18388-03-9

Basic information

• Product Name: 2-CHLOROMETHYL-3-TRIMETHYLSILYL-1-PROPENE
• Synonyms: 2-CHLOROMETHYL-3-TRIMETHYLSILYL-1-PROPENE;2-(CHLOROMETHYL)ALLYL-TRIMETHYLSILANE;2-(TRIMETHYLSILYLMETHYL)ALLYL CHLORIDE;2-(Chloromethyl)-3-trimethylsilyl-1-propene, 2-(Trimethylsilylmethyl)allyl chloride;[2-(Chloromethyl)-2-propenyl]trimethylsilane;2-(Trimethylsilylmethyl)-2-propenyl chloride;2-(Trimethylsilylmethyl)-3-chloro-1-propene;2-Methylene-3-chloropropyltrimethylsilane
• CAS NO: 18388-03-9
• Molecular Formula: C₇H₁₅ClSi
• Molecular Weight: 162.73
• Mol File: 18388-03-9.mol

Chemical Properties

• Boiling Point: 162-163 °C768 mm Hg(lit.)
• Flash Point: 110 °F
• Appearance: light yellow transparent liquid
• Density: 0.899 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.575mmHg at 25°C
• Refractive Index: n20/D 1.453(lit.)
• Storage Temp.: 2-8°C
• BRN: 1747038
• CAS DataBase Reference: 2-CHLOROMETHYL-3-TRIMETHYLSILYL-1-PROPENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROMETHYL-3-TRIMETHYLSILYL-1-PROPENE(18388-03-9)
• EPA Substance Registry System: 2-CHLOROMETHYL-3-TRIMETHYLSILYL-1-PROPENE(18388-03-9)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• TSCA: No
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 18388-03-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Chloromethyl-3-trimethylsilyl-1-propene is used as a building block for the synthesis of more complex molecules, particularly in the field of organic chemistry. Its unique structure and reactivity make it a valuable component in creating useful substances.
Used in Chemical Research:
In the scientific community, 2-chloromethyl-3-trimethylsilyl-1-propene is used as a research tool to study the properties and reactions of organosilicon compounds. Its specific structure allows for the exploration of various biochemical interactions and the development of new synthetic pathways.
Used in Pharmaceutical Industry:
2-Chloromethyl-3-trimethylsilyl-1-propene is used as an intermediate in the synthesis of pharmaceutical compounds. Its organosilicon and chloromethyl groups can be utilized to create novel drug molecules with potential therapeutic applications.
Used in Material Science:
In the field of material science, 2-chloromethyl-3-trimethylsilyl-1-propene is used to develop new materials with unique properties. Its organosilicon nature can contribute to the creation of advanced materials with improved performance in various applications.
Safety Considerations:
Due to its potential health and safety factors, the usage and handling of 2-chloromethyl-3-trimethylsilyl-1-propene require careful consideration. Specific data about its properties, safety measures, and exact applications can be expected to be found in material safety data sheets and specialized chemical databases.

InChI:InChI=1/C8H13Br/c1-2-3-4-5-6-7-8-9/h2-5,8H2,1H3

Upstream product

• 18147-84-7 2-(chloromethyl)-3-(trichlorosilyl)propene 
• 676-58-4 methylmagnesium chloride 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 96-34-4 methyl chloroacetate 
• 74532-54-0 3-trimethylsilyl-2-(methylsulphonyloxymethyl)prop-1-ene 
• 4206-67-1 iodo(trimethylsilyl)methane 
• 105-53-3 diethyl malonate 
• 81302-80-9 2-(trimethylsilylmethyl)prop-2-en-1-ol 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 77517-77-2 3-(2-Chloromethyl-allyl)-2-phenylsulfanyl-cyclopentanone 
• 77517-76-1 3-(2-Chloromethyl-allyl)-2-phenylsulfanyl-cyclohexanone 
• 143006-54-6 (4S,5S)-5-((tert-butoxycarbonyl)amino)-2-(chloromethyl)-6-phenyl-1-hexen-4-ol 
• 161758-23-2 (4S,5S)-5-((tert-Butoxycarbonyl)amino)-1-chloro-6-phenyl-2-((trimethylsilyl)methyl)-1-hexen-4-ol 
• 72047-94-0 [2-(acetoxymethyl)prop-2-enyl]trimethylsilane 
• 114377-79-6 (1S,2S)-2-Methyl-4-methylene-cyclopentanecarboxylic acid phenethyl ester 
• 114377-79-6 (1S,2R)-2-Methyl-4-methylene-cyclopentanecarboxylic acid phenethyl ester 
• 155219-86-6 1-benzyl-1-(2-<(trimethylsilyl)methyl>-2-propenyl)-2-hydrazinecarboxylic acid allyl ester 
• 23740-61-6 2-(phenylsulfanyl)-2-cyclohexanone 
• 178427-87-7 [(S)-1-((1S,2S)-1-Benzyl-2-hydroxy-4-trimethylsilanylmethyl-pent-4-enylcarbamoyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 178427-88-8 {(S)-1-[(4S,5S)-4-Benzyl-2,2-dimethyl-5-(2-trimethylsilanylmethyl-allyl)-oxazolidine-3-carbonyl]-2-methyl-propyl}-carbamic acid tert-butyl ester 
• 1185729-91-2 (2S,5R,6S)-6-(2-chloromethylallyl)-5-hydroxypiperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 

