Identification and Related Records
- 【CAS Registry number】
- 【Molecular Formula】
- C10H5ClN2 (Products with the same molecular formula)
Chemical and Physical Properties
- 【Storage temp】
- Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
- 【Computed Properties】
- Molecular Weight:188.6131 [g/mol]
Rotatable Bond Count:1
Topological Polar Surface Area:47.6
Heavy Atom Count:13
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Ring Count:1
Effective Rotor Count:1
Conformer Sampling RMSD:0.4
CID Conformer Count:4
Safety and Handling
Poison by ingestion, intraperitoneal, and intravenous routes. Moderately toxic by inhalation. Human systemic effects by inhalation: conjunctiva irritation, cough, and unspecified respiratory system effects. A human skin and eye irritant. Human exposure data suggest relatively low systemic toxicity, but intense irritation of eyes, skin, and mucous membranes. Mutation data reported. A tear gas used for riot control. When heated to decomposition it emits very toxic fumes of Cl−, NOx, and CN−.
Hazard Codes: Xi,T
Risk Statements: 36/37/38-42/43-25
R36/37/38:Irritating to eyes, respiratory system and skin.
R42/43:May cause sensitization by inhalation and skin contact.
R25 :Toxic if swallowed.
Safety Statements: 26-27-37/39-45-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S27:Take off immediately all contaminated clothing.
S37/39:Wear suitable gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 3448 6.1/PG 2
WGK Germany: 3
- 【Skin, Eye, and Respiratory Irritations】
- A human skin, eye irritant.
Human volunteers experienced greater ocular and respiratory irritation from 0.9 u than from 60 u particles. However, with the larger particles the ocular irritation predominated and required a longer recovery time than with the smaller particles.
- 【Cleanup Methods】
- 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 RECLAIMED; HOWEVER, 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/WATER; OR (B) BY ADDING FLAKE SODIUM HYDROXIDE TO A SOLUTION OR SLURRY OF THE SPILL IN ISOPROPYL ALCOHOL; OR (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.
- Available both unground and ground with 5% silica aerogel or treated Cab-O-Sil.
- 【DOT Emergency Guidelines】
- If ... THERE IS NO FIRE, go directly to the Table of Initial Isolation and Protective Action Distances /(see table below)/ ... to obtain initial isolation and protective action distances. IF THERE IS A FIRE, or IF A FIRE IS INVOLVED, go directly to the appropriate guide /(see guide(s) below)/ and use the evacuation information shown under PUBLIC SAFETY. Table of Initial Isolation and Protective Action Distances for CS (when used as a weapon)
Small Spills (from a small package or small leak from a large package) -------------------- First ISOLATE in all Directions 60 meters (200 feet) Then PROTECT persons Downwind during DAY: 0.4 kilometers (0.2 miles) Then PROTECT persons Downwind during NIGHT: 1.2 kilometers (0.7 miles) ==================== Large Spills (from a large package or from many small packages) -------------------- First ISOLATE in all Directions 240 meters (800 feet) Then PROTECT persons Downwind during DAY: 2.6 kilometers (1.6 miles) Then PROTECT persons Downwind during NIGHT: 5.7 kilometers (3.5 miles)
/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.
/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.
/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.
/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.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Evacuation: ... Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire: Small fires: Dry chemical, CO2 or water spray. Large fires: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.
- 【Reactivities and Incompatibilities】
- Strong oxidizers.
The finely powdered nitrile is a significant dust explosion hazard.
- 【Other Preventative Measures】
- The 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.
All nitriles should be handled under carefully controlled conditions and only by personnel having a thorough understanding and knowledge of safe handling techniques. Because of the nature of nitrile cmpd and the lack of complete toxicity data on many nitriles, care should be exercised in handling these cmpd to avoid inhalation of the vapors, ingestion, and contact with the skin. /Nitriles/
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.
- 【Protective Equipment and Clothing】
- Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Any supplied-air respirator with a full facepiece. Recommendations for respirator selection. Max concn for use: 2 mg/cu m: Respirator Classes: Any supplied-air respirator operated in a continuous flow mode. Eye protection needed. Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted canister providing protection against the compound of concern and having a high-efficiency particulate filter. Any self-contained breathing apparatus with a full facepiece.
Recommendations for respirator selection. Condition: Emergency or planned entry into unknown concn or IDLH conditions: Respirator Classes: Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive pressure mode. Any supplied-air respirator with a full face piece and operated in pressure-demand or other positive pressure mode in combination with an auxiliary self-contained breathing apparatus operated in pressure-demand or other positive pressure mode.
Recommendations for respirator selection. Condition: Escape from suddenly occurring respiratory hazards: Respirator Classes: Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted canister providing protection against the compound of concern and having a high-efficiency particulate filter. Any appropriate escape-type, self-contained breathing apparatus.
O-Chlorobenzylidene malononitrile , with a CAS name of 2698-41-1, it has some synonyms like 2-[(2-chlorophenyl)methylene]malononitrile or ((2-Chlorophenyl)methylene)propanedinitrile.
O-Chlorobenzylidene malononitrile (CAS NO.2698-41-1) is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should immediately flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water.Then, get medical aid. Or in the eyes: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously get medical aid. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. Immediately While, it's inhaled: Immediately leave the contaminated area; take deep breaths of fresh air.Then, get medical aid. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used. Then you have the ingesting of the product : If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical. Get medical aid immediately. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. Do not induce vomiting. Transport the victim immediately to a hospital.
O-Chlorobenzylidene malononitrile (CAS NO.2698-41-1) was reported in EPA TSCA Inventory. Cyanide and its compounds are on the Community Right-To-Know List.
- 【Disposal Methods】
- 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.
Use and Manufacturing
- 【Use and Manufacturing】
- Methods of Manufacturing
o-Chlorobenzaldehyde + malononitrile (carbonyl condesation)
Prepn: B.B. Corson, R.W. Stoughton, J Am Chem Soc 50: 2825 (1928)
- It is used primarily as an incapacitating agent, both by military & law enforcement personnel. It can be disseminated in burning grenades & weapon-fired projectiles, as an aerosol from the finely divided solid chemical, or from a solution of the chemical dissolved in methylene chloride or acetone.
- 【Sampling Procedures】
- NIOSH Method 304. Analyte: 2-Chlorobenzylidene malononitrile. Matrix: Air. Procedure: Filter/sorbent collection, extraction with 20% methylene chloride in hexane. Flow rate: 1.5 l/min. Sample size: 90 liters.
NIOSH Method: 304. Analyte: o-Chlorobenzylidene malononitrile. Matrix: Air. Procedure: Filter/sorbent collection, extraction with 20% methylene chloride in hexane. Flow Rate: 1.5 l/min. Sample Size: 90 liters.
Biomedical Effects and Toxicity
- 【Pharmacological Action】
- - Chemical substances which are employed during a riot in order to control or disperse the rioting parties.
Environmental Fate and Exposure Potential
- 【Environmental Fate/Exposure Summary】
- 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 forest; more 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 deg C and 14.5 min at 25 deg 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 deg C and 14.5 min at 25 deg 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 deg 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 deg 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 hydrolysis; half-lives range from 281.7-14.5 minutes at 0-25 deg C(4). Therefore, dissolution of the compound into clouds or rain will contribute to its atmospheric removal(SRC).