Glycolonitrile - Wikipedia

Glycolonitrile

Names
Preferred IUPAC name Hydroxyacetonitrile
Other names Cyanomethanol[1] Formaldehyde cyanohydrin[1] Glycolic nitrile[1] Hydroxyacetonitrile[1] Hydroxyethylnitrile[citation needed]
Identifiers
CAS Number	107-16-4 Y
3D model (JSmol)	Interactive image
Beilstein Reference	605328
ChEBI	CHEBI:137685
ChemSpider	7569 N
ECHA InfoCard	100.003.155
EC Number	203-469-1
MeSH	glycolonitrile
PubChem CID	7857
UNII	ZCI474BE63 N
CompTox Dashboard (EPA)	DTXSID3025417
InChI InChI=1S/C2H3NO/c3-1-2-4/h4H,2H2 YKey: LTYRAPJYLUPLCI-UHFFFAOYSA-N Y
SMILES OCC#N
Properties
Chemical formula	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
Solubility in water	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	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). N verify (what is YN ?) Infobox references

Chemical compound

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

[edit]

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

[edit]

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

References

[edit]

1. ^ 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.
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. ^ 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.
5. ^ 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
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.

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 Imidogen Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur mononitride 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 Methylidynephosphane N2H+ Nitrous oxide Nitroxyl Ozone Potassium cyanide Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Trihydrogen cation Water Fouratoms Acetylene Ammonia Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methyl cation Methyl radical Methylene amidogen Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thiocyanic acid Thioformaldehyde Tricarbon monosulfide Tricarbon monoxide Fiveatoms Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster Sixatoms Acetonitrile Cyanobutadiynyl radical Cyclopropenone Diacetylene E-Cyanomethanimine Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene Sevenatoms Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Methyl isocyanate Methylamine Propyne Vinyl alcohol Eightatoms Acetic acid Acrolein Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methyl formate Methylcyanoacetylene Nineatoms Acetamide Cyanohexatriyne Dimethyl ether Ethanethiol Ethanol Methyldiacetylene N-Methylformamide Octatetraynyl radical Propene Propionitrile Tenatomsor more Acetone Benzene Benzonitrile Buckminsterfullerene (C60, C60+, fullerene, buckyball) Butyronitrile C70 fullerene Cyanodecapentayne Ethyl formate Ethylene glycol Heptatrienyl radical Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Pyrimidine
Deuteratedmolecules	Ammonia Ammonium ion Formaldehyde Formyl radical Heavy water Hydrogen cyanide Hydrogen deuteride Hydrogen isocyanide N2D+ Propyne Trihydrogen cation
Unconfirmed	Anthracene Dihydroxyacetone Glycine Graphene H2NCO+ Hemolithin Linear C5 Methoxyethane 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 Iron–sulfur world theory Kerogen Molecules in stars Nexus for Exoplanet System Science Organic compound Outer space PAH world hypothesis Photodissociation region Polycyclic aromatic hydrocarbon (PAH) Pseudo-panspermia RNA world hypothesis Spectroscopy Tholin
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