2-Chlorobenzylidenemalononitrile

188.61

188.61

220-278-9

D8317IAV7Q

1065

637336|542

2810|3276

DTXSID9020297

White crystalline solid

2926909090

47.6

2.35

O-chlorobenzylidene malononitrile appears as white crystalline solid or light beige powder. Odor of pepper. (NTP, 1992)

1.3±0.1 g/cm3

95-96 °C

310-315 °C

148.0±18.0 °C

1.624

H2O: 0.1-0.5 g/100 mL at 16 ºC

Vapour pressure, Pa at ?°C: 0.0045

6.52

Oral-rat LD50: 178 mg/kg; Oral-Mouse LD50: 282 mg/kg

Flammable; thermal decomposition emits toxic nitrogen oxides, chloride fumes

Pepper-like odor.

The finely powdered nitrile is a significant dust explosion hazard. Slightly soluble in water.

Nitriles

O-CHLOROBENZYLIDENE MALONONITRILE may react with strong oxidizers. (NTP, 1992)

Combustible Solid

I

6.1(a)

UN 3448 6.1/PG 2

3

36/37/38-42/43-25

26-27-37/39-45-36/37/39

OO3675000

Xi,T

The warehouse is ventilated and dry at low temperature; stored separately from food raw materials and oxidants; dedicated management

Stable. Incompatible with strong oxidizing agents. Combustible.

P260, P261, P264, P270, P271, P273, P280, P284, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P314, P320, P321, P330, P363, P391, P403+P233, P405, P501

H302

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.

Strong oxidizers.|The finely powdered nitrile is a significant dust explosion hazard.

JONES G RN; CS (2,CHLOROBENZYLIDENE MALONONITRILE) AND ITS CHEMICAL RELATIVES; NATURE (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 RP; Toxicol Appl Pharmacol 84 (3): 533-540 (1986). Pathways for the bioactivation of aliphatic nitriles to free cyanide in mice.|DHHS/NTP; Toxicology & 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

Flash point data for this chemical are not available, but it is probably combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

|Danger|H301 (98.39%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P284, P285, P301+P310, P302+P352, P304+P340, P304+P341, P305+P351+P338, P310, P312, P320, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 62 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P280, P284, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P314, P320, P321, P330, P363, P403+P233, P405, and P501|P260, P261, P264, P270, P271, P272, P280, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P307+P311, P310, P320, P321, P330, P332+P313, P333+P313, P337+P313, P363, P403+P233, P405, and P501|P260, P261, P264, P270, P272, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P310, P314, P321, P330, P333+P313, P363, P391, P405, and P501

Fires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)|Use powder, carbon dioxide.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: 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. SPILL: If this material is being used as a weapon, see ERG Table 1 - Initial Isolation and Protective Action Distances on the UN/NA 2810 datasheet. Otherwise increase, in the downwind direction, as necessary, the isolation distance shown above. 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. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures, and keep it away from oxidizing materials. (NTP, 1992)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. The worker should wash daily at the end of each work shift. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. (NIOSH, 2016)|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.|(See protection codes)

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.

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.|For more Preventive Measures (Complete) data for 2-CHLOROBENZALMALONONITRILE (6 total), please visit the HSDB record page.

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.|/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.|For more DOT Emergency Guidelines (Complete) data for 2-CHLOROBENZALMALONONITRILE (9 total), please visit the HSDB record page.

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.

Permissible 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.

Recommended Exposure Limit: Ceiling value: 0.05 ppm (0.4 mg/cu m), skin

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Vacuum spilled material with specialist equipment.

Separated from food and feedstuffs. Keep in a well-ventilated room.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.

Lachrymation. The substance is severely irritating to the eyes, skin and respiratory tract. The substance may cause effects on the lungs.

Repeated or prolonged contact with skin may cause dermatitis. Repeated or prolonged contact may cause skin sensitization.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

PREVENT DISPERSION OF DUST!

Use local exhaust.

Protective gloves. Protective clothing.

Wear safety goggles or face shield.

