Glycolonitrile

Glycolonitrile

Names
IUPAC name 2-Hydroxyacetonitrile[1]
Other names Cyanomethanol[2] Formaldehyde cyanohydrin[2] Glycolic nitrile[2] Hydroxyacetonitrile[2] Hydroxymethylnitrile
Identifiers
Beilstein Reference	605328
CAS Registry Number	107-16-4 Y
ChemSpider	7569 N
EC number	203-469-1
InChI InChI=1S/C2H3NO/c3-1-2-4/h4H,2H2 Y Key: LTYRAPJYLUPLCI-UHFFFAOYSA-N Y
Jmol-3D images	Image
MeSH	glycolonitrile
PubChem	7857
SMILES OCC#N
Properties
Molecular formula	C2H3NO
Molar mass	57.05 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
Solubility in water	soluble[3]
Vapor pressure	1 mmHg (62.78°C)[3]
Related compounds
Related alkanenitriles	Hydrogen cyanide Thiocyanic acid Cyanogen iodide Cyanogen bromide Cyanogen chloride Cyanogen fluoride Acetonitrile Aminoacetonitrile Cyanogen Propanenitrile Aminopropionitrile Malononitrile Pivalonitrile Acetone cyanohydrin
Related compounds	DBNPA
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

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.

Synthesis and reactions

Glycolonitrile is produced by reacting formaldehyde with hydrogen cyanide under acidic conditions. This reaction is catalysed by base.^[5] Gylcolonitrile 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.^[5]

References