624-79-3

Usage

Uses

Used in Toxicology:
Ethyl isocyanide is used as a reagent in toxicology for the characterization of cytochrome P450 isozymes. It plays a crucial role in understanding the behavior and function of these enzymes, which are essential for the metabolism of various drugs and toxins in the body.
Used in Enzyme Research:
Ethyl isocyanide is used as a probe molecule in enzyme research, particularly for studying the properties of cytochrome P450 enzymes. When ethyl isocyanide interacts with the reduced form of cytochrome P450, it forms a characteristic optical difference spectrum with two peaks in the Soret region (type III). The pH equilibrium point, which is the pH at which the two peaks are of equal height, varies between different isozymes, providing valuable information about their structure and function.

Preparation

CAUTION: The reaction and distillation should be conducted behind a safety shield. Precautions for handling toxic cyanides should be observed.To a three-necked flask equipped with a condenser and ground glass stirrer (or Hershberg stirrer) is added 116 gm (0.75 mole) of ethyl iodide and 100 gm (0.75 mole) of silver cyanide. The mixture is refluxed for 2 hr, the stirrer blade raised, the mixture cooled, filtered (see Note a), the solid washed with ether, dried, and 260 gm of a 50% solution of potassium cyanide (2.0 moles) added. The reaction mixture is distilled to afford a mixture of isonitrile and water (see Note b). The crude isonitrile 49.5- 52.3 gm (90-95%) is separated after being salted out of the water. The isonitrile is washed twice with 24-ml portions of ice-cold saturated sodium chloride solution, dried over magnesium sulfate, and fractionally distilled, to afford 25.9-30.3 gm (47-55%), b.p. 77-79°C (760 mm Hg).

InChI:InChI=1/C3H5N/c1-3-4-2/h3H2,1H3

Upstream product

• 74-90-8 hydrogen cyanide 
• 74-85-1 ethene 
• 5014-40-4 N-chloro-N-ethylacetamide 
• 67-66-3 chloroform 
• 75-04-7 ethylamine 
• 5610-59-3 fulminic acid ; silver-salt 
• 75-03-6 ethyl iodide 
• 506-64-9 silver(I) cyanide 
• 542-85-8 Ethyl isothiocyanate 
• 554-70-1 triethylphosphine 
• 64-17-5 ethanol 
• 627-45-2 N-formylethylamine 
• 39150-84-0 N-Ethyl-formimidoylcyanid 
• 63442-64-8 bis(dimethylamino)malononitrile 

Downstream Products

• 73418-67-4 N-ethyl-5-methyl-2,4-dinitro-aniline 
• 25108-33-2 1-ethyl-1H-tetrazole 
• 74-90-8 hydrogen cyanide 
• 542-85-8 Ethyl isothiocyanate 
• 627-45-2 N-formylethylamine 
• 75-04-7 ethylamine 
• 64-18-6 formic acid 
• 107-12-0 propiononitrile 
• 115485-42-2 2,2,4,4-Tetraphenyl-5-aethyliminocyclopentan-1,3-dion 
• 339551-11-0 4-methyl-5-styryl-4,5-dihydro-oxazole 
• 74-87-3 methylene chloride 
• 148759-19-7 6-chloro-4,5-diimino-6-(methylthio)-1,6-dihydro-2-pyrimidinethione 
• 124-38-9 carbon dioxide 
• 10035-10-6 hydrogen bromide 

Relevant academic research and scientific papers

Ortho Amides, XLVI. - Contributions to the Chemistry of Bis(dialkylamino)malononitriles

The reaction of chloroformamidinium chlorides 2 with sodium cyanide in the two-phase system ether/water affords bis(dialkylamino)malononitriles 3 with good yields.From 3a and morpholine or aniline the guanidines 5 and 6 can be obtained, respectively.Alcohol-free sodium ethoxide transforms 3a into the urea acetal 10b, whereas in the reaction of 3a with alkoxides in alcohol ortho carbamic esters 11a, b are produced.The malonic esters and acetoacetic esters 12 react with 3a in the presence of two equivalents of sodium hydride to give the ketene aminals 13.The reactionof 3a with malononitrile furnishes the guanidinium salt 14, which cyclized by hydrogen chloride to the pyridinetricarbonitrile 15.In the presence of sodium hydride, 3a and malononitrile or cyanoacetic esters 17 from the ketene aminal 16 and the 1,2,3-tricyanopropenides 18a-c, respectively.The analogous salts 20 and 21 result from the reaction of 3a with the barbituric acid derivatives 19a, and b, respectively.Hydrogen chloride reacts in ether with 3a to afford the piperazinetetracarbonitrile 22.Reaction of carboxylic acid chlorides yields the cyanoformamidinium salt 28a; byproducts are acyl cyanides 29 and dimeric acyl cyanides 30.Triethyloxonium tetrafluoroborate transforms 3a into the salt 28b.Bromine and iodine react with 3a to produce the salts 28c, d and 28e, f, respectively, depending on the stoichiometric ratios of the starting materials.The thiocyanate 28g is prepared from sulfur and 3a.

The Question of Tautomerism of Alkylnitrile and Isonitrile Cations

The isomeric pairs+. and +. and +. and +. have been established as stable, noninterconverting structures.The conclusion derives from studies of collision induced decomposition spectra.The same conclusion pertains for the ions +. and +., and for +., +. and HNCCHCHCNH>+..The energy barrier of a -hydrogen shift, a possible isomerization mechanism, is determined to be at least 163kJ mol-1 for the +. and +. pair, and the barrier may be as high as 318kJ*mol-1.The C3H5N and C4H4N2 radical cations decompose before they can be activated with 318 kJ mol-1 of internal energy.