p-Chloroacetophenone
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p-Chloroacetophenone
structure -
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CAS No:
99-91-2
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Formula:
C8H7ClO
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Chemical Name:
p-Chloroacetophenone
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Synonyms:
Ethanone,1-(4-chlorophenyl)-;Acetophenone,4′-chloro-;Acetophenone,p-chloro-;1-(4-Chlorophenyl)ethanone;p-Chloroacetophenone;4′-Chloroacetophenone;Methyl p-chlorophenyl ketone;p-Chlorophenyl methyl ketone;Methyl 4-chlorophenyl ketone;1-Acetyl-4-chlorobenzene;4-Chlorophenyl methyl ketone;4-Acetylchlorobenzene;p-Acetylchlorobenzene;1-(4-Chlorophenyl)-1-ethanone;1-Chloro-4-acetylbenzene;4-Acetyl-1-chlorobenzene;NSC 6115;1-(p-Chlorophenyl)ethanone;4-Acetylphenyl chloride;p-Chlorohypnone;4-Chlorohypnone;4-Chloro-1-acetylbenzene;4-Chlorobenzene methyl ketone
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CAS No:
p-Chloroacetophenone Basic Attributes
154.594
154.59
202-800-7
ZV4A71K303
6115
DTXSID1052668
LIQUID
2914700090
Characteristics
17.07000
2.35
colorless to light yellow liquid
1.1922 g/cm3 @ Temp: 20 °C
20-21 °C
237 °C
107.1±11.0 °C
1.532
111 mg/L (25 ºC)
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Flammables-area.
8 mm Hg ( 90 °C)
Henry's Law constant= 9.3X10-4 atm cu-m/mole @ 25 °C (est)
Safety Information
II
6.1
UN 3416 6.1/PG 2
3
R26;R36/37/38
S26-S28-S36/37/39-S45-S28A
KM5600000
T+,Xn
Stable at room temperature in closed containers under normal storage and handling conditions.
P260-P280-P284-P305 + P351 + P338-P310
H302-H315-H318-H330-H335
The following wastewater treatment technologies have been investigated for acetophenone: concentration process: activated carbon. /Acetophenone/|The following wastewater treatment technologies have been investigated for acetophenone: concentration process: resin adsorption. /Acetophenone/
|Danger|H302 (82.56%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P280, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 173 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Chloroacetophenone; Chloroacetophenone, liquid; Chloroacetophenone, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. 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. /Chloroacetophenone; Chloroacetophenone, liquid; Chloroacetophenone, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Chloroacetophenone; Chloroacetophenone, liquid; Chloroacetophenone, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Chloroacetophenone; Chloroacetophenone, liquid; Chloroacetophenone, solid/|For more DOT Emergency Guidelines (Complete) data for P-CHLOROACETOPHENONE (8 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
HIGHLY IRRITATING TO EYES, MUCOUS MEMBRANES.
p-Chloroacetophenone was qualitatively detected in advanced wastewater treatment effluent samples obtained from Pomona, CA, 1974(1). It was detected in the emissions of a improperly regulated kerosene space heater, but not properly adjusted ones, at a rate of 40 ng/kJ(2).
Toxicity
p-Chloroacetophenone is of anthropogenic origin and it is not known to be produced by natural sources. (SRC)
p-Chloroacetophenone is a commercially important ketone prepared by the Friedel-Crafts chlorination of a acetophenone(1). It may be released to the environment as a fugitive emission during its production and use(SRC).
TERRESTRIAL FATE: If released to soil, an estimated soil adsorption coefficient for p-chloroacetophenone of 436 obtained from an experimental log octanol/water partition coefficient of 2.32(1) and an appropriate regression equation(2), indicates that it will display moderate mobility in soil(3). An estimated Henry's Law constant of 9.3X10-4 atm cu-m/mole at 25 °C(4,SRC) indicates that p-chloroacetophenone will rapidly volatilize from moist soil to the atmosphere(SRC). An estimated vapor pressure of 0.51 mm Hg at 25 °C(1-2,4,SRC) indicates that p-chloroacetophenone will only slowly volatilize from dry soil to the atmosphere(SRC).|AQUATIC FATE: If released to water, p-chloroacetophenone is expected to rapidly volatilize to the atmosphere. Based on an estimated Henry's Law constant of 9.3X10-4 atm cu-m/mole at 25 °C(1,SRC), the estimated half-life for volatilization of p-chloroacetophenone from a model river 1 m deep flowing at 1 m/sec with a wind speed of 3 m/sec is 4.8 hrs(2,SRC). A bioconcentration factor of 34 estimated from an experimental log octanol/water partition coefficient of 2.32(3) using an appropriate regression equation(2) indicates that p-chloroacetophenone will not bioconcentrate in fish and aquatic organisms(SRC). An estimated soil adsorption coefficient of 436(2-3,SRC) indicates that it may weakly adsorb to sediment and suspended organic matter(SRC).|ATMOSPHERIC FATE: If released to the atmosphere, an estimated rate constant for the gas-phase reaction of p-chloroacetophenone with photochemically produced hydroxyl radicals of 1.16X10-12 cu-cm/ molec sec(1,SRC) translates to an atmospheric half-life of 13.8 days using an average atmospheric hydroxyl radical concn of 5X10+5 molec/cu-cm(1,SRC).
An estimated rate constant for the gas-phase reaction of p-chloroacetophenone with photochemically produced hydroxyl radicals of 1.16X10-12 cu-cm/molec sec(1,SRC) translates to an atmospheric half-life of 13.8 days(SRC) using an average atmospheric hydroxyl radical concn of 5X10+5 molec/cu-cm(1).
