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
Names
	IUPAC names Aminoacetonitrile; Glycinonitrile
	Other names 2-Aminoacetonitrile
Identifiers
CAS Number	540-61-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	10439 ;
ECHA InfoCard	100.007.957
EC Number	208-751-8;
MeSH	Aminoacetonitrile
PubChem CID	10901;
RTECS number	AL7750000;
UNII	3739OQ10IJ ;
CompTox Dashboard (EPA)	DTXSID90202314 ;
	InChI InChI=1S/C2H4N2/c3-1-2-4/h1,3H2 Key: DFNYGALUNNFWKJ-UHFFFAOYSA-N ;
	SMILES NCC#N;
Properties
Chemical formula	C2H4N2
Molar mass	56.068 g·mol−1
Appearance	Colourless liquid
Boiling point	58.1 °C; 136.5 °F; 331.2 K at 2.0 kPa
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332, H351
Precautionary statements	P280
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). verify (what is ?) 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

^ ^a ^b 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.
^ 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
^ 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.
^ 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.

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[iupac2013-1] 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.

[Ullmann-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.

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