(1-Bromovinyl)trimethylsilane

Base Information

• Chemical Name: (1-Bromovinyl)trimethylsilane
• CAS No.: 13683-41-5
• Molecular Formula: C5H11BrSi
• Molecular Weight: 179.132
• Hs Code.: 2931900090
• European Community (EC) Number: 237-195-9
• DSSTox Substance ID: DTXSID00159966
• Nikkaji Number: J277.990K
• Wikidata: Q83028343
• Mol file: 13683-41-5.mol

Synonyms:(1-Bromovinyl)trimethylsilane;13683-41-5;Silane, (1-bromoethenyl)trimethyl-;1-bromovinyltrimethylsilane;1-bromoethenyl(trimethyl)silane;(1-bromoethenyl)trimethylsilane;EINECS 237-195-9;C5H11BrSi;1-Bromo-1-trimethylsilylethylene;C5-H11-Br-Si;1-Bromovinyl(trimethyl)silane;SCHEMBL1493208;alpha-Trimethylsilylvinyl Bromide;(1-Bromoethenyl)trimethyl-silane;AMY1247;DTXSID00159966;alpha-(Trimethylsilyl)vinyl bromide;1-bromo-1-(trimethylsilyl)ethylene;(1-Bromovinyl)trimethylsilane, 97%;MFCD00014927;AKOS015833910;BS-20805;B1769;BB 0260988;CS-0204005;FT-0694114;EN300-214083;J-500135;J-802028

Chemical Property of (1-Bromovinyl)trimethylsilane

Chemical Property:

• Appearance/Colour: clear light yellow liquid
• Vapor Pressure: 14.6mmHg at 25°C
• Refractive Index: n20/D 1.458(lit.)
• Boiling Point: 124.9 °C at 760 mmHg
• Flash Point: 22.2 °C
• PSA: 0.00000
• Density: 1.156 g/cm³
• LogP: 2.77240
• Storage Temp.: 2-8°C
• Solubility.: completely miscible with THF and Et2O.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 177.98134
• Heavy Atom Count: 7
• Complexity: 80.6

Purity/Quality:

98%, ^*data from raw suppliers

(1-Bromovinyl)trimethylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)C(=C)Br
• 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.

Technology Process of (1-Bromovinyl)trimethylsilane

There total 11 articles about (1-Bromovinyl)trimethylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.2%

ethenyltrimethylsilane (754-05-2) → 1-bromo-1-(trimethylsilyl)ethene (13683-41-5)

Guidance literature:

With bromine; triethylamine; In dichloromethane; at -10 - -5 ℃; Temperature; Reflux;

Reference yield: 82.0%

(1,2-dibromoethyl)trimethylsilane (18146-08-2) → 1-bromo-1-(trimethylsilyl)ethene (13683-41-5)

Guidance literature:

With diethylamine; for 168h;

Reference yield: 60.0%

chloro-trimethyl-silane (75-77-4) + Vinyl bromide (593-60-2,25951-54-6) → 1-bromo-1-(trimethylsilyl)ethene (13683-41-5) + Bis(trimethylsilyl)ethyne (14630-40-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; at -100 ℃; for 3h;

DOI:10.1246/bcsj.60.777

upstream raw materials:

(vi-1-Br)SiCl₃

methylmagnesium bromide

methyl magnesium iodide

(1,2-dibromoethyl)trimethylsilane

Downstream raw materials:

1,1-Diphenyl-2-trimethylsilyl-2-propen-1-ol

3-methyl-3-<1-(trimethylsilyl)-1-vinyl>cyclohexanone

(E)-1,3-bis(trimethylsilyl)-1,3-butadiene

1-<α-(trimethylsilyl)vinyl>cyclohexan-1-ol

Refernces

• 1、 Fritz,Grobe. "". . p. 77. Retrieved 1961.
• 2、 Ottolenghi,A. et al.. "-". . p. 2977 - 2982. Retrieved 1963.
• 3、 Ding, Yi-Xiang,Weber, William P.. "Stereospecific 1,4-polymerization of 2,3-bis(trimethylsilyl)-1,3-butadiene". . p. 267 - 272. Retrieved 1988.
• 4、 -. "Trimethylsilylacetylene synthesis process". Paragraph 0022; 0023. . Retrieved 2021/01/11.
• 5、 Mu, Wenbo,Zou, Yue,Zhou, Lijun,Wang, Quanrui,Goeke, Andreas. "Removable Silyl Group as a "masked Proton" in Oxy-2-oxonia(azonia)-Cope Rearrangement: Applications in Stereoselective Total Synthesis of Natural Macrolides". supporting information. p. 4982 - 4989. Retrieved 2015/08/03.