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HCID 17604作成日：2026年10月27日

2-(2-クロロベンジリデン)プロパンジニトリル

2-(2-クロロベンジリデン)プロパンジニトリル · (2-クロロベンジリデン)マロノニトリル · 2-(2-クロロベンジリデン)マロノニトリル · 2-クロロBMN · 2-[(2-クロロフェニル)メチレン]プロパンジニトリル · CS【催涙物質】 · 2-(2-クロロフェニル)エテン-1,1-ジカルボニトリル · o-クロロベンジリデンマロノニトリル

https://huagongshe.com/ja/chemical/17604

2-(2-クロロベンジリデン)プロパンジニトリル の分子構造式

識別子と物理属性

CAS No.2698-41-1
分子式C10H5ClN2
平均分子量188.61 g/mol
単同位体質量188.01412584 g/mol
SMILESN#CC(C#N)=Cc1ccccc1Cl
InChIKeyJJNZXLAFIPKXIG-UHFFFAOYSA-N
PubChem CID17604
ChEMBLCHEMBL1256101
ChEBICHEBI:188626
EC No.220-278-9
DTXSIDDTXSID9020297
現地名2-(2-クロロベンジリデン)プロパンジニトリル

化学・物理的性質

XLogP2.3
極性表面積47.6
水素結合供与体数0
水素結合受容体数2
回転可能結合数1
重原子数13
形式電荷0
複雑度283
物質分類Toxic Gases & Vapors -> Tear Gas Agents
臭いPepper-like odor.
Color/FormWhite crystalline solid
溶解度1 to 5 mg/mL at 61 °F (NTP, 1992)Sparingly soluble in waterSoluble in acetone, dioxane, methylene chloride, ethyl acetate, benzeneSolubility in water, g/100ml at 20 °C: 0.1-0.5Insolubleアセトン、ベンゼン、1,4-ジオキサン、酢酸エチル、およびジクロロメタンに可溶 (Windholz et al., 1983)16℃で0.1～0.5g/100mL
沸点590 to 599 °F at 760 mmHg (NTP, 1992)310-315 °C590-599 °F313 °C @760 [mm Hg]126 °C0.1 mm Hg(lit.)
DecompositionWhen heated to decomposition it emits very toxic fumes of /hydrogen chloride, nitrogen oxides and cyanides./
融点203 °F (NTP, 1992)95-96 °C93-96 °C203-205 °F95 °C68-70 °C(lit.)
蒸気密度6.52 (NTP, 1992) - Heavier than airwill sink (Relative to Air)Relative vapor density (air = 1): 6.5
蒸気圧3.4e-05 mmHg at 68 °F (NTP, 1992)0.00003 [mmHg]3.4X10-5 mm Hg at 20 °CVapor pressure, Pa at ? °C: 0.00450.00003 mmHg0.00003 [mm Hg] @20 °C3 x 10-5 mmHg at 20 °C (NIOSH, 1997)
Physical DescriptionO-chlorobenzylidene malononitrile appears as a chemical warfare tear gas agent. White crystalline solid or light beige powder. Odor of pepper. (NTP, 1992)White crystalline solid with a pepper-like odor[NIOSH]WHITE CRYSTALLINE POWDER WITH CHARACTERISTIC ODOUR.White crystalline solid with a pepper-like odor.
密度1.2906 (rough estimate)
屈折率1.5500 (estimate)
貯蔵条件2-8°C
外観・状態白色、結晶性固体
色胡椒のようなにおいのある白色の結晶性固体
ヘンリー定数9.9×102 mol/(m3Pa) at 25℃, HSDB (2015)
安定性安定。強力な酸化剤とは相容れない。可燃性。
CAS データベース2698-41-1(CAS DataBase Reference)
NISTの化学物質情報2-Chlorobenzalmalononitrile(2698-41-1)
EPAの化学物質情報o-Chlorobenzylidene malononitrile (2698-41-1)

化学的特性

o-Chlorobenzylidene malonitrile is a combustible, white crystalline solid with a pepper-like odor. It is the defining component of tear gas (CS gas).

