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.)

Flash point:

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.

InChI

1S/C8H7ClO/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2

InChIKey

VMZCDNSFRSVYKQ-UHFFFAOYSA-N

SMILES

ClC(=O)Cc1ccccc1

LogP

1.628 (est)

CAS DataBase Reference

103-80-0(CAS DataBase Reference)

NIST Chemistry Reference

Benzeneacetyl chloride(103-80-0)

EPA Substance Registry System

Benzeneacetyl 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

F 

21

TSCA 

TSCA listed

HazardClass 

8

PackingGroup 

II

HS Code 

29163900

Storage Class

8A - Combustible corrosive hazardous materials

Hazard Classifications

Eye Dam. 1
Met. Corr. 1
Skin Corr. 1B
STOT SE 3

MSDS

• Language:English Provider:Benzeneacetyl chloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Phenylacetyl chloride Usage And Synthesis

Chemical Properties

colourless liquid

Uses

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.

Uses

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.

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 Description

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.

Air & Water Reactions

Soluble in water. Fumes in air. Decomposes in water or steam to form very corrosive hydrogen chloride gas.

Reactivity Profile

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].

Health Hazard

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.

Fire Hazard

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.

Synthesis

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.

Phenylacetyl chloride(103-80-0)Related Product Information

• Trichloroacetyl chloride
• Ammonium chloride
• Acetyl chloride
• Acetoxyacetyl chloride
• Thionyl chloride
• Bromoacetyl chloride
• Phenoxyacetyl chloride
• 2-Phenylacetamide
• Calcium chloride
• Benzyloxyacetyl chloride
• Sodium chloride
• Choline chloride
• Polyvinyl chloride
• Chloroacetyl chloride
• Phenylhydrazine hydrochloride
• Potassium chloride
• Phenylmalonic acid
• Phenylhydrazine