768-33-2

Basic information

• Product Name: Chlorodimethylphenylsilane
• Synonyms: PHENYLDIMETHYLCHLOROSILANE;CHLORODIMETHYLPHENYLSILANE;DMPSCI;DIMETHYLPHENYLSILYLCHLORIDE;DIMETHYLPHENYL-CHLOROSILANE;chlorodimethylphenyl-silan;CP0160;Dimethylphenylchlorosilane~Dimethylphenylsilyl chloride~DMPSCl~Phenyldimethylchlorosilane
• CAS NO: 768-33-2
• Molecular Formula: C₈H₁₁ClSi
• Molecular Weight: 170.71
• EINECS: 212-193-0
• Product Categories: Monochlorosilanes;Si (Classes of Silicon Compounds);Si-Cl Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 768-33-2.mol
• Article Data: 48

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 194-198 °C
• Flash Point: 143 °F
• Appearance: clear colorless to light yellow liquid
• Density: 1.017 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.572mmHg at 25°C
• Refractive Index: n20/D 1.509(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Miscible with tetrahydrofuran, ether and hexane.
• Water Solubility: MAY DECOMPOSE
• Sensitive: Moisture Sensitive
• BRN: 606292
• CAS DataBase Reference: Chlorodimethylphenylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: Chlorodimethylphenylsilane(768-33-2)
• EPA Substance Registry System: Chlorodimethylphenylsilane(768-33-2)

Safety Data

• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2987 8/PG 2
• WGK Germany: 1
• F: 10-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 768-33-2(Hazardous Substances Data)

Usage

Chemical Description

Chlorodimethylphenylsilane is an organosilicon compound used as a reagent in organic synthesis.

Chemical Properties

clear colorless to light yellow liquid

Uses

Chlorodimethylphenylsilane is used in the synthesis of enantioenriched allenylsilanes through an ortho-ester Claisen rearrangement of chiral and silylpropargylic alcohols.

Purification Methods

Fractionate it through a 1.5 x 18inch column packed with stainless steel helices, or a spinning band column. [Daudt & Hyde J Am Chem Soc 74 386 1952, Lewis et al. J Am Chem Soc 70 1115 1948, Eaborn J Chem Soc 494 1953.] It is used for standardising MeLi or MeMgBr which form Me3PhSi which is estimated by GC. [Maienthal et al. J Am Chem Soc 76 6392 1954, House & Respess J Organomet Chem 4 95 1965, Beilstein 16 IV 1475.] TOXIC and MOISTURE SENSITIVE.

InChI:InChI=1/C8H11ClSi/c1-10(2,9)8-6-4-3-5-7-8/h3-7H,1-2H3

Upstream product

• 676-58-4 methylmagnesium chloride 
• 75-78-5 dimethylsilicon dichloride 
• 1825-58-7 dimethyl(ethoxy)phenylsilane 
• 75-36-5 acetyl chloride 
• 108-86-1 bromobenzene 
• 1558-25-4 (chloromethyl)trichlorosilane 
• 766-77-8 Dimethylphenylsilane 
• 5272-18-4 dimethylphenylsilanol 
• 778-24-5 Dimethyldiphenylsilane 
• 56-33-7 1,1,3,3-tetramethyl-1,3-diphenyldisiloxane 
• 37865-47-7 dimethylphenyl(trimethylgermyl)silane 
• 76-83-5 trityl chloride 
• 4342-61-4 1,2-dichlorotetramethylsilane 
• 98-88-4 benzoyl chloride 

Downstream Products

• 75-78-5 dimethylsilicon dichloride 
• 75-77-4 chloro-trimethyl-silane 
• 58309-61-8 dimethyl(2-methyl-1,3-dithiacyclohexan-2-yl)phenylsilan 
• 138142-29-7 1-Methyl-3-dimethylphenylsilyl-2-pyrrolidone 
• 78823-77-5 3-methyl-4-(dimethylphenylsilyl)pyridine 
• 127611-95-4 (Dimethyl-phenyl-silanyl)-ethyl-amine 
• 143810-34-8 2,5-Bis-(dimethyl-phenyl-silanyl)-thiophene 
• 125828-08-2 2-(dimethylphenylsilyl)-2,3-dihydrofuran 
• 4774-69-0 N-n-butyldimethylphenylsilylamine 
• 7036-89-7 N,N'-Bis-(dimethyl-phenyl-silyl)-aethylendiamin 
• 15164-36-0 1,3-bis-{[3-(dimethyl-phenyl-silanyl)-2,2-dimethyl-[1,3,2]diazasilolidin-1-yl]-dimethyl-silanyl}-2,2-dimethyl-[1,3,2]diazasilolidine 
• 7036-85-3 1,3-bis-(dimethyl-phenyl-silanyl)-2,2-dimethyl-[1,3,2]diazasilolidine 
• 43019-63-2 3-(phenyldimethylsilyl)prop-2-yn-1-ol 
• 17920-00-2 Acetylphosphonsaeure-aethylester-(dimethyl-phenyl-silylester) 

Relevant articles and documents

A General and Selective Synthesis of Methylmonochlorosilanes from Di-, Tri-, and Tetrachlorosilanes

Direct catalytic transformation of chlorosilanes into organosilicon compounds remains challenging due to difficulty in cleaving the strong Si-Cl bond(s). We herein report the palladium-catalyzed cross-coupling reaction of chlorosilanes with organoaluminum reagents. A combination of [Pd(C3H5)Cl]2 and DavePhos ligand catalyzed the selective methylation of various dichlorosilanes 1, trichlorosilanes 5, and tetrachlorosilane 6 to give the corresponding monochlorosilanes.

Neutral-Eosin-Y-Photocatalyzed Silane Chlorination Using Dichloromethane

Chlorosilanes are versatile reagents in organic synthesis and material science. A mild pathway is now reported for the quantitative conversion of hydrosilanes to silyl chlorides under visible-light irradiation using neutral eosin Y as a hydrogen-atom-transfer photocatalyst and dichloromethane as a chlorinating agent. Stepwise chlorination of di- and trihydrosilanes was achieved in a highly selective fashion assisted by continuous-flow micro-tubing reactors. The ability to access silyl radicals using photocatalytic Si?H activation promoted by eosin Y offers new perspectives for the synthesis of valuable silicon reagents in a convenient and green manner.

Nickel-Catalyzed Selective Cross-Coupling of Chlorosilanes with Organoaluminum Reagents

Nickel-catalyzed cross-coupling reactions of chlorosilanes with organoaluminum reagents were developed. An electron-rich Ni(0)/PCy3 complex was found to be an effective catalyst for the desired transformation. The reaction of dichlorosilanes 1 proceeded to give the corresponding monosubstituted products 2. Trichlorosilanes 4 underwent selective double substitution to furnish the corresponding monochlorosilanes 2. Overall, the selective synthesis of a series of alkylmonochlorosilanes 2 from di- and trichlorosilanes was achieved using the present catalytic systems.