially. The reaction mixture was continued to be stirred at the same temperature for 30 min. Subsequently, the excess TEA was removed by vacuum evaporation and the pH was adjusted to 1 by adding 1 N hydrochloric acid. extraction was carried out with ethyl acetate (EtOAc) and water, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate (MgSO4). After evaporation of the solvent, the residue was purified by column chromatography (eluent: hexane) to afford the target compound (4-bromophenyl ethynyl)trimethylsilane (21.00 g, 98% yield) as a white solid.1H NMR (CDCl3, 500 MHz): δ 7.19-7.06 (4H, m, ArH), 0.00 (9H, s, Si(CH3)3); 13C NMR (CDCl3, 125 MHz): δ 133.5, 131.6, 122.8, 122.3, 104.0, 95.7, 0.00.

References

[1] Journal of Organic Chemistry, 2015, vol. 80, # 8, p. 4097 - 4107
[2] Dalton Transactions, 2013, vol. 42, # 2, p. 338 - 341
[3] Organometallics, 2014, vol. 33, # 18, p. 4947 - 4963
[4] Synlett, 1999, # 6, p. 750 - 752
[5] Tetrahedron Letters, 2005, vol. 46, # 1, p. 27 - 30

(4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

(4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE Suppliers

Americas 1 China 99 Europe 1 Germany 1 India 3 Japan 1 Singapore 1 Switzerland 1 United States 8 Global 116
SIGMA-RBI
Tel
--
Fax
--
Country
Switzerland
ProdList
6896
Advantage
91
More
Less

View Lastest Price from (4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
(4-Bromophenylethynyl)trimethylsilane 16116-78-2
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27
Career Henan Chemical Co
Product
[(4-Bromophenyl)ethynyl](trimethyl)silane 16116-78-2
Price
US $1.00/g
Min. Order
1g
Purity
Min98% HPLC
Supply Ability
g/kg/ton
Release date
2019-12-28

16116-78-2, (4-BROMOPHENYLETHYNYL)TRIMETHYLSILANERelated Search:

(4-ethenylphenyl)Methyl-triMethylsilane TERT-BUTYL(4-IODOBUTOXY)DIMETHYLSILANE METHYLSILANE (3-BROMOPHENYLETHYNYL)TRIMETHYLSILANE (2-BROMOPHENYLETHYNYL)TRIMETHYLSILANE (2-BROMOPHENYLETHYNYL)TRIMETHYLSILANE, 9 8% 4-Bromophenylacetylene PHENYLETHYNYLDIMETHYLSILANE (4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE 1-PHENYL-2-(TRIMETHYLSILYL)ACETYLENE

  • (4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE
  • (4-BROMOPHENYLETHYNYL)TRIMETHYLSILANE, 9 8%
  • (4-BroMophenylethynyl)triMethylsilane 98%
  • 1-Bromo-4-[2-(trimethylsilyl)ethynyl]benzene
  • (2-(4-bromophenyl)ethynyl)trimethylsilane
  • (4-Bromophenyl)Trimethylsilylacetylene
  • (4-Bromophenylethynyl) trimethylsilane, 98% white to yellow powder
  • Benzene, 1-bromo-4-[2-(trimethylsilyl)ethynyl]-
  • DK567
  • (4-<WBR>Bromophenylethynyl)<WBR>trimethylsilane
  • ((4-Bromophenyl)ethynyl)trimethylsilane - [B54598]
  • 16116-78-2
  • BrC6H4CCSiCH33
  • Halogenated Hydrocarbons
  • Organic Building Blocks
  • Building Blocks
  • Alkynyl
  • Alkynyl
  • Halogenated Hydrocarbons
  • Organic Building Blocks