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Aminoacetonitrile

Aminoacetonitrile is the organic compound 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 derivative, i.e., [NCCH2NH3]+Cl− and [NCCH2NH3]+HSO4−.{{cite book|chapter=2-Aminoacetonitrile

Production and applications

Industrially aminoacetonitrile is produced from glycolonitrile by reaction with ammonia: :HOCH2CN + NH3 → H2NCH2CN + H2O The aminoacetonitrile can be hydrolysed to give glycine: 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, aminoacetonitrile was discovered in the Large Molecule Heimat, 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

References

  1. [[International Union of Pure and Applied Chemistry]]. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013". [[Royal Society of Chemistry.
  2. (2016). "CRC Handbook of Chemistry and Physics". [[CRC Press]].
  3. (2002). "Nitriles".
  4. (2008). "A new class of anthelmintics effective against drug-resistant nematodes". Nature.
  5. (2008). "Detection of amino acetonitrile in Sgr B2(N)". Astronomy and Astrophysics.
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