|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||57.052 g·mol−1|
|Appearance||Colourless, oily liquid|
|Density||1.10 g/mL (18.89°C)|
|Melting point||< −72 °C; −98 °F; 201 K|
|Boiling point||99.6 °C; 211.2 °F; 372.7 K at 2.3 kPa|
|Vapor pressure||1 mmHg (62.78°C)|
|Occupational safety and health (OHS/OSH):|
|forms cyanide in the body|
|NIOSH (US health exposure limits):|
|C 2 ppm (5 mg/m3) [15-minute]|
IDLH (Immediate danger)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
(what is ?)
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. 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.
Glycolonitrile is produced by reacting formaldehyde with hydrogen cyanide under acidic conditions. This reaction is catalysed by base.[clarification needed]. 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:
The industrially important chelating agent EDTA is prepared from glycolonitrile and ethylenediamine followed by hydrolysis of the resulting tetranitrile. Nitrilotriacetic acid is prepared similarly.