Trimethylvinylsilan

TRIMETHYLVINYLSILANE · Vinyltrimethysilane · DK385 · CH2=CHSi(CH3)3 · VINYLTRIMETHYLSILANE · Trimethylsilylethene · ETHENYLTRIMETHYLSILANE · ethenyltrimethyl-silan

https://huagongshe.com/de/chemical/79102

Identifikatoren & physikalische Daten

CAS No.	754-05-2
Summenformel	C5H12Si
Durchschnittliche Molmasse	100,23 g/mol
Monoisotopische Masse	100,07082691 g/mol
SMILES	C=C[Si](C)(C)C
InChIKey	GCSJLQSCSDMKTP-UHFFFAOYSA-N
PubChem CID	79102
EC No.	212-042-9
DTXSID	DTXSID1061071
Lokaler Name	Trimethylvinylsilan

Chemische & physikalische Eigenschaften

Polarare Oberfläche (TPSA)	0
H-Brücken-Donoren	0
H-Brücken-Akzeptoren	0
Frei drehbare Bindungen	1
Schwere Atome	6
Formalladung	0
Komplexität	49,4
Stoffklassen	Metals -> Metalloid Compounds (Silicon)
SpringerMaterials Properties	29Si nuclear magnetic resonance spectrum
Physical Description	LiquidClear liquid with an unpleasant odor[Air Products MSDS]
Schmelzpunkt	-132°C
Siedepunkt	55 °C (lit.)
Dichte	0.684 g/mL at 25 °C (lit.)
Dampfdruck	4.44 psi ( 20 °C)
Brechungsindex	n20/D 1.391(lit.)
Flammpunkt	<-30 °C
Lagerbedingungen	Inert atmosphere,2-8°C
Löslichkeit	Miscible with tetrahydrofuran, diethyl ether, benzene and dichloromethane.
Aggregatzustand	liquid
Wichte	0.6903
Farbe	Colorless to Almost colorless
BRN	956572
InChI	1S/C5H12Si/c1-5-6(2,3)4/h5H,1H2,2-4H3
InChIKey	GCSJLQSCSDMKTP-UHFFFAOYSA-N
SMILES	C[Si](C)(C)C=C
CAS Datenbank	754-05-2(CAS DataBase Reference)
NIST chemische Informationen	Silane, ethenyltrimethyl-(754-05-2)
EPA chemische Informationen	Silane, ethenyltrimethyl- (754-05-2)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 73 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische Informationen	Chemical: Silane, ethenyltrimethyl-Silane, ethenyltrimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Silane, ethenyltrimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 26-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21677Trimethylvinylsilane: HSNO Approval: HSR006887 Approved with controls
Gefahrenübersicht	FlammableA mild irritantMay decompose to form flammable or explosive mixtures with airLethal-dose study of rats at 2,000 mg/kg produced diarrhea on the day of administration and no deathsLethal-concentration study of rats at 20,030 mg/m3 (4,886 ppm) caused no clinical signs of toxicity or irritation and no deaths[Air Products MSDS] May contain up to 3% tetrahydrofuran (with BHT inhibitor) as residual impurity of productionHighly flammableAn irritantHarmful by ingestionTargets kidneys, liver, and CNS[Aldrich MSDS]
Hazard Classes and Categories	Flam. Liq. 2 (100%)
Minimum Risk Level	Intermediate Oral: 0.3 mg/kg/day (L134) Chronic Oral: 0.3 mg/kg/day (L134)
Treatment	Zinc poisoning is treated symptomatically, often by administering fluids such as water or milk, or with gastric lavage. (L49)

Anwendungen & Verwendung

Verwenden

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.

Herstellung & Synthese

synthetische

Prepared in 67–91% yield from vinylmagnesium bromide and chlorotrimethylsilane in THF.