基本情報
- 標準SMILES
CC(=O)c1ccc(Cl)cc1- InChIKey
BUZYGTVTZYSBCU-UHFFFAOYSA-N- 分子式
- C8H7ClO
- 平均分子量
- 154.59 g/mol
- 単同位体質量
- 154.01854252
概要
P-chloroacetophenone is an organic molecular entity.
名称と識別子
- 優先名称
- P-Chloroacetophenone
- IUPAC
- 1-(4-chlorophenyl)ethanone
- 現地名
- 4'-クロロアセトフェノン
- 英語名
- 4'-Chloroacetophenone
- 分子式
- C8H7ClO
- 分子量
- 154.59
名称と別名
名称をさらに表示
データベース識別子
- CAS
99-91-2- PubChem CID
- 7467
- DTXSID
DTXSID1052668- ChEMBL
CHEMBL608419- ChEBI
CHEBI:230611- UNII
- ZV4A71K303
- EC Number
- 202-800-7
- Nikkaji
- J38.176D
物性
構造計算による物性
- XLogP
- 2.3
- 極性表面積
- 17.1 Ų
- 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
実験および物理化学的性質
LogP
log Kow= 2.32 (experimental)
2.35
物理化学的性質
- 融点
- 14 · 14-18 °C (lit.)
- 沸点
- 232 °C · 232 °C (lit.)
- 比重(密度)
- 1.192 g/mL · 1.192 g/mL at 25 °C (lit.)
- 蒸気圧
- 8 mm · 8 mm Hg ( 90 °C)
- 屈折率
- 20 · n20/D 1.554(lit.)
- 闪点
- 194 °F · 194 °F
- 貯蔵温度
- Sealed in dry,Room Temperature
- 溶解性
- 111 mg/l · 111mg/l(遅分解)
- 外見
- 融解後の液体
- 色
- 無色透明~黄色
- 臭い (Odor)
- 100 %で。甘くマイルドなアセトフェノン干し草 · 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
- 水溶解度
- 111 mg/L · 111mg/L(25℃)
- Merck
- 14 · 14,2116
- BRN
- 386014 · 386014
- InChI
- 1S/C8H7ClO/c1-6(10)7-2-4-8(9)5-3-7/h2-5H,1H3
- InChIKey
- BUZYGTVTZYSBCU-UHFFFAOYSA-N
- SMILES
- CC(=O)c1ccc(Cl)cc1
- LogP
- 2.32 at · 2.32 at 20℃
- CAS データベース
- 99 · 99-91-2(CAS DataBase Reference)
- NISTの化学物質情報
- 1 · Ethanone, 1-(4-chlorophenyl)-(99-91-2)
- EPAの化学物質情報
- 4 · 4'-Chloroacetophenone (99-91-2)
化学的性質
化学的特性clear colourless to yellowish liquid after melting
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 0.5% (1 of 216) of reports.
Danger
H302 (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.
Warning
危険有害性情報
Regulatory Information
Chemical: Ethanone, 1-(4-chlorophenyl)-
Status: Active Update: 17-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21493
4'-Chloroacetophenone: Does not have an individual approval but may be used under an appropriate group standard
DOT Emergency Guidelines
/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.
Hazard Classes and Categories
Acute Tox. 4 (86.1%)
Acute toxicity (Oral) - Category 4
Flammable liquids - Category 4
Shipment Methods and Regulations
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.
Shipping Name/ Number DOT/UN/NA/IMO
UN 1697; Chloroacetophenone
IMO 6.1; Chloroacetophenone
安全と保護具
Disposal Methods
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 Measures
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.
毒性情報
Environmental Fate
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).
Effluent Concentrations
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).
Soil Adsorption/Mobility
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).
Human Toxicity Excerpts
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/
Environmental Bioconcentration
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).
Volatilization from Water/Soil
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).
Non-Human Toxicity Excerpts
A 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 Degradation
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).
安全データ
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- KM5600000
- ridadr
- UN 3416 6.1/PG 2
- hs_code
- 29147090
- risk_code
- 22-26-37/38-41-36/37/38-36/37
- 化審法
- (3)-1241
- 消防法
- 危-4-3-III
- hazard_code
- T+,Xn
- safety_code
- 26-28-36/37/39-45-28A-36
- hazard_class
- 6.1
- packing_group
- II
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2STOT SE 3
- ストレージクラス
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- 有毒物質データの
- 99-91-2(Hazardous Substances Data)
化学と産業
薬理情報
用途と製造
Uses
Used as a chemical intermediate for pharmaceuticals; [HSDB]
CHEM INT FOR PHARMACEUTICALS
応用分野
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
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義ChEBI: P-chloroacetophenone is an organic molecular entity.
関連反応
関連ノート
読み込み中…