Aminoacetonitrile is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula NCCH₂NH₂. 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 The ammonium cation is a positively-charged polyatomic ion with the chemical formula or . It is formed by the protonation of ammonia (). Ammonium is also a general name for positively charged or protonated substituted amines and quaternary a ...

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 (carbamic acid is unstable), with the chemical formula NH2‐ CH2‐ COOH. Glycine is one of the proteinogeni ...

: Being bifunctional, it is useful in the synthesis of diverse nitrogen-containing

heterocycle A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different chemical element, elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis ...

s. 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 celestial objects at radio frequencies. The first detection of radio waves from an astronomical object was in 1933, when Karl Jansky at Bell Telephone Laboratories reported radiation coming f ...

, aminoacetonitrile was discovered in the

Large Molecule Heimat The Large Molecule Heimat is a dense gas cloud located in the molecular cloud Sagittarius B2. Many species of molecule, including aminoacetonitrile (a molecule related to glycine), ethyl formate, and butyronitrile Butyronitrile or butanenitril ...

, a giant gas cloud near the galactic center 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 physical sci ...

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