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.

highly toxic

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/

LD50 Rat iv 28 mg/kg|LD50 Rat ip 48 mg/kg|LD50 Rat (male) oral 1366 mg/kg|LD50 Rat (female) oral 1284 mg/kg

Toxicology and carcinogenesis studies were conducted by exposing 50 F344/N rats and 50 B6C3F1 mice of each sex to ... (94% o-chlorobenzalmalononitrile) /by inhalation/. ... Exposure concentrations for the 2 yr studies were 0, 0.075, 0.25, or 0.75 mg/cu m for 6 hr/day, 5 days/wk for 105 wk for groups of 50 rats of each sex. Groups of 50 mice of each sex were exposed to 0, 0.75, or 1.5 mg/cu m on the same schedule. ... Under the conclusions of these inhalation studies, there was no evidence of carcinogenic activity ... for male or female F344/N rats exposed to 0.075, 0.25, or 0.75 mg/cu m for 2 yr. There was no evidence of carcinogenic activity for male or female B6C3F1 mice exposed to 0.75 or 1.5 mg/cu m in air for up to 2 yr.|Toxicology and carcinogenesis studies were conducted by exposing groups of F344/N rats and B6C3F1 mice of each sex for 6 hours per day, 5 days per week for 2 weeks, 13 weeks, or 2 years, to a CS2 (94% o-chlorobenzalmalonitrile [CS]; 5% Cab-O-Sil colloidal silica; 1% hexamethyldissilizane), aerosol. ... No compound-related clinical signs were observed. No significant differences in survival were seen for any group of rats or mice of either sex. ... Compound-related nonneoplastic lesions occurred in the nasal passage of exposed rats and mice. In exposed rats, hyperplasia and squamous metaplasia of the respiratory epithelium and degeneration of the olfactory epithelium with ciliated columnar and/or squamous metaplasia were observed. Focal chronic inflammation and proliferation of the periosteum of the turbinate bones were increased slightly in rats at the top exposure concentration. Suppurative inflammation with hyperplasia and squamous metaplasia of the respiratory epithelium occurred in exposed mice. The were no compound-related increased incidences of neoplasms in rats or mice. ... In exposed female mice, there were pronounced decreases in the incidences of adenomas of the pituitary pars distalis (control, 13/47; 0.75 mg/cu m, 5/46; 1.5 mg/cu m, 1/46) and decreased incidences of malignant lymphomas (21/50; 12/50; 8/50).

2-Chlorobenzalmalononitrile's production and use as a riot control agent(1) may result in its release to the environment through various waste streams(SRC).

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 °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 hydrolysis; half-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).

The rate constant for the vapor-phase reaction of 2-chlorobenzalmalononitrile with photochemically-produced hydroxyl radicals has been estimated as 3.5X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 110 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The first-order hydrolysis rate constants of 2-chlorobenzalmalononitrile in seawater at 0, 15, and 25 °C were experimentally determined to be 4.10X-5, 2.30X10-4, and 7.97X10-4 per sec, respectively(2); these rate constants correspond to respective half-lives of 281.7, 50.2, and 14.5 minutes(SRC). However, the degradation rate in water may be much longer than the hydrolysis rates would suggest(2); 2-chlorobenzalmalononitrile is produced as fine particles whose size and surface coatings greatly affect the rate at which it dissolves in water(2). 2-Chlorobenzalmalononitrile released to water could float and travel for considerable distances before it dissolves(2). Once it is dissolved, hydrolysis will proceed rapidly(2). o-Chlorobenzaldehyde was detected as a hydrolysis product(2).

An estimated BCF of 30 was calculated for 2-chlorobenzalmalononitrile(SRC), using an estimated log Kow of 2.76(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Using 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.

The Henry's Law constant for 2-chlorobenzalmalononitrile is estimated as 1.0X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-chlorobenzalmalononitrile is expected to be essentially nonvolatile from water surfaces(2). 2-Chlorobenzalmalononitrile's Henry's Law constant(1) indicates that volatilization from moist soil surfaces will not occur(SRC). 2-Chlorobenzalmalononitrile is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.4X10-5 mm Hg(3).

Occupational exposure to 2-chlorobenzalmalononitrile may occur through dermal contact with this compound at workplaces where 2-chlorobenzalmalononitrile is produced or used. Exposure to the general population may occur through eye and dermal contact due to its use as a riot control agent. (SRC)

Chemical substances which are employed during a riot in order to control or disperse the rioting parties. (See all compounds classified as Riot Control Agents, Chemical.)

... Rats exposed to CS aerosols at concn of 14-245 mg/cu m for 5 min absorbed measurable quantities of the compound. Both CS and a reduction product, 2-chlorobenzyl malononitrile, were detected in the blood.

