 | |||
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name Hydroxyacetonitrile | |||
Other names
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| Identifiers | |||
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3D model (JSmol) | |||
| 605328 | |||
| ChEBI | |||
| ChemSpider |
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| ECHA InfoCard | 100.003.155 | ||
| EC Number |
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| MeSH | glycolonitrile | ||
| UNII | |||
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| Properties | |||
| C2H3NO | |||
| Molar mass | 57.052 g·mol−1 | ||
| Appearance | Colourless, oily liquid | ||
| Odor | odorless[2] | ||
| Density | 1.10 g/mL (18.89°C)[2] | ||
| Melting point | < −72 °C; −98 °F; 201 K[2] | ||
| Boiling point | 99.6 °C; 211.2 °F; 372.7 K at 2.3 kPa | ||
| soluble[2] | |||
| Vapor pressure | 1 mmHg (62.78°C)[2] | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards | forms cyanide in the body[2] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) | none[2] | ||
REL (Recommended) | C 2 ppm (5 mg/m3) [15-minute][2] | ||
IDLH (Immediate danger) | N.D.[2] | ||
| Related compounds | |||
Related alkanenitriles | |||
Related compounds | DBNPA | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Glycolonitrile, also calledhydroxyacetonitrile orformaldehyde cyanohydrin, is theorganic compound with the structure HOCH2CN. It is the simplestcyanohydrin, being derived fromformaldehyde. It is a colourless liquid that dissolves in water andether, and is useful in production of several industrially important chemicals. Because glycolonitrile decomposes readily into formaldehyde andhydrogen cyanide, it is listed as anextremely hazardous substance. In January 2019, astronomers reported the detection of glycolonitrile, another possiblebuilding block of life amongother such molecules, inouter space.[3]
Glycolonitrile is produced by combiningformaldehyde withhydrogen cyanide at near-neutral pH. The reaction is catalyzed by base.[4][5] Glycolonitrile polymerizes under alkaline conditions.
Glycolonitrile can react with ammonia to giveaminoacetonitrile, which can be hydrolyzed to giveglycine. The general process for reaction of an aldehyde, hydrogen cyanide, and ammonia, followed by hydrolysis, to give an amino acid is the industrially importantStrecker amino acid synthesis:
Ethylenediaminetetraacetic acid widely used as achelating agent, can be prepared from glycolonitrile andethylenediamine followed by hydrolysis of the resulting tetranitrile.Nitrilotriacetic acid is prepared similarly.[5]
Glycolonitrile rapidly forms variousdimers,trimers, and higheroligomers inalkaline solution.[6]
