Glycolonitrile

Glycolonitrile
	Skeletal formula of glycolonitrile
Ball and stick model of glycolonitrile	Spacefill model of glycolonitrile
Names
	Preferred IUPAC name Hydroxyacetonitrile
	Other names Cyanomethanol; Formaldehyde cyanohydrin; Glycolic nitrile; Hydroxyacetonitrile; Hydroxyethylnitrile;
Identifiers
CAS Number	107-16-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	605328
ChEBI	CHEBI:137685;
ChemSpider	7569 ;
ECHA InfoCard	100.003.155
EC Number	203-469-1;
MeSH	glycolonitrile
PubChem CID	7857;
UNII	ZCI474BE63 ;
CompTox Dashboard (EPA)	DTXSID3025417 ;
	InChI InChI=1S/C2H3NO/c3-1-2-4/h4H,2H2 Key: LTYRAPJYLUPLCI-UHFFFAOYSA-N ;
	SMILES OCC#N;
Properties
Chemical formula	C2H3NO
Molar mass	57.052 g·mol−1
Appearance	Colourless, oily liquid
Odor	odorless
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
Solubility in water	soluble
Vapor pressure	1 mmHg (62.78°C)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	forms cyanide in the body
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	C 2 ppm (5 mg/m3) [15-minute]
IDLH (Immediate danger)	N.D.
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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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]

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]

Reactivity

4-Amino-2-hydroxy-2-hyroxymethyloxazolidine, the trimer of glycolonitrile

Glycolonitrile rapidly forms various dimers, trimers, and higher oligomers in alkaline solution.^[6]

References

^ ^a ^b ^c ^d "Glycolonitrile". NIOSH Pocket Guide to Chemical Hazards. USA: Centers for Disease Control and Prevention. 4 April 2011. Retrieved 8 November 2013.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ NIOSH Pocket Guide to Chemical Hazards. "#0304". National Institute for Occupational Safety and Health (NIOSH).
^ Queen Mary University of London (23 January 2019). "Astronomers find star material could be building block of life". EurekAlert!. Retrieved 24 January 2019.
^ Gaudry, R. (1955). "Glycolonitrile". Organic Syntheses; Collected Volumes, vol. 3, p. 436.
^ ^a ^b 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
^ Arrhenius, Gustaf; Bladridge, Kim K.; Richards-Gross, Sarah; Siegel, Jay S. (1997). "Glycolonitrile Oligomerization: Structure of Isolated Oxazolines, Potential Heterocycles on the Early Earth". The Journal of Organic Chemistry. 62 (16): 5522–5525. doi:10.1021/jo962185r. PMID 11543606.

[pocket-1] "Glycolonitrile". NIOSH Pocket Guide to Chemical Hazards. USA: Centers for Disease Control and Prevention. 4 April 2011. Retrieved 8 November 2013.

[PGCH-2] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ NIOSH Pocket Guide to Chemical Hazards. "#0304". National Institute for Occupational Safety and Health (NIOSH).

[EA-20190123-3] Queen Mary University of London (23 January 2019). "Astronomers find star material could be building block of life". EurekAlert!. Retrieved 24 January 2019.

[4] Gaudry, R. (1955). "Glycolonitrile". Organic Syntheses; Collected Volumes, vol. 3, p. 436.

[Ullmann-5] 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

[6] Arrhenius, Gustaf; Bladridge, Kim K.; Richards-Gross, Sarah; Siegel, Jay S. (1997). "Glycolonitrile Oligomerization: Structure of Isolated Oxazolines, Potential Heterocycles on the Early Earth". The Journal of Organic Chemistry. 62 (16): 5522–5525. doi:10.1021/jo962185r. PMID 11543606.

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