(1-BROMOVINYL)TRIMETHYLSILANE Chemical Properties

Boiling point:

124 °C745 mm Hg(lit.)

Density 

1.156 g/mL at 25 °C(lit.)

vapor density 

>1 (vs air)

refractive index 

n20/D 1.458(lit.)

Flash point:

49 °F

storage temp. 

2-8°C

solubility 

completely miscible with THF and Et2O.

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Specific Gravity

1.163

Hydrolytic Sensitivity

4: no reaction with water under neutral conditions

BRN 

1742258

CAS DataBase Reference

13683-41-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

F

Risk Statements 

11

Safety Statements 

16-23-24/25

RIDADR 

UN 1993 3/PG 2

WGK Germany 

3

F 

8-10-21

TSCA 

No

HS Code 

2931.90.9010

HazardClass 

3.1

PackingGroup 

II

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

(1-BROMOVINYL)TRIMETHYLSILANE Usage And Synthesis

Chemical Properties

CLEAR LIGHT YELLOW LIQUID

Physical properties

bp 124°C/745 mmHg; d 1.156 g cm?3.

Uses

Numerous nucleophiles react with (1-bromovinyl)trimethylsilane in the presence of palladium complexes. The bromine has been substituted by phenylthio,vinyl,and aryl groups. This approach gives reasonable yields of the desired products. However, the substitution reactions sometimes lack regiospecificity. For example, a mixture of regioisomers was obtained in eq 6. Two mechanisms have been proposed for the formation of the β-substituted product. One involves an elimination step to give trimethylsilylacetylene as an intermediate, which then undergoes catalyzed additions with the nucleophile at either the α- or β-positions.The other mechanism involves the formation of a pentacoordinated palladium intermediate, leading to the formation of isomeric products.

Preparation

prepared, in good yield, from the reaction of vinyltrimethylsilane with bromine at low temperature followed by dehydrohalogenation in the presence of an amine base.Alternative syntheses and reagents, i.e. (1-bromovinyl)- triphenylsilane and (1-bromovinyl)triethylsilane, are also known.

General Description

Tetrakis(triphenylphosphine)palladium(0) catalyzed coupling reactions of (1-bromovinyl)trimethylsilane with organozinc bromides were studied.

(1-BROMOVINYL)TRIMETHYLSILANE(13683-41-5)Related Product Information

• (2-BROMOVINYL)TRIMETHYLSILANE
• (2-BROMOVINYL)TRIMETHYLSILANE, 98%, PRED OMINANTLY TRANS,(2-BROMOVINYL)TRIMETHYLSILANE(CIS+TRANS)
• Dimethylvinylsilane
• Vinyl bromide
• (BROMOMETHYL)TRIMETHYLSILANE
• vinylsilane
• Vinyltrimethylsilane
• (E)-1,2-DIBROMO-1,2-BIS-TRIMETHYLSILANYL-ETHENE
• (1-BROMOVINYL)TRIMETHYLSILANE