2-Chloracetophenon

Bezeichnung:2-Chloracetophenon

CAS-Nr532-27-4

Englisch Name:2-Chloroacetophenone

CBNumberCB9387386

SummenformelC8H7ClO

Molgewicht154.59

MOL-Datei532-27-4.mol

Synonyma

2-Chloracetophenon

2-Chlor-1-phenylethanon

alpha-Chloracetophenon

2-Chloracetophenon physikalisch-chemischer Eigenschaften

Schmelzpunkt	54-56 °C(lit.)
Siedepunkt	244-245 °C(lit.)
Dichte	1.324 g/mL at 25 °C(lit.)
Dampfdruck	4 at 20 °C, 14 at 30 °C (quoted, Verschueren, 1983)
Brechungsindex	1.5438
Flammpunkt	118°C
Löslichkeit	Soluble in acetone (Weast, 1986). Freely soluble in alcohol, benzene, and ether (Windholz et al., 1983)
Aggregatzustand	Colorless crystals
Wasserlöslichkeit	insoluble. <0.1 g/100 mL at 19 ºC
Sensitive	Moisture Sensitive
Merck	14,2115
BRN	507950
Expositionsgrenzwerte	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).
Stabilität	May decompose upon exposure to air or water. Incompatible with bases, amines, alcohols.
InChIKey	IMACFCSSMIZSPP-UHFFFAOYSA-N
LogP	1.724 (est)
CAS Datenbank	532-27-4(CAS DataBase Reference)
NIST chemische Informationen	Ethanone, 2-chloro-1-phenyl-(532-27-4)
EPA chemische Informationen	2-Chloroacetophenone (532-27-4)

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	25-36/37/38-42/43-23/25-36-23/24/25
S-Sätze:	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-Nr.	AM6300000
F	9-19
TSCA	Yes
HazardClass	6.1
PackingGroup	II
Giftige Stoffe Daten	532-27-4(Hazardous Substances Data)
Toxizität	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

Gefahreninformationscode (GHS)

2-Chloroacetophenone Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
FARBLOSEBIS GRAUE KRISTALLE.
CHEMISCHE GEFAHREN
Zersetzung beim Verbrennen unter Bildung giftiger und ätzender Rauche mit Chlorwasserstoff.
ARBEITSPLATZGRENZWERTE
TLV: 0.05 ppm (als TWA); Krebskategorie A4 (nicht klassifizierbar als krebserzeugend für den Menschen); (ACGIH 2005).
MAK nicht festgelegt (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20 °C tritt langsam eine gesundheitsschädliche Kontamination der Luft ein.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Tränenreizend. Die Substanz reizt stark die Augen. Die Substanz reizt die Haut und die Atemwege. Inhalation von Dampf oder Aerosol kann zu Lungenödem führen (s.Anm.). Die Auswirkungen treten u.U. verzögert ein. ärztliche Beobachtung notwendig.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Hautkontakt kann zu Dermatitis und Hautsensibilisierung führen.
LECKAGE
Verschüttetes Material in abdichtbaren Kunststoffbehältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen. Persönliche Schutzausrüstung: Umgebungsluftunabhängiges Atemschutzgerät.
R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
R23/25:Giftig beim Einatmen und Verschlucken.
R36:Reizt die Augen.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S7/9:Behälter dicht geschlossen an einem gut gelüfteten Ort aufbewahren.
Beschreibung
Chloroacetophenone is contained in tear gases (lacrimators). This substance has an important irritative potential but can also be a sensitizer.
Chemische Eigenschaften
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
Physikalische Eigenschaften
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).
Verwenden
Chemical warfare agent (CN); principal constituent in riot control agent Mace; in tear gas formulations for personal protection devices
Verwenden
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.
Verwenden
Riot control agent.
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
Allgemeine Beschreibung
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)
Brandgefahr
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.
Kontakt-Allergie
w-Chloroacetophenone is contained in tear gases (lacrimators). This substance has important irritative potential, but can also be a sensitizer.
Sicherheitsprofil
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.
mögliche Exposition
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.
Erste Hilfe
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).
Lager
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.
Versand/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.
läuterung methode
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.
Inkompatibilitäten
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 alcoholwater solution. Hydrogen sulfide is liberated and collected by an alkaline scrubber.

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