Cyanoacetic acid

This chemical does not meet GHS hazard criteria for 1.2% (3 of 245) of reports.

H302+H332 (21.2%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]

H302 (98.4%): Harmful if swallowed [Warning Acute toxicity, oral]

H314 (98.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

H318 (67.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H332 (86.9%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H412 (12.2%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 245 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 3 of 245 reports by companies.

There are 21 notifications provided by 242 of 245 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

INHALATION: move to fresh air.

INGESTION: give large amounts of water; get medical attention.

EYES: flush with water for at least 15 min.

SKIN: flush with water. (USCG, 1999)

Fire Extinguishing Agents: Water, foam, dry chemical, carbon dioxide (USCG, 1999)

... Water ... effective in controlling fire; however, resulting liquid ... extremely corrosive ...

Use water spray, dry chemical, or carbon dioxide. Use water spray to keep fire-exposed containers cool. Control corrosive runoff and isolate discharged material for proper disposal. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

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: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.

FIRE: If tank, rail tank car or highway tank 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, 2024)

Stop or control the leak, if this can be done without undue risk. Absorb in noncombustible material for proper disposal.

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.

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.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2024)

Protect against physical damage. Separate from other storage ... /Store/ away from any area where fire hazard may be acute. Outside or detached storage is preferred ...

Store in a cool, dry, well-ventilated location. Separate from acids, alkalies, oxidizing materials, reducing agents.

Dust mask; goggles or face shield; rubber gloves (USCG, 1999)

... Full protective clothing except that in absence of heat self-contained breathing apparatus is not required.

Wear special protective clothing and positive pressure self-contained breathing apparatus.

Cyanoacetic acid is a yellow-brown liquid with an unpleasant odor. Sinks and mixes with water. (USCG, 1999)

White hygroscopic solid; [Hawley] White crystalline solid; [MSDSonline]

Hygroscopic crystals

108 °C at 15 mm Hg

151 °F (USCG, 1999)

Sol in water, alcohol, ether; slightly sol in benzene, chloroform

Slightly sol in acetic acid

greater than 1.1 at 68 °F (USCG, 1999)

0.03 [mmHg]

log Kow = -0.76

Decomposes at 320 °F (160 °C) with release of acetonitrile.

When heated to decomposition it emits toxic fumes of /nitrogen oxide and hydrogen cyanide/.

pKa = 2.45 at 25 °C

Hygroscopic; decomp at 160 °C into CO2 and acetonitrile

15N nuclear magnetic resonance spectrum

Chemical shift

Corrosion

Dielectric constant

Nuclear quadrupole resonance spectroscopy

Quadrupole coupling

Spin-spin coupling constant

Other Classes -> Organic Acids

Water soluble.

Acids, Carboxylic

Nitriles

Acids, Weak

White, moderately toxic solid, combustible. When heated to decomposition it emits toxic fumes of nitrile and oxides of nitrogen. A stirred mixture with furfuryl alcohol exploded violently upon heating [MCA Case History No 858].

An explosion occurred in a laboratory when cyanoacetic acid was reacted with furfuryl alcohol in an attempt to form the ester, furfuryl cyanoacetate. The explosion occurred a few min after the agitator was turned on and the heat applied. /Furfuryl alcohol/

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

No indication of carcinogenicity to humans (not listed by IARC).

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

Oral (L96) ; inhalation (L96) ; dermal (L96)

Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Other Poison - Chemical Asphyxiant

Dermatotoxin - Skin burns.

Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

LD50: 1500 mg/kg (Oral, Rat) (T31)

LD50: 200 mg/kg (Intraperitoneal, Mouse) (T29)

LD50 Rat oral 1500 mg/kg

LD50 Mouse ip 200 mg/kg

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)

/SIGNS AND SYMPTOMS/ Corrosive. Causes severe eye and skin burns. May be harmful if absorbed through skin or inhaled. Irritating to skin, eyes, and respiratory system.

/OTHER TOXICITY INFORMATION/ ...Acetonitrile /formed when cyanoacetic acid is heated/ is irritating to skin... high concentration ...rapidly fatal.

/LABORATORY ANIMALS: Acute Exposure/ ... /Cyanoacetic acid/ was reported ... to have caused histologic demonstrable lesions in optic nerves and tracts of 2 out of 15 severely poisoned rats. ... In rabbits no effect on ERG /(Electroretinogram)/ ...

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... Rats were given drinking water containing 2 mg cyanoacetic acid/mL daily for 7 wk. No toxic effects of any sort were noted ...

