From Wikipedia, the free encyclopedia
Chemical compound
Aminoacetonitrile
is the
organic compound
with the formula
H
2
N?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., [NCCH
2
NH
3
]
+
Cl
?
and [NCCH
2
NH
3
]
+
HSO
4
?
.
[3]
Production and applications
[
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]
Industrially aminoacetonitrile is produced from
glycolonitrile
by reaction with ammonia:
- HOCH
2
CN + NH
3
→ H
2
NCH
2
CN + H
2
O
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
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]
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
[
edit
]
- ^
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, Gerard; 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.; Muller, 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
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]