Ethyl cyanoacetate
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Ethyl cyanoacetate
structure -
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CAS No:
105-56-6
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Formula:
C5H7NO2
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Chemical Name:
Ethyl cyanoacetate
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Synonyms:
Acetic acid,2-cyano-,ethyl ester;Acetic acid,cyano-,ethyl ester;Cyanoacetic acid ethyl ester;Cyanoacetic ester;Ethyl cyanoacetate;Ethyl cyanoethanoate;Malonic acid ethyl ester nitrile;Ethyl cyanacetate;Ethyl 2-cyanoacetate;Ethyl α-cyanoacetate;NSC 8844;(Ethoxycarbonyl)acetonitrile;3-Ethoxy-3-oxopropanenitrile;2-Cyanoacetic acid ethyl ester;1427280-50-9
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CAS No:
Description
Ethyl cyanoacetate is a colorless to straw colored liquid with a mild pleasant odorA colorless liquid. Denser than water. Contact may irritate skin, eyes and mucous membranes. Flash point 210°F. May be toxic by ingestion. Used to make other chemicals.
Ethyl cyanoacetate appears as a colorless liquid. Denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals.|Liquid
Ethyl cyanoacetate appears as a colorless liquid. Denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals.
Ethyl cyanoacetate Basic Attributes
113.11
113.11
605871
203-309-0
X9N006U0F8
8844
3276|2666
DTXSID9026718
Colorless liquid|Colorless to pale straw-colored liquid
2926 90 70
Characteristics
50.1
0.06
Clear Liquid
1.0560 g/cm3 @ Temp: 25 °C
-22 °C
206.0 °C @ Press: 760 Torr
>230 °F
n 20/D 1.418(lit.)
H2O: 20 g/L (20 ºC)
Store below +30°C.
1 mm Hg ( 67.8 °C)
3.9 (vs air)
Oral-rat LDL0: 400 mg/kg
Open flame is flammable; emits toxic cyanide gas when exposed to heat or acid; emits toxic and flammable gas when exposed to water
Slight, pleasant odor
Henry's Law constant = 2.89X10-7 atm-cu m/mol at 25 °C (est)
Specific gravity: 1.0560 at 25 °C/4 °C; 1.0306 at 50 °C/4 °C; 1.0110 at 70 °C/|Hydroxyl radical reaction rate constant = 1.72X10-12 cu cm/molecule-sec at 25 °C (est)
Slightly soluble in water.
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
ETHYL CYANOACETATE is both a nitrile and an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.
Safety Information
3276
1
20/21/22-36/38
36/37-37/39-26
AG4110000
Xn,Xi
The warehouse is ventilated, low temperature and dry; stored and transported separately from food, oxidants and acids
P280
H302-H312-H332
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.
Will react with water or steam to produce toxic and flammable vapors.|Can react with oxidizing materials|Materials to avoid: Strong acids, strong bases, strong oxidizing agents, strong reducing agents.
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways. (ERG, 2016)|Reactive - 1st degree
|Warning|H302 (85.25%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501|Aggregated GHS information provided by 237 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
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)
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: 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. Cover with plastic sheet to prevent spreading. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: 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)|Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|For prolonged or repeated contact use protective gloves.|Face shield and safety glasses.
Combustible when exposed to heat or flame
Carbon dioxide, dry chemical|Water or foam may cause frothing.|Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.|Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.
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.|Avoid contact with skin and eyes. Avoid inhalation of vapor or mist.|Choose body protection according to the amount and concentration of the dangerous substance at the work place.|Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.|/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Health: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat which will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.|/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Public Safety: CALL Emergency Response Telephone Number ... As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.|/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Protective Clothing: 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.|For more DOT Emergency Guidelines (Complete) data for ETHYL CYANOACETATE (8 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 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.
Ethyl cyanoacetate at ... /an/ aerosol concentration of 7380 mg/cu m ... /produced/ irritation of the eyes and upper respiratory tract.
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. Ethyl cyanoacetate is produced, as an intermediate or a final product, by process units covered under this subpart.
| 1 - Materials that, under emergency conditions, can cause significant irritation.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.
Toxicity
highly toxic
Ethyl cyanoacetate is the ethyl ester of cyanoacetic acid. Ethyl cyanoacetate hydrolyzes rapidly under neutral and alkaline conditions to cyanoacetic acid and ethanol ... , while in acid pH the half life is considerably longer. It also is likely that unspecific esterases in the body catalyze the hydrolysis to cyanoacetic acid and ethanol ... As the acid and the ester have different physical chemical properties due to their chemical nature, effects that are related to the acidity of the acid (e.g. ecotoxicity data, local irritating effects) have to be assessed separately. The environmental and toxicokinetic distribution can however be expected to range in a similar order of magnitude due to the similar polarity, vapor pressure and log Kow. ... Human Health. From the physical chemical properties of both cyanoacetic acid and ethyl cyanoacetate it can be expected that both substances will be moderately absorbed by all exposure routes. A relatively even distribution between tissues and also to embryonic tissues of pregnant rats was observed after oral administration of cyanoacetic acid. A similar behavior can be expected for ethyl cyanoacetate. Ethyl cyanoacetate is likely to be metabolized by unspecific esterases of different tissues, in particular in the liver to cyanoacetic acid and ethanol. While no mortality and no signs of toxicity were observed in a 7-hour vapor inhalation study in rats with saturated vapors of cyanoacetic acid, the 4-hour LC50 in rats for an aerosol of 50% cyanoacetic acid in water was 1900 mg/cu m. The most prominent symptoms were signs of severe irritation of eyes, mouth and respiratory tract. In a 1-hour inhalation study with ethyl cyanoacetate at the maximum attainable aerosol concentration of 7380 mg/cu m the only substance related findings were reversible signs of irritation of the eyes and the upper respiratory tract. For cyanoacetic acid a dermal LD50 > 2000 mg/kg bw in rabbits was reported. In this study with limited documentation local irritant effects on the skin and some systemic effects (dyspnea, behavioral changes) were reported, indicating a possible systemic toxicity after dermal exposure. For ethyl cyanoacetate a dermal LD50 > 1000 and > 2000 mg/kg bw was reported in rabbits and rats, respectively ... . No treatment related findings except for slight local skin irritation in the study in rabbits were observed. An acute oral LD50 value in rats of 1010 mg/kg bw has been reported for cyanoacetic acid. Symptoms including dyspnea, labored breathing, apathy and staggered gait were observed from doses of 1000 mg/kg bw and necropsy revealed local effects in the stomach. Only systemic effects similar to those reported for cyanoacetic acid were observed with ethyl cyanoacetate at a limit dose of 2000 mg/kg bw in rats. Cyanoacetic acid was corrosive to rabbit skin ... and eyes ... while ethyl cyanoacetate was not irritating to rabbit skin ... and moderately irritating to rabbit eyes... . Based on the results of the inhalation toxicity studies, cyanoacetic acid can be regarded as highly irritating to the mucous membranes of the respiratory tract while ethyl cyanoacetate only had a slight irritant effect on the respiratory tract. Both substances were not skin sensitizing in a Buehler test in guinea pigs ... . One 90-day oral (gavage) study in rats ... has been conducted with ethyl cyanoacetate at doses of 0, 100, 300 and 1000 mg/kg bw/day. The NOAEL in this study was 100 mg/kg bw/day for female rats and 300 mg/kg bw/day for male rats. A significant dose related reduction in hemoglobin values was observed at dose levels of 300 and 1000 mg/kg bw/day in female animals. In males of the 1000 mg/kg bw/day dose group increased urine volume and reversible pathological changes in liver (chronic peribiliary inflammation) and adrenals (vacuolization in the zona fasciculata of the adrenals) were observed. An additional examination of sperm counts and sperm motility in high dosed males revealed an apparently treatment related decrease in the percentage of motile sperms and sperm counts in the epididymis (changes within 2 standard deviations of the historical control data, no significant changes in organ weights or pathological findings in testes or epididymis). No effects were observed on female sex organs and estrous cycle. Both cyanoacetic acid and ethyl cyanoacetate were not mutagenic in the standard Ames assay in bacteria with and without metabolic activation. Neither Salmonella typhimurium TA102 nor E. coli WP2 were tested in these Ames tests, however, this is an acceptable restriction, because it can be assumed that neither cyanoacetic acid nor ethyl cyanoacetate has oxidizing or cross-linking potential, which may be detected by TA102 or E. coli WP2. Ethyl cyanoacetate did not show any clastogenic activity in the in vitro cytogenetic assay with V79 Chinese Hamster lung cells in the presence and absence of a metabolic activation system. All tests with ethyl cyanoacetate were conducted according to OECD or EC guidelines and GLP. For both substances, there is no structural alert for genotoxicity. In conclusion, from the available information, there is no indication of a genotoxic potential of the substances, both for gene mutations and chromosomal aberrations. No data are available on carcinogenicity. No specific studies on fertility are available for cyanoacetic acid or ethyl cyanoacetate. In a 90-day oral gavage study ... with ethyl cyanoacetate that included a histopathological evaluation of the gonads as well as additional investigations on sperm motility and sperm counts a NOAEL for these fertility related endpoints of 300 mg/kg bw/day was derived. A decrease of sperm motility and epididymal sperm counts observed in this study at 1000 mg/cu m (LOAEL) were not accompanied by significant reductions in testicular, epididymal, ovary or uterus weights, or any histopathological findings in these organs. Moreover, these effects are observed together with systemic toxicity. In a developmental toxicity study with ethyl cyanoacetate ... the NOAEL for embryotoxic or fetotoxic effects was 100 mg/kg bw/day based on an increase in minor skeletal anomalies in litters of the 300 and 1000 mg/kg bw/day dose groups and a reduced mean fetal weight at 1000 mg/kg bw/day. The NOAEL for maternal toxicity in this study was 300 mg/kg bw/day. Maternal toxicity in this study was however, only defined based on clinical signs, body weight development and macroscopic organ changes. Therefore it can not be excluded that the observed developmental effects are due to maternal toxicity. Studies on repeated dose toxicity and developmental toxicity conducted with ethyl cyanoacetate are considered relevant for cyanoacetic acid as well, as the ester will be rapidly metabolized to cyanoacetic acid and ethanol and its toxicity is likely to be mediated predominantly by cyanoacetic acid. Furthermore the study of the ester represents a "worst case" assumption for the acid as it can be assumed that the slightly more lipophilic ethyl ester is more readily absorbed than the corresponding acid and the maximum applicable dose of the ester is not limited by local irritation to mucous membranes. Therefore the ester can be administered at higher dose levels and is assumed to have a better bioavailability than the acid.
LD50 Rat dermal 1010 mg/kg|LD50 Rat dermal >2000 mg/kg|LD50 Rabbit dermal >1000 mg/kg bw|LC50 Rat inhalation >7380 mg/cu m 1hr|LD50 Mouse intraperitoneal 500 mg/kg
/AQUATIC SPECIES/ Acute toxicity data for 3 trophic levels of the aquatic environment are available for ethyl cyanoacetate ... . A 96 h LC50 of 59 mg/L was derived (Danio rerio). This test was conducted under flow-through conditions to ensure stability of the test concentration. The 48 hr EC50 for Daphnia magna was ... 471 mg/L for ethyl cyanoacetate (nominal concentration). The 72 hr ErC50 /median effective concentration for growth rate/ for algae (Scenedesmus subspicatus) was 142 mg/L (72 hr EbC50 /median effective concentration for biomass/ 72.4 mg/L) and the NOEC based on growth rate was 17 mg/L for ethyl cyanoacetate. It can reasonably be assumed that hydrolysis of the ester occurred in this study and the acid and the lowered pH have contributed considerably to the toxicity. Therefore the data of the ester are relevant for cyanoacetic acid as well.|/PLANTS/ No growth inhibition of ethyl cyanoacetate to terrestrial plants in soil was observed up to concentrations of >100 mg/kg soil (dry weight) and no toxicity to Eisenia fetida /(earthworm)/ was observed at concentrations of 1000 mg ethyl cyanoacetate /kg soil (dry weight) after 14 days of exposure.
Ethyl cyanoacetate's production and use in organic synthesis, pharmaceuticals, and dyes(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4(SRC), determined from a structure estimation method(2), indicates that ethyl cyanoacetate is expected to have very high mobility in soil(SRC). Volatilization of ethyl cyanoacetate from moist soil surfaces is expected to be a moderate fate process(SRC) given an estimated Henry's Law constant of 2.9X10-7 atm-cu m/mole(SRC), based upon its vapor pressure, 3.88X10-2 mm Hg(3), and water solubility, 2.0X10+4 mg/L(4). Ethyl cyanoacetate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). A 68% of its theoretical BOD in 28 days in the Japanese MITI test(5) indicates that biodegradation may be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4(SRC), determined from a structure estimation method(2), indicates that ethyl cyanoacetate 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 2.9X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 3.9X10-2 mm Hg(4), and water solubility, 2.0X10+4 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4 months and 2.7 years, respectively(SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 0.02(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 68% of its theoretical BOD in 28 days in the Japanese MITI test(9) indicates that biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl cyanoacetate, which has a vapor pressure of 3.88X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl cyanoacetate 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 6 days(SRC), calculated from its rate constant of 1.7X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Ethyl cyanoacetate does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of ethyl cyanoacetate with photochemically-produced hydroxyl radicals has been estimated as 1.7X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Ethyl cyanoacetate is expected to undergo hydrolysis in the environment due to the presence of functional groups that hydrolyze under environmental conditions(2). A base-catalyzed second-order hydrolysis rate constant of 11.8 L/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 7 days and 16 hours at pH values of 7 and 8, respectively(3). Ethyl cyanoacetate does not contains chromophores that absorb at wavelengths >290 nm(2), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3 was calculated in fish for ethyl cyanoacetate(SRC), using an estimated log Kow of 0.02(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 ethyl cyanoacetate can be estimated to be 4(SRC). According to a classification scheme(2), this estimated Koc value suggests that ethyl cyanoacetate is expected to have very high mobility in soil.
The Henry's Law constant for ethyl cyanoacetate is estimated as 2.9X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 3.88X10-2 mm Hg(1), and water solubility, 2.0X10+4 mg/L(2). This Henry's Law constant indicates that ethyl cyanoacetate is expected to volatilize slowly from water surfaces(3). 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)(3) is estimated as 4 months(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 2.7 years(SRC). Ethyl cyanoacetate's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Ethyl cyanoacetate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of ethyl cyanoacetate is 1 to 99; the data may be greatly underestimated(1).|Occupational exposure to ethyl cyanoacetate may occur through inhalation and dermal contact with this compound at workplaces where ethyl cyanoacetate is produced or used. (SRC)
Drug Information
From the physical chemical properties of both cyanoacetic acid and ethyl cyanoacetate it can be expected that both substances will be moderately absorbed by all exposure routes. A relatively even distribution between tissues and also to embryonic tissues of pregnant rats was observed after oral administration of cyanoacetic acid. A similar behavior can be expected for ethyl cyanoacetate.
Ethyl cyanoacetate is likely to be metabolized by unspecific esterases of different tissues, in particular in the liver to cyanoacetic acid and ethanol.
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)
Immediate first aid: 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. /Esters 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. Provide a low-stimulus environment. Monitor for shock 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 ... . Treat frostbite by rapid rewarming ... . /Esters and related compounds/|Advanced treatment: 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 ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . 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 ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Esters and related compounds/
ethyl cyanoacetate
Ethyl cyanoacetate Use and Manufacturing
The preparation method is obtained by the action of cyanoacetic acid and ethanol. The cyanoacetic acid, ethanol and catalyst sulfuric acid were added to the reactor to reflux for 3h, and the temperature was lowered to 10°C, then washed with water, separated into layers, dried, and distilled under reduced pressure to obtain a finished product. NCCH2COOH+C2H5OH[H2SO4]→NCCH2COOC2H5+H2O
Reagent used in labelled pyrimidine and purine synthesis.
Adhesives and sealant chemicals
Adhesives and sealants
500,000 - 1,000,000 lb|Acetic acid, cyano-, ethyl ester is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4168]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Acetic acid, 2-cyano-, ethyl ester. Aggregated National Production Volume: 1 to < 10 million lbs.
Grade: Reagent, technical
Adhesive manufacturing|Acetic acid, 2-cyano-, ethyl ester: ACTIVE|Method of purification: Vacuum distillation.|Ethyl cyanoacetate is the ethyl ester of cyanoacetic acid. Ethyl cyanoacetate hydrolyzes rapidly under neutral and alkaline conditions to cyanoacetic acid and ethanol (and so it does under most physiological and environmental conditions), while in acid pH the half life is considerably longer. It also is likely that unspecific esterases in the body catalyze the hydrolysis to cyanoacetic acid and ethanol, as it has been shown for the structurally related ethyl acetate, which is rapidly hydrolyzed in vitro and in vivo by various esterases to yield ethanol and acetic acid. Ethanol is a physiological substance that is metabolized via physiological pathways. Ethanol (CAS. 64-17- 5) was evaluated within the OECD HPV Chemicals Programme. It can be assumed that for most endpoints cyanoacetic acid will be the common metabolite that determines the toxicity of both substances. Furthermore the production and use pattern of both, ester and acid, are comparable. As the acid and the ester have different physical chemical properties due to their chemical nature, effects that are related to the acidity of the acid (e.g. ecotoxicity data, local irritating effects) have to be assessed separately. The environmental and toxicokinetic distribution can however be expected to range in a similar order of magnitude due to the similar polarity, vapor pressure and log Kow. The biodegradation behavior is also expected to be comparable as the ester is probably cleaved and the metabolites further degraded.
Fire Hazards -> Reactive - 1st degree
Computed Properties
Molecular Weight:113.11
XLogP3:0.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:113.047678466
Monoisotopic Mass:113.047678466
Topological Polar Surface Area:50.1
Heavy Atom Count:8
Complexity:122
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Price Analysis
- Data: 2026-08-15
- Price: 12000.00Yuan/ton
- Change: 0
Recommended Suppliers of Ethyl cyanoacetate
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Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, ethyl ester, (1alpha,3R,4alpha,5R)- (9CI)
463325-95-3
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260261-27-6
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3-CYCLOPROPYL-2-METHYL-3-OXO-PROPIONIC ACID ETHYL ESTER
21741-37-7
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Cyclopropanecarboxylic acid, 1-amino-2-phenyl-, ethyl ester, (1R,2R)-rel- (9CI) Formula
669058-57-5
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Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, ethyl ester, (1R,2S)-rel- (9CI) Formula
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Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, ethyl ester, hydrochloride (9CI) Formula
681807-60-3
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3-Cyclopentene-1-carboxylic acid, 1-(chlorocarbonyl)-, ethyl ester (9CI) Structure
76910-09-3
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Cyclopropanecarboxylic acid, 2-propyl-, ethyl ester, (1R,2S)- (9CI) Structure
492468-18-5
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What is Cyclopentanecarboxylic acid, 2-(formylhydrazono)-, ethyl ester, (Z)- (9CI)
163352-99-6
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What is 2-[(2,6-Dichlorophenyl)sulfonyl]acetic acid ethyl ester
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