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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,2H2Key: LTYRAPJYLUPLCI-UHFFFAOYSA-N
SMILES OCC#N
Properties
Chemical formula	C2H3NO
Molar mass	57.052 g·mol
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/m)
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 , 100 kPa). N verify (what is  ?) 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. 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. In January 2019, astronomers reported the detection of glycolonitrile, another possible building block of life among other such molecules, in outer space.

Synthesis and reactions

Glycolonitrile is produced by reacting formaldehyde with hydrogen cyanide at near-neutral pH, but with small amounts of catalytic base. Glycolonitrile 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.

References

1. ^ "Glycolonitrile". NIOSH Pocket Guide to Chemical Hazards. USA: Centers for Disease Control and Prevention. 4 April 2011. Retrieved 8 November 2013.
2. ^ 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.
4. Queen Mary University of London (23 January 2019). "Astronomers find star material could be building block of life". EurekAlert!. Retrieved 24 January 2019.
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

v t e Molecules detected in outer space
Molecules	Diatomic Aluminium monochloride Aluminium monofluoride Aluminium(II) oxide Argonium Carbon cation Carbon monophosphide Carbon monosulfide Carbon monoxide Cyano radical Diatomic carbon Fluoromethylidynium Helium hydride ion Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Imidogen Sulfur mononitride Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur monoxide Titanium(II) oxide Triatomic Aluminium(I) hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene N2H Nitrous oxide Nitroxyl Ozone Methylidynephosphane Potassium cyanide Trihydrogen cation Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water Four atoms Acetylene Ammonia Isocyanic acid Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl cation Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon monosulfide Thiocyanic acid Five atoms Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster Six atoms Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene Seven atoms Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Propyne Methylamine Methyl isocyanate Vinyl alcohol Eight atoms Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methylcyanoacetylene Methyl formate Acrolein Nine atoms Acetamide Cyanohexatriyne Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Ethanethiol Propionitrile N-Methylformamide Ten atoms or more Acetone Benzene Benzonitrile Buckminsterfullerene (C60, C60, fullerene, buckyball) C70 fullerene Cyanodecapentayne Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Butyronitrile Pyrimidine Heptatrienyl radical
Deuterated molecules	Ammonia Ammonium ion Formaldehyde Formyl radical Heavy water Hydrogen cyanide Hydrogen deuteride Hydrogen isocyanide Propyne N2D Trihydrogen cation
Unconfirmed	Anthracene Dihydroxyacetone Methoxyethane Glycine Graphene Hemolithin H2NCO Linear C5 Naphthalene cation Phosphine Pyrene Silylidyne
Related	Abiogenesis Astrobiology Astrochemistry Atomic and molecular astrophysics Chemical formula Circumstellar dust Circumstellar envelope Cosmic dust Cosmic ray Cosmochemistry Diffuse interstellar band Earliest known life forms Extraterrestrial life Extraterrestrial liquid water Forbidden mechanism Homochirality Intergalactic dust Interplanetary medium Interstellar medium Photodissociation region Iron–sulfur world theory Kerogen Molecules in stars Nexus for Exoplanet System Science Organic compound Outer space PAH world hypothesis Pseudo-panspermia Polycyclic aromatic hydrocarbon (PAH) RNA world hypothesis Spectroscopy Tholin
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