安全性と法規制

GHS 分類DangerH301 (98.5%): Toxic if swallowed [Danger Acute toxicity, oral]P233, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P391, P403, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 65 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302: Harmful if swallowed [Warning Acute toxicity, oral]
規制情報Status: Active Update: 09-04-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/26045o-Chlorobenzylidene malononitrile: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
輸送ラベル（DOT）Poison
火災危険For information on chemical warfare tear gas agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.
健康有害性For information on chemical warfare tear gas agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)
有害性の概要This is the active ingredient in the CS type of tear gas. No CS-related deaths have been reported. [NIOSH Guidelines for Chemical Hazards] A potential skin sensitizerSufficient data not available to recommend a SEN notationMedian incapacitating dose is 12-20 mg/m3Incapacitating symptoms within 20 seconds and persist for 5-10 minutes after removal to fresh air[ACGIH] A lachrymator[HSDB] A skin sensitizerSeverely irritating to the eyes, skin, and respiratory tract[ICSC]The major hazards encountered in the use and handling of 2-chlorobenzalmalononitrile stem from its toxicologic properties. Toxic primarily by inhalation and dermal contact, exposure to this pepper-smelling, white crystalline substance may occur from its production or use as an incapacitating agent by military and law enforcement personnel. Effects from exposure may include lacrimation, headache, contact burns to the eyes and skin, bronchospasm, laryngospasm, hypersensitivity reactions, and pulmonary edema. Some effects may be delayed. OSHA has established a Ceiling exposure limit of 0.4 mg/cu m for this substance. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water.

用途

用途

催涙性物質

説明

CS, also known as o-chlorobenzylidene malononitrile, is a riot control agent (RCA) currently used by U.S. military forces. It was synthesized in 1928 and named 'CS' after its creators, Corson and Stoughton. CS replaced chloroacetophenone (CN) in 1959 as the primary RCA due to its higher safety ratio. It is more potent and safer than CN. CS can be disseminated pyrotechnically or in powder formulations like CS1 and CS2.

使用

2-Chlorobenzylidenemalononitrile has found extensive application in exploring the effects of irritants on the human body. It is used as a tear gas and riot control agent.

一般的な説明

White crystalline solid or light beige powder. Odor of pepper.

