Chloroacetonitrile
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Chloroacetonitrile
structure -
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CAS No:
107-14-2
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Formula:
C2H2ClN
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Chemical Name:
Chloroacetonitrile
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Synonyms:
Acetonitrile,2-chloro-;Acetonitrile,chloro-;2-Chloroacetonitrile;Chloroacetonitrile;Chloromethyl cyanide;α-Chloroacetonitrile;Monochloroacetonitrile;Chloracetonitrile;NSC 6180;Cyanomethyl chloride;1867-10-3
- Categories:
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CAS No:
Description
It is colorless, transparent fuming liquid with a pungent choking smell. It is soluble in alcohol and ether. colourless liquid A clear, colorless liquid. Pungent odor.A colorless liquid with a pungent odor. Flash point 118°F. Insoluble in water and denser than water. Hence, sinks in water. Very toxic by ingestion, inhalation and skin absorption. A lachrymator. Used to make other chemicals and as a fumigant.Chloroacetonitrile, also known as ''cyanide chloromethane'' has its chemical formu
Chloroacetonitrile appears as a colorless liquid with a pungent odor. Flash point 118°F. Insoluble in water and denser than water. Hence, sinks in water. Very toxic by ingestion, inhalation and skin absorption. A lachrymator. Used to make other chemicals and as a fumigant.|COLOURLESS LIQUID WITH PUNGENT ODOUR.
Chloroacetonitrile appears as a colorless liquid with a pungent odor. Flash point 118°F. Insoluble in water and denser than water. Hence, sinks in water. Very toxic by ingestion, inhalation and skin absorption. A lachrymator. Used to make other chemicals and as a fumigant.|Chloroacetonitrile is a nitrile.
Chloroacetonitrile Basic Attributes
75.495
75.50
203-467-0
CN524K9DXD
0844
6180
2668
DTXSID7021524
Colorless liquid
29269095
Characteristics
23.8
0.23
Chloroacetonitrile appears as a colorless liquid with a pungent odor. Flash point 118°F. Insoluble in water and denser than water. Hence, sinks in water. Very toxic by ingestion, inhalation and skin absorption. A lachrymator. Used to make other chemicals and as a fumigant.
1.1930 g/cm3
<25 °C
126.5 °C
47°C
n 20/D 1.422(lit.)
H2O: INsoluble
Store in a cool, dry well-ventilated location. Separate from acids, alkalies, oxidizing materials, and reducing agents. Outside or detached storage preferred.
Vapour pressure, kPa at 20°C: 1.16
Relative vapour density (air = 1): 2.61
Oral-rat LD50: 220 mg/kg; Oral-Mouse LD50: 139 mg/kg.
Combustible upon fire with thermal decomposition into toxic nitrogen compounds, chloride and cyanide gas.
vol% in air: 1.0
Pungent odor
Henry's Law constant = 1.08X10-5 atm-cu m/mol at 25 °C (est)
The substance decomposes on heating producing toxic and flammable vapors including hydrogen cyanide . Reacts with strong oxidants, reducing agents, acids, bases, steam, producing highly toxic and flammable fumes.|Hydroxyl radical reaction rate constant = 6.74X10-14 cu cm/molecule-sec at 25 °C (est)
Flammable. Insoluble in water and denser than water. Hence, sinks in water. Reacts with water and steam to produce toxic vapors of hydrogen chloride.
Halogenated Organic Compounds
Highly Flammable
CHLOROACETONITRILE reacts with water, steam, strong acids or acid fumes to produce toxic vapors of hydrogen chloride. When heated to decomposition, it emits highly toxic fumes of hydrogen cyanide and hydrogen chloride [Sax, 2nd ed., 1963, p. 600].
Safety Information
II
6.1
UN2668 Chloroaceto nitrile Hazard class: 6.1, Labels: 6.1-Poison Inhalation Hazard, 3-Flammable liquid Inhalation Hazard Zone B.UN 2668 6.1/PG 2
3
R23/24/25;R51/53
45-61
AL8225000
T,N
Treasury: ventilated and low-temperature and dry; store it separately from oxidants, acids and food additives.
Stable, but reacts with water. Combustible. Incompatible with water, moisture, strong oxidizing agents, acids.
