Phenylacetyl chloride is used as a key precursor in the total synthesis of vialinin B. It is employed as a linker to prepare dendrimers and also used in the synthesis of various conjugated aromatic small molecules.
Phenylacetyl chloride is used in the preparation of 1,2-diphenyl-ethanone by reaction with iodobenzene using tetrabutylammonium tetrafluoroborate as a phase transfer catalyst. It is widely used in the chemical industry for manufacturing dyes and pharmaceutical products. It plays an important role in the preparation of penicillin. Further, it is used to prepare esters for flavorings.
Journal of the American Chemical Society, 96, p. 6469, 1974
DOI: 10.1021/ja00827a034Organic Syntheses, Coll. Vol. 2, p. 156, 1943
A colorless volatile liquid with a strong odor. Denser than water. Contact may severely irritate skin, eyes and mucous membranes. May be toxic by ingestion. May also be combustible.
Soluble in water. Fumes in air. Decomposes in water or steam to form very corrosive hydrogen chloride gas.
Phenylacetyl chloride is incompatible with strong oxidizing agents, alcohols, bases (including amines). May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
First, weigh 0.136 kg (1.0 mol) of phenylacetic acid and place it in a 250 mL four-necked flask equipped with a thermometer, a tail gas pipe, a phosgene receiving tube, and a mechanical stirrer. Then add a catalyst accounting for 1%–2% of the total mass. Place the reaction flask in an oil bath and heat it to 78 °C, the melting point of phenylacetic acid. Start slow stirring after the phenylacetic acid dissolves gradually. Next, connect the phosgene receiving tube to a 500 mL PTFE bottle containing liquid phosgene. Given that phosgene has a boiling point of only 8.2 °C, it can be vaporized spontaneously at room temperature and then introduced into the reaction flask to react with the raw material at a certain temperature. After the introduction of phosgene is completed, maintain the temperature for a period of reaction. During this process, phosgene can be quantified by weighing with an analytical balance to control the ratio of raw materials. The completion of the reaction can be determined by the results of gas chromatography (GC) analysis. Subsequently, carry out vacuum distillation to remove low-boiling-point impurities. After all volatile substances are eliminated, collect the fraction at 85–90 °C under a pressure of -0.096 MPa, and the target product, phenylacetyl chloride, is thus obtained.
