105-56-6 Usage
Description
Ethyl cyanoacetate, also known as the ethyl ester of cyanoacetic acid, is a colorless to straw-colored liquid with a mild pleasant odor. It is denser than water and may irritate skin, eyes, and mucous membranes upon contact. Ethyl cyanoacetate hydrolyzes rapidly under neutral and alkaline conditions to cyanoacetic acid and ethanol, and it may be toxic by ingestion. It is primarily used to make other chemicals.
Uses
1. Used in Chemical Synthesis:
Ethyl cyanoacetate is used as a reagent for the synthesis of ethyl glyoxylate, which is an important intermediate in the production of various chemicals and pharmaceuticals.
2. Used in Organic Chemistry:
Ethyl cyanoacetate is used as a reagent in the Knoevenagel condensation reactions, a carbon-carbon bond-forming reaction that involves the condensation of an active methylene compound with an aldehyde or a ketone. It was used to investigate the Knoevenagel condensation reactions in microreactors using zeolite catalysts obtained by grafting amino groups onto NaX and CsNaX zeolites.
3. Used in Labelled Pyrimidine and Purine Synthesis:
Ethyl cyanoacetate is employed as a reagent in the synthesis of labelled pyrimidine and purine compounds, which are essential for various research applications in biochemistry and molecular biology.
4. Used in Pharmaceutical Industry:
Ethyl cyanoacetate may be used in the development of new drugs and pharmaceutical compounds, given its role in the synthesis of various chemical intermediates.
Preparation
Ethyl 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.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
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.
Hazard
Toxic by ingestion and inhalation.
Health Hazard
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 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 Hazard
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.
Safety Profile
oison 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 Exposure
A nitrile used to manufacture dyes,
pharmaceuticals, and other chemicals.
Purification Methods
Shake the ester several times with aqueous 10% Na2CO3, wash it well with water, dry with Na2SO4 and fractionally distil it. [Beilstein 2 IV 1889.]
Incompatibilities
Incompatible 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 Disposal
Consult 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.
Check Digit Verification of cas no
The CAS Registry Mumber 105-56-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 5 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 105-56:
(5*1)+(4*0)+(3*5)+(2*5)+(1*6)=36
36 % 10 = 6
So 105-56-6 is a valid CAS Registry Number.
InChI:InChI:1S/C5H7NO2/c1-2-8-5(7)3-4-6/h2-3H2,1H3
105-56-6Relevant articles and documents
Synthesis of novel semi-squaraine derivatives and application in efficient dye-sensitized solar cells
Kabanakis, Antonios N.,Bidikoudi, Maria,Elsenety, Mohamed M.,Vougioukalakis, Georgios C.,Falaras, Polycarpos
, p. 308 - 318 (2019)
A series of novel semi-squaraine sensitizers with various architectures and anchors have been synthesized and utilized in dye-sensitized solar cells. These dyes combine indole- or carboline-based electron rich units with strongly electron-withdrawing cyanoacetate moieties or other functional anchoring moieties. They were thoroughly characterized as per their structural, optical and electrochemical properties and the behavior of the as-prepared solar cells were examined in detail using linear sweep voltammetry, electrochemical impedance spectroscopy and DFT calculations. Amongst the herein reported dyes, AKSq1, incorporating a free hydroxyl group directly attached to the squarate ring, exerts the optimum performance in dye-sensitized solar cells, despite the fact that this dye presents the lowest extinction coefficient among the molecules under study. AKSq1 demonstrates power conversion efficiency of 2.63%, about 14% higher than the efficiency obtained with the corresponding reference dye, the commercially available, high-performance, metal-free dye D35, under the same cell fabrication and measuring conditions. This result is attributed to the presence of free squaryl hydroxyl moiety ensuring efficient dye chemisorption and the existence of a lipophilic dodecyl group preventing the aggregation of the squaraine sensitizer onto the semiconductor's surface either by itself, or via increased intercalation of the C12 chain with the chenodeoxycholic acid coadsorbent.
-
Smith,McGrath
, p. 395 (1976)
-
NITROAZINES 25. SPECTRAL STUDY OF THE REACTION OF THE TRANSFORMATION OF 6-NITROAZOLOPYRIMIDINES BY CH-ACTIVE NITRILES
Rusinov, V. L.,Pilicheva, T. L.,Tumashov, A. A.,Egorova, L. G.,Chupakhin, O. N.
, p. 213 - 217 (1994)
The methods of 1H and 13C NMR and UV spectroscopy were utilized to investigate the structure of products of the transformation of 6-nitroazolopyrimidines by CH-active nitriles.The mechanism of reactions is discussed.
PROCESS FOR PREPARING CYANOACETATES
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Paragraph 0041; 0044-0045, (2021/06/22)
This invention relates to a process for producing cyanoacetates involving contacting a salt of an alkyl, alkenyl, alkynyl or aryl formyl acetate with a hydroxyl amine acid under appropriate conditions and for a time sufficient to yield a cyanoacetate.
PROCESS FOR PREPARING CYANOACETATES
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Paragraph 0027-0030, (2020/10/27)
This invention relates to a process for producing cyanoacetates using a cyanoacetamide as a precursor.