Glycolonitrile

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| Watchedfields = changed

| verifiedrevid = 434561909

| ImageFile = Glycolonitrile-2D-skeletal.png

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 100

| ImageName = Skeletal formula of glycolonitrile

| ImageFileL1 = Glycolonitrile-3D-balls-A.png

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| ImageNameL1 = Ball and stick model of glycolonitrile

| ImageFileR1 = Glycolonitrile-3D-vdW-A.png

| ImageFileR1_Ref = {{chemboximage|correct|??}}

| ImageNameR1 = Spacefill model of glycolonitrile

| PIN = Hydroxyacetonitrile

| OtherNames = {{Unbulleted list|Cyanomethanol{{Cite web|title=Glycolonitrile |url=https://www.cdc.gov/niosh/npg/npgd0304.html|work=NIOSH Pocket Guide to Chemical Hazards|publisher=Centers for Disease Control and Prevention|access-date=8 November 2013|location=USA|date=4 April 2011}}|Formaldehyde cyanohydrin|Glycolic nitrile|Hydroxyacetonitrile|Hydroxyethylnitrile{{Citation needed|date=June 2012}}

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|Section1={{Chembox Identifiers

| CASNo = 107-16-4

| CASNo_Ref = {{cascite|correct|??}}

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = ZCI474BE63

| PubChem = 7857

| ChemSpiderID = 7569

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| EINECS = 203-469-1

| MeSHName = glycolonitrile

| Beilstein = 605328

| ChEBI = 137685

| SMILES = OCC#N

| StdInChI = 1S/C2H3NO/c3-1-2-4/h4H,2H2

| StdInChI_Ref = {{chemspidercite|correct|chemspider}}

| StdInChIKey = LTYRAPJYLUPLCI-UHFFFAOYSA-N

| StdInChIKey_Ref = {{chemspidercite|correct|chemspider}}

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|Section2={{Chembox Properties

| C=2 | H=3 | N=1 | O=1

| Appearance = Colourless, oily liquid

| BoilingPtK = 372.7

| BoilingPt_notes = at 2.3 kPa

| MeltingPt = <

| MeltingPtF = -98

| MeltingPt_ref =

| Odor = odorless

| Solubility = soluble

| VaporPressure = 1 mmHg (62.78°C)

| Density = 1.10 g/mL (18.89°C)

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|Section3={{Chembox Hazards

| PEL = none{{PGCH|0304}}

| IDLH = N.D.

| REL = C 2 ppm (5 mg/m³) [15-minute]

| MainHazards = forms cyanide in the body

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|Section4={{Chembox Related

| OtherFunction_label = alkanenitriles

| OtherFunction = {{Unbulleted list|Hydrogen cyanide|Thiocyanic acid|Cyanogen iodide|Cyanogen bromide|Cyanogen chloride|Cyanogen fluoride|Acetonitrile|Aminoacetonitrile|Cyanogen|Propanenitrile|Aminopropionitrile|Malononitrile|Pivalonitrile|Acetone cyanohydrin}}

| OtherCompounds = DBNPA

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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.{{OrgSynth | author = Gaudry, R. | title = Glycolonitrile | collvol = 3 | collvolpages