Missing Phrase - N15.00950417-P210-P280-P302 + P352 + P312-P304 + P340 + P312-P370 + P378
H226-H301 + H311 + H331-H411
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste numbers D003 and P030 must conform with USEPA regulations in storage, transportation, treatment and disposal of waste. /Cyanides (soluble cyanide salts), not otherwise specified/|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|A poor candidate for incineration. /Cyanides/
Incompatible with strong oxidizers such as acids, acid salts, chlorates and nitrates. /Cyanides/
Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016)|Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 47 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|H226 (69.28%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P337+P313, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 166 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P262, P264, P270, P273, P280, P301+P310, P302+P350, P303+P361+P353, P305+P351+P338, P310, P321, P322, P330, P337+P313, P361, P363, P370+P378, P391, P403+P235, P405, and P501
Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. SPILL: See ERG Table 1 - Initial Isolation and Protective Action Distances on the UN/NA 2668 datasheet. 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)
Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. SMALL SPILL: Absorb with earth, sand or other non-combustible material and transfer to containers for later disposal. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)
Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: 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. (ERG, 2016)|Wear special protective clothing and positive pressure self-contained breathing apparatus. Butyl rubber, polyvinyl alcohol, or Viton barrier recommended.|Personnel protection: Wear positive pressure self-contained breathing apparatus.|Wear appropriate equipment to prevent: Any possibility of skin contact. /Cyanides/|Wear eye protection to prevent: Any possibility of eye contact. /Cyanides/|For more Personal Protective Equipment (PPE) (Complete) data for CHLOROACETONITRILE (8 total), please visit the HSDB record page.
Flammable liquid.
Combustible liquid.|Explosive limits , vol% in air: 1.0-?
Use water spray, dry chemical, foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products.|If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Extinguish fire using agent suitable for type surrounding fire(Material itself using agent does not burn or burns with difficulty). Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.
Releases may require isolation or evacuation. Eliminate all ignition sources. Stop or control the leak, if this can be done with undue risk. Use water sprat or foam to cool and disperse vapors and protect personnel. Approach from upwind. Control runoff and isolate discharged material for proper disposal.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.|Evacuation: If material leaking (not on fire) consider evacuation from downwind area based on amount of material spilled, location and weather conditions.|Personnel protection: Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. Do not handle broken packages unless wearing appropriate personal protective equipment.|For more Preventive Measures (Complete) data for CHLOROACETONITRILE (9 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 131: FLAMMABLE LIQUIDS - TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.|/GUIDE 131: FLAMMABLE LIQUIDS - TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.|/GUIDE 131: FLAMMABLE LIQUIDS - TOXIC/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.|For more DOT Emergency Guidelines (Complete) data for CHLOROACETONITRILE (9 total), please visit the HSDB record page.
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.
Irritating to skin, eyes, and respiratory system.
Evacuate danger area! Consult an expert! Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.
Fireproof. Separated from strong oxidants, strong bases, strong acids and food and feedstuffs. Well closed. Cool. Ventilation along the floor.
A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the cellular respiration. This may result in cyanosis. The effects may be delayed. Medical observation is indicated.
NO open flames, NO sparks and NO smoking. Above 47 °C use a closed system and ventilation.
STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!
Use ventilation, local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear face shield or eye protection in combination with breathing protection.
D003; A waste containing hexachlorobutadiene may (or may not) be characterized a hazardous waste following testing for the reactivity characteristics as prescribed by the Resource Conservation and Recovery Act (RCRA) regulations.|P030; An acute hazardous waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate. /Cyanides (soluble cyanide salts), not otherwise specified/
P030; As stipulated in 40 CFR 261.33, when chloroacetonitrile, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)). /Cyanides (soluble cyanide salts), not otherwise specified/
Chloroacetonitrile has been qualitatively detected in a wastewater effluent collected from the electronics industry (source and sampling date not reported)(1); and in the effluents from water treatment facilities that use chlorination(2).