Based on an experimental log octanol/water partition coefficient of 2.32(1) a bioconcentration factor of 34 can be calculated for p-chloroacetophenone using an appropriate regression equation(2). This value indicates that p-chloroacetophenone will not bioconcentrate in fish and aquatic organisms(SRC).
Based on an experimental log octanol/water partition coefficient of 2.32(1) a soil adsorption coefficient of 436 can be calculated for p-chloroacetophenone using an appropriate regression equation(2,SRC). This value indicates that it will display moderate mobility in soil(3).
An estimated Henry's Law constant of 9.3X10-4 atm cu-m/mole at 25 °C(1,SRC) indicates that p-chloroacetophenone will rapidly volatilize from both moist soil and water to the atmosphere(SRC). The estimated half-life for volatilization from a model river 1 m deep flowing at 1 m/sec with a wind speed of 3 m/sec is 4.8 hrs(2,SRC). An estimated vapor pressure for p-chloroacetophenone of 0.51 mm Hg at 25 °C(2,SRC) obtained in turn from its estimated Henry's Law constant and estimated water solubility, 111 mg/L at 25 °C(SRC), which was obtained from its experimental log octanol/water partition coefficient and an appropriate regression equation(3), indicates that this compound will only slowly volatilize from dry soil to the atmosphere(SRC).
The probable routes of exposure to p-chloroacetophenone are by inhalation and dermal contact during its production, formulation and use(SRC). Members of the general population may be exposed to p-chloroacetophenone during the use of improperly maintained kerosene space heaters(1,SRC).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 28 workers may be exposed to p-chloroacetophenone in the USA(1).
Drug Information
P-CHLOROACETOPHENONE YIELDS IN RABBITS 1-(P-CHLOROPHENYL)ETHANOL. /FROM TABLE/
EXPTL USE: 4'- CHLOROACETOPHENONE TESTED FOR ABILITY TO INHIBIT CYTOPATHOGENIC CHANGES IN CELL CULTURES OF HUMAN EMBRYONIC KIDNEYS INDUCED BY POLIOVIRUS TYPES 1 & 2. 4'-CHLOROACETOPHENONE WAS MOST EFFECTIVE @ REDUCING POLIOVIRUS TYPE 1.|A case of allergic contact sensitivity following a single exposure to the tear gas chloroacetophenone in a 24 year old police officer was presented. The officer accidentally discharged the tear gas from a container he kept in his right trouser pocket, and immediately washed the site of contact with water for 5 minutes. A localized erythema with a burning sensation occurred instantly on the right upper thigh and a blistering reaction developed within 2 days. After 2 weeks of treatment with a topical steroid, the center of the lesion was faint, but the borders had extended and persisted for 4 weeks. Testing with chloroacetophenone and orthochlorbenzylidine malonitrile one month after symptoms disappeared gave positive test results to chloroacetophenone but negative to orothochlorbenzylidine malonitrile. The normal exposure to this compound as a gas has not been reported to cause sensitivity reactions except in 1 in about 10,000 servicemen exposed in gas chamber drills. However, application of this compound in high concentration and in the presence of moisture indicates that it is a powerful skin irritant as evidenced not only by this report but by other earlier reports in literature. /Chloroacetophenone/|/A case of acute contact dermatitis caused by exposure to 2-chloroacetophenone tear gas in the face /is reported/. Within 3 days the contact dermatitis had dissappeared without medical treatment, but 7 days after exposure, a scaly pruritic eruption developed at the site of the original exposure although no new contact with 2-chloroacetophenone had taken place. /2-Chloroacetophenone/|Chloroacetophenone is used as a tear gas for riot control and as a kind of chemical mace against small groups or individuals. Among other side effects, choroacetophenone can evoke toxic and allergic contact dermatitis, and more rarely exanthematous or anaphylactic reactions. It is difficult to distinguish between toxic and allergic reactions both in the clinical picture of dermatitis as well as on the basis of skin test reactions. A /report of a/ patient with allergic contact dermatitis, which first appeared 5 days after exposure to choroacetophenone as a sign of primary sensitization, leading to an intense eczematous reaction in skin tests. Allergy to choroacetophenone does not appear to represent a handicap in normal daily life because it is solely used as tear gas and is of little significance with regards to "cross allergies" to substances in the environment. /Chloroacetophenone/|When the lacrimatory agent chloroacetophenone was released into 44 prisoner cells, 8 prisoners required hospitalization and 20 more received outpatient physician care for injuries. Contact with water contributed to the injuries caused by chloroacetophenone, but prolonged exposure in a confined space was probably the principal cause of morbidity. In a confined space the lacrimatory agent chloroacetophenone is relatively toxic. /Chloroacetophenone/
4-chloroacetophenone
p-Chloroacetophenone Use and Manufacturing
REACTION OF CHLOROBENZENE AND ACETIC ANHYDRIDE CATALYZED BY ALUMINUM CHLORIDE, AND SEPARATION OF ISOMERS.
CHEM INT FOR PHARMACEUTICALS
(1972) PROBABLY GREATER THAN 4.54X10+5 G (EST)|(1975) PROBABLY GREATER THAN 4.54X10+5 G
Ethanone, 1-(4-chlorophenyl)-: ACTIVE
SUBSTITUTED ACETOPHENONES (INCLUDING P-CHLOROACETOPHENONE) WERE DETECTED IN ATMOSPHERE BY GAS CHROMATOGRAPHY; RESPONSES OF THESE COMPOUNDS WERE MEASURED BY FLAME IONIZATION, ELECTRON CAPTURE, AND THERMIONIC DETECTORS.
Computed Properties
Molecular Weight:154.59
XLogP3:2.3
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:154.0185425
Monoisotopic Mass:154.0185425
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Complexity:125
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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