Vinyltrimethylsilane

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

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

식별자 및 물리적 특성

CAS No.	754-05-2
분자식	C5H12Si
평균 분자량	100.23 g/mol
단동위원소 질량	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

화학 및 물리적 성질

극성 표면적	0
수소 결합 공여자 수	0
수소 결합 수용자 수	0
회전 가능 결합 수	1
무거운 원자 수	6
형식 전하	0
복잡도	49.4
물질 분류	Metals -> Metalloid Compounds (Silicon)
SpringerMaterials Properties	29Si nuclear magnetic resonance spectrum
Physical Description	LiquidClear liquid with an unpleasant odor[Air Products MSDS]
녹는점	-132°C
끓는 점	55 °C (lit.)
밀도	0.684 g/mL at 25 °C (lit.)
증기압	4.44 psi ( 20 °C)
굴절률	n20/D 1.391(lit.)
인화점	<-30 °C
저장 조건	Inert atmosphere,2-8°C
용해도	테트라히드로푸란, 디에틸 에테르, 벤젠 및 디클로로메탄과 혼합 가능.
물리적 상태	액체
비중	0.6903
색상	무색 내지 거의 무색
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
NIST	Silane, ethenyltrimethyl-(754-05-2)
EPA	Silane, ethenyltrimethyl- (754-05-2)

화학적 성질

clear colourless liquid

안전 및 규제

GHS 분류	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.
규제 정보	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
유해성 요약	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)
건강 영향	Chronic exposure to zinc causes anemia, atazia, lethargy, and decreases the level of good cholesterol in the body. It is also believed to cause pancreatic and reproductive damage. (L49)

용도

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.

제조 및 합성 방법

제조 방법

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