Toxicity
Highly tox
LD50 Rat oral 220 mg/kg|LD50 Mouse oral 139 mg/kg|LD50 Mouse intraperitoneal 100 mg/kg
Chloroacetonitrile's production and use as a chemical intermediate in the synthesis of the cardiovascular drug guanethidine and the insecticide fenoxycarb(1) may result in its release to the environment through various waste streams(SRC). Chloroacetonitrile has been detected in the wastewater effluent from the electronics industry(2) and in the effluents from water treatment facilities that use chlorination(3). Chloroacetonitrile is reported to be a disinfectant by-product of drinking water chlorination(4,5).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9(SRC), determined from a structure estimation method(2), indicates that chloroacetonitrile is expected to have very high mobility in soil(SRC). Volatilization of chloroacetonitrile from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.08X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Chloroacetonitrile is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8 mm Hg at 20 °C(3). Based on studies using pure culture soil methylotroph Methylosirius trichosporium OB-3b, chloroacetonitrile is expected to biodegrade in soil(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9(SRC), determined from a structure estimation method(2), indicates that chloroacetonitrile is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.08X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 days and 25 days, respectively(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow of 0.45(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The aqueous hydrolysis rate constant for chloroacetonitrile at 20 °C and pH 8.7 was experimentally determined to be 1.2X10-6/sec(6) which corresponds to a half-life of 6.68 days(SRC); hydrolysis rates at neutral or acidic conditions is much slower(6) by approximately one to two orders of magnitude based on observed hydrolysis rates of the nine haloacetonitriles used in the study(SRC). Based on studies using pure culture soil methylotroph Methylosirius trichosporium OB-3b, chloroacetonitrile is expected to biodegrade in water(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chloroacetonitrile, which has a vapor pressure of 8 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase chloroacetonitrile 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 240 days(SRC), calculated from its rate constant of 6.74X10-14 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).
The rate constant for the vapor-phase reaction of chloroacetonitrile with photochemically-produced hydroxyl radicals has been estimated as 6.74X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 240 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The aqueous hydrolysis rate constant for chloroacetonitrile at 20 °C and pH 8.7 was experimentally determined to be 1.2X10-6/sec(2) which corresponds to a half-life of 6.68 days(SRC). Hydrolysis rates at neutral or acidic conditions is much slower(2) by approximately one to two orders of magnitude based on observed hydrolysis rates of the nine haloacetonitriles used in the study(SRC). Under basic conditions, aqueous hydrolysis of chloroacetonitrile yields the corresponding acetamide, which in basic media can be further hydrolyzed to the corresponding acid(2).
An estimated BCF of 3 was calculated for chloroacetonitrile(SRC), using a log Kow of 0.45(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(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of chloroacetonitrile can be estimated to be 9(SRC). According to a classification scheme(2), this estimated Koc value suggests that chloroacetonitrile is expected to have very high mobility in soil.
The Henry's Law constant for chloroacetonitrile is estimated as 1.08X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that chloroacetonitrile is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 2 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 25 days(SRC). Chloroacetonitrile's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). Chloroacetonitrile is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8 mm Hg at 20 °C(3).
DRINKING WATER: Chloroacetonitrile was detected not quantified in drinking water samples collected in Miami, FL on February 3, 1976(1). The compound was selected as a priority disinfection by-product to be included in a US nantionwide occurrence study. Chloroacetonitrile was not detected (method reporting limit = 0.1 ug/L) in two treatment plant operations sampled on Oct 30, 2000; the plants are located in EPA Region 9 (Pacific Southwest). Disinfection systems used were ozone-chlorine-chloramines and chlorine-chloramines, respectively. Sampling on July 1, 2001 and March 19, 2002 resulted in no detections at plant 1. At plant 2, chloracetonitrile was detected at 0.1 ug/L both in the treatment tank and finished water when sampled on July 1, 2001 and March 19, 2002. A concentration of 0.2 ug/L was reported in a clearwell sample from a plant located in EPA Region (South Central), sampled on September 10, 2001; the plant employed chlorine dioxide- chlorine-chloramine disinfection(2,3).
