| Identification | More | [Name]
(1-BROMOVINYL)TRIMETHYLSILANE | [CAS]
13683-41-5 | [Synonyms]
(1-BROMOVINYL)TRIMETHYLSILANE
α-(trimethylsilyl)vinyl bromide
(1-Bromoethenyl)trimethylsilane
Trimethyl(1-bromoethenyl)silane
(1-Bromoethynl) trimethylsilane
α-(trimethylsilyl)vinyl bromide
1-BROMO-1-TRIMETHYLSILYLETHYLENE
1-Bromo-1-(trimethylsilyl)ethene
(1-Bromovinyl)trimethylsilane,97%
(1-BroMovinyl)triMethylsilane 97%
ALPHA-TRIMETHYLSILYLVINYL BROMIDE
(1-Bromovinyl)trimethylsilane >
Silane, (1-bromoethenyl)trimethyl-
1-Bromo-1-trimethylsilylethylene
alpha-Trimethylsilylvinyl Bromide | [EINECS(EC#)]
237-195-9 | [Molecular Formula]
C5H11BrSi | [MDL Number]
MFCD00014927 | [Molecular Weight]
179.13 | [MOL File]
13683-41-5.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR LIGHT YELLOW LIQUID | [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.)
| [Fp ]
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 Data | Back Directory | [Hazard Codes ]
F | [Risk Statements ]
R11:Highly Flammable. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes . | [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 |
| Hazard Information | Back Directory | [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. |
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