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hydroxyacetonitrile
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hydroxyacetonitrile

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Also known as Cyanomethanol, Formaldehyde cyanohydrin, Glycolic nitrile, Glyconitrile, Glycolonitrile

Glycolonitrile, also called hydroxyacetonitrile or formaldehyde cyanohydrin, is the organic compound with the structure HOCH2CN. It is the simplest cyanohydrin, being derived from formaldehyde. It is a colourless liquid that dissolves in water and ether, and is useful in production of several industrially important chemicals. Because glycolonitrile decomposes readily into formaldehyde and hydrogen cyanide, it is listed as an extremely hazardous substance. In January 2019, astronomers reported the detection of glycolonitrile, another possible building block of life among other such molecules, i

Wikidata facts

Subclass of
nitrile
Mass
57.021
Show 10 more facts
chemical formula
C₂H₃NO
Commons category
Glycolonitrile
NIOSH Pocket Guide ID
0304
density
1.10
melting point
-98
decomposition point
361
vapor pressure
1
ceiling exposure limit
5
canonical SMILES
C(C#N)O
has characteristic
flammable liquid
Sources (3)

via Wikidata · CC0

~2 min read

Encyclopedic overview

3 sections
Contents
  • Synthesis and reactions
  • Reactivity
  • References

Glycolonitrile, also called hydroxyacetonitrile or formaldehyde cyanohydrin, is the organic compound with the structure HOCH2CN. It is the simplest cyanohydrin, being derived from formaldehyde. It is a colourless liquid that dissolves in water and ether, and is useful in production of several industrially important chemicals. Because glycolonitrile decomposes readily into formaldehyde and hydrogen cyanide, it is listed as an extremely hazardous substance. In January 2019, astronomers reported the detection of glycolonitrile, another possible building block of life among other such molecules, in outer space.

==Synthesis and reactions== Glycolonitrile is produced by combining formaldehyde with hydrogen cyanide at near-neutral pH. The reaction is catalyzed by base. Glycolonitrile polymerizes under alkaline conditions.

Excerpted from Wikipedia’s “hydroxyacetonitrile” article, available under the CC BY-SA 4.0 licence.