Glycolonitrile

Glycolonitrile, also called hydroxyacetonitrile or formaldehyde cyanohydrin, is the organic compound with the formula HOCH2CN. It is the simplest cyanohydrin and it is derived from formaldehyde.[4] It is a colourless liquid that dissolves in water and ether. 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.[5]

Glycolonitrile
Ball and stick model of glycolonitrile
Spacefill model of glycolonitrile
Names
IUPAC name
2-Hydroxyacetonitrile[1]
Other names
  • Cyanomethanol[2]
  • Formaldehyde cyanohydrin[2]
  • Glycolic nitrile[2]
  • Hydroxyacetonitrile[2]
  • Hydroxymethylnitrile
Identifiers
3D model (JSmol)
605328
ChEBI
ChemSpider
ECHA InfoCard 100.003.155
EC Number
  • 203-469-1
MeSH glycolonitrile
UNII
Properties
C2H3NO
Molar mass 57.052 g·mol−1
Appearance Colourless, oily liquid
Odor odorless[3]
Density 1.10 g/mL (18.89°C)[3]
Melting point < −72 °C; −98 °F; 201 K [3]
Boiling point 99.6 °C; 211.2 °F; 372.7 K at 2.3 kPa
soluble[3]
Vapor pressure 1 mmHg (62.78°C)[3]
Hazards
Main hazards forms cyanide in the body[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 none[3]
REL (Recommended)
 C 2 ppm (5 mg/m3) [15-minute][3]
IDLH (Immediate danger)
 N.D.[3]
Related compounds
Related alkanenitriles
Related compounds
 DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Synthesis and reactions

Glycolonitrile is produced by reacting formaldehyde with hydrogen cyanide under acidic conditions. This reaction is catalysed by base.[6] Glycolonitrile polymerizes under alkaline conditions above pH 7.0. As the product of polymerization is an amine with a basic character, the reaction is self-catalysed, gaining in speed with ongoing conversion.

Glycolonitrile can react with ammonia to give aminoacetonitrile, which can be hydrolysed to give glycine:

HOCH2CN + NH3 → H2NCH2CN + H2O
H2NCH2CN + 2 H2O → H2NCH2CO2H + NH3

The industrially important chelating agent EDTA is prepared from glycolonitrile and ethylenediamine followed by hydrolysis of the resulting tetranitrile. Nitrilotriacetic acid is prepared similarly.[6]

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References
  1. "glycolonitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 5 June 2012.
  2. "Glycolonitrile". NIOSH Pocket Guide to Chemical Hazards. USA: Centers for Disease Control and Prevention. 4 April 2011. Retrieved 8 November 2013.
  3. NIOSH Pocket Guide to Chemical Hazards. "#0304". National Institute for Occupational Safety and Health (NIOSH).
  4. Gaudry, R. (1955). "Glycolonitrile". Organic Syntheses.; Collective Volume, 3, p. 436
  5. Queen Mary University of London (23 January 2019). "Astronomers find star material could be building block of life". EurekAlert!. Retrieved 24 January 2019.
  6. 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
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