13683-41-5

Basic information

• Product Name: (1-BROMOVINYL)TRIMETHYLSILANE
• Synonyms: ALPHA-TRIMETHYLSILYLVINYL BROMIDE;1-BROMO-1-TRIMETHYLSILYLETHYLENE;(1-BROMOVINYL)TRIMETHYLSILANE;Silane, (1-bromoethenyl)trimethyl-;α-(trimethylsilyl)vinyl bromide;(1-Bromoethenyl)trimethylsilane;1-Bromo-1-(trimethylsilyl)ethene;Trimethyl(1-bromoethenyl)silane
• CAS NO: 13683-41-5
• Molecular Formula: C₅H₁₁BrSi
• Molecular Weight: 179.13
• EINECS: 237-195-9
• Product Categories: Industrial/Fine Chemicals;Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Vinylsilanes, Allylsilanes
• Mol File: 13683-41-5.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 124 °C745 mm Hg(lit.)
• Flash Point: 49 °F
• Appearance: clear light yellow liquid
• Density: 1.156 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: 14.6mmHg at 25°C
• Refractive Index: n20/D 1.458(lit.)
• Storage Temp.: 2-8°C
• Solubility: completely miscible with THF and Et2O.
• BRN: 1742258
• CAS DataBase Reference: (1-BROMOVINYL)TRIMETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: (1-BROMOVINYL)TRIMETHYLSILANE(13683-41-5)
• EPA Substance Registry System: (1-BROMOVINYL)TRIMETHYLSILANE(13683-41-5)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-23-24/25
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• F: 8-10-21
• TSCA: No
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 13683-41-5(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C5H11BrSi/c1-7(2,3)5-4-6/h4-5H,1-3H3/b5-4+

Upstream product

• 917-64-6 methyl magnesium iodide 
• 18038-34-1 (vi-1-Br)SiCl₃ 
• 75-77-4 chloro-trimethyl-silane 
• 593-60-2 Vinyl bromide 
• 111-71-7 heptanal 
• 123-38-6 propionaldehyde 
• 103-64-0 bromostyrene 
• 754-05-2 ethenyltrimethylsilane 
• 5654-07-9 1,1-bis(trimethylsilyl)ethylene 
• 18146-08-2 (1,2-dibromoethyl)trimethylsilane 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 71785-82-5 3-methyl-3-<1-(trimethylsilyl)-1-vinyl>cyclohexanone 
• 71785-85-8 2-Methyl-5-(1-trimethylsilylvinyl)-cyclohexanon 
• 71785-83-6 2-Isopropyl-5-(1-trimethylsilylvinyl)-cyclohexanon 
• 71785-86-9 3-(1-Trimethylsilylvinyl)-4-t-butyl-cyclohexanon 
• 22472-36-2 2,3-bis(trimethylsilyl)-buta-1,3-diene 
• 51666-96-7 1-phenyl-2-(trimethylsilyl)-2-propen-1-ol 
• 58649-14-2 1-Cyclohexyl-2-trimethylsilyl-2-propen-1-ol 
• 1923-01-9 trimethyl(1-phenylvinyl)silane 
• 80868-65-1 2-Trimethylsilyl-1-(4-methoxy-2-methylphenyl)prop-2-en-1-ol 
• 77461-49-5 1-(Phenylseleno)-1-(trimethylsilyl)ethene 
• 19372-00-0 1-(trimethylsilyl)-2-phenylethene 
• 62762-20-3 1-phenylthio-1-trimethylsilylethene 
• 7671-24-1 2-(trimethylsilyl)-1-(phenylthio)ethene 
• 1121-55-7 3-vinylpyridine 

Relevant articles and documents

RADICAL REACTIONS OF (2-TRIMETHYLSILYLALLYL)TRIPHENYLSTANNANE WITH ALKYL HALIDES: A NEUTRAL ACETONE ENOLATE EQUIVALENT

Facile transfer of 2-trimethylsilylallyl group is achieved when (2-trimethylsilylallyl)triphenylstannane is reacted with some halides under radical reaction conditions.

Synthesis of (1-Halo-1-alkenyl)trimethylsilanes via gem-Trimethylsilylation of Vinyl Halides

Various vinyl halides including enol silyl ethers of α-halo ketones and esters give the corresponding (1-halo-1-alkenyl)trimethylsilanes in fair to good yields on treatment with lithium diisopropylamide at Dry Ice temperature in the presence of chlorotrimethylsilane.

An efficient synthesis of 2-trimethylsilyl-2-propenal, a useful three- carbon synthon

A formal efficient synthesis of 2-trimethylsilyl-2-propenal (2), a potentially useful synthetic reagent, is hereby described. The readily available α-bromovinyltrimethylsilane can be converted into 2- trimethylsilyl-2-propen-1-ol (1) via Grignard formation followed by addition of paraformaldehyde. The alcohol 1 can be oxidized using Jones reagent or PCC to yield the desired aldehyde 2.

Intermediate for preparing halichondrin compound and preparation method thereof

The invention relates to an intermediate for preparing a halichondrin compound and a preparation method thereof. The invention particularly relates to an intermediate for preparing halichondrin, eribulin or analogues thereof, and a preparation method and application of the intermediate. The intermediate as well as the preparation method and application thereof are used for constructing C20-C26 structural fragments of the halichondrin compound. The initial raw materials of the synthesis route are cheap, easy to obtain, stable in source and reliable in quality; the structural characteristics ofreactants are fully utilized in the selection of a chiral center construction method, so that the synthesis efficiency is practically improved, and the difficulty and risk of product quality control are reduced; and the use of a high-toxicity and expensive organic tin catalyst is avoided, so that the cost and the environmental friendliness are remarkably improved.

Catalytic asymmetric Claisen rearrangement in natural product synthesis: Synthetic studies toward (-)-xeniolide F

(Chemical Equation Presented) The catalytic asymmetric Claisen rearrangement (CAC) of a highly substituted and functionalized α-alkoxycarbonyl-substituted allyl vinyl ether has been exploited to gain access to an advanced building block for the projected total synthesis of (-)-xeniolide F, the enantiomer of a xenicane diterpene isolated from a coral of the genus Xenia.