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Aminoacetonitrile

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Title: Aminoacetonitrile  
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Subject: Anthelmintic, Hydrogen cyanide, Acetonitrile, Methanol, Methyl isocyanide
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Aminoacetonitrile

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
Identifiers
CAS number  YesY
PubChem
ChemSpider  YesY
UNII  YesY
EC number
MeSH
RTECS number AL7750000
Jmol-3D images Image 1
Properties
Molecular formula 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
GHS hazard statements H302, H312, H332, H351
GHS precautionary statements P280
EU classification Harmful Xn
R-phrases R20/21/22, R40
S-phrases S36
Related compounds
Related alkanenitriles
Related compounds DBNPA
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY   YesY/N?)

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

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 anthelmintics. They act as nematode specific ACh agonists[3] causing a spastic paralysis and rapid expulsion from the host.

Occurrent in the interstellar medium

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

Property data at the National Institute of Standards and Technology NIST

References

  1. ^ "Aminoacetonitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 5 June 2012. 
  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.  
  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.  
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