Aminoacetonitrile

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Aminoacetonitrile
Skeletal formula of aminoacetonitrile with an implicit carbon shown
Stereo, skeletal formula of aminoacetonitrile with all implicit carbons shown, and all explicit hydrogens added
Ball and stick model of aminoacetonitrile
Spacefill model of aminoacetonitrile
Names
IUPAC names
Aminoacetonitrile[1]
Glycinonitrile[1]
Other names
2-Aminoacetonitrile
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.957
EC Number 208-751-8
MeSH Aminoacetonitrile
RTECS number AL7750000
UNII
Properties
C2H4N2
Molar mass 56.07 g·mol−1
Appearance Colourless liquid
Boiling point 58.1 °C; 136.5 °F; 331.2 K at 2.0 kPa
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
H302, H312, H332, H351
P280
Related compounds
Related alkanenitriles
Related compounds
DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Aminoacetonitrile is a simple organic compound containing both nitrile and amino groups. It is somewhat similar to the simplest amino acid, glycine. This compound is commercially available as the chloride and sulfate salts.

Production and applications[edit]

Industrially aminoacetonitrile is produced from glycolonitrile by reaction with ammonia:

HOCH2CN + NH3 → H2NCH2CN + H2O

The aminoacetonitrile can be hydrolysed to give glycine:[2]

Aminoacetonitrile derivatives are useful antihelmintics. They act as nematode specific ACh agonists[3] causing a spastic paralysis and rapid expulsion from the host.

Occurrence in the interstellar medium[edit]

In 2008, aminoacetonitrile was discovered in the Large Molecule Heimat, a giant gas cloud near the galactic center in the constellation Sagittarius by the Max Planck Institute for Radio Astronomy.[4] This discovery is significant to the debate on whether glycine exists widely in the universe.

External links[edit]

References[edit]

  1. ^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 903, 1408. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001. 
  2. ^ Peter Pollak, Gérard Romeder, Ferdinand Hagedorn, Heinz-Peter Gelbke "Nitriles" Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_363
  3. ^ 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. PMID 18337814. doi:10.1038/nature06722. 
  4. ^ 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. Bibcode:2008A&A...482..179B. arXiv:0801.3219Freely accessible. doi:10.1051/0004-6361:20079203.