1833-31-4

Basic information

• Product Name: Benzylchlorodimethylsilane
• Synonyms: BENZYLCHLORODIMETHYLSILANE;BENZYLDIMETHYLCHLOROSILANE;benzylchlorodimethyl-silan;chlorodimethyl(phenylmethyl)-silan;Dimethylchlorobenzylsilane;Benzyldimethylchlorisilane;Benzene, [(chlorodiMethylsilyl)Methyl]-
• CAS NO: 1833-31-4
• Molecular Formula: C₉H₁₃ClSi
• Molecular Weight: 184.74
• Product Categories: Monochlorosilanes;Protection & Derivatization Reagents (for Synthesis);Si (Classes of Silicon Compounds);Si-Cl Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Protecting and Derivatizing Reagents;Protection and Derivatization;Silicon-Based
• Mol File: 1833-31-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 101-103 °C18 mm Hg(lit.)
• Flash Point: 194 °F
• Appearance: /
• Density: 1.018 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.225mmHg at 25°C
• Refractive Index: n20/D 1.511(lit.)
• CAS DataBase Reference: Benzylchlorodimethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: Benzylchlorodimethylsilane(1833-31-4)
• EPA Substance Registry System: Benzylchlorodimethylsilane(1833-31-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2987 8/PG 2
• WGK Germany: 3
• RTECS: VV1810000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1833-31-4(Hazardous Substances Data)

Usage

Description

Benzylchlorodimethylsilane is an organosilicon compound with the chemical formula C9H13ClSi. It is a colorless to pale yellow liquid and is commonly used in various chemical reactions and processes due to its unique properties.

Uses

Used in Chemical Synthesis:
Benzylchlorodimethylsilane is used as a reagent for the preparation of various organic compounds, such as:
1. A ferrocene-based mesoporous catalyst, which is applicable in the oxidation of styrene. This application is significant because it aids in the development of efficient and selective catalysts for industrial chemical processes.
2. Silylbissulfide named 3-(benzyldimethylsilyl)-1,3-bis(phenylthio)-1-propene, which is an important intermediate in the synthesis of various organic compounds and materials.
3. Silyl enyne by reacting with 6-hept-1-yne and nBu-Li, which can be further used in the intramolecular cross-metathesis to yield silicon-substituted diene. This process is valuable for the synthesis of complex organic molecules and materials with specific properties.
Used in Pharmaceutical Industry:
Benzylchlorodimethylsilane can be utilized as a building block for the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and therapies.
Used in Material Science:
In the field of material science, benzylchlorodimethylsilane can be employed in the synthesis of novel materials with unique properties, such as improved thermal stability, chemical resistance, or electrical conductivity.

Safety Profile

Poison by intravenous route.When heated to decomposition it emits toxic vapors ofCl- .

InChI:InChI=1/C9H13ClSi/c1-11(2,10)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H3

Upstream product

• 75-78-5 dimethylsilicon dichloride 
• 6921-34-2 benzylmagnesium chloride 
• 100-44-7 benzyl chloride 
• 56633-16-0 1,1-dimethylphenylmethylsilanol 
• 17881-63-9 chlorodimethyl(4-methylphenyl)silane 
• 2355-86-4 (4-fluorophenyl)chlorodimethylsilane 
• 100-39-0 benzyl bromide 
• 4342-61-4 1,2-dichlorotetramethylsilane 
• 6376-86-9 dimethylsilylene 
• 122887-70-1 Benzyl(chlorformyloxymethyl)methylsilan 
• 768-33-2 phenyldimethylsilyl chloride 
• 13528-88-6 1,1,2-trichloro-1,2,2-trimethyldisilane 
• 1719-57-9 Chloro(chloromethyl)dimethylsilane 
• 71-43-2 benzene 

