Cyanoacetic acid

85.06

85.06

506325

206-743-9

QZT550H2Y9

5571

1759

DTXSID0027149

Hygroscopic crystals

2926909090

61.1

-0.76

White to light beige Adhering Crystalline Solid

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

66 °C

108 °C @ Press: 15 Torr

226 °F

1.440

H2O: soluble 50mg/mL, clear, colorless to very faintly yellow

Store at 0-5°C

0.1 mm Hg ( 100 °C)

Oral-Rat LD50: 1500 mg/kg; peritoneal-mouse LD50: 200 mg/kg

Open flame is flammable; high heat emits toxic nitrogen oxides and cyanide gas

Henry's Law constant = 2.3X10-10 atm-cu m/mol at 25 °C (est)

pKa = 2.45 at 25 °C

Hygroscopic; decomp at 160 °C into CO2 and acetonitrile|Hydroxyl radical reaction rate constant = 6.5X10-13 cu cm/molec-sec at 25 °C (est)

Water soluble.

Acids, Carboxylic

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].

II

8

UN 3261 8/PG 2

2

22-31-34-52/53-20/22

26-36/37/39-45-61-20

AG3675000

C

The warehouse is ventilated at low temperature and dry; stored separately from oxidants, acids and food additives

P280-P305 + P351 + P338-P310

H302 + H332-H314

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.

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/

Special Hazards of Combustion Products: Toxic oxides of nitrogen and toxic and flammable acetonitrile vapors may form in fire. (USCG, 1999)

|Danger|H302+H332 (23.04%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]|P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P405, and P501|Aggregated GHS information provided by 220 companies from 20 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, P301+P312, P330, and P501

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

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

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.

Combustible solid. When heated to decomp, emits ... flammable acetonitrile vapor.

... 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.

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

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.

Irritating to skin, eyes, and respiratory system.|...Acetonitrile /formed when cyanoacetic acid is heated/ is irritating to skin... .

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Cyanoacetic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

moderately toxic

LD50 Rat oral 1500 mg/kg|LD50 Mouse ip 200 mg/kg

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).

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).

... In vivo and in vitro metabolism of 3-dimethylaminopropionitrile (DMAPN) and its urotoxic effect on male Sprague-Dawley rats /were investigated/. Rats were given 175, 350, or 525 mg/kg DMAPN or DMAPN metabolites orally for 5 days, and urinary metabolites and volumes were measured. By day 5, 44% of the DMAPN dose was excreted unchanged. Beta-aminopropionitrile and cyanoacetic acid were the major urinary metabolites, as identified by gas chromatography. /It was/ concluded that DMAPN is metabolized via a cytochrome P450 mixed-function oxidase system and the urotoxic effects of DMAPN may be related to its metabolism.|... Cyanoacetic acid has been studied with reference to its possible role in the production of the symptoms of lathyrism by 3-aminopropionitrile. Injection of 14C-labeled 3-aminopropionitrile in rats showed that 25-30% could be recovered as cyanoacetic acid ... /However/ cyanoacetic acid is not responsible for the skeletal deformities, and such produced by feeding 3-aminopropionitrile.

Contact irritates eyes and may irritate skin. (USCG, 1999)

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)

/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.

cyanoacetic acid

Acetic acid, 2-cyano-: ACTIVE