(4-Chlorobut-3-en-2-yl)(trimethyl)silane

Base Information

• Chemical Name: (4-Chlorobut-3-en-2-yl)(trimethyl)silane
• CAS No.: 116399-78-1
• Molecular Formula: C₇H₁₅ClSi
• Molecular Weight: 162.735
• DSSTox Substance ID: DTXSID10699520
• Mol file: 116399-78-1.mol

Synonyms:(4-Chlorobut-3-en-2-yl)(trimethyl)silane;DTXSID10699520

Chemical Property of (4-Chlorobut-3-en-2-yl)(trimethyl)silane

Chemical Property:

• Vapor Pressure: 2.22mmHg at 25°C
• Refractive Index: 1.432
• Boiling Point: 167.7°C at 760 mmHg
• Flash Point: 49.1°C
• PSA: 0.00000
• Density: 0.881g/cm³
• LogP: 3.46720
• Solubility.: freely sol organic solvents.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 162.0631547
• Heavy Atom Count: 9
• Complexity: 102

Purity/Quality:

((E)-3-CHLORO-1-METHYLPROPENYL)TRIMETHYLSILANE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C=CCl)[Si](C)(C)C
• Physical properties: bp 92–94°C/74 mmHg.
• Uses: (E)-(3-Chloro-1-methyl-1-propenyl)- trimethylsilane acts as the alkylative equivalent of 3-buten-2-one (methyl vinyl ketone), permitting regiospecific enolate alkylation under nonequilibrating conditions. As a vinylsilane it can be converted,via the corresponding α,β-epoxy silane, into a 3-oxobutyl moiety, and hence used in an alkylative equivalent of Robinson annulation.Application of such methodology can be seen (eq 1) in the preparation of bicyclodecenones via the alkylation of dihydrocarvone with this reagent.Apart from this application, and its use in combination with potassium iodide, it has seen little use so far.

Technology Process of (4-Chlorobut-3-en-2-yl)(trimethyl)silane

There total 3 articles about (4-Chlorobut-3-en-2-yl)(trimethyl)silane 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: 66.0%

(2E)-3-(trimethylsilyl)crotyl alcohol (52685-50-4) → ((E)-3-chloro-1-methylpropenyl)trimethylsilane (116399-78-1)

Guidance literature:

With N-chloro-succinimide; triphenylphosphine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/jo0480803

Reference yield:

(Z)-(3)-(trimethylsilyl)-3-iodo-2-propen-1-ol (105575-91-5,97632-90-1) → ((E)-3-chloro-1-methylpropenyl)trimethylsilane (116399-78-1)

Guidance literature:

Multi-step reaction with 2 steps

2: CCl₄, Ph₃P

With tetrachloromethane; triphenylphosphine;

DOI:10.1021/ja00818a071

Reference yield:

3-trimethylsilyl-2-propyn-1-ol (5272-36-6) → ((E)-3-chloro-1-methylpropenyl)trimethylsilane (116399-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1: CuI / diethyl ether

2: Ph₃P, CCl₄

With tetrachloromethane; copper(l) iodide; triphenylphosphine; In diethyl ether;

DOI:10.1055/s-1976-24200

upstream raw materials:

(2E)-3-(trimethylsilyl)crotyl alcohol

3-trimethylsilyl-2-propyn-1-ol

(Z)-⁽³⁾-(trimethylsilyl)-3-iodo-2-propen-1-ol

Downstream raw materials:

2-Methyl-2-(3-trimethylsilyl-2-butenyl)-cyclohexanon

(E)-(3-iodo-1-methyl-1-propenyl)-trimethylsilane