| Identification | More | [Name]
2-Chloroacetophenone | [CAS]
532-27-4 | [Synonyms]
2-CHLORO-1-PHENYLETHANONE
2-CHLOROACETOPHENONE
A-CHLOROACETOPHENONE
ALPHA-CHLOROACETOPHENONE
a-phenacyl chloride
BETA-CHLOROACETOPHENONE
Chloromethyl phenylketone
OMEGA-CHLOROACETOPHENONE
PHENACYLCHLORID
PHENACYL CHLORIDE
W-CHLOROACETOPHENONE
"teargas"[qr]
1-Chloroacetophenone
1-chloroacetophenone[qr]
2-Chloro-1-oxoethyl)benzene
2-chloro-1-phenyl-ethanon
2-chloro-1-phenylethanone[qr]
2-chloro-acetophenon
Acetophenone, 2-chloro-
acetophenone,2-chloro- | [EINECS(EC#)]
208-531-1 | [Molecular Formula]
C8H7ClO | [MDL Number]
MFCD00000933 | [Molecular Weight]
154.59 | [MOL File]
532-27-4.mol |
| Chemical Properties | Back Directory | [Definition]
A strong lachrymator. | [Appearance]
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 | [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 | [Fp ]
118°C | [solubility ]
Soluble in acetone (Weast, 1986). Freely soluble in alcohol, benzene, and ether (Windholz et al.,
1983) | [form ]
Colorless crystals | [Stability:]
May decompose upon exposure to air or water. Incompatible with bases, amines, alcohols. | [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). | [Contact allergens]
w-Chloroacetophenone is contained in tear gases (lacrimators).
This substance has important irritative
potential, but can also be a sensitizer. | [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]
532-27-4(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
tan crystalline powder | [Uses]
Riot control agent. | [General Description]
Colorless liquid, odorless to fruity. | [Hazard]
Strong irritant to eyes and tissue as gas
or liquid. Skin and upper respiratory tract irritant.
Questionable carcinogen. | [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) | [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. | [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. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
Medical observation is recommended for 24 to 48 hours
after breathing overexposure, as pulmonary edema may be
delayed. As first aid for pulmonary edema, a doctor or
authorized paramedic may consider administering a drug or
other inhalation therapy. | [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. | [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. | [Description]
Chloroacetophenone is contained in tear gases (lacrimators).
This substance has an important irritative
potential but can also be a sensitizer. | [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 alcoholwater
solution. Hydrogen sulfide is liberated and collected by an
alkaline scrubber. | [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). | [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 | [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. | [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. |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R42/43:May cause sensitization by inhalation and skin contact .
R23/25:Toxic by inhalation and if swallowed .
R36:Irritating to the eyes.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S7/9:Keep container tightly closed and in a well-ventilated place . | [RIDADR ]
UN 1693 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
AM6300000
| [F ]
9-19 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [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. | [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 |
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