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化工社化工社 化学情報印刷レポート · 研究参考用
HCID 7467作成日：2026年10月27日

4'-クロロアセトフェノン

4'-クロロアセトフェノン · 1-(4-クロロフェニル)アセトアルデヒド · メチル(4-クロロフェニル)ケトン · 1-クロロ-4-アセチルベンゼン · (4-クロロフェニル)(メチル)ケトン · p-クロロアセトフェノン · メチル(p-クロロフェニル)ケトン · 1-(4-クロロフェニル)エタノン

https://huagongshe.com/ja/chemical/7467

4'-クロロアセトフェノン の分子構造式

識別子と物理属性

CAS No.99-91-2
分子式C8H7ClO
平均分子量154.59 g/mol
単同位体質量154.01854252 g/mol
SMILESCC(=O)c1ccc(Cl)cc1
InChIKeyBUZYGTVTZYSBCU-UHFFFAOYSA-N
PubChem CID7467
ChEMBLCHEMBL608419
ChEBICHEBI:230611
EC No.202-800-7
DTXSIDDTXSID1052668
現地名4'-クロロアセトフェノン

化学・物理的性質

XLogP2.3
極性表面積17.1
水素結合供与体数0
水素結合受容体数1
回転可能結合数1
重原子数10
形式電荷0
複雑度125
物質分類Other Classes -> Aromatic Ketones, Halogenated
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP（分配係数）log Kow= 2.32 (experimental)2.35
密度1.1922 @ 20 °C/4 °C1.192 g/mL at 25 °C (lit.)
Color/FormLIQUID
溶解度PRACTICALLY INSOL IN WATERMISCIBLE WITH ALC, ETHER111mg/l（遅分解）111mg/L（25℃）
沸点237 °C232 °C (lit.)
融点20-21 °C14-18 °C (lit.)
蒸気圧0.12 [mmHg]8 mm Hg ( 90 °C)
屈折率INDEX OF REFRACTION: 1.5550 @ 20 °C/Dn20/D 1.554(lit.)
Physical DescriptionLiquid[Merck Index] Colorless liquid[MSDSonline]
引火点194 °F
貯蔵条件Sealed in dry,Room Temperature
外観・状態融解後の液体
色無色透明～黄色
臭い100.00%で。甘くマイルドなアセトフェノン干し草
においのタイプ花柄
Merck14,2116
BRN386014
InChI1S/C8H7ClO/c1-6(10)7-2-4-8(9)5-3-7/h2-5H,1H3
InChIKeyBUZYGTVTZYSBCU-UHFFFAOYSA-N
SMILESCC(=O)c1ccc(Cl)cc1
LogP（分配係数）2.32 at 20℃
CAS データベース99-91-2(CAS DataBase Reference)
NISTの化学物質情報Ethanone, 1-(4-chlorophenyl)-(99-91-2)
EPAの化学物質情報4'-Chloroacetophenone (99-91-2)

化学的特性

clear colourless to yellowish liquid after melting

安全性と法規制

GHS 分類This chemical does not meet GHS hazard criteria for 0.5% (1 of 216) of reports.DangerH302 (86.1%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P261, P264, P264+P265, P270, P271, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P320, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 216 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
規制情報Chemical: Ethanone, 1-(4-chlorophenyl)-Status: Active Update: 17-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/214934'-Chloroacetophenone: Does not have an individual approval but may be used under an appropriate group standard
有害性の概要Highly irritating to eyes[Merck Index] May cause allergic contact dermatitis[HSDB] An irritantEffects in high-dose animal studies include lacrimation and acute pulmonary edema[MSDSonline] See alpha-Chloroacetophenone.
DOT Emergency Guidelines/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXICinhalation, 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. /ChloroacetophenoneChloroacetophenone, liquidChloroacetophenone, 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/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

用途

用途

医薬品の中間体

用途

有機合成原料。

使用

Chloroacetophenone is used as a tear gas for riot control and as a kind of chemical mace against small groups or individuals

