Benzoyl chloride Chemical Properties

Melting point:

-1 °C

Boiling point:

198 °C(lit.)

Density 

1.211 g/mL at 25 °C(lit.)

vapor density 

4.88 (vs air)

vapor pressure 

1 mm Hg ( 32 °C)

refractive index 

n20/D 1.553(lit.)

Flash point:

156 °F

storage temp. 

Store at 0-5°C

form 

Liquid

color 

Clear

Odor

Pungent characteristic.

PH

2 (1g/l, H2O, 20℃)

PH Range

2 at 1 g/l

explosive limit

2.5-27%(V)

Water Solubility 

reacts

FreezingPoint 

-1℃

Sensitive 

Moisture Sensitive

Merck 

14,1112

BRN 

471389

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents, water, alcohols, strong bases. Reacts violently with DMSO and vigorously with alkalies.

InChIKey

PASDCCFISLVPSO-UHFFFAOYSA-N

CAS DataBase Reference

98-88-4(CAS DataBase Reference)

IARC

2A (Vol. 29, Sup 7, 71) 1999

NIST Chemistry Reference

Benzoyl chloride(98-88-4)

EPA Substance Registry System

Benzoyl chloride (98-88-4)

Safety Information

Hazard Codes 

C

Risk Statements 

34-43-20/21/22

Safety Statements 

26-45-36/37/39

RIDADR 

UN 1736 8/PG 2

WGK Germany 

1

RTECS 

DM6600000

Autoignition Temperature

600 °C

Hazard Note 

Corrosive

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29310095

Hazardous Substances Data

98-88-4(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 2460 mg/kg LD50 dermal Rabbit 790 mg/kg

MSDS

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

Benzoyl chloride Usage And Synthesis

Physical and Chemical Properties

Its pure product is a colorless and transparent flammable liquid, which is smoking exposed to air in the air. In Industry, it is slightly pale yellow, with a strong pungent odor. Its steam has a strong stimulating effect for eye mucous membranes, skin and respiratory tract, by stimulating the mucous membranes and eyes tear. Benzoyl chloride Melting point is-1.0 ℃, boiling point is 197.2 ℃, and the relative density is 1.212 (20 ℃), while a flash point is 72 ℃, and refractive index (n20) is 1.554. It is soluble in the ether, chloroform, benzene and carbon disulfide. It can gradually decomposed in water or ethanol, ammonia, which generates benzoic acid, generating benzamide, ethyl benzoate and hydrogen chloride. In the laboratory, it can be obtained by distillation of benzoic acid and phosphorus pentachloride under anhydrous conditions. Industrial production process can be obtained by the use of thionyl chloride benzaldehyde. Benzoyl chloride is an important intermediate for preparing dyes, perfumes, organic peroxides, resins and drugs. It is also used in photography and artificial tannin production, which was formerly used as an irritant gas in chemical warfare.

Application

• Used for dye intermediates, initiator, UV absorbers, rubber additives, medicine etc.
• Benzoyl chloride is intermediate of herbicide metamitron, and insecticide propargite, benzene hydrazine or intermediate food.
• Benzoyl chloride is used for organic synthesis, dye and pharmaceutical raw material, manufacturing initiator benzoyl peroxide, t-butyl peroxybenzoate, pesticides and herbicides. In pesticides, it is a new insecticide, which is inducible isoxazole parathion (Isoxathion, Karphos) intermediate. Benzoyl chloride is an important benzoyl and benzyl reagent. Most of benzoyl chloride is used in the production of benzoyl peroxide, and secondly for the production of benzophenone, benzyl benzoate, benzyl cellulose. Benzoyl peroxide catalyzes polymerization initiator for the monomer plastic, polyester, epoxy, acrylic resin production, self-curing agent, which is a glass fiber material, fluorine rubber, silicone crosslinking agents, oil refined, bleached flour, fiber decolorizing Wait. Domestic original benzoyl chloride manufacturing enterprises are more than 20. Some of the manufacturers also produce acid chloride, and the production capacity is 10,000t. However, according to the 2003 survey, the profit is too low, because of the use of small polluting production line, while the use of polluting route is controlled by the government restrictions, and a further raw material price increases. Therefore most of the manufacturers stop the production. Further reaction with the acid chloride can also produce acid anhydride,  and benzoic acid anhydride is the main purpose for acylation agents, which can also be used as a bleaching agent and flux of a component, as well as it can also be used for the preparation of benzoyl peroxide over.
• Reagents for the analysis, but also for spices, organic synthesis.

Chemical Properties

Transparent, colorless liquid; pungent odor; vapor causes tears. Soluble in ether and carbon disulfide; decomposes in water. Combustible.

Chemical Properties

Benzoyl chloride is a colorless to slight brown liquid with a strong, penetrating odor.