Downstream Products

• 18765-45-2 bis-{[4-(3-carboxy-propionyl)-benzyl]-dimethyl-silanyl}-ether 
• 18876-51-2 bis-{[4-(2-carboxy-benzoyl)-benzyl]-dimethyl-silanyl}-ether 
• 18052-78-3 benzyl-but-3-en-1-ynyl-dimethyl-silane 
• 18753-40-7 1,3-bis-(4-acetyl-benzyl)-1,1,3,3-tetramethyl-disiloxane 
• 18832-01-4 1,3-bis-(4-benzoyl-benzyl)-1,1,3,3-tetramethyl-disiloxane 
• 67176-44-7 BnMe₂SiOOtBu 
• 67564-65-2 Benzyl-dimethyl-(2,2,2-trichloro-ethoxy)-silane 
• 17151-27-8 benzyl(ethoxy)dimethylsilane 
• 17964-80-6 benzyl(4-bromophenyl)dimethylsilane 
• 71958-71-9 Acetoxymethylbenzylmethylsilan 
• 69397-63-3 1-Benzyl-1,1-dimethyl-2,2,2-triphenyl-disilane 
• 18752-27-7 Benzyl-dimethyl--silan 
• 20156-42-7 1,2-dibenzyl-1,1,2,2-tetramethyldisilane 
• 58061-21-5 benzyldimethylsilyl peroxide 

Relevant articles and documents

Synthesis of C14-Desmethylene Corialactone D and Discovery of Inhibitors of Nerve Growth Factor Mediated Neurite Outgrowth

An asymmetric synthesis of C14-desmethylene corialactone D is described on the basis of strategic application of a metallacycle-mediated annulative cross-coupling reaction, a Still [2,3]-Wittig rearrangement, and Morken's hydroxyl-directed diboration reac

Synthesis of Cyclic Alkenyl Dimethylsiloxanes from Alkynyl Benzyldimethylsilanes and Application in Polyene Synthesis

Cyclic dimethylalkenylsiloxanes, useful motifs for (Z)-selective Hiyama cross-coupling, are accessed from alkynyl benzyldimethylsilanes featuring adjacent allylic or homoallylic oxygen substituents by semihydrogenation/debenzylation/cyclization. While formation of 5- and 6-membered rings can be achieved from the free alcohols using fluoride or silanolate, allylic acetate precursors to 5-membered rings display distinct modes of activation. The utility of these compounds is demonstrated through the preparation of a variety of (Z)-alkene-containing polyenes and application to a concise total synthesis of leukotriene B3.

Effect of the substituents at the silicon of (ω-chloroalkyl)silanes on the alkylation to benzene

(ω-Chloroalkyl)silanes [Cl3-mMemSi(CH2)n-Cl: m=0-3, n=1-3] underwent Friedel-Crafts alkylation with benzene in the presence of aluminum chloride to give alkylated products. Such alkylation reactions took place at temperatures ranging from room temperature (m=0-1, n=2, 3; m=3, n=1) to 80 (m=1, 2; n=1) and 200°C (m=0; n=1), depending on the substituent(s) of the silicon and the alkylene-chain spacer between the silicon and C-Cl bond of (ω-chloroalkyl)silanes. In the alkylation to benzene, the reactivities of (ω-chloroalkyl)silanes increase as the number (m) of methyl-group(s) at the silicon and the alkylene length between the silicon and C-Cl bond increases. While decomposition of alkylation products was observed at two more methyl groups substituted at silicon in the cases of (chloromethyl)silanes such as (chloromethyl)dimethylchlorosilane and (chloromethyl)trimethylsilane. The reaction with (chloromethyl)trimethylsilane occurred at room temperature to give trimethylchlorosilane, toluene and xylene via a decomposition reaction of the products. No (trimethylsilylmethyl)benzene was formed. In the alkylation to benzene, the reactivity of (ω-chloroalkyl)silanes decreases in the following order: m=3>2>1>0; n=3>2?1. The results are consistent with the stability of the carbocation generated by the complexation of (ω-chloroalkyl)silanes with aluminum chloride.