/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
For more DOT Emergency Guidelines (Complete) data for P-CHLOROACETOPHENONE (8 total), please visit the HSDB record page.
Hazard Classes and CategoriesAcute Tox. 4 (86.1%)Acute toxicity (Oral) - Category 4Flammable liquids - Category 4
Shipment Methods and RegulationsNo 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.
Shipping Name/ Number DOT/UN/NA/IMOUN 1697ChloroacetophenoneIMO 6.1
Skin, Eye, and Respiratory IrritationsHIGHLY IRRITATING TO EYES, MUCOUS MEMBRANES.
処分方法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/
Preventive MeasuresSRP: 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.
環境中動態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).
有害作用Skin Sensitizer - An agent that can induce an allergic reaction in the skin.
Effluent Concentrationsp-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).
Soil Adsorption/MobilityBased 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).
Natural Pollution Sourcesp-Chloroacetophenone is of anthropogenic origin and it is not known to be produced by natural sources. (SRC)
Human Toxicity ExcerptsEXPTL 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/
Artificial Pollution Sourcesp-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).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental BioconcentrationBased 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).
Volatilization from Water/SoilAn 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).
Non-Human Toxicity ExcerptsA DIRECT CORRELATION WAS OBSERVED BETWEEN HYPNOTIC STRENGTH & LIPOPHILICITY OF P-CHLOROACETOPHENONE IN RANA TEMPORARIA TADPOLES.The biochemical changes in blood samples of rats at different intervals after o-chloroacetophenone and dibenz(b,f)-1,4-oxazepine were studied. After a single subacute (1/10 LC50) exposure, both the compounds induced hyperglycemia which was abolished within 24 hr. The level of plasma urea was unaltered. o-Chloroacetophenone exposed animals did not show any significant changes in plasma SGOT, acid and alkaline phosphatase activities at different intervals. However, in dibenz(b,f)-1,4-oxazepine exposed animals, a significant elevation of the activities of SGOT, GPT, acid and alkaline phosphatase was observed at different intervals. All the parameters became normal within seven days after the exposure. Inhalation of dibenz(b,f)-1,4-oxazepine aerosols can thus lead to tissue damaging effects in rats. /o-Chloroacetophenone/Three ketones ie p-chloroacetophenone, p-bromo-acetophenone and 2-bromo-4-nitroacetophenone were evaluated by the olfacto-gustatory method to determine their repellent properties at nine concentrations ranging from 0.0625 to 5.0 g/l. The basis of this method was total and differential feeding by bees at 30% sugar water and chemical sugar solutions. This method provided an indication to the extent and manner of response of the olfacto-gustatory system to the repellent chemicals. The lower concentrations exercised less repellency while higher concentrations worked in the opposite direction. However, the increase in repellency was limited to a certain concentration, then the increase almost stabilized. Out of all the compounds, p-bromoacetophenone showed higher repellency.Effects of 2-chloroacetophenone on the morphology of the mouse exorbital lacrimal gland were studied using light and electron microscopic techniques. Exposure to 2-chloroacetophenone vapor causes rapid exocytosis of acinar cell granules as well as vacuolation of the secretory and ductal epithelial cells. Concomitantly, intralobular ductal epithelial cells which are normally cuboidal in shape, enlarge in size and release electron dense granules into the duct lumen. Within 15 min after exposure, acinar cells show a preponderance of cells containing only pale granules and the ductal epithelium returns to a more cuboidal shape. By 60 min after exposure, the gland is not readily distinguishable from the unexposed, control gland. /2-Chloroacetophenone/Solutions of various concentrations of chloroacetophenone (dissolved in 1,1,1-trichloroethane) were trickled on the corneas of rabbits. The substance was either applied to the center or to the limbus, or simultaneously to the center and limbus of the cornea. After surgical removal of the cornea on day 21, the alterations were examined by a light microscope. When chloracetophenone was applied to the middle of the cornea, signs of intensified epithelial regeneration were observed, even to the point of a severe granulating and necrotic infection with ulceration. The severity of these changes depended on the concentration used and showed that repair of a corneal defect had been attempted. The same changes were observed when the same concentrations of chloracetophenone were applied to the limbus, but with greater severity. Some of these alterations led to perforation of the cornea when the substance was applied to center and limbus. These results are discussed in reference to the correlation of the changes seen in animal tests to those in the human eye. /Chloroacetophenone/
Environmental Abiotic DegradationAn 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).
水環境危害等級（WGK）3
TSCA 収載状態TSCA listed
RTECS 番号KM5600000
輸送番号（UN）UN 3416 6.1/PG 2
税関コード29147090
危険文句（R）22-26-37/38-41-36/37/38-36/37
化審法(3)-1241
消防法危-4-3-III
危険表示T+,Xn
安全措置（S）26-28-36/37/39-45-28A-36
危険等級6.1Acute Tox. 4 OralEye Irrit. 2STOT SE 3
包装等級II
貯蔵分類6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
有害物質データ99-91-2(Hazardous Substances Data)