Uses

Benzoyl Chloride is used in the manufacturing of dye intermediates.

Uses

For acylation, i.e., introduction of the benzoyl group into alcohols, phenols, and amines (Schotten-Baumann reaction); in the manufacture of benzoyl peroxide and of dye intermediates. In organic analysis for making benzoyl derivatives for identification purposes.

Definition

A liquid acyl chloride used as a benzoylating agent.

Production Methods

Benzoyl chloride can be prepared from benzoic acid by reaction with PCl5 or SOCl2, from benzaldehyde by treatment with POCl3 or SO2 Cl2, from benzotrichloride by partial hydrolysis in the presence of H2SO4 or FeCl3, from benzal chloride by treatment with oxygen in a radical source, and from several other miscellaneous reactions. Benzoyl chloride can be reduced to benzaldehyde, oxidized to benzoyl peroxide, chlorinated to chlorobenzoyl chloride and sulfonated to m-sulfobenzoic acid. It will undergo various reactions with organic reagents. For example, it will add across an unsaturated (alkene or alkyne) bond in the presence of a catalyst to give the phenylchloroketone:图

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 702, 1951 DOI: 10.1021/ja01146a061
Synthesis, p. 306, 1983 DOI: 10.1055/s-1983-30314

General Description

A colorless fuming liquid with a pungent odor. Flash point 162°F. Lachrymator, irritating to skin and eyes. Corrosive to metals and tissue. Density 10.2 lb / gal. Used in medicine and in the manufacture of other chemicals.

Reactivity Profile

Benzoyl chloride reacts violently with protic solvents such as alcohols, with amines and amides (for example dimethylformamide [Bretherick 1979 p. 6] ) and with inorganic bases. Causes the violent decomposition of dimethyl sulfoxide [Chem. Eng. News 35(9): 87 1957]. 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]. Friedel-Crafts acylation of naphthalene using Benzoyl chloride, catalyzed by AlCl3, must be conducted above the melting point of the mixture, or the reaction may be violent [Clar, E. et al., Tetrahedron, 1974, 30, 3296].

Hazard

Highly toxic. Strong irritant to skin, eyes, and mucous membranes, and via ingestion, inhala- tion. Upper respiratory tract irritant. Probable car- cinogen.

Health Hazard

INHALATION: may irritate eyes, nose and throat. INGESTION: causes acute discomfort. SKIN: causes irritation and burning.

Chemical Reactivity

Reactivity with Water Slow reaction with water to produce hydrochloric acid fumes. The reaction is more rapid with steam; Reactivity with Common Materials: Slow corrosion of metals but no immediate danger; Stability During Transport: Not pertinent; Neutralizing Agents for Acids and Caustics: Soda ash and water, lime; Polymerization: Does not occur; Inhibitor of Polymerization: Not pertinent.

Safety Profile

Confirmed carcinogen withexperimental tumorigenic data by skin contact. Humansystemic effects by inhalation: unspecified effects onolfaction and respiratory systems. Corrosive effects on theskin, eyes, and mucous membranes by inhalation.Flammable whe

Potential Exposure

Benzoyl chloride is used as a chemical intermediate; in organic synthesis; to produce other chemicals, dyes, perfumes, herbicides, and medicines.

Shipping

UN 1736 Benzoylchloride, Hazard class: 8; Labels: 8—Corrosive material.

Purification Methods

A solution of benzoyl chloride (300mL) in *C6H6 (200mL) is washed with two 100mL portions of cold 5% NaHCO3 solution, separated, dried with CaCl2 and distilled [Oakwood & Weisgerber Org Synth III 113 1955]. Repeated fractional distillation at 4mm Hg through a glass helices-packed column (avoiding porous porcelain or silicon-carbide boiling chips, and hydrocarbon or silicon greases on the ground joints) gave benzoyl chloride that did not darken on addition of AlCl3. Further purification is achieved by adding 3 mole% each of AlCl3 and toluene, standing overnight, and distilling off the benzoyl chloride at 1-2mm [Brown & Jenzen J Am Chem Soc 80 2291 1958]. Refluxing for 2hours with an equal weight of thionyl chloride before distillation has also been used. [Beilstein 9 IV 721.] Strong IRRITANT. Use in a fume cupboard.

Incompatibilities

May form explosive mixture with air. Contact with heat, hot surfaces, and flames causes decomposition, forming phosgene and hydrogen chloride. Water contact may be violent; forms hydrochloric acid. Reactions with amines, alcohols, alkali metals, dimethyl sulfoxide, strong oxidizers, and metal salts may be violent, causing fire and explosions. Attacks metals in the presence of moisture, forming explosive hydrogen gas. Attacks some plastics, rubber or coatings.

Waste Disposal

Pour into sodium bicarbonate solution and flush to sewer.

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