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
	Preferred IUPAC name Aminoacetonitrile
	Other names Glycinonitrile; 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	NH2CH2CN
Molar mass	56.068 g·mol−1
Appearance	Colourless liquid
Boiling point	15 °C (59 °F; 288 K) at 15 mm/Hg
Acidity (pKa)	5.34 (conjugate acid; H2O)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332, H351
Precautionary statements	P280
Related compounds
Related alkanenitriles	Acetonitrile; Cyanogen; Aminopropionitrile;
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 the organic compound with the formula H₂N−CH₂−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⁻.^[3]

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:^[4] Being bifunctional, it is useful in the synthesis of diverse nitrogen-containing heterocycles.^[3]

Aminoacetonitrile derivatives are useful antihelmintics. They act as nematode specific ACh agonists^[5] 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.^[6] This discovery is significant to the debate on whether glycine exists widely in the universe.

References

^ ^a ^b 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.
^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 978-1498754286.
^ ^a ^b 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). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_363. ISBN 978-3527306732.
^ 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. S2CID 4428834.
^ 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. S2CID 21809828.

External links

Property data at the National Institute of Standards and Technology (NIST)

[IUPAC2014-1] 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.

[CRC97-2] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 978-1498754286.

[eros-3] Tauber, Johannes; Opatz, Till (2015). "2-Aminoacetonitrile". E-EROS Encyclopedia of Reagents for Organic Synthesis: 1–4. doi:10.1002/047084289X.rn01752. ISBN 9780470842898.

[Ullmann-4] Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2002). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_363. ISBN 978-3527306732.

[5] 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. S2CID 4428834.

[6] 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. S2CID 21809828.

[1]

[2]

[3]

[4]

[5]

[6]