輸送番号・ガイド（DOT）2810 153
反応性グループNitriles
UN 分類UN Hazard Class: 6.1UN Pack Group: III
Special ReportsJONES G RNCS (2,CHLOROBENZYLIDENE MALONONITRILE) AND ITS CHEMICAL RELATIVESNATURE (LOND) 235 (5336): 257 (1972). THIS REVIEW ARTICLE SURVEYS THE PRINCIPAL ASPECTS OF THE CHEMICAL PROPERTIES OF BENZYLIDENE MALONONITRILES AND THEIR EFFECTS ON THE INTERACTIONS WITH LIVING ORGANISMS (HUMAN AND ANIMAL).Kaplita PV and Smith RPToxicol Appl Pharmacol 84 (3): 533-540 (1986). Pathways for the bioactivation of aliphatic nitriles to free cyanide in mice.DHHS/NTPToxicology & Carcinogenesis Studies of CS (94% o-Chlorobenzalmalononitrile) in F344/N Rats and B6C3F1 Mice (Inhalation Studies)Technical Report Series No. 377 (1990) NIH Publication No. 90-2832
OSHA StandardsPermissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 0.05 ppm (0.4 mg/cu m).Vacated 1989 OSHA PEL Ceiling limit 0.05 ppm (0.4 mg/cu m), skin designation, is still enforced in some states.
Reactivity ProfileO-CHLOROBENZYLIDENE MALONONITRILE may react with strong oxidizers. (NTP, 1992)
Chemical DangersReacts with strong bases and strong acids. This produces ammonia. Decomposes on burning. This produces toxic fumes including hydrogen chloride, hydrogen cyanide and nitrogen oxides. Reacts violently with strong oxidants. This generates fire and explosion hazard.
消火For information on chemical warfare tear gas agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)Use powder, carbon dioxide.
応急処置措置Fresh air, rest.Remove contaminated clothes. Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Give one or two glasses of water to drink. Refer for medical attention .
応急処置For information on chemical warfare tear gas agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)(General first aid procedures)
安全保管Separated from food and feedstuffs. Keep in a well-ventilated room.
暴露管理・個人防護4.0 [ppm]
清掃方法1. VENTILATE AREA OF SPILL. 2. FOR SMALL QUANTITIES, SWEEP ONTO PAPER OR OTHER SUITABLE MATERIAL, PLACE IN APPROPRIATE CONTAINER & BURN IN SAFE PLACE (SUCH AS FUME HOOD). LARGE QUANTITIES MAY BE RECLAIMEDHOWEVER, IF THIS IS NOT PRACTICAL, DISSOLVE IN FLAMMABLE SOLVENT (SUCH AS ALCOHOL) & ATOMIZE IN SUITABLE COMBUSTION CHAMBER EQUIPPED WITH APPROPRIATE EFFLUENT GAS CLEANING DEVICE. 3. DECONTAMINATE AREA OF SPILL: (A) BY WASHING WITH A 5% SOLUTION OF SODIUM HYDROXIDE IN 50/50 ETHYL ALCOHOL/WATEROR (B) BY ADDING FLAKE SODIUM HYDROXIDE TO A SOLUTION OR SLURRY OF THE SPILL IN ISOPROPYL ALCOHOLOR (C) BY COVERING THE SPILL WITH A 10% SOLUTION OF SODIUM HYDROXIDE IN 50/50 ISOPROPYL ALCOHOL/WATER & LETTING STAND 20 MINUTES BEFORE FLUSHING WITH WATER.CHEMICAL DISPOSAL METHOD FOR CS WAS DEVELOPED. THE RECOMMENDED REACTION IS AQ ALKALINE HYDROLYSIS OF CS TO O-CHLOROBENZALDEHYDE.
非火災時の漏出対応For information on chemical warfare tear gas agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)
処分方法SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.1. BY MAKING PACKAGES OF O-CHLOROBENZYLIDENE MALONONITRILE IN PAPER OR OTHER FLAMMABLE MATERIAL & BURNING IN SUITABLE COMBUSTION CHAMBER EQUIPPED WITH AN APPROPRIATE EFFLUENT GAS CLEANING DEVICE. 2. BY DISSOLVING O-CHLOROBENZYLIDENE MALONONITRILE IN FLAMMABLE SOLVENT (SUCH AS ALCOHOL) & ATOMIZING IN SUITABLE COMBUSTION CHAMBER EQUIPPED WITH APPROPRIATE EFFLUENT GAS CLEANING DEVICE. 3. BY MIXING SOLID WITH 5 PARTS OF 10% SOLUTION OF MONOETHANOLAMINE IN WATER CONTAINING 0.3% OF NONIONIC DETERGENT. 4. BY STIRRING 1 LB OF SOLID FOR 2 HOURS IN 1 GALLON OF A 5-15% SOLUTION OF SODIUM HYDROXIDE IN ETHYLENE GLYCOL, ETHYL ALCOHOL, OR METHYL ALCOHOL.
漏出処分Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Vacuum spilled material with specialist equipment.
Preventive MeasuresThe worker should immediately wash the skin when it becomes contaminated.The worker should wash daily at the end of each work shift.Work clothing that becomes wet or significantly contaminated should be removed or replaced.Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.For more Preventive Measures (Complete) data for 2-CHLOROBENZALMALONONITRILE (6 total), please visit the HSDB record page.
Isolation and EvacuationFor initial isolation and protective action distances for chemical warfare tear gas agents see the Chemical Warfare Agents table in the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)
Eye PreventionWear safety goggles or face shield.
相互作用When CS is applied in a solvent, its effect on the cornea is very much influenced by the nature of the solvent, less injury resulting from solutions in trichloroethane or tri(2-ethylhexyl)phosphate than in methylene dichloride, corn oil, or polyethylene glycol 300.The toxic mechanism of nitriles and the effect of metabolic modifiers in mice were studied in relation to their physicochemical properties. All the test nitriles liberated cyanide both in vivo and in vitro, with the exception of benzonitrile, although the extent of liberation and the effect of carbon tetrachloride pretreatment on the mortality of animals differed among nitriles. From these results, test compounds were tentatively divided into 3 groups. In group 1, acute toxicity was greatly reduced by carbon tetrachloride pretreatment, in group 2, toxicity was not significantly changed or was somewhat enhanced, and in group 3, benzonitrile only, toxicity was clearly enhanced. The amount of cyanide was higher at death in the brains of mice given group 1 compounds, the level being comparable to that found in mice killed by dosing with potassium cyanide. The relation between log (1/LD50) and log p for the compounds in group 1 fitted a parabolic plot, while that for compounds in group 2 was linear. For most nitriles, the in vitro metabolism was inhibited when the incubation mixture contained either SKF-525A, carbon monoxide, or microsomes from mice treated with carbon tetrachloride. When mice were dosed with ethyl alcohol, metabolic enhancement of nitriles was seen compared with the control. However, ethyl alcohol, when added to the incubation mixture, inhibited the in vitro metabolism of nitriles. /Nitriles/
