| Identification | More | [Name]
Vinyltrimethylsilane | [CAS]
754-05-2 | [Synonyms]
ETHENYLTRIMETHYLSILANE
(TRIMETHYLSILYL)ETHYLENE
TRIMETHYLVINYLSILANE
VINYLTRIMETHYLSILANE
CH2=CHSi(CH3)3
ethenyltrimethyl-silan
Silane, trimethylvinyl-
silane,trimethylvinyl-
Vinyltrimethysilane
TRIMETHYLVINYLSILANE
97%
Vinyltrimethylsilane,99%
Silane, ethenyltrimethyl-
VINYLTRIMETHYLSILANE 97%
(Trimethylsilyl)ethylene, Ethenyltrimethylsilane, Trimethyl(vinyl)silane
(Trimethylsilyl)ethylene, Ethenyltrimethylsilane
(Trimethylsilyl)ethene
1-(Trimethylsilyl)ethene
2-(Trimethylsilyl)ethene
Trimethylsilylethene | [EINECS(EC#)]
212-042-9 | [Molecular Formula]
C5H12Si | [MDL Number]
MFCD00008606 | [Molecular Weight]
100.23 | [MOL File]
754-05-2.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colourless liquid | [Melting point ]
-132°C | [Boiling point ]
55 °C (lit.) | [density ]
0.684 g/mL at 25 °C(lit.) | [vapor pressure ]
4.44 psi ( 20 °C)
| [refractive index ]
n20/D 1.391(lit.)
| [Fp ]
<-30 °C
| [storage temp. ]
Flammables area | [solubility ]
Miscible with tetrahydrofuran, diethyl ether, benzene and dichloromethane. | [form ]
liquid | [Specific Gravity]
0.6903 | [Hydrolytic Sensitivity]
1: no significant reaction with aqueous systems | [BRN ]
956572 | [InChIKey]
GCSJLQSCSDMKTP-UHFFFAOYSA-N | [CAS DataBase Reference]
754-05-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Silane, ethenyltrimethyl-(754-05-2) | [EPA Substance Registry System]
754-05-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
F,Xn | [Risk Statements ]
R11:Highly Flammable.
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S33:Take precautionary measures against static discharges .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 1993 3/PG 1
| [WGK Germany ]
1
| [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colourless liquid | [Physical properties]
bp 55–57 °C; d20
4 0.691 g cm?3; n20
D 1.391. | [Uses]
Preparation of silyl-ethers by Rh(I) catalysis.1 | [Uses]
Vinyltrimethylsilane is ethylene equivalent in electrophilic substitution reactions;
precursor to 3-trimethylsilyl-3-buten-2-one, a methyl vinyl ketone
surrogate for Robinson annulations; homologation of aldehydes
to α,β-unsaturated aldehydes. It takes part in the reactions of Synthesis of Vinyl Aryl Sulfides, Synthesis of 3-Triethylsilyl-3-buten-2-one, Synthesis of α,β-Unsaturated Primary Amides, Synthesis of α,β-Unsaturated Aldehydes, Synthesis of Bicyclopentenones, Synthesis of 1-Chlorocyclopropene, Radical Addition Reactions of Vinyltrimethylsilane, Reaction of Vinyltrimethylsilane with 2-Azaallylanions, Regioselective Hydroesterification of Vinyltrimethylsilane, 3 + 2 Cycloaddition of Vinyltrimethylsilane with Nitrones, Addition of α-Iodo-α,α-Difluoroketones to Vinyltrimethylsilane, Addition of α-Iodosulfones to Vinyltrimethylsilane, Titanium-mediated Formation of Trimethylsilylcyclopropanols, β-Trimethylsilyl Ketones and Cyclopropenes, Hydrogen Acceptor Catalyst in the Conversion of Alcohols
to Hydrogenated Wittig Adducts, Formation of 2-Trimethylsilylaziridines, Formation of Sulfonyl Chlorides, Improved Synthesis of 2-Trimethylsilylethylsulfonyl
Chloride, Formation of an Iron Carbonyl Trienone Complex, Synthesis of 2-Phenyl-2-Trimethylsilylethanol, Synthesis of 2-Vinylanilines, Decarbonylative Vinylation of an Aromatic Ester, Asymmetric Epoxidation of Vinyltrimethylsilane, Direct Silylation of Heteroarylcarbonyl Compounds, Trimethylsilylation of Vinylboronates, etc. | [Preparation]
Prepared in 67–91% yield from vinylmagnesium bromide and chlorotrimethylsilane in THF. | [Flammability and Explosibility]
Flammable | [Purification Methods]
If the 1H NMR spectrum shows impurities, then dissolve it in Et2O, wash it with aqueous NH4Cl solution, dry over CaCl2, filter, evaporate and distil it at atmospheric pressure in an inert atmosphere. It is used as a co-polymer and may polymerise in the presence of free radicals. It is soluble in CH2Cl2. [Nagel & Post J Org Chem 17 1379 1952, Beilstein 4 IV 3922.] |
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