Occupational exposure to chloroacetonitrile may occur through inhalation and dermal contact with this compound at workplaces where chloroacetonitrile is produced or used. Chloroacetonitrile is reported to be a disinfectant by-product of drinking water chlorination; therefore, the general population may be exposed to chloroacetonitrile through tap water containing this by-product. (SRC)
Drug Information
... Male Sprague-Dawley rats were treated with a tracer dose of 2-(14)C-/chloroacetonitirile (CAN)/ (i.v., 88 muCi/kg, spec. act 4.07 mCi/mM). At various time intervals (0.08, 1, 3, 6, 12, 24, and 48 hr) after treatment, rats were processed for WBA, /whole body autoradiography/. Over 12 hr after administration, the radioactivity excreted in urine, feces, and exhaled as (14)CO2 accounted for 51%, 2.7%, and 12% of the dose, respectively. Only 0.8% of the administered dose was exhaled as unchanged CAN. At an early time interval (5 min) extensive accumulation of radioactivity was observed in liver, kidney, and gastrointestinal (G.I.) walls. In addition, high levels of (14)C were detected in the thyroid gland, lung bronchioles, adrenal cortex, salivary gland, and testes. At 1 hr following administration, the olfactory bulb, olfactory receptor area of the brain and lumbar cistern showed high accumulations of radioactive CAN or its equivalents. At 3, 6, and 12 hr after treatment, the radioactivity diffused homogeneously in all tissues and reconcentrated in several organs at later time periods (24 and 48 hr). ... The retention of radioactivity in the tissues of the thyroid gland, G.I., testes, brain and eye suggest that those organs are potential target sites of CAN toxicity.|... /Investigators sought to/ understand the potential mechanisms involved in such molecular interactions by examining the disposition, transplacental uptake and covalent interaction of the chemical in normal and GSH depleted pregnant mice (at 13th day of gestation). Both normal and GSH depleted (by administration of Diethylmaleate (DEM), 0.6 mL/kg, i.p.) pregnant mice were given an equitoxic i.v. dose of 2-(14)C-CAN (333 uCi/kg equivalent to 77 mg/kg). Animals were processed for whole-body autoradiography (WBA) at 1, 8 and 24 hr after treatment. Tissue distribution of radioactivity in the autoradiographs was quantitated using computer aided image analysis. With few exceptions, a rapid high uptake (at 1 hr) of radioactivity was observed in all major maternal (liver, lung, urinary bladder, gastrointestinal mucosa, cerebellum, uterine luminal fluid) and fetal (liver, brain) organs of both normal and GSH depleted mice. This pattern of distribution was observed, with lesser intensity, at 8 hr following treatment. At a later time period (24 hr), there was a significant higher retention and covalent interaction of radioactivity in GSH depleted mouse tissues especially in the liver as compared to normal mouse. This study suggests that 2-(14)C-CAN and/or its metabolites are capable of crossing the placental barrier. The observed higher uptake and retention of the radioactivity in the maternal liver, kidney, cerebellum, nasal turbinates and fetal liver may pose toxicity of the chemical to these organs. The increased covalent interaction of radioactivty in GSH depleted mice liver may indicate the potential utilization of GSH pathway by this organ in the detoxication of CAN derived metabolites and thus exerting hepatotoxicity.
Chloroacetonitirile is metabolized to hydrogen cyanide by mouse hepatic microsomal fractions.|Approximately 14% of a single oral dose to rats of 57 mg/kg body weight of chloroacetonitrile was excreted in urine within 24 hours as thiocyanate, the product of released cyanide metabolized by rhodanese.|Haloacetonitriles, contaminants present in chlorinated drinking water, were administered orally to rats, and the urinary excretion of thiocyanate was measured as an index of cyanide release. The urinary excretion of thiocyanate accounted for 14.2% of the dose of monochloroacetonitrile ...
