Glycolonitrile
Chemical compound
From Wikipedia, the free encyclopedia
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.[3]
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| Names | |||
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| Preferred IUPAC name
Hydroxyacetonitrile | |||
Other names
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| Identifiers | |||
3D model (JSmol) |
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| 605328 | |||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.003.155 | ||
| EC Number |
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| MeSH | glycolonitrile | ||
PubChem CID |
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| UNII | |||
CompTox Dashboard (EPA) |
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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 |
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Related compounds |
DBNPA | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and reactions
Glycolonitrile is produced by combining formaldehyde with hydrogen cyanide at near-neutral pH. The reaction is catalyzed by base.[4][5] Glycolonitrile polymerizes under alkaline conditions.
Glycolonitrile can react with ammonia to give aminoacetonitrile, which can be hydrolyzed to give glycine. The general process for reaction of an aldehyde, hydrogen cyanide, and ammonia, followed by hydrolysis, to give an amino acid is the industrially important Strecker amino acid synthesis:
- HOCH2CN + NH3 → H2NCH2CN + H2O
- H2NCH2CN + 2 H2O → H2NCH2CO2H + NH3
Ethylenediaminetetraacetic acid widely used as a chelating agent, can be prepared from glycolonitrile and ethylenediamine followed by hydrolysis of the resulting tetranitrile. Nitrilotriacetic acid is prepared similarly.[5]
