|Molecular formula||C 5 H 9 NO|
|Density||911 kg/m³; 0,911 g/cm³|
|Molar mass||99.13 g / mol|
|Melting point||−22 °C (251 K)|
|Boiling point||171 °C (444 K)|
|Vapor pressure||2,5 mmHg|
|Refractive index (n D )||1,408|
|Solubility in water||230 g/L|
|Family||Nitrile , ether|
|Flash point||336,15 K (63 °C)|
|nitrilos|| hexanonitrile |
|dinitrilos|| 3,3'-oxidipropionitrilo |
|Values in the SI and under standard conditions|
(25 ℃ and 1 atm ), unless otherwise indicated.
The 3-ethoxypropionitrile , also called 3-etoxipropanonitrilo and 3-etoxipropiononitrilo , it is an organic compound of molecular formula C 5 H 9 N O . [ 2 ] Its chemical structure corresponds to a nitrile and an ether , being the atom of oxygen attached to an ethyl group and a cyanoethyl group (-CH 2 -CH 2 -C≡N).
Physical and chemical properties
At room temperature , 3-ethoxypropionitrile is a colorless liquid [ 3 ] with a density lower than that of water (ρ = 0.911 g / cm³ ). It has its boiling point at 171 ° C while its melting point is -22 ° C. The value of the logarithm of its partition coefficient , log P = 0.09, indicates a very similar solubility in polar solvents and in nonpolar solvents.. Its solubility in water is 230 g / L (estimated value). [ 4 ] [ 5 ]
Synthesis and uses
3-Ethoxypropionitrile can be synthesized by adding ethanol to acrylonitrile . To remove steric inhibition, this reaction must take place at high pressures in the presence of tributylphosphine as a catalyst . Even under these conditions, the chemical yield of the reaction is only 10%. [ 7 ] Also, the Heck reaction between iodobenzene and acrylonitrile catalyzed nanoparticles of Pd (0) stabilized by polyvinyl pyrrolidone(Pd-PVP) in ethanol , results in various phenyl- and diphenylpropionitriles in addition to 3-ethoxypropionitrile. [ 8 ]
In turn, 3-ethoxypropionitrile can be a precursor in the synthesis of ethyl cyanoacetate : it is reacted with O 2 , N -hydroxyphthalimide, acetonitrile and cobalt acetate tetrahydrate, the latter as a catalyst. [ 9 ]
The use of 3-ethoxypropionitrile has been proposed in the manufacture of organic electroluminescence devices, devices that consist of two electrodes with an organic layer arranged between them; said layer can be manufactured using a solution that includes the organic compound contained in the layer and an organic solvent . Among the solvents to be used are various nitriles such as valeronitrile , heptanonitrile or 3-ethoxypropionitrile. [ 11 ]
- CAS number
- [TZ4680000 3-Ethoxypropionitrile] (PubChem)
- 3-Ethoxypropionitrile (Chemical Book)
- 3-Ethoxypropionitrile (ChemSpider)
- 3-Ethoxypropiononitrile (EPA)
- 3-Ethoxypropionitrile. MSDS (Alfa Aesar)
- Jenner, G. (2001). «Synthesis of hindered functionalized ethers via high-pressure addition of alcohols to acrylic compounds». Tetrahedron Letters 42 (29): 4807-4810. Consultado el 3 de abril de 2017.
- Daniela de L. Martins; Heiddy M. Alvarez; Lúcia C.S. Aguiar; Octavio A.C. Antunes (2011). «Heck reactions catalyzed by Pd(0)-PVP nanoparticles under conventional and microwave heating». Applied Catalysis A: General 408 (1-2): 47-53. Consultado el 3 de abril de 2017.
- Method for producing cyanoacetic acid esters. Paul Hanselmann, Stefan Hildbrand (2004). Patente US 6700010 B1
- Umemoto, T.; Wada, T. (2004). «Oligoribonucleotide synthesis by the use of 1-(2-cyanoethoxy)ethyl (CEE) as a 2'-hydroxy protecting group». Nucleic Acids Symp Ser (Oxf) 48: 9-10. Consultado el 3 de abril de 2017.
- Method for producing electroluminescence device (2015). Kakimoto, H.; et al. Patente US 9,093,667