Aminoacetonitrile

Aminoacetonitrile

Aminoacetonitrile

Chemical compound

Aminoacetonitrile is the organic compound with the formula H2N−CH2−C≡N. 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−.[3]

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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:[4] Being bifunctional, it is useful in the synthesis of diverse nitrogen-containing heterocycles.[3]

Aminoacetonitrile derivatives are useful antihelmintics. They act as nematode specific ACh agonists[5] 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.[6] This discovery is significant to the debate on whether glycine exists widely in the universe.

References

  1. [1]
    International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. pp. 902−903. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. [2]
    Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 978-1498754286.
  3. [3]
    Tauber, Johannes; Opatz, Till (2015). "2-Aminoacetonitrile". E-EROS Encyclopedia of Reagents for Organic Synthesis: 1–4. doi:10.1002/047084289X.rn01752. ISBN 9780470842898.
  4. [4]
    Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2002). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_363. ISBN 978-3527306732.
  5. [5]
    Kaminsky, R.; Ducray, P.; Jung, M.; Clover, R.; Rufener, L.; Bouvier, J.; Weber, S. S.; Wenger, A.; Wieland-Berghausen, S.; et al. (2008). "A new class of anthelmintics effective against drug-resistant nematodes". Nature. 452 (7184): 176–180. Bibcode:2008Natur.452..176K. doi:10.1038/nature06722. PMID 18337814. S2CID 4428834.
  6. [6]
    Belloche, A.; Menten, K. M.; Comito, C.; Müller, H. S. P.; Schilke, P.; Ott, J.; Thorwirth, S.; Hieret, C. (2008). "Detection of amino acetonitrile in Sgr B2(N)" (PDF). Astronomy and Astrophysics. 482 (1): 179–196. arXiv:0801.3219. Bibcode:2008A&A...482..179B. doi:10.1051/0004-6361:20079203. S2CID 21809828.
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