... To examine the mechanism of /chloroacetonitrile (CAN)/ toxicity, /investigators/ studied its effect on glutathione (GSH) homeostasis and its impact on oxidative DNA damage in gastric mucosal cells of rats. Following a single oral dose (38 or 76 mg/kg) of CAN, animals were sacrificed at various times (0-24 hr), and mucosa from pyloric stomach were collected. The effects of CAN treatment on gastric GSH contents and the integrity of genomic gastric DNA were assessed. Oxidative damage to gastric DNA was evaluated by measuring the levels of 8-Hydroxydeoxyguanosine (8-OHdG) in hydrolyzed DNA by HPLC-EC. The results indicate that CAN induced a significant, dose- and time-dependent, decrease in GSH levels in pyloric stomach mucosa at 2 and 4 hours after treatment (56 and 39% of control, respectively). DNA damage was observed electrophoretically at 6 and 12 hours following CAN administration. CAN (38 mg/kg) induced significant elevation in levels of 8-OHdG in gastric DNA. Maximum levels of 8-OHdG in gastric DNA were observed at 6 hours after CAN treatment [9.59+/-0.60 (8-OHdG/10(5)dG) 146% of control]. When a high dose of CAN (76 mg/Kg) was used, a peak level of 8-OHdG [11.59+/-1.30 (8-OHdG/10(5)dG) 177% of control] was observed at earlier times (2 h) following treatment. When CAN was incubated with gastric mucosal cells, a concentration-dependent cyanide liberation and significant decrease in cellular ATP levels were detected. These data indicate that a mechanism for CAN-induced toxicity may be partially mediated by depletion of glutathione, release of cyanide, interruption of the energy metabolism, and induction of oxidative stress that leads to oxidative damage to gastric DNA.|Distinct dichloromethane dehalogenases from Methylobacterium sp. strain DM4 and Methylophilus DM11 were inhibited by low concentrations of haloacetonitriles. Chloroacetonitrile (ClCH2CN) showed maximal inhibition at a stoichiometry of 1 mol inhibitor:1 mol holoenzyme for both enzymes. This stoichiometry is suggestive of one active site per holoenzyme or extreme negative cooperativity amongst the subunits. Radiolabelled ClCH2CN dissociated completely or partially from the two dehalogenases, respectively, during chromatography. This suggested ClCH2CN was bound non-covalently.|Acetonitrile (AN) and seven of its halogenated derivatives known to be water disinfectant by-products were evaluated for their action on hepatic cytosolic glutathione S-transferase (GST) activity using 1-chloro-2,4-dinitrobenzene (CDNB) as substrate. Increasing concentrations of acetonitrile, monofluoroacetonitrile (MFAN), monochloroacetonitrile (MCAN), and monobromoacetonitrile (MBAN) up to 10 mM failed to produced 50% inhibition of the activity of GST enzyme. ...|Haloacetonitriles, which are water chlorination by-products, are mutagens, carcinogens and teratogens. In vitro, the reaction of the haloacetonitriles bromoacetonitrile (BAN), chloroacetonitrile (CAN), dichloroacetonitrile (DCAN) and trichloroacetonitrile (TCAN) with calf thymus DNA produced fluorescent DNA derivatives. The reactivity of haloacetonitriles towards DNA was in the order of BAN > CAN > DCAN > TCAN. ... The DNA interaction was dependent on haloacetonitrile concentration. Higher affinity of haloacetonitriles towards single-stranded DNA (SS-CT-DNA) than towards double-stranded DNA (DS-CT-DNA) was observed. ... A major fluorescent peak was detected in the enzymatic hydrolysate that was not present in unreacted DNA. In the acid hydrolysate, one fluorescent peak was detected that was not present in unreacted DNA. Authentic 7-(cyanomethyl)guanine was synthesized by the reaction of CAN with 2'-deoxyguanosine and the product was purified and characterized spectroscopically. The product, 7-(cyanomethyl)guanine, was found to be chromatographically and spectroscopically identical to the fluorescence product that was obtained following haloacetonitrile-DNA interaction. This study shows that haloacetonitriles, in vitro, are capable of alkylating DNA at the guanine moiety to form a 7-(cyanomethyl)guanine adduct.
Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. 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. 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. Be prepared to transport the victim to a hospital if advised by a physician. 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. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Immediate first aid: Remove patient from contact with the material. Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Cyanide and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Administer amyl nitrite ampules as per protocol and physician order ... . Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . /Cyanide and related compounds/|Advanced treatment: Consider Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer cyanide antidote kit as per protocol and physician order ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Cyanide and related compounds/
/GENOTOXICITY/ Chlorinated and brominated haloacetonitriles (HAN) were investigated for genotoxic activity. The HAN produced DNA strand breaks in cultured human lymphoblastic (CCRF-CEM) cells, bound to the nucleophilic trapping agent 4-(p-nitrobenzyl)pyridine and formed a covalent bond to polyadenylic acid in a cell-free reaction system. Thus, /it was/ demonstrated that these chemicals are genotoxic, which would indicate a potential for carcinogenic activity and for human health hazard. /haloacetonitriles/|/GENOTOXICITY/ The alkylating potential of the HAN to react with the electrophile-trapping agent, 4-(p-nitrobenzyl)pyridine, followed the order dibromoacetonitrile (DBAN) greater than bromochloroacetonitrile (BCAN) greater than chloroacetonitrile (CAN) greater than dichloroacetonitrile (DCAN) greater than trichloroacetonitrile (TCAN). ... The HAN produced DNA strand breaks in cultured human lymphoblastic (CCRF-CEM) cells. TCAN was the most potent DNA strand breaker, and BCAN greater than DBAN greater than DCAN greater than CAN, which was only marginally active. DCAN reacted with polyadenylic acid and DNA to form adducts in a cell-free system; however, the oral administration of DBAN or DCAN to rats did not result in detectable adduct formation in liver DNA. ...|/ALTERNATIVE and IN VITRO TESTS/ The present studies were initiated to measure the permeation coefficients (K(p)) for haloacetonitriles (HANs) and chloral hydrate (CH), important cytotoxic DBPs. The K(p) values measured using fully hydrated dermatomed torso skin at 37 °C for the HANs ranged from 0.099 to 0.17 cm h(-1) , and was 0.0039 cm h(-1) for CH. Of the HANs, dibromoacetonitrile had the highest permeability while chloroacetonitrile had the lowest permeability and a direct relationship was observed between their K(p) and their octanol/water partition coefficients (K(ow) ). The K(p) values of the HANs were also approximately 30 times that of CH. The monthly dermal and ingestion doses of HANs and CH of an average American population were estimated using Monte Carlo simulations. The dermal doses of HANs from showering and bathing ranged from 0.39 to 0.78 times their ingestion doses but only approximately 0.02 times their ingestion doses for CH, assuming that the K(p) values determined are applicable to shorter water contact times. However, that ratio can vary markedly with chlorinated swimming pool exposures, with a range of 0.30-2.3 for HANs and 0.19-0.25 for CH. Dermal exposure to HANs and CH seems to be a significant route of exposure and should be considered when evaluating their total exposure during the routine usage of water for bathing and swimming. /haloacetonitriles/|/OTHER TOXICITY INFORMATION/ Sister chromatid exchange was induced in one study using Chinese hamster ovary (CHO) cells, and DNA strand breaks (weakly) were induced in another using a human lymphoblast cell line.
chloroacetonitrile
The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.
Sore throat. Cough. Headache. Laboured breathing. Weakness. Unconsciousness.
MAY BE ABSORBED! Redness. Further see Inhalation.
Redness.
Chloroacetonitrile Use and Manufacturing
Chloroacetonitrile can be selectively obtained by the photochemical chlorination of acetonitrile with chlorine in the presence of, for example, SnCl4. Another method is based on the dehydration of chloroacetamide with, e.g., phosphorous pentoxide.
1. It can be used as raw material of organic synthesis and analytical reagents.
2. It can be used as pharmaceutical intermediates, pesticides.
Fumigant, intermediate.
Acetonitrile, 2-chloro-: ACTIVE
Method: EPA-NERL 524.2; Procedure: gas chromatography/mass spectrometry; Analyte: chloroacetonitrile; Matrix: surface water, ground water, and drinking water in any stage of treatment; Detection Limit: 0.12 ug/L.|EPA Method 1624. Isotope Dilution Purge and Trap Gas Chromatography/Mass Spectrometry. This method is applicable for the determination of volatile organic compounds in municipal and industrial discharges. By adding a known amount of an isotopically labeled compound to every sample prior to purging, a correction of recovery of the pollutant can be made. If isotopically labeled compounds are not available, an internal standard method is used. Under the prescribed conditions, chloroacetonitrile has an estimated detection limit of 10 ug/l in solids at high level and 10 ug/l in water with no interferences present as defined by EPA.
Fire Hazards -> Flammable - 2nd degree
Computed Properties
Molecular Weight:75.50
XLogP3:0.5
Hydrogen Bond Acceptor Count:1
Exact Mass:74.9875768
Monoisotopic Mass:74.9875768
Topological Polar Surface Area:23.8
Heavy Atom Count:4
Complexity:41.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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