Phenylacetyl chloride

Phenylacetyl chloride Basic information
Product Name:Phenylacetyl chloride
Synonyms:Acetyl chloride, phenyl-;alpha-Phenylacetyl chloride;alpha-Toluyl chloride;phenylacetyl;-Toluylchloride;AKOS BBS-00003909;A-TOLUYL CHLORIDE;LABOTEST-BB LT00643802
CAS:103-80-0
MF:C8H7ClO
MW:154.59
EINECS:203-146-5
Product Categories:Pharmaceutical Intermediates;Acid Halides;Carbonyl Compounds;Organic Building Blocks
Mol File:103-80-0.mol
Phenylacetyl chloride Structure
Phenylacetyl chloride Chemical Properties
Melting point 264-266 °C(Solv: N,N-dimethylformamide (68-12-2))
Boiling point 94-95 °C/12 mmHg (lit.)
density 1.169 g/mL at 25 °C (lit.)
refractive index n20/D 1.5325(lit.)
Fp 217 °F
storage temp. 2-8°C
solubility Miscible with alcohol and ether.
form clear liquid
color Colorless to Light yellow
Sensitive Moisture Sensitive
BRN 742254
Stability:Stable. Reacts with water. Incompatible with amines, most common metals, moisture, strong oxidizing agents.
LogP1.628 (est)
CAS DataBase Reference103-80-0(CAS DataBase Reference)
NIST Chemistry ReferenceBenzeneacetyl chloride(103-80-0)
EPA Substance Registry SystemBenzeneacetyl chloride (103-80-0)
Safety Information
Hazard Codes C
Risk Statements 34-37-14
Safety Statements 26-36/37/39-45-25-27
RIDADR UN 2577 8/PG 2
WGK Germany 3
21
TSCA Yes
HazardClass 8
PackingGroup II
HS Code 29163900
MSDS Information
ProviderLanguage
Benzeneacetyl chloride English
SigmaAldrich English
ACROS English
ALFA English
Phenylacetyl chloride Usage And Synthesis
Chemical Propertiescolourless liquid
UsesPhenylacetyl 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.
UsesPhenylacetyl 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.
Synthesis Reference(s)Journal of the American Chemical Society, 96, p. 6469, 1974 DOI: 10.1021/ja00827a034
Organic Syntheses, Coll. Vol. 2, p. 156, 1943
General DescriptionA 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.
Air & Water ReactionsSoluble in water. Fumes in air. Decomposes in water or steam to form very corrosive hydrogen chloride gas.
Reactivity ProfilePhenylacetyl 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].
Health HazardTOXIC; 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.
Fire HazardCombustible 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.
Methylene Chloride Phenoxyacetyl chloride 2-Phenylacetamide Bromoacetyl chloride Calcium chloride Sodium chloride Acetyl chloride Choline chloride Chloroacetyl chloride Trichloroacetyl chloride Ammonium chloride Phenylacetyl chloride Polyvinyl chloride Potassium chloride Benzyloxyacetyl chloride Thionyl chloride Acetoxyacetyl chloride 2-​[[(2-​ethylphenyl)​(2-​hydroxyethyl)​amino]​methyl]​-​3,​3-​difluoro-Propanenitrile

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