Aminoacetonitrile

Aminoacetonitrile

Names
IUPAC names Aminoacetonitrile[1] Glycinonitrile[1]
Other names 2-Aminoacetonitrile
Identifiers
CAS Number	540-61-4
3D model (Jmol)	Interactive image
ChemSpider	10439
ECHA InfoCard	100.007.957
EC Number	208-751-8
MeSH	Aminoacetonitrile
PubChem	10901
RTECS number	AL7750000
UNII	3739OQ10IJ
InChI InChI=1S/C2H4N2/c3-1-2-4/h1,3H2 Key: DFNYGALUNNFWKJ-UHFFFAOYSA-N
SMILES NCC#N
Properties
Chemical 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
GHS signal word	WARNING
GHS hazard statements	H302, H312, H332, H351
GHS precautionary statements	P280
EU classification (DSD)	Xn
R-phrases	R20/21/22, R40
S-phrases	S36
Related compounds
Related alkanenitriles	Hydrogen cyanide Thiocyanic acid Cyanogen iodide Cyanogen bromide Cyanogen chloride Cyanogen fluoride Acetonitrile Glycolonitrile Cyanogen Propanenitrile Aminopropionitrile Malononitrile Pivalonitrile Acetone cyanohydrin
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

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

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. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 903, 1408. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
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. doi:10.1038/nature06722. PMID 18337814.
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. arXiv:0801.3219. Bibcode:2008A&A...482..179B. doi:10.1051/0004-6361:20079203.