Relevant articles and documents

A bidirectional SE′ strategy for 1,5- syn and 1,5- anti stereocontrol toward the synthesis of complex polyols

Studies report a bidirectional SE′ strategy applicable for the stereocontrolled synthesis of nonracemic 1,5-syn and 1,5-anti diols and their derivatives. Nonracemic 1,3,2-diazaborolidine auxiliaries are incorporated by chemoselective tin-boron exchange to provide reactive allylic boranes. The convergent pathway utilizes sequential reactions with two aldehydes producing stereochemical outcomes from cyclic, closed, and open transition state preferences, respectively. Synthesis of fragment 16 of peloruside A is accomplished in four steps from readily available aldehydes 9 and 13.

THE CERIUM (III) MEDIATED REACTION OF TRIMETHYLSILYLMETHYL MAGNESIUM CHLORIDE WITH ESTERS AND LACTONES: THE EFFICIENT SYNTHESIS OF SOME FUNCTIONALISED ALLYLSILANES OF USE IN ANNULATION REACTIONS

The use of cerium (III) chloride alters the chemoselectivity of the reaction of trimethylsilylmethyl magnesium chloride with ester-acetals and also greatly improves the efficiency of reaction with lactones.In addition it gives improved preparations of the useful intermediates (7), (13), (18), (20) and (22) and gives direct access to the valuable functionalised allylsilanes (1) to (3) of use in annulation reactions.

DIRECT ACCESS TO FUNCTIONALISED ALLYLSILANES: THE CERIUM(III) MEDIATED GRIGNARD REACTION OF FUNCTIONALISED ESTERS AND LACTONES

The use of cerium (III) chloride alters the chemoselectivity of the reaction of the Grignard reagent (1) with ester-acetals and also greatly improves the efficiency of reaction with lactones.In addition it gives improved preparations of the useful intermediates (8), (11) and (12) giving direct access to valuable functionalised allylsilanes of use in annulation reactions.

TRIMETHYLENEMETHANE METAL COMPLEXES. PART1. SYNTHESIS OF RUTHENIUM, OSMIUM, RHODIUM, AND IRIDIUM COMPLEXES

1--3-trimethylsilylprop-1-ene, available from 2-methylprop-2-en-1-ol, serves as a new entry into trimethylenemethane (tmm) metal complexes.Reaction with low-valent metal complexes affords the first tmm metal complexes of ruthenium, osmium, rhodium, and iridium: 4-tmm)> (M=Ru or Os), 4-tmm)>, 4-tmm)> (M=Rh or Ir), and 4-tmm)> (X=Cl, L=PPh3 or AsPh3; X=Br, L=PPh3).The desilylation of an η3-allyl intermediate rationalises the results and has been verified by the reaction of sodium fluoride with 3-CH2C(CH2SiMe3))CH2>Cl(CO)(PMe2Ph)2>BPH4 in aqueous methyl cyanide which gave the complex 4-tmm)>BPh4 in quantitative yield.N.m.r. data (1H, 13C-) are reported and variable-temperature 1H n.m.r. spin-magnetisation transfer experiments have been used to set a lower limit of ca. 90 kJ mol-1 for the activation energies for trimethylenemethane rotation.

A Annulation Procedure for Methylenecyclopentanes

A two step sequence converts certain cyclic enones to fused methylenecyclopentanes using the annulation reagent 2-chloromethyl-3-trimethylsilylpropene.