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[citation needed];
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 formula HOCH₂CN and the simplest cyanohydrin. It is a colorless 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 combining formaldehyde with hydrogen cyanide at near-neutral pH. The reaction is catalyzed by base.^[3]^[4] Glycolonitrile polymerizes under alkaline conditions.

Glycolonitrile can react with ammonia to give aminoacetonitrile, which can be hydrolyzed to give glycine. This two-step process is the core industrial production of amino acids known as the Strecker Synthesis:

HOCH₂CN + NH₃ → H₂NCH₂CN + H₂O

H₂NCH₂CN + 2 H₂O → H₂NCH₂CO₂H + NH₃

The industrially important chelating agent EDTA can be prepared from glycolonitrile and ethylenediamine followed by hydrolysis of the resulting tetranitrile. Nitrilotriacetic acid is prepared similarly.^[4]

Reactivity

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

Glycolonitrile rapidly polymerizes near neutral pH. One intermediate in this conversion is the trimer 4-amino-2-hydroxy-2-hydroxymethyloxazolidine.^[5]

Glycolonitrile has been recognized as a possible building block of life. ^[6] A key characteristic of this reaction is that the synthesis of all α-amino acids, except for glycine, typically yields a racemic mixture (50:50 mixture of L and D enantiomers).^[7]

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).
^ 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.
^ Thrush, Kyra L.; Kua, Jeremy (2018-08-23). "Reactions of Glycolonitrile with Ammonia and Water: A Free Energy Map". The Journal of Physical Chemistry A. 122 (33): 6769–6779. Bibcode:2018JPCA..122.6769T. doi:10.1021/acs.jpca.8b05900. ISSN 1089-5639. PMID 30063827.
^ Huang, Jun; Yu, Lian (2006-02-01). "Effect of Molecular Chirality on Racemate Stability: α-Amino Acids with Nonpolar R Groups". Journal of the American Chemical Society. 128 (6): 1873–1878. Bibcode:2006JAChS.128.1873H. doi:10.1021/ja0571693. ISSN 0002-7863. PMID 16464087.

[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).

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

[Ullmann-4] 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

[5] 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.

[6] Thrush, Kyra L.; Kua, Jeremy (2018-08-23). "Reactions of Glycolonitrile with Ammonia and Water: A Free Energy Map". The Journal of Physical Chemistry A. 122 (33): 6769–6779. Bibcode:2018JPCA..122.6769T. doi:10.1021/acs.jpca.8b05900. ISSN 1089-5639. PMID 30063827.

[7] Huang, Jun; Yu, Lian (2006-02-01). "Effect of Molecular Chirality on Racemate Stability: α-Amino Acids with Nonpolar R Groups". Journal of the American Chemical Society. 128 (6): 1873–1878. Bibcode:2006JAChS.128.1873H. doi:10.1021/ja0571693. ISSN 0002-7863. PMID 16464087.

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