10557-71-8

Basic information

• Product Name: P-CHLOROPHENYLTRIMETHYLSILANE
• Synonyms: 1-CHLORO-4-(TRIMETHYLSILYL)BENZENE;P-CHLOROPHENYLTRIMETHYLSILANE;(4-Chlorophenyl)(trimethyl)silane;(4-chlorophenyl)trimethyl-silan;(4-chloro-phenyl)-trimethyl-silane;p-chlorophenyltrimethylsilane7%;1-(Trimethylsilyl)-4-chlorobenzene;Trimethyl(4-chlorophenyl)silane
• CAS NO: 10557-71-8
• Molecular Formula: C₉H₁₃ClSi
• Molecular Weight: 184.74
• Mol File: 10557-71-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: °C
• Boiling Point: 98-100 °C20 mm Hg(lit.)
• Flash Point: 171 °F
• Appearance: /
• Density: 0.995 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.301mmHg at 25°C
• Refractive Index: n20/D 1.509(lit.)
• CAS DataBase Reference: P-CHLOROPHENYLTRIMETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: P-CHLOROPHENYLTRIMETHYLSILANE(10557-71-8)
• EPA Substance Registry System: P-CHLOROPHENYLTRIMETHYLSILANE(10557-71-8)

Safety Data

• Statements: 11-36/38
• Safety Statements: 16-26-36/37/39
• RIDADR: 1993
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 10557-71-8(Hazardous Substances Data)

Usage

General Description

P-Chlorophenyltrimethylsilane is a type of organosilicon compound, which is specifically a silyl ether. This chemical compound is formed by substituting one hydrogen atom of trimethylsilane with a p-chlorophenyl group. Its molecular formula is C9H11ClSi. It is commonly used in organic synthesis as a protecting agent or coupling agent. P-Chlorophenyltrimethylsilane can also act as a precursor for other chemical compounds. Safety measures should be taken while handling this compound, as it is harmful if inhaled, ingested, or contacted with skin. In its pure form, it appears as a clear colorless to yellow liquid.

InChI:InChI=1/C9H13ClSi/c1-11(2,3)9-6-4-8(10)5-7-9/h4-7H,1-3H3

Upstream product

• 106-46-7 para-dichlorobenzene 
• 825-94-5 trichloro(p-chlorophenyl)silane 
• 676-58-4 methylmagnesium chloride 
• 75-77-4 chloro-trimethyl-silane 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 637-87-6 1-Chloro-4-iodobenzene 
• 106-39-8 bromochlorobenzene 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 54711-92-1 trimethylsilanide ion 
• 17955-46-3 trimethylsilyltributyltin 
• 3098-83-7 (4-chlorophenyl)pentamethyldisilane 
• 917-54-4 methyllithium 

Downstream Products

• 13183-70-5 1,4-bis-(trimethylsilyl)benzene 
• 453-54-3 2-chloro-5-(trimethylsilyl)benzotrifluoride 
• 115603-78-6 2-(trimethylsilyl)-5-chlorobenzotrifluoride 
• 34557-54-5 methane 
• 41866-81-3 trimethylsiloxide anion 
• 108-90-7 chlorobenzene 
• 18713-58-1 1-(4-chlorophenyl)-2-methylpropan-1-one 
• 2204-98-0 (4-chlorophenyl)(cyclopentyl)methanone 
• 3277-80-3 (4-chlorophenyl)(cyclohexyl)methanone 
• 184910-50-7 p-(trans-4-n-pentyl-4-silacyclohexyl)-bromobenzene 
• 959706-73-1 2-phenyl-2-[4-(trimethylsilyl)phenyl]propanal 
• 959706-62-8 4-(5,5-dimethyl-1,3-dioxan-2-yl)-2-[4-(trimethylsilyl)phenyl]butanal 
• 18764-94-8 diphenyl-bis-(4-trimethylsilanyl-phenyl)-silane 
• 75-77-4 chloro-trimethyl-silane 

Relevant articles and documents

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Reactions of trimethylstannide and trimethylsiliconide anions with aromatic and heteroarornatic substrates

A parallel study was carried out on the reactions of Me3Sn- and Me3Si- ions towards aromatic and heteroaromatic substrates in hexamethylphosphoramide (HMPA) as solvent. It was found that Me3Si- ions are more reactive and therefore less selective than Me3Sn- ions. In HMPA, PhI and PhBr react with Me3Sn- ions through an HME pathway. PhCl also reacts by an HME reaction, but under photostimulation the SRN1 mechanism competes with the HME process, With PhF as sabstrate, Me3Sn- ions afford (4-fluorophenyl)trimethylstannane, presumably through a hypervalent tin species. Under irradiation, the SRN1 mechanism operates concurrently with the formation of the hypervalent tin species. Me3Si- ions, on the other hand, react with PhX (X = Cl, Br, I) to yield the ipso substitution product, presumably through the intermediacy of a hypervalent silicon species. PhF affords, upon reaction with Me3Si- ions, o- and p-fluorotrimethylsilylbenzenes together with the ipso substitution product PhSiMe3. A novel type of nucleophilic substitution mechanism takes place with Me3Si- ions upon reaction with aromatic and heteroaromatic substrates without classical leaving groups in HMPA. Copyright

General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP

A new and general nickel-catalyzed cyanation of hetero(aryl) chlorides using less toxic Zn(CN)2 as the cyanide source has been developed. The reaction relies on the use of inexpensive NiCl2·6H2O/dppf/Zn as the catalytic system and DMAP as the additive, allowing the cyanation to occur under mild reaction conditions (50-80 °C) with wide functional group tolerance. DMAP was found to be crucial for successful transformation, and the reaction likely proceeds via a Ni(0)/Ni(II) catalysis based on mechanistic studies. The method was also successfully extended to aryl bromides and aryl iodides.

Palladium-catalyzed direct CH bond arylation of simple arenes with aryltrimethylsilanes

Direct CH bond arylation of arenes with aryltrimethylsilanes catalyzed by PdCl2 in the presence of CuCl2 as an oxidant has been developed. In addition to the role as the oxidant, CuCl2 is found to be necessary for the selective crosscoupling reaction.