3-Aminocrotononitrile

Chemical Properties

Yellowish flakes. 3-Amino-3-methylacrylonitrile [1118-61- 2], b-iminobutyronitrile, b-aminocrotononitrile, diacetonitrile, 3-amino-2-butenenitrile, NCCH=C (NH2) CH3, Mr 82.11, mp (cis-form) 79 – 83℃, mp (trans-form) 52 – 53℃, d774 0.9519, is a yellowish solid soluble in ethanol and diethyl ether; it is sparingly soluble in benzene and water.

Uses

3-Aminocrotononitrile is used as intermediate for the syntheses of heterocycles (e.g. pyridines and pyrimidines) and for the production of polyurethane). It is used in the pharmaceutical (e.g. production of sulfsomizole) and dyestuff industries. Product Data Sheet

Uses

3-Aminocrotononitrile reacts with ferrocenyl-1,2-enones to form ferrocenyl pyridines. It undergoes diazotization coupling reaction with p-substituted anilines to give 2-arylhydrazone-3-ketimino-butyronitriles.3-Aminocrotononitrile, (E)+(Z), is used in reaction with aryldiazonium salts gave, instead of the expected triazene, 2-arylhydrazono-3-ketobutyronitrile by electrophilic attack at the -carbon and hydrolysis of the resulting imine. It is also used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. 3-Aminocrotononitrile was used as bisnucleophilic reagent which on cyclocondensation with hexafluoroacetone(ethoxycarbonylimine) forms bis(trifluoromethyl)pyrimidinones.

Biochem/physiol Actions

3-Aminocrotononitrile reacts with ferrocenyl-1,2-enones to form ferrocenyl pyridines. It undergoes diazotization coupling reaction with p-substituted anilines to give 2-arylhydrazone-3-ketimino-butyronitriles.