標的器官Eyes, skin, respiratory system
健康影響2-Chlorobenzylidene malononitrile can cause severe pulmonary damage and damage of the heart and liver.
生態毒性値LC50 Rainbow trout 1.28 mg/l/12 hr. /Conditions of bioassay not specified/LC50 RAINBOW TROUT > 0.1 MG/L < 1 WK.
環境中動態TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1700(SRC), determined from a structure estimation method(2), indicates that 2-chlorobenzalmalononitrile is expected to have low mobility in soil(SRC). 2-Chlorobenzalmalononitrile was applied to snow surfaces in a Norwegian forestmore than 10% remained after 28 days(5). 2-Chlorobenzalmalononitrile was found in Norwegian snow samples 70 m downwind and for as long as 29 days following the detonation of a grenade containing this compound(5). Dusts or powders of 2-chlorobenzalmalononitrile that have settled to the ground after its use as a riot control agent can remain active for as long as 5 days(6)if the compound was formulated with a silicone water repellent, it may persist for as long as 45 days(6). Volatilization of 2- chlorobenzalmalononitrile from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.0X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The major degradation process for 2-chlorobenzalmalononitrile in moist soil is expected to be hydrolysis(SRC)half-lives of 281.7 min at 0 °C and 14.5 min at 25 °C have been determined(7). Actual environmental degradation rates may be much slower because the rate at which 2-chlorobenzalmalononitrile dissolves in water can be very slow(7). 2-Chlorobenzalmalononitrile is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.4X10-5 mm Hg(4).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1700(SRC), determined from an estimation method(2), indicates that 2-chlorobenzalmalononitrile is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.0X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). 2-Chlorobenzalmalononitrile is expected to hydrolyze in aquatic environments forming 2-chlorobenzaldehyde. Aqueous hydrolysis experiments in seawater have determined hydrolysis half-lives of 281.7 min at 0 °C and 14.5 min at 25 °C(8). However, actual environmental degradation rates may be much slower because the rate at which 2-chlorobenzalmalononitrile dissolves in water can be very slow(8). 2-Chlorobenzalmalononitrile released to water could float and travel for considerable distances before it dissolves(8)once it is dissolved, hydrolysis will proceed rapidly. Bioconcentration is not expected when 2-chlorobenzalmalononitrile is present in the dissolved form as hydrolysis will occur so rapidly(SRC). According to a classification scheme(5), an estimated BCF of 30(SRC), from an estimated log Kow of 2.76(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. Aquatic volatilization and adsorption to sediment are not expected to be environmentally important(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-chlorobenzalmalononitrile, which has a vapor pressure of 3.4X10-5 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2-chlorobenzalmalononitrile is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 110 hrs(SRC), calculated from its rate constant of 3.5X10-12 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3). Particulate-phase 2-chlorobenzalmalononitrile may be removed from the air by wet and dry deposition(SRC). 2-Chlorobenzalmalononitrile when dissolved in water is susceptible to rapid hydrolysishalf-lives range from 281.7-14.5 minutes at 0-25 °C(4). Therefore, dissolution of the compound into clouds or rain will contribute to its atmospheric removal(SRC).
有害作用Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.
暴露経路The substance can be absorbed into the body by inhalation, through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contact
毒性の概要Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)
Signs and SymptomsCough. Dizziness. Headache. Laboured breathing. Nausea. Sore throat. Vomiting.Redness. Burning sensation. Pain. Blisters.Watering of the eyes. Redness. Pain.Burning sensation in the throat and chest.Pain, burn eyes, lacrimation (discharge of tears), conjunctivitiserythema (skin redness) eyelids, blepharospasmirritation throat, cough, chest tightnesserythema (skin redness), vesiculation skinSymptoms include eye irritation, tearing, burning sensation on the nose and throat, rhinorrhoea, excess salivation, constricting sensations in the chest, sneezing, coughing, and stinging or burning sensations in exposed skin.
Ongoing Test StatusThe following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=2698-41-1]
ICSC Environmental DataThe substance is very toxic to aquatic organisms.
Soil Adsorption/MobilityUsing a structure estimation method based on molecular connectivity indices(1), the Koc for 2-chlorobenzalmalononitrile can be estimated to be 1700(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-chlorobenzalmalononitrile is expected to have low mobility in soil.
職業暴露限界（OEL）Ceiling: 0.05 ppm (0.4 mg/m3) [skin]
水環境危害等級（WGK）3
生命健康即時危険濃度2 mg/m3
TSCA 収載状態TSCA listed
RTECS 番号OO3675000
輸送番号（UN）UN 3448 6.1/PG 2
毒性LD50 in rats (mg/kg): 28 i.v., 48 i.p.LC50 in rats: 88,480 mg/min/m3 (Ballantyne, Swanston)
危険文句（R）36/37/38-42/43-25
危険表示Xi,T
安全措置（S）26-27-37/39-45-36/37/39
危険等級6.1(a)
包装等級I
有害物質データ2698-41-1(Hazardous Substances Data)