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Ethyl cyanoacetate

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Identification
Molecular formula
C5H7NO2
CAS number
105-56-6
IUPAC name
ethyl 2-cyanoacetate
State
State

At room temperature, ethyl cyanoacetate is typically found as a liquid.

Melting point (Celsius)
-17.00
Melting point (Kelvin)
256.15
Boiling point (Celsius)
206.50
Boiling point (Kelvin)
479.65
General information
Molecular weight
113.12g/mol
Molar mass
113.1160g/mol
Density
1.0558g/cm3
Appearence

Ethyl cyanoacetate is a colorless to slightly yellow liquid. It may emit an odor that is described as fruity or sweet.

Comment on solubility

Solubility of Ethyl 2-Cyanoacetate

Ethyl 2-cyanoacetate, with the chemical formula C5H7N1O2, is known for its interesting solubility properties. This compound is considered to be:

  • Soluble in organic solvents: Ethyl 2-cyanoacetate shows good solubility in aprotic solvents such as dimethyl sulfoxide (DMSO), ethanol, and acetone, which makes it suitable for various organic reactions.
  • Limited solubility in water: This compound has low solubility in water due to its hydrophobic ethyl group and the electron-withdrawing cyano group which reduces its interaction with polar water molecules.
  • Polarity considerations: The solubility behavior can be attributed to the compound’s polarity. The cyano group (-C≡N) is quite polar, yet the overall molecule's hydrophobic characteristics dominate in aqueous solutions.

As a result, one can generally say that while ethyl 2-cyanoacetate may be readily utilized in organic synthesis, care should be taken when considering its use in aqueous environments due to its limited solubility. Therefore, understanding these solubility attributes is crucial for effective experimental design and applications in chemistry.

Interesting facts

Interesting Facts about Ethyl 2-Cyanoacetate

Ethyl 2-cyanoacetate is a fascinating compound that plays an important role in organic synthesis and the field of medicinal chemistry. Known for its versatile reactivity, this compound is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals. Here are some compelling aspects of ethyl 2-cyanoacetate:

  • Versatile Reagent: Ethyl 2-cyanoacetate serves as a key intermediate in the synthesis of α-amino acids, which are essential for protein synthesis in living organisms.
  • Synthesis of Heterocycles: This compound can facilitate the formation of diverse heterocyclic compounds, which are crucial in the development of many drugs and agrochemicals.
  • Reaction Types: Ethyl 2-cyanoacetate is involved in a variety of reactions such as Michael additions and cyclocondensations, showcasing its versatility in chemical transformations.
  • Biological Activity: There is ongoing research into the potential biological activities of derivatives of ethyl 2-cyanoacetate, which may yield new pharmaceutical developments.
  • Common Use in Synthesis: It is frequently employed in the synthesis of other important compounds, including barbiturates, which are known for their sedative and anesthetic properties.

As one of the most important building blocks in organic chemistry, ethyl 2-cyanoacetate exemplifies the intricate relationship between chemical synthesis and the discovery of new medicinal compounds. Its utility in various chemical reactions makes it an essential compound in both academic and industrial settings.

Through exploring its chemistry and applications, scientists continue to unlock the potential of this compound to contribute to advancements in health and agriculture.

Synonyms
ETHYL CYANOACETATE
105-56-6
Ethyl 2-cyanoacetate
Ethyl cyanacetate
Cyanoacetic ester
Cyanoacetic acid ethyl ester
Ethyl cyanoethanoate
Acetic acid, cyano-, ethyl ester
Cyanacetate ethyle
USAF KF-25
Estere cianoacetico
ethyl cyano acetate
Cyanacetate ethyle [German]
NSC 8844
Ethylester kyseliny kyanoctove
Cyanoacetic acid, ethyl ester
Estere cianoacetico [Italian]
ETHYLCYANOACETATE
2-cyanoacetic acid ethyl ester
Malonic acid ethyl ester nitrile
HSDB 2769
EINECS 203-309-0
UN2666
Ethylester kyseliny kyanoctove [Czech]
UNII-X9N006U0F8
BRN 0605871
ethyl-2-cyanoacetate
DTXSID9026718
AI3-19027
Malonic acid, ethyl ester nitrile
ethyl alpha-cyanoacetate
X9N006U0F8
NSC-8844
NCCH2COOC2H5
Acetic acid, 2-cyano-, ethyl ester
DTXCID506718
ETHYL CYANOACETATE [MI]
Ethyl ester of cyanoacetic acid
ACID ETHYL ESTER NITRILE
ETHYL CYANOACETATE [HSDB]
EC 203-309-0
ACETIC ACID,CYANO,ETHYL ESTER
MFCD00001940
UN 2666
Ethyl2-Cyanoacetate-13C15N
CYANACETATE ETHYLE (GERMAN)
ethyl-cyanoacetate
ethyl 2 cyanoacetate
ethyl cyanoacetic acid
ethyl 2-cyanoethanoate
cyanoacetic acid ethylester
cyano acetic acid ethylester
WLN: NC1VO2
SCHEMBL70685
cyano acetic acid ethyl ester
cyano-acetic acid ethyl ester
Ethyl cyanoacetate, >=98%
CHEMBL3186698
Acetic acid, cyano, ethyl ester
ethyl cyanoacetate, 14C-labeled
NSC8844
Acetic acid,2-cyano-, ethyl ester
BCP25865
STR00038
Tox21_200434
BBL012203
STL163545
AKOS000118956
NCGC00248613-01
NCGC00257988-01
CAS-105-56-6
DB-012763
NS00008396
EN300-19206
C90336
Ethyl 2-cyanoacetate;Cyanoacetic acid ethyl ester
Q1146961
Ethyl cyanoacetate [UN2666] [Keep away from food]
F0001-0108
203-309-0