Aminoacetonitrile is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula . The compound is a colorless liquid. It is unstable at room temperature, owing to the incompatibility of the amine nucleophile and the nitrile electrophile. For this reason it is usually encountered as the chloride and bisulfate salts of the

ammonium Ammonium is a modified form of ammonia that has an extra hydrogen atom. It is a positively charged (cationic) polyatomic ion, molecular ion with the chemical formula or . It is formed by the protonation, addition of a proton (a hydrogen nucleu ...

derivative, i.e., CCH₂NH₃sup>+Cl⁻ and CCH₂NH₃sup>+HSO₄⁻.

Production and applications

Industrially aminoacetonitrile is produced from

glycolonitrile Glycolonitrile, also called hydroxyacetonitrile or formaldehyde cyanohydrin, is the organic compound with the formula HOCH2CN. It is the simplest cyanohydrin and it is derived from formaldehyde. It is a colourless liquid that dissolves in water an ...

by reaction with ammonia: :HOCH₂CN + NH₃ → H₂NCH₂CN + H₂O The aminoacetonitrile can be hydrolysed to give

glycine Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid. Glycine is one of the proteinogenic amino acids. It is encoded by all the codons starting with GG (G ...

: Being bifunctional, it is useful in the synthesis of diverse nitrogen-containing heterocycles. Aminoacetonitrile derivatives are useful antihelmintics. They act as nematode specific ACh agonists causing a spastic paralysis and rapid expulsion from the host.

Occurrence in the interstellar medium

Using

radio astronomy Radio astronomy is a subfield of astronomy that studies Astronomical object, celestial objects using radio waves. It started in 1933, when Karl Jansky at Bell Telephone Laboratories reported radiation coming from the Milky Way. Subsequent observat ...

, aminoacetonitrile was discovered in the Large Molecule Heimat, a giant gas cloud near the

Galactic Center The Galactic Center is the barycenter of the Milky Way and a corresponding point on the rotational axis of the galaxy. Its central massive object is a supermassive black hole of about 4 million solar masses, which is called Sagittarius A*, a ...

in the constellation Sagittarius. This discovery is significant to the debate on whether glycine exists widely in the universe.

References

External links

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National Institute of Standards and Technology The National Institute of Standards and Technology (NIST) is an agency of the United States Department of Commerce whose mission is to promote American innovation and industrial competitiveness. NIST's activities are organized into Outline of p ...

(NIST) {{Molecules detected in outer space Nitriles Amines