Cyanoacetic acid's production and use in the manufacture of the fungicide cymoxanil, the cough remedy dextromethorphan, and the production of barbital may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 0.035 mm Hg at 25 °C indicates cyanoacetic acid will exist solely as a vapor in the ambient atmosphere. Vapor-phase cyanoacetic acid will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 25 days. If released to soil, cyanoacetic acid is expected to have very high mobility based upon an estimated Koc of 1. The pKa of cyanoacetic acid is 2.45, which indicates it will exist as an anion under environmental conditions. Volatilization from moist soil surfaces will not be an important fate process because anions do not volatilize. Cyanoacetic acid is not expected to volatilize from dry soil surfaces based upon its estimated vapor pressure. Cyanoacetic acid was readily degraded in 2 weeks in a screening test that used an activated sludge inoculum, suggesting that it will be susceptible to biodegradation in the environment. If released into water, cyanoacetic acid is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization will not be an important fate process in water since anions do not volatilize. Cyanoacetic acid is highly reactive in chlorinated waters such as municipal drinking water systems, rapidly degrading to dichloroacetic acid, dichloromalonic acid, and trichloroacetic acid at pH range of 4 to 10. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Occupational exposure to cyanoacetic acid may occur through inhalation and dermal contact with this compound at workplaces where cyanoacetic acid is produced or used. (SRC)

Cyanoacetic acid's production and use for the manufacture of the fungicide cymoxanil, the cough remedy dextromethorphan(1), and the production of barbital(2) 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 1(SRC), determined from a structure estimation method(2), indicates that cyanoacetic acid is expected to have very high mobility in soil(SRC). Furthermore, the pka of cyanoacetic acid is 2.45(3), indicating it will exist as an anion under environmental conditions and anions generally have greater mobility in soils than neutral compounds(4). Volatilization from moist soil surfaces will not be an important environmental fate process since anions do not volatilize(SRC). The potential for volatilization of cyanoacetic acid from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 0.035 mm Hg determined from a fragment constant method(5). Cyanoacetic acid was readily degraded in 2 weeks using an activated sludge inoculum and the Japanese MITI test, suggesting that it will be susceptible to biodegradation in soil(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that cyanoacetic acid is not expected to adsorb to suspended solids and sediment(SRC). The pka of cyanoacetic acid is 2.45(3), indicating it will exist as an anion under environmental conditions. Volatilization from water surfaces is not an important environmental fate process since anions do not volatilize(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from a log Kow of -0.76(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Cyanoacetic acid is highly reactive in chlorinated water, rapidly degrading to dichloroacetic acid, dichloromalonic acid, and trichloroacetic acid at pH 4-10(7). Cyanoacetic acid was readily degraded in 2 weeks using an activated sludge inoculum and the Japanese MITI test, suggesting that it will be susceptible to biodegradation in water(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyanoacetic acid, which has an estimated vapor pressure of 0.035 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cyanoacetic acid 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 25 days(SRC), calculated from its rate constant of 6.5X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

AEROBIC: Cyanoacetic acid, present at 100 mg/L, reached 90% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(1).

The rate constant for the vapor-phase reaction of cyanoacetic acid with photochemically-produced hydroxyl radicals has been estimated as 6.5X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 25 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Cyanoacetic acid is highly reactive in the presence of chlorine resulting in production of dichloroacetic acid, dichloromalonic acid, and trichloroacetic acid(2,3). Cyanoacetic acid was completely degraded in buffered solutions containing chlorine at pH 4,7, and 10 within 1 hour(2,3).

An estimated BCF of 3 was calculated for cyanoacetic acid(SRC), using a log Kow of -0.76(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(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for cyanoacetic acid can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that cyanoacetic acid is expected to have very high mobility in soil(SRC). In addition, the pKa of cyanoacetic acid is 2.45(3), indicating that this compound will exist primarily as an anion in the environment, and anions generally possess higher mobility in soil than their neutral counterpart(4).

The pKa of cyanoacetic acid is 2.45(1), indicating that this compound will exist as an anion under environmental conditions. Volatilization will not occur from water and moist soils since anions do not volatilize(SRC). Cyanoacetic acid is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 0.035 mm Hg at 25 °C(SRC) determined from a fragment constant method(2).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 919 workers (306 of these are female) are potentially exposed to cyanoacetic acid in the US(1). Occupational exposure to cyanoacetic acid may occur through inhalation or dermal contact with this compound at workplaces where it is produced or used(SRC).

Cyanoacetic acid's production and use in the manufacture of the fungicide cymoxanil, the cough remedy dextromethorphan, and the production of barbital may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 0.035 mm Hg at 25 °C indicates cyanoacetic acid will exist solely as a vapor in the ambient atmosphere. Vapor-phase cyanoacetic acid will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 25 days. If released to soil, cyanoacetic acid is expected to have very high mobility based upon an estimated Koc of 1. The pKa of cyanoacetic acid is 2.45, which indicates it will exist as an anion under environmental conditions. Volatilization from moist soil surfaces will not be an important fate process because anions do not volatilize. Cyanoacetic acid is not expected to volatilize from dry soil surfaces based upon its estimated vapor pressure. Cyanoacetic acid was readily degraded in 2 weeks in a screening test that used an activated sludge inoculum, suggesting that it will be susceptible to biodegradation in the environment. If released into water, cyanoacetic acid is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization will not be an important fate process in water since anions do not volatilize. Cyanoacetic acid is highly reactive in chlorinated waters such as municipal drinking water systems, rapidly degrading to dichloroacetic acid, dichloromalonic acid, and trichloroacetic acid at pH range of 4 to 10. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Occupational exposure to cyanoacetic acid may occur through inhalation and dermal contact with this compound at workplaces where cyanoacetic acid is produced or used. (SRC)

Cyanoacetic acid's production and use for the manufacture of the fungicide cymoxanil, the cough remedy dextromethorphan(1), and the production of barbital(2) 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 1(SRC), determined from a structure estimation method(2), indicates that cyanoacetic acid is expected to have very high mobility in soil(SRC). Furthermore, the pka of cyanoacetic acid is 2.45(3), indicating it will exist as an anion under environmental conditions and anions generally have greater mobility in soils than neutral compounds(4). Volatilization from moist soil surfaces will not be an important environmental fate process since anions do not volatilize(SRC). The potential for volatilization of cyanoacetic acid from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 0.035 mm Hg determined from a fragment constant method(5). Cyanoacetic acid was readily degraded in 2 weeks using an activated sludge inoculum and the Japanese MITI test, suggesting that it will be susceptible to biodegradation in soil(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that cyanoacetic acid is not expected to adsorb to suspended solids and sediment(SRC). The pka of cyanoacetic acid is 2.45(3), indicating it will exist as an anion under environmental conditions. Volatilization from water surfaces is not an important environmental fate process since anions do not volatilize(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from a log Kow of -0.76(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Cyanoacetic acid is highly reactive in chlorinated water, rapidly degrading to dichloroacetic acid, dichloromalonic acid, and trichloroacetic acid at pH 4-10(7). Cyanoacetic acid was readily degraded in 2 weeks using an activated sludge inoculum and the Japanese MITI test, suggesting that it will be susceptible to biodegradation in water(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyanoacetic acid, which has an estimated vapor pressure of 0.035 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cyanoacetic acid 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 25 days(SRC), calculated from its rate constant of 6.5X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

AEROBIC: Cyanoacetic acid, present at 100 mg/L, reached 90% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(1).

The rate constant for the vapor-phase reaction of cyanoacetic acid with photochemically-produced hydroxyl radicals has been estimated as 6.5X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 25 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Cyanoacetic acid is highly reactive in the presence of chlorine resulting in production of dichloroacetic acid, dichloromalonic acid, and trichloroacetic acid(2,3). Cyanoacetic acid was completely degraded in buffered solutions containing chlorine at pH 4,7, and 10 within 1 hour(2,3).

An estimated BCF of 3 was calculated for cyanoacetic acid(SRC), using a log Kow of -0.76(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(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for cyanoacetic acid can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that cyanoacetic acid is expected to have very high mobility in soil(SRC). In addition, the pKa of cyanoacetic acid is 2.45(3), indicating that this compound will exist primarily as an anion in the environment, and anions generally possess higher mobility in soil than their neutral counterpart(4).

The pKa of cyanoacetic acid is 2.45(1), indicating that this compound will exist as an anion under environmental conditions. Volatilization will not occur from water and moist soils since anions do not volatilize(SRC). Cyanoacetic acid is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 0.035 mm Hg at 25 °C(SRC) determined from a fragment constant method(2).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 919 workers (306 of these are female) are potentially exposed to cyanoacetic acid in the US(1). Occupational exposure to cyanoacetic acid may occur through inhalation or dermal contact with this compound at workplaces where it is produced or used(SRC).

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.

Corrosive