... METABOLITE IN BLOOD OF CATS & RATS, TO WHICH CS, O-CHLOROBENZYLIDENE MALONONITRILE, HAD BEEN ADMINISTERED, HAS ... BEEN /IDENTIFIED/ ... AS O-CHLOROBENZYLMALONONITRILE. REDUCTION OF THE BENZYLIDENE DOUBLE BOND, WHICH OCCURS IN THE ERYTHROCYTE CYTOPLASM, IS ASSOCIATED WITH THE DETOXIFICATION OF CS.|IN RABBITS ADMINISTERED IV DOSES 2 REACTIONS TAKE PLACE HYDROLYSIS & REDUCTION. O-CHLOROBENZALDEHYDE & MALONONITRILE ARE PRODUCTS OF HYDROLYSIS & O-CHLOROBENZYL MALONONITRILE IS PRODUCT OF REDUCTION. BIOTRANSFORMATION TAKES PLACE MAINLY IN THE BLOOD, BUT LIVER, IN CONTRAST TO KIDNEYS, IS ALSO IMPORTANT IN THE TRANSFORMATION. O-CHLOROBENZYLIDENE MALONONITRILE & ITS BASIC METABOLITES, O-CHLOROBENZALDEHYDE & O-CHLOROBENZYL MALONONITRILE HAVE SHORT HALF-LIVES IN THE BLOOD.|MICE RECEIVED O-CHLOROBENZYLIDENE MALONONITRILE BY IP INJECTION (0.5 LD50) OR BY AEROSOL EXPOSURE (20000 MG/MIN/CU M). INCREASED EXCRETION OF THIOCYANATE IN THE URINE WAS OBSERVED, INDICATING A TRANSFORMATION OF CS TO CYANIDE IN VIVO.|The fate of (3)H-ring labeled, (14(C-cyanide labeled, and (14C=C) side chain-labeled CS was studied in Porton rats given intraperitoneal or gavage doses ranging from 0.08 to 159 umol/kg. In most cases, the largest proportion (44%-100%) of the dose was eliminated in the urine. The major urinary metabolites identified were 2-chlorohippuric acid, 1-O-(2-chlorobenzyl)glucuronic acid, 2-chlorobenzyl cysteine, and 2-chlorobenzoic acid. Minor metabolites identified included 2-chlorobenzyl alcohol and 2-chlorophenyl-2-cyanopropionate.|... Six male volunteers /were exposed/ to CS at concn of 0.5-1.5 mg/cu m for 90 min. Neither CS nor 2-chlorobenzaldehyde was detected in the blood of those persons, and only in one was a trace of 2-chlorobenzyl malononitrile detected.

2-CHLOROBENZYLIDENEMALONONITRILE HAS 2 DISTINCT ... /MECHANISMS/ OF TOXICITY IN MICE; ONE, OF SHORT TERM DURATION, WHICH IS THE MORE TOXIC OF THE TWO, INVOLVES LIBERATION OF CYANIDE WITHIN THE BODY, AND IS REVERSED BY SODIUM THIOSULFATE; THE OTHER IS OF LONG-TERM DURATION, THE MECHANISM OF WHICH HAS NOT BEEN DETERMINED.|The high toxicity of CS when given by the intraperitoneal or intravenous routes was due to its rapid metabolism, which leads to high levels of cyanide and thiocyanate in the urine.|Many of the changes seen in the lungs with CS smoke are similar in quality to those produced by other irritant smokes. The lethality of CS is probably dependent on two main factors: its alkylating properties and its cyanogenic potential. On the first point, CS reacts with glutathione, and also lipoic acid and cysteine, and ... the alkylating properties of the molecule are major determinants of the toxicity of CS after intravenous administration. There is also evidence that cyanide contributes to the toxicity of CS.

Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Symptoms: Pain, burn eyes, lacrimation (discharge of tears), conjunctivitis; erythema (skin redness) eyelids, blepharospasm; irritation throat, cough, chest tightness; headache; erythema (skin redness), skin vesiculation Target Organs: Eyes, skin, respiratory system (NIOSH, 2016)

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 calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. 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. (NTP, 1992)|(See procedures)

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.

Rapid support of respiration and circulation is essential to successful treatment of cyanide intoxication. Massive cyanide overdoses have survived with only good supportive care. Immediate attention should be directed toward assisted ventilation, administration of 100% oxygen, insertion of intravenous lines, and institution of cardiac monitoring. Obtain an arterial blood gas immediately and correct any severe metabolic acidosis (pH below 7.15). Oxygen (100%) should be used routinely in moderate or severely symptomatic patients even in the presence of a normal pO2, since 100% O2 increases O2 delivery, may reactivate cyanide-inhibited mitochondrial enzymes, and potentiates the effect of thiosulfate. Avoid mouth to mouth resuscitation during CPR in order to prevent self poisoning. /Cyanides/|Amyl nitrite perles are designed to produce 3% to 5% methemoglobinemia while an iv line is established for iv sodium nitrite. As a temporizing measure, the patient inhales the vapors until the sodium nitrite is ready. Because of the variability in methemoglobin production and the potential for cardiovascular collapse, this step may be omitted if sodium nitrite is readily available and the patient is not in extremes. Adequate ventilation and oxygenation are more important than administration of amyl nitrite. One perle (0.2 ml) is crushed and inhaled for 30 seconds every minute until iv nitrite is given. Sodium nitrite (3% solution), as 10 ml of a 3% solution (eg, 300 mg), is administered iv slowly over 4 minutes to produce a 20% methemoglobin level in adults. Children should receive 0.33 ml of the 3% solution per kilogram initially at an infusion rate of 2.5 ml/min, up to a maximum of 10 ml. Administer sodium nitrite doses to children on the basis of body weight, since fatal methemoglobinemia has occurred in children. /Cyanides/

