Ethyl cyanoacetate

Ethyl cyanoacetate Basic information
Product Name:Ethyl cyanoacetate
Synonyms:2-cyano-aceticacidethylester;Acetic acid,2-cyano-, ethyl ester;Aceticacid,cyano-,ethylester;Cyanacetate ethyle;cyanacetateethyle;ethylcyanacetate;Ethylcyanoacetat;Ethylester kyseliny kyanoctove
CAS:105-56-6
MF:C5H7NO2
MW:113.11
EINECS:203-309-0
Product Categories:C2 to C5;Carbonyl Compounds;Esters;Alpha Sort;Chemical Class;E;Pharmaceutical Intermediates;E-LAlphabetic;EQ - EZAnalytical Standards;EstersAnalytical Standards;Nitriles;Volatiles/ Semivolatiles;organic chemical;Halogenated Heterocycles;1
Mol File:105-56-6.mol
Ethyl cyanoacetate Structure
Ethyl cyanoacetate Chemical Properties
Melting point -22 °C (lit.)
Boiling point 208-210 °C (lit.)
density 1.063 g/mL at 25 °C (lit.)
vapor density 3.9 (vs air)
vapor pressure 1 mm Hg ( 67.8 °C)
refractive index n20/D 1.418(lit.)
Fp >230 °F
storage temp. Store below +30°C.
solubility 20g/l
form Liquid
pka3.19±0.10(Predicted)
color Clear
Water Solubility 20 g/L (20 ºC)
Merck 14,3786
BRN 605871
LogP-0.119-1.05 at 23-25℃ and pH6.1
Surface tension70.2mN/m at 1.034g/L and 23℃
CAS DataBase Reference105-56-6(CAS DataBase Reference)
NIST Chemistry ReferenceAcetic acid, cyano-, ethyl ester(105-56-6)
EPA Substance Registry SystemEthyl cyanoacetate (105-56-6)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 20/21/22-36/38
Safety Statements 36/37-37/39-26
RIDADR 3276
WGK Germany 1
RTECS AG4110000
10
Autoignition Temperature460 °C
TSCA Yes
HS Code 2926 90 70
Hazardous Substances Data105-56-6(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: > 2000 mg/kg
MSDS Information
ProviderLanguage
Ethyl 2-cyanoacetate English
SigmaAldrich English
ACROS English
ALFA English
Ethyl cyanoacetate Usage And Synthesis
DescriptionEthyl cyanoacetate is the ethyl ester of cyanoacetic acid. Ethyl cyanoacetate hydrolizes 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.
Knoevenagel condensation of ethyl cyanoacetate with aldehyde is reported. Microwave enhanced Knoevenegal condensation reaction of ethyl cyanoacetate with an aldehyde, P2O5, piperidine and chlorobenzene is reported.
Chemical PropertiesEthyl cyanoacetate is a colorless to straw colored liquid with a mild pleasant odor
UsesEthyl cyanoacetate may be used in the synthesis of ethyl glyoxylate. It was used to investigate the Knoevenagel condensation reactions in microreactor using zeolite catalysts obtained by grafting amino groups onto NaX and CsNaX zeolites.
UsesReagent used in labelled pyrimidine and purine synthesis. Ethyl cyanoacetate is an ester. It may be used in the synthesis of ethyl glyoxylate.It was used to investigate the Knoevenagel condensation reactions in microreactor using zeolite catalysts obtained by grafting amino groups onto NaX and CsNaX zeolites.
PreparationEthyl cyanoacetate can be prepared by the action of sodium or potassium cyanide on ethyl chloroacetate, and by the action of sodium cyanide on sodium chloroacetate, followed by esterification.
General DescriptionA 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.
Air & Water ReactionsSlightly soluble in water.
Reactivity ProfileEthyl 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.
HazardToxic by ingestion and inhalation.
Health HazardTOXIC; 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 that 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.
Fire HazardCombustible 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.
Safety Profileoison by ingestion. Moderately toxic by intraperitoneal and subcutaneous routes. Combustible when exposed to heat or flame; can react with oxidzing materials. Wdl react with water or steam to produce toxic and flammable vapors. To fight fire, use CO2, dry chemical. When heated to decomposition or on contact with acid or acid fumes it emits highly toxic fumes of CN-. See also NITRILES.
Potential ExposureA nitrile used to manufacture dyes, pharmaceuticals, and other chemicals.
ShippingUN3276 Nitriles, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required, Potential Inhalation Hazard (Special Provision 5).
Purification MethodsShake the ester several times with aqueous 10% Na2CO3, wash it well with water, dry with Na2SO4 and fractionally distil it. [Beilstein 2 IV 1889.]
IncompatibilitiesIncompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, and reducing agents. 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. Reacts with moisture, water, and steam, forming toxic fumes.
Waste DisposalConsult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.
Ethyl cyanoacetate Preparation Products And Raw materials
Raw materialsEthanol-->Hydrochloric acid-->Sulfuric acid-->Sodium cyanide-->Chloroacetic acid-->Ethyl chloroacetate-->Sodium chloroacetate-->Cyanoacetic acid
Preparation ProductsEthyl 4-amino-2-(ethylthio)-5-pyrimidinecarboxylate-->2-AMINO-5-ISOPROPYL-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER-->2-AMINO-4-ETHYL-5-METHYL-THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER-->Dacarbazine-->Triamterene-->2-AMINO-4,6-DIMETHYL-3-PYRIDINECARBOXAMIDE-->Allopurinol-->5-AMINO-4-CYANO-3-METHYL-THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER-->6-AMINO-2-MERCAPTO-PYRIMIDIN-4-OL-->3-AMINO-2,2-DIMETHYL-1-PROPANOL-->ETHYL 2-AMINO-4,5-DIMETHYLTHIOPHENE-3-CARBOXYLATE-->1-Cyclohexyl-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbonitrile ,97%-->6-AMINO-3-METHYLURACIL-->2-AMINO-6-METHYL-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER-->1,2,3,5-TETRAHYDRO-8-THIA-5,7-DIAZA-CYCLOPENTA[A]INDENE-4-ONE-->5,6-Diamino-1-methyluracil-->6-AMINO-2-METHYLTHIO-3-METHYLURACIL-->5-CYANO-6-HYDROXY-4-METHOXYMETHYL-2-METHYLPYRIDINE-->GUANINE SULFATE-->6-AMINO-1-METHYL-5-NITROSOURACIL-->6-CHLORO-5-CYANO-4-METHOXYMETHYL-3-NITRO-2-PICOLINE-->Ethyl α-cyanoacrylate instantaneous adhesive-->2-CHLORO-4-METHYLQUINOLINE-3-CARBONITRILE-->ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE-->6-Amino-1-methyluracil-->2-Amino-4-trifluoromethylbenzonitrile-->ETHYL 5-AMINO-1-PYRIDIN-2-YL-1H-PYRAZOLE-4-CARBOXYLATE-->2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER-->2-(4,6-diamino-1,3,5-triazin-2-yl)acetic acid-->5-AMINO-3-METHYL-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER-->1-ETHYL-1-METHYLSUCCINIC ACID-->6-Aminouracil-->Disperse Yellow S-3GL-->Amiloride hydrochloride-->ETHYL 2-CYANO-3-METHYL-2-PENTENOATE-->ETHYL(Z)-2-CYANO-3-ETHOXY-2-PROPENOATE-->4-Amino-6-hydroxy-2-mercaptopyrimidine monohydrate
Cyanoacetic acid Ethyl acetoacetate Trinexapac-ethyl Ethanol Ethyl propionate Ethyl formate Tetraethyl orthosilicate METHOXY ETHYL CYANOACETATE Ethylparaben Ethyl cyanoglyoxylate-2-oxime ISOXADIFEN-ETHYL 2-Ethoxyethanol Diethyl ether Ethyl isocyanoacetate Ethyl acetate Ethyl acrylate Ethyl (ethoxymethylene)cyanoacetate Ethyl cyanoacetate

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