Chemistry:Aminoacetonitrile
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| Names | |||
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| Preferred IUPAC name
Aminoacetonitrile[1] | |||
Other names
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| Identifiers | |||
3D model (JSmol)
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| EC Number |
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| MeSH | Aminoacetonitrile | ||
PubChem CID
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| Properties | |||
| NH 2CH 2CN | |||
| Molar mass | 56.068 g·mol−1 | ||
| Appearance | Colourless liquid | ||
| Boiling point | 15 °C (59 °F; 288 K) at 15 mm/Hg | ||
| Hazards | |||
| GHS pictograms |  
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| GHS Signal word | WARNING | ||
| H302, H312, H332, H351 | |||
| P280 | |||
| Related compounds | |||
Related alkanenitriles
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Related compounds
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DBNPA | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
 verify (what is   ?)
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| Infobox references | |||
Aminoacetonitrile is the organic compound with the formula H
2N–CH
2–C≡N. The compound is a colorless liquid. It is unstable at room temperature, owing to the incompatibility of the amine nucleophile and the nitrile electrophile. For this reason it is usually encountered as the chloride and bisulfate salts of the ammonium derivative, i.e., [NCCH2NH3]+Cl− and [NCCH2NH3]+HSO4−.[2]
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:[3] Being bifunctional, it is useful in the synthesis of diverse nitrogen-containing heterocycles.[2]
Aminoacetonitrile derivatives are useful antihelmintics. They act as nematode specific ACh agonists[4] causing a spastic paralysis and rapid expulsion from the host.
Occurrence in the interstellar medium
Using radio astronomy, aminoacetonitrile was discovered in the Large Molecule Heimat, a giant gas cloud near the Galactic Center in the constellation Sagittarius.[5] This discovery is significant to the debate on whether glycine exists widely in the universe.
References
- ↑ 1.0 1.1 International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. pp. 902−903. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
- ↑ 2.0 2.1 Tauber, Johannes; Opatz, Till (2015). "2-Aminoacetonitrile". E-EROS Encyclopedia of Reagents for Organic Synthesis: 1–4. doi:10.1002/047084289X.rn01752. ISBN 9780470842898.
- ↑ Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2002). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_363.
- ↑ Kaminsky, R. et al. (2008). "A new class of anthelmintics effective against drug-resistant nematodes". Nature 452 (7184): 176–180. doi:10.1038/nature06722. PMID 18337814. Bibcode: 2008Natur.452..176K.
- ↑ 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)". Astronomy and Astrophysics 482 (1): 179–196. doi:10.1051/0004-6361:20079203. Bibcode: 2008A&A...482..179B. http://www.aanda.org/articles/aa/pdf/2008/16/aa9203-07.pdf.
External links
- Property data at the National Institute of Standards and Technology (NIST)
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