... HUMAN VOLUNTEERS /WERE EXPOSED/ TO CS AEROSOLS DISPERSED FROM A 10% SOLUTION IN METHYLENE CHLORIDE, OR FROM PURE MOLTEN COMPOUND. ... 3 OF 4 MEN EXPOSED FOR 90 MINUTES AT 1.5 MG/CU M CS DEVELOPED HEADACHES, & 1 ... DEVELOPED SLIGHT EYE & NOSE IRRITATION. TWO ... EXPERIENCED HEADACHE FOR 24 HR FOLLOWING EXPOSURE. ... INCREASING TEMPERATURE & RELATIVE HUMIDITY AS WELL AS HYPERVENTILATION CAUSED DECREASE IN TOLERANCE TIME TO CS EFFECTS. MAJOR EXPOSURE SYMPTOMS WERE EYE IRRITATION, CONJUNCTIVITIS, LACRIMATION & SKIN BURNING.|TWENTY FIVE OF 28 WORKERS IN A CHEMICAL PLANT MANUFACTURING ORTHO-CHLOROBENZYLIDENE MALONONITRILE GAVE A HISTORY OF DERMATITIS INVOLVING THE ARMS AND NECK. TWO OF 25 WORKERS SHOWED POSITIVE PATCH TEST REACTIONS WHEN TESTED TO A 1:1000 DILUTION OF ORTHO-CHLOROBENZYLIDENE MALONONITRILE IN OLIVE OIL.|PULMONARY EDEMA COMPLICATED BY PNEUMONIA, HEART FAILURE & HEPATOCELLULAR DAMAGE WERE OBSERVED IN A 43 YR OLD MALE EXPOSED TO CS TEAR GAS.|A 4 MO OLD MALE INFANT DEVELOPED PNEUMONITIS FOLLOWING A PROLONGED EXPOSURE TO TEAR GAS. THE PAIENT HAD A PERSISTENT LEUKOCYTOSIS (WHITE BLOOD CELL COUNT 20000 TO 30000/CU MM) WITH A PREDOMINANCE OF LYMPHOCYTES ON PERIPHERAL BLOOD SMEAR.|For more Human Toxicity Excerpts (Complete) data for 2-CHLOROBENZALMALONONITRILE (8 total), please visit the HSDB record page.

2 Chlorobenzylidene Malonitrile

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

Pain, burn eyes, lacrimation (discharge of tears), conjunctivitis; erythema (skin redness) eyelids, blepharospasm; irritation throat, cough, chest tightness; headache; erythema (skin redness), vesiculation skin

Cough. Dizziness. Headache. Laboured breathing. Nausea. Sore throat. Vomiting.

Redness. Burning sensation. Pain. Blisters.

Watering of the eyes. Redness. Pain.

Eyes, skin, respiratory system

Available both unground and ground with 5% silica aerogel or treated Cab-O-Sil.

Propanedinitrile, 2-[(2-chlorophenyl)methylene]-: ACTIVE

CAN BE EXTRACTED FROM CHEMICAL PROTECTION SPRAYS WITH METHANOL. ANALYSIS IS BY GC/MS.|REVERSED-PHASE HPLC IS DESCRIBED. A CONCENTRATION OF 1-10 NG CAN BE DETECTED AT 313 NM.|NIOSH Method: 304. Analyte: o-Chlorobenzylidene malononitrile. Matrix: Air. Procedure: HPLC. Method Evaluation: Method was validated over the range of 0.1472 to 0.819 mg/cu m using a 90 liter sample. Method detection limit: 0.3 ug/sample. Precision (CVt): 0.102. Interferences: No specific interferences.

CONCENTRATIONS OF 2-CHLOROBENZALMALONONITRILE & ITS METABOLITES WERE DETERMINED IN BLOOD BY GC.