227936-62-1

Basic information

• Product Name: (3-CHLOROPHENYLETHYNYL)TRIMETHYLSILAN&
• Synonyms: (3-CHLOROPHENYLETHYNYL)TRIMETHYLSILAN&;(2-(3-chlorophenyl)ethynyl)trimethylsilane;1-Chloro-3-[2-(trimethylsilyl)ethynyl]benzene
• CAS NO: 227936-62-1
• Molecular Formula: C₁₁H₁₃ClSi
• Molecular Weight: 208.75942
• Product Categories: Alkynyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 227936-62-1.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 240-241 °C(lit.)
• Flash Point: 225 °F
• Appearance: /
• Density: 0.995 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0614mmHg at 25°C
• Refractive Index: n20/D 1.537(lit.)
• CAS DataBase Reference: (3-CHLOROPHENYLETHYNYL)TRIMETHYLSILAN&(CAS DataBase Reference)
• NIST Chemistry Reference: (3-CHLOROPHENYLETHYNYL)TRIMETHYLSILAN&(227936-62-1)
• EPA Substance Registry System: (3-CHLOROPHENYLETHYNYL)TRIMETHYLSILAN&(227936-62-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 227936-62-1(Hazardous Substances Data)

Usage

General Description

(3-Chlorophenylethynyl)trimethylsilane is a chemical compound with the formula C11H13ClSi. It is a colorless liquid with a pungent odor, and is used as a reagent in the synthesis of various organic compounds. (3-Chlorophenylethynyl)trimethylsilane reacts readily with nucleophiles, and has been used in the synthesis of pharmaceuticals and agrochemicals. It is also used as a crosslinking agent in the preparation of silicone resins and polymers. Additionally, this compound has been studied for potential applications in materials science and as a building block in the development of new chemical structures.

InChI:InChI=1/C11H13ClSi/c1-13(2,3)8-7-10-5-4-6-11(12)9-10/h4-6,9H,1-3H3

Upstream product

• 625-99-0 3-iodochlorobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 108-37-2 1-bromo-3-chlorobenzene 
• 75-77-4 chloro-trimethyl-silane 
• 766-83-6 m-chlorophenylacetylene 

Downstream Products

• 808773-38-8 4-(3-chloro-phenylethynyl)-2-methyl-1H-imidazole 
• 766-84-7 3-chloro-benzonitrile 
• 1459714-42-1 5-(3-chlorophenyl)-3-methylenepent-4-yn-1-ol 
• 80221-18-7 1,4-bis(3-chlorophenyl)buta-1,3-diyne 
• 1354640-26-8 2,5-bis(3-chlorophenyl)thiophene 
• 1279694-62-0 4,6-di(3-chlorophenyl)-[1,2]-oxathiine 2,2-dioxide 
• 1279694-90-4 4,6-di(3-chlorophenyl)-3-(phenylethynyl)-1,2-oxathiine 2,2-dioxide 

Relevant articles and documents

Synthesis, Characterization of Spirocyclic λ3-Iodanes and Their Application to Prepare 4,1-Benzoxazepine-2,5-diones and 1,3-Diynes

Herein, a [3+2] cycloaddition of aza-oxyallylic cations with ethynylbenziodoxolones for synthesis of new λ3-iodanes containing spirocyclic 4-oxazolidinone has been developed. This cyclic λ3-iodanes display stability in air and excellent solubility in organic solvent. Using them as substrate, both the 4,1-benzoxazepine-2,5-diones and symmetrical 1,3-diynes derivatives were afforded in high yield under copper(I)-catalyzed conditions.

Sustainable Ligand-Free Heterogeneous Palladium-Catalyzed Sonogashira Cross-Coupling Reaction in Deep Eutectic Solvents

The commercially available and cheap Pd/C was found to promote Sonogashira couplings in the environmentally friendly choline chloride/glycerol eutectic mixture in the absence of external ligands. Under heterogeneous conditions, (hetero)aryl iodides were successfully coupled with both aromatic and aliphatic alkynes in yields ranging from 50 to 99 % within 3 h at 60 °C. The aforementioned catalytic system proved to be effective also towards electron-rich iodides, which are notoriously known to be poorly reactive in Pd-catalyzed Sonogashira coupling reactions. The eutectic mixture and the catalyst could easily and successfully be recycled up to four times with an E-factor as low as 24.4.

Iridium-Catalyzed Asymmetric Transfer Hydrogenation of Alkynyl Ketones Using Sodium Formate and Ethanol as Hydrogen Sources

A green and efficient iridium-catalyzed asymmetric transfer hydrogenation of alkynyl ketones to chiral propargylic alcohols has been developed. By using sodium formate and ethanol as hydrogen sources, a series of alkynyl ketones were hydrogenated by chira