Trichloroacetonitrile

144.379

144.39

208-885-7

6397DL8869

66405

3276

DTXSID0021672

Colorless liquid|Liquid

2926909090

23.8

2.09

Trichloroacetonitrile is a clear pale yellow liquid. (NTP, 1992)

1.44 g/cm³ @ Temp: 25 °C

-42 °C

85.7 °C

383 dec F (195 deg C) (closed cup)

1.489

H2O: <0.1 g/100 mL at 21.5°C

Keep tightly closed.

58 mm Hg ( 20 °C)

LD50 orally in rats: 0.25 g/kg (Smyth)

Henry's Law constant = 1.34X10-6 atm-cu m/mol at 25 °C (est)

Conversion factor: mg/cu m = 5.91 X ppm

Highly flammable. Insoluble in water.

Halogenated Organic Compounds

Highly Flammable

May be sensitive to light and heat. This compound may react with water, steam, acid or acid fumes. It may hydrolyze under acidic or alkaline conditions. (NTP, 1992). The reaction of benzene and trichloroacetonitrile evolves toxic chloroform and HCl gases. (Hagedorn, F., H.-P. Gelbke, and Federal Republic of Germany. 2002. Nitriles. In Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. KGaA.).

II

8

UN 3276 6.1/PG 3

3

R23/24/25;R51/53

S45-S61

AM2450000

T:Toxic

Stable, but water sensitive. Incompatible with acids, water, steam. May hydrolyze in alkali or acid conditions. Flammable.

Missing Phrase - N15.00950417-P261-P280-P302 + P352 + P312-P304 + P340 + P312-P403 + P233

H301 + H311 + H331-H315-H319-H411

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|Observe all federal, state, and local environmental regulations.

This chemical is combustible. (NTP, 1992)

|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|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 115 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P302+P352, P312, P321, P322, P330, P332+P313, P362, P363, and P501|P201, P202, P261, P264, P270, P271, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501

Excerpt from ERG Guide 151 [Substances - Toxic (Non-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: See ERG Table 1 - Initial Isolation and Protective Action Distances on the UN/NA 3276 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)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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 protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: When working with this chemical, wear a NIOSH-approved full face chemical cartridge respirator equipped with the appropriate organic vapor cartridges. If that is not available, a half face respirator similarly equipped plus airtight goggles can be substituted. However, please note that half face respirators provide a substantially lower level of protection than do full face respirators. RECOMMENDED GLOVE MATERIALS: It is recommended that two different glove types be used for best protection. However, if this chemical makes direct contact with your gloves, or if a tear, puncture or hole develops, remove them at once. SUGGESTED GLOVES: PVA (NTP, 1992)|ENGINEERING CONTROLS. Safety shower and eye bath. Use only in a chemical fume hood.|PERSONAL PROTECTIVE EQUIPMENT. Other: Wear appropriate government approved respirator, chemical-resistant gloves, safety goggles, other protective clothing.

FIREFIGHTING. Protective Equipment: Wear self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes.|EXTINGUISHING MEDIA. Carbon dioxide, dry chemical powder, or appropriate foam.

Emits toxic fumes under fire conditions.

Absorb on sand or vermiculite and place in closed containers for disposal.

SRP: When working with strong solutions of acids or bases or other caustic or corrosive materials, always wear a full face mask. When working with caustic or corrosive gases or vapors, a full face mask will not protect the eyes or prevent inhaling the material. A full face respirator is required.|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.|Do not breathe vapor. Do not get in eyes, on skin, on clothing.|Wear self-contained breathing apparatus, rubber boots, and heavy rubber gloves. In case of leak or spill, evacuate area.|For more Preventive Measures (Complete) data for TRICHLOROACETONITRILE (7 total), please visit the HSDB record page.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ When administered by gavage to pregnant Long-Evans rats in a medium-chain triglyceride vehicle, tricaprylin oil (Tricap), at a volume of 10 mL/kg, trichloroacetonitrile (TCAN) induced fetal cardiovascular anomalies at doses as low as 1 mg/kg/d ... . A slight but possibly biologically significant increase over the water control group in adverse pregnancy outcomes (resorptions, reduced fetal weight, and anomalies) was observed in the Tricap control group. This led .. to /reexamination of/ the development effects of TCAN in a second vehicle, corn oil (CO). Five groups of approximately 20 pregnant female rats received TCAN in CO at 15, 35, 55, and 75 mg/kg/d, and in Tricap at 15 mg/kg/d (10 mL/kg dosing volume). Corn oil, Tricap, and water served as vehicle controls. Animals were treated by oral intubation on gestation d 6-18 (vaginal plug = d 0). Five out of 20 dams (75 mg/kg) died during treatment. Adjusted maternal weight gain was lower in females receiving 35 mg/kg TCAN or greater. The mean percent of nonlive implants per litter was elevated at 55 and 75 mg/kg TCAN (CO). ... Fetal weight was reduced at 15 mg/kg TCAN (Tricap) and at > or = 55 mg/kg TCAN (CO). When TCAN was administered in CO, the mean frequency of soft-tissue malformations decreased with significantly fewer septal and great vessel cardiovascular defects observed. /It was hypothesized/ that the volatile haloacetonitrile, TCAN, may interact with the Tricap vehicle in such a way that effects on the developing cardiovascular system are potentiated. The lowest observed adverse effect level for TCAN (CO) was determined to be 35 kg/kg.

Trichloroacetonitrile's production and use as a chemical intermediate(1) may result in its release to the environment through various waste streams. Trichloroacetonitrile formation in small amounts during the chlorination of water(2,3) will result in its release to the environment through various waste streams(SRC). Its former use as an insecticide(4) resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 330(SRC), determined from a log Kow of 2.09(2) and a regression-derived equation(3), indicates that trichloroacetonitrile is expected to have moderate mobility in soil(SRC). Volatilization of trichloroacetonitrile from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Trichloroacetonitrile is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 74.1 mm Hg(5). Trichloroacetonitrile is a by-product of water chlorination and hydrolyzes quickly; therefore, biodegradation is not expected to be an important fate in the environment(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 330(SRC), determined from a log Kow of 2.09(2) and a regression-derived equation(3), indicates that trichloroacetonitrile is 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 1.3X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 33 and 240 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 8(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Trichloroacetonitrile has a hydrolysis rate constant of 2.0X10-6/sec, 1.5X10-4/sec and 3.9X10-4/sec at pH of 5.4, 7.2 and 8.7, respectively(7), corresponding to half-lives of 4 days, 1.3 hours, and 29 minutes, respectively(SRC). Trichloroacetonitrile is a by-product of water chlorination and hydrolyzes quickly; therefore, biodegradation is not expected to be an important fate in the environment(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trichloroacetonitrile, which has a vapor pressure of 74.1 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. There is no mechanistic process by which tichloroacetonitrile can be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(2). Trichloroacetonitrile does not contain chromophores that absorb at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

There is no mechanistic process by which tichloroacetonitrile can be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(1). Trichloroacetonitrile has a hydrolysis rate constant of 2.0X10-6/sec, 1.5X10-4/sec and 3.9X10-4/sec at pH of 5.4, 7.2 and 8.7, respectively(2), corresponding to half-lives of 4 days, 1.3 hours, and 29 minutes, respectively(SRC). Trichloroacetonitrile does not contain chromophores that absorb at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 8 was calculated in fish for trichloroacetonitrile(SRC), using a log Kow of 2.09(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).

The Koc of trichloroacetonitrile is estimated as 330(SRC), using a log Kow of 2.09(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that trichloroacetonitrile is expected to have moderate mobility in soil.

The Henry's Law constant for trichloroacetonitrile is estimated as 1.3X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that trichloroacetonitrile 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 33 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 240 days(SRC). Trichloroacetonitrile's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Trichloroacetonitrile is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 74.1 mm Hg(3).

DRINKING WATER: The concn of trichloroacetonitrile in two water treatment plants using chlorine and a combination of chlorination and ozonation were all <0.012 ug/L(1). Based on a study of 35 water utilities across the U.S. by the EPA and State of California Department of Health Services, the quarterly median concns of trichloroacetonitrile from the spring of 1988 through the winter of 1989 were <0.012, <0.012, <0.029, and <0.029 ug/L(2). The quarterly trichloroacetonitrile concns in the facility with the highest bromide level ranged from <0.012 to <0.029 ug/L(2). Trichloroacetonitrile was not detected in raw water, pre-chlorinated, sand filters, ozone, at the granulated carbon filter stage, or post-chlorinated stages at a water treatment plant in Barcelona, Spain(3). Trichloroacetonitrile, studied in 5 locations in each of 3 treatment plants for a one year period from Jan to Dec 1994, contained concns of <0.1 ug/L in 2 plants with source water from the Ottawa River one using chlorine/chloramine treatment and one using chlorine/chlorine treatment and at concns of <0.1-0.2 ug/L in a plant with source water from LaLievre River using ozone/chlorine treatment(4). Trichloroacetonitrile was found in 9% of samples taken from 53 water treatment facilities throughout Canada, at concns of <5 ug/L(5). Trichloroacetonitrile was not detected when using chlorine dioxide, chlorine dioxide with bromide, chloramination, chloramination with bromide, chlorine, chlorine with bromide, ozone, or ozone with bromide treatments(6).

Occupational exposure to trichloroacetonitrile may occur through inhalation and dermal contact with this compound at workplaces where trichloroacetonitrile is produced. Monitoring data indicate that the general population may be exposed to small amounts of trichloroacetonitrile via ingestion of and dermal contact with drinking water. (SRC)

About 2% of a single oral dose of 108 mg/kg bw trichloroacetonitrile to rats was excreted in urine within 24 hr as thiocyanate, the product of released cyanide metabolized by rhodanese

When administered orally to rats, the haloacetonitriles (HAN) were metabolized to cyanide and excreted in the urine as thiocyanate. The extent of thiocyanate excretion was chloroacetonitrile (CAN) greater than bromochloroacetonitrile (BCAN) greater than dichloroacetonitrile (DCAN) greater than dibromoacetonitrile (DBAN) much greater than trichloroacetonitrile (TCAN).

SYMPTOMS: Severe eye irritation is likely with permanent major residual eye injury. Major lung damage may result and is likely to be permanent despite prompt medical treatment. Minor residual skin injury may result despite prompt medic treatment. ACUTE/CHRONIC HAZARDS: This material is a lachrymator and can cause severe irritation of the eyes, skin and lungs. It is readily absorbed through this skin and evolves hazardous fumes on contact with acid or acid fumes and when heated to decomposition. (NTP, 1992)

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 volatile chemicals have a high risk of being aspirated into the victim's lungs during vomiting. Thus, the risk of increasing the medical problems by inducing vomiting of a volatile corrosive chemical is very high. 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. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

/SRP:/ 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/|/SRP:/ 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/|/SRP:/ 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 (sodium nitrite, amyl nitrite, sodium thiosulfate) as per protocol and physician order ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Cyanide and related compounds/|Emergency and supportive measures. Treat all cyanide exposures as potentially lethal. Maintain an open airway and assist ventilation if necessary. Administer supplemental oxygen. Treat coma, hypotension, and seizures if they occur. Start an intravenous line and monitor the patient's vital signs and ECG closely. /Cyanide/|For more Antidote and Emergency Treatment (Complete) data for TRICHLOROACETONITRILE (6 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ Multiple Routes: Harmful if swallowed, inhaled, or absorbed through skin.|/SIGNS AND SYMPTOMS/ Material is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and skin. Inhalation may result in spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting.|/GENOTOXICITY/ ... The ability of halogenated acetonitriles (HAN) to induce single-strand breaks on the DNA of HeLa S3 cells was investigated using the single-cell gel electrophoresis (SCGE) assay, which could be a good tool with which to evaluate the genotoxicity of chlorinated water. The results were compared to those obtained in the Ames fluctuation test using the Salmonella typhimurium TA100 strain without activation. With the Ames fluctuation test, a mutagenic effect was observed for chloroacetonitrile (MCAN), dichloroacetonitrile (DCAN), and trichloroacetonitrile (TCAN). No mutagenic effect was found with bromoacetonitrile (MBAN) or dibromoacetonitrile (DBAN). In the SCGE assay, all five HANs induced DNA damage in HeLa S3 cells, increasing the mean tail moment significantly. For each compound, a dose-effect relation was observed. ... Brominated acetonitriles were more genotoxic than chlorinated acetonitriles in the SCGE assay, and the genotoxicity increased with the number of halogenated atoms of the compound. This behavior had already been found with other genotoxicity tests.|/GENOTOXICITY/ The haloacetonitriles produced DNA strand breaks in cultured human lymphoblastic (CCRF-CEM) cells. Trichloroacetonitrile (TCAN) was the most potent DNA strand breaker, and bromochloroacetonitrile (BCAN) greater than dibromoacetonitrile (DBAN) greater than dichloroacetonitrile (DCAN) greater than chloroacetonitrile (CAN), which was only marginally active.|/GENOTOXICITY/ Chlorinated and brominated haloacetonitriles (HAN) ... produced DNA strand breaks in cultured human lymphoblastic (CCRF-CEM) cells /treated for 1 hr with up to 3.0 mM dibromoacetonitrile/. /Chlorinated & brominated haloacetonitriles/

trichloroacetonitrile

Acetonitrile, 2,2,2-trichloro-: ACTIVE|Haloacetonitriles ... are chemical by-products of chlorine disinfection of drinking water. /Halogenated acetonitriles/

Method: EPA-OGWDW/TSC 551.1; Procedure: gas chromatography with electron capture detector; Analyte: trichloroacetonitrile; Matrix: finished drinking water, drinking water during intermediate stages of treatment, and raw source water; Detection Limit: 0.002 ug/L.