2-Chloroacetophenone Chemical Properties

Melting point:

54-56 °C(lit.)

Boiling point:

244-245 °C(lit.)

Density 

1.324 g/mL at 25 °C(lit.)

vapor pressure 

4 at 20 °C, 14 at 30 °C (quoted, Verschueren, 1983)

refractive index 

1.5438

Flash point:

118°C

solubility 

Soluble in acetone (Weast, 1986). Freely soluble in alcohol, benzene, and ether (Windholz et al., 1983)

form 

Colorless crystals

Water Solubility 

insoluble. <0.1 g/100 mL at 19 ºC

Sensitive 

Moisture Sensitive

Merck 

14,2115

BRN 

507950

Exposure limits

NIOSH REL: TWA 0.3 mg/m³ (0.05 ppm), IDLH 15 mg/m³; OSHA PEL: TWA 0.05 ppm (0.3 mg/m³); ACGIH TLV: TWA 0.05 ppm (adopted).

Stability:

May decompose upon exposure to air or water. Incompatible with bases, amines, alcohols.

InChIKey

IMACFCSSMIZSPP-UHFFFAOYSA-N

LogP

1.724 (est)

CAS DataBase Reference

532-27-4(CAS DataBase Reference)

NIST Chemistry Reference

Ethanone, 2-chloro-1-phenyl-(532-27-4)

EPA Substance Registry System

2-Chloroacetophenone (532-27-4)

Safety Information

Hazard Codes 

T

Risk Statements 

25-36/37/38-42/43-23/25-36-23/24/25

Safety Statements 

22-26-36/37/39-45-28A-7/9

RIDADR 

UN 1693 6.1/PG 2

OEB

C

OEL

TWA: 0.3 mg/m3 (0.05 ppm)

WGK Germany 

3

RTECS 

AM6300000

F 

9-19

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

Hazardous Substances Data

532-27-4(Hazardous Substances Data)

Toxicity

LD50 in rats (mg/kg): 41 i.v., 36 i.p., 127 orally; LC50 in rats: 8750 mg/min/m3 (Ballantyne, Swanston)

IDLA

15 mg/m3

MSDS

• Language:English Provider:2-Chloroacetophenone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloroacetophenone Usage And Synthesis

Description

Chloroacetophenone is contained in tear gases (lacrimators). This substance has an important irritative potential but can also be a sensitizer.

Chemical Properties

2-Chloroacetophenone (CN) is a combustible, colorless-to-gray solid. CN has a sharp, irritating odor, has been described as smelling like “apple blossoms.” It may be dissolved in a solvent

Physical properties

Colorless to gray crystalline solid with a sharp, penetrating, irritating odor. The low odor and high odor threshold concentrations were 102 and 150 μg/m³, respectively (Ruth, 1986).

Uses

2-Chloroacetophenone is used as a nonlethal or less-than-lethal chemical in riot control situations to distract, deter, incapacitate, disorient, or disable disorderly people; to clear facilities or areas; to deny areas; or for hostage rescue. It can also be used in peacekeeping operations. It is also used in military training as a confidence builder for the protective mask.

Uses

Riot control agent.

Uses

Chemical warfare agent (CN); principal constituent in riot control agent Mace; in tear gas formulations for personal protection devices

Definition

A strong lachrymator.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 2032, 1984 DOI: 10.1021/jo00185a046
Tetrahedron, 51, p. 703, 1995 DOI: 10.1016/0040-4020(94)00989-8
Tetrahedron Letters, 13, p. 4661, 1972

General Description

2-chloroacetophenone appears as a white crystalline solid. Denser than water and insoluble in water. Hence sinks in water. A lachrymator: vapors are very irritating to the eyes. Has a floral odor. Used as a riot control agent.

Hazard

The main uses for 2-chloroacetophenone are in tear gas and in chemical Mace. It is a potent eye, throat, and skin irritant. Acute (short-term) inhalation exposure of humans causes burning of the eyes with lacrimation, some degree of blurred vision, possible corneal damage, irritation and burning of the nose, throat, and skin, and burning in the chest with dyspnea. Acute dermal exposure is irritating and can result in first, second, and third degree chemical burns in humans. Squamous hyperplasia of the nasal respiratory epithelium was reported in rats chronically exposed (long-term) via inhalation. EPA has not classified 2-chloroacetophenone with respect to potential carcinogenicity.

Health Hazard

Median lethal dose (mg-min/m3): 11000 (estimated). Median incapacitating dose: 80. Eye/skin toxicity: Temporarily severe eye irritation; mild skin irritation. Rate of action: Instantaneous. Physiological action: Powerfully lacrimatory. Detoxification rate: Rapid. (ANSER)

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Contact allergens

w-Chloroacetophenone is contained in tear gases (lacrimators). This substance has important irritative potential, but can also be a sensitizer.

Safety Profile

A human poison by inhalation. An experimental poison by ingestion, inhalation, intraperitoneal, and intravenous routes. Human systemic effects by inhalation: lachrymation, conjunctiva irritation, and unspecified eye effects, cough, and dyspnea. A severe eye and moderate skin irritant. Questionable carcinogen with experimental neoplastigenic data by skin contact. A riot control agent. When heated to decomposition it emits toxic fumes of Cl-. See also KETONES.

Potential Exposure

Chloroacetophenone is used as a chemical warfare agent (Agent CN) and as a principal ingredient in the riot control agent Mace. It is also used as a pharmaceutical intermediate. The United States considers agent CN and its mixtures with various chemicals to be obsolete for military deployment.

First aid

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin,remove contaminated clothing and wash immediately withsoap and water. Seek medical attention immediately. If thischemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart actionhas stopped. Transfer promptly to a medical facility. Whenthis chemical has been swallowed, get medical attention.Give large quantities of water and induce vomiting. Do notmake an unconscious person vomit. Medical observation isrecommended for 24-48 h after breathing overexposure, aspulmonary edema may be delayed. As first aid for pulmonaryedema, a doctor or authorized paramedic may consideradministering a corticosteroid spray.

Environmental Fate

Chemical/Physical. Releases toxic chloride fumes when heated to decomposition (Sax and Lewis, 1987).

storage

Color Code—Blue: Health Hazard: Store in asecure poison location. Prior to working with this chemicalyou should be trained on its proper handling and storage.Store in tightly closed containers in a refrigerator or cool,well-ventilated area away from oxidizers, heat, water, andsteam. Metal containers involving the transfer of this chemical should be grounded and bonded. Drums must beequipped with self-closing valves, pressure vacuum bungs,and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers ofthis chemical. Sources of ignition, such as smoking andopen flames, are prohibited where this chemical is used,handled, or stored in a manner that could create a potentialfire or explosion hazard.

Shipping

UN1697 Chloroacetophenone, solid, (CN), Hazard Class: 6.1; Labels: 6.1-Poison Inhalation. UN3416 Chloroacetophenone, liquid, (CN), Hazard Class: 6.1;Labels: 6.1-Poisonous materials. Hazard. Military driver shall be given full and complete information regarding shipment and conditions in case of emergency. AR 50-6 deals specifically with the shipment of chemical agents. Shipments of agent will be escorted in accordance with AR 740-32.

Purification Methods

Crystallise it from MeOH [Tanner J Org Chem 52 2142 1987]. [Beilstein 7 IV 641.]

Toxicity evaluation

CN has a half-life under aerobic conditions of 672 h and can be biodegraded in most moist, nutrient-rich soil.
Biodegradation in water is similar to degradation in soil. Howard et al. (1991) reports the same 672 h half-life for CN in aerobic surface water. This half-life is extended up to 2688 h for anaerobic aqueous degradation.
Volatile losses of CN from surface waters can be another significant process for CN disappearance in water. For instance, Olajos and Stopford (2004) calculated that CN contamination in a river would have a half-life of approximately 14 days, while CN contamination in a lake would have a half-life of approximately 110 days.

Incompatibilities

Keep away from water, steam, strong oxidizers. CN reacts with water, forming hydrochloric acid. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. CN reacts slowly with metals, causing mild corrosion and may evolve flammable hydrogen gas.

Waste Disposal

Tear gas-containing waste is dissolved in an organic solvent and sprayed into an incinerator equipped with an afterburner and alkaline scrubber utilizing reaction with sodium sulfide in an alcohol
water solution. Hydrogen sulfide is liberated and collected by an alkaline scrubber.

2-Chloroacetophenone(532-27-4)Related Product Information

• Sulfuryl chloride
• Calcium chloride
• Phenoxyacetyl chloride
• 3-Nitroacetophenone
• N-Acetylsulfanilyl chloride
• Potassium chloride
• Diethylstilbestrol
• Choline chloride
• Sodium chloride
• 4-Nitroacetophenone
• 4'-Hydroxyacetophenone
• Trichloroacetyl chloride
• 2-Bromoacetophenone
• 4'-Bromoacetophenone
• Phenylacetyl chloride
• Acetyl chloride
• 2',4'-Dichloroacetophenone
• Ferric chloride