Aminoacetonitrile
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| Names | |||
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| IUPAC names | |||
| Other names
2-Aminoacetonitrile
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| Identifiers | |||
540-61-4  |
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| ChemSpider | 10439 |
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| ECHA InfoCard | 100.007.957 | ||
| EC Number | 208-751-8 | ||
| Jmol 3D model | Interactive image | ||
| MeSH | Aminoacetonitrile | ||
| PubChem | 10901 | ||
| RTECS number | AL7750000 | ||
| UNII | 3739OQ10IJ |
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| 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 |   |
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| GHS signal word | WARNING | ||
| H302, H312, H332, H351 | |||
| P280 | |||
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EU classification (DSD)
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 Xn |
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| R-phrases | R20/21/22, R40 | ||
| S-phrases | S36 | ||
| Related compounds | |||
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Related alkanenitriles
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Related compounds
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DBNPA | ||
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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.
Contents
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 anthelmintics. 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]
- Property data at the National Institute of Standards and Technology (NIST)
References[edit]
- ^ 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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