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105-56-6

Basic Information
CAS No.: 105-56-6
Name: Ethyl cyanoacetate
Article Data: 109
Cas Database
Molecular Structure:
Molecular Structure of 105-56-6 (Ethyl cyanoacetate)
Formula: C5H7NO2
Molecular Weight: 113.116
Synonyms: Ethyl cyanoacetate [UN2666] [Keep away from food];Ethylester kyseliny kyanoctove [Czech];Cyanoacetic ester;Cyanoacetic acid, ethyl ester;Stearate Methyl;Cyanoacetic acid ethyl ester;Cyanacetate ethyle [German];Usaf kf-25;Malonic acid ethyl ester nitrile;Malonic acid, ethyl ester nitrile;Ethyl cyanacetate;Estere cianoacetico [Italian];ethyl 2-cyanoacetate;Ethyl cyanoethanoate;Acetic acid, cyano-, ethyl ester;Cyanacetate ethyle;
EINECS: 203-309-0
Density: 1.047 g/cm3
Melting Point: -22 °C
Boiling Point: 203.6 °C at 760 mmHg
Flash Point: 84.1 °C
Solubility: 20 g/L (20 °C) in water
Appearance: Clear to very yellow liquid
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 20/21/22-36/38
Safety: 36/37/39-26
Transport Information: UN 3276
PSA: 50.09000
LogP: 0.46318
Synthetic route
2141-62-0

3-(ethoxy)propionitrile

105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With N-hydroxyphthalimide; cobalt(II) acetate In acetonitrile at 190℃; under 6750.68 Torr; for 7h;

sodium 3-ethoxy-3-oxoprop-1-en-1-olate

105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With hydroxylamine hydrochloride In ethanol at 90℃; for 4h; pH=2; pH-value; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;81%
64-17-5

ethanol

372-09-8

cyanoacetic acid

105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With sulfuric acid In dichloromethane for 18h; Heating;95%
With sulfuric acid In dichloromethane for 18h; Reflux; Dean-Stark;95%
With sulfuric acid; sulfur trioxide at 20 - 70℃; for 4h; Temperature; Reflux;93.6%
74-90-8

hydrogen cyanide

105-39-5

chloroacetic acid ethyl ester

105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With triethylamine at 15℃; for 4.83333h; Concentration; Reagent/catalyst; Solvent; Temperature; Time;94.2%
773837-37-9

sodium cyanide

105-39-5

chloroacetic acid ethyl ester

A

10359-15-6

diethyl 2-cyanosuccinate

B

20822-61-1

triethyl 2-cyano-1,2,3-propanetricarboxylate

C

105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With tetrabutylammomium bromide In dichloromethane; water at 20℃; for 4h;A 10.4%
B 5.4%
C 44%
64-17-5

ethanol

107-91-5

cyanoacetic acid amide

105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With sulfuric acid for 3h; Time; Reflux;97%
With sulfuric acid for 3h; Reflux;97%
773837-37-9

sodium cyanide

74-90-8

hydrogen cyanide

105-39-5

chloroacetic acid ethyl ester

105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With tetrabutylammomium bromide In water; acetonitrile at 55℃; for 2h; Product distribution / selectivity;93.2%
64-17-5

ethanol

372-09-8

cyanoacetic acid

A

105-56-6

ethyl 2-cyanoacetate

B

105-53-3

diethyl malonate

Conditions
ConditionsYield
With sulfuric acid In hexane; ethyl acetate at 30 - 62℃; for 5h; Temperature; Solvent; Dean-Stark;A 105.2 g
B 1.8 g
21860-86-6

aspartic acid 4-ethyl ester

105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With trichloroisocyanuric acid; sodium hydroxide In water at 20℃; for 6h; Temperature;85%
75-05-8

acetonitrile

105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With sodium ethanolate; sodium amide; Diethyl carbonate at 140 - 160℃;
With sodium ethanolate; sodium amide; Diethyl carbonate at 140 - 160℃;
With sodium ethanolate; sodium amide; Diethyl carbonate at 140 - 160℃;
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Analytical Methods

  Ethyl cyanoacetate (CAS No.105-56-6) is both a nitrile and an ester.
  As esters , it can 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.
  As nitriles Ethyl cyanoacetate (CAS No.105-56-6) is 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.

Specification

The CAS registry number of Ethyl cyanoacetate is 105-56-6. Its EINECS registry number is 203-309-0. The IUPAC name is ethyl 2-cyanoacetate. In addition, the molecular formula is C5H7NO2 and the molecular weight is 113.11. What's more, it belongs to the classes of Pharmaceutical Intermediates; EQ - EZ Analytical Standards; Esters Analytical Standards; Nitriles; Volatiles/ Semivolatiles. It can be used as intermediates in the preparation of vitamin B6 and caffeine. Besides, it also can be used as raw materials for organic synthesis.

Physical properties about this chemical are: (1)ACD/LogP: 0.06; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 3; (7)#Freely Rotating Bonds: 3; (8)Polar Surface Area: 50.09 Å2; (9)Index of Refraction: 1.412; (10)Molar Refractivity: 26.9 cm3; (11)Molar Volume: 107.9 cm3; (12)Polarizability: 10.66 ×10-24cm3; (13)Surface Tension: 35.8 dyne/cm; (14)Density: 1.047 g/cm3; (15)Flash Point: 84.1 °C; (16)Enthalpy of Vaporization: 43.99 kJ/mol; (17)Boiling Point: 203.6 °C at 760 mmHg; (18)Vapour Pressure: 0.275 mmHg at 25°C .

Preparation of Ethyl cyanoacetate: it can be prepared by ethyl chloroacetate and sodium cyanide. The ethyl chloroacetate can be obtained by chloroacetic acid and ethanol through esterification reaction. The equation is as follows:

Ethyl cyanoacetate can be prepared by ethyl chloroacetate and sodium cyanide

Uses of Ethyl cyanoacetate: it can react with 2-hydroxy-benzaldehyde to get 2-imino-2H-chromene-3-carboxylic acid ethyl ester. This reaction will need catalyst AlPO4-Al2O3. The reaction time is 1 hour with ambient temperature. The yield is about 58%.

Ethyl cyanoacetate can react with 2-hydroxy-benzaldehyde to get 2-imino-2H-chromene-3-carboxylic acid ethyl ester

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: N#CCC(=O)OCC
(2)InChI: InChI=1/C5H7NO2/c1-2-8-5(7)3-4-6/h2-3H2,1H3
(3)InChIKey: ZIUSEGSNTOUIPT-UHFFFAOYAI

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo subcutaneous 4200mg/kg (4200mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 5, Pg. 161, 1899.
guinea pig LD50 subcutaneous 1115mg/kg (1115mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

GASTROINTESTINAL: NAUSEA OR VOMITING
Medicina del Lavoro. Industrial Medicine. Vol. 47, Pg. 192, 1956.
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   National Technical Information Service. Vol. AD277-689,
rabbit LDLo subcutaneous 1410mg/kg (1410mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 5, Pg. 161, 1899.
rat LDLo oral 400mg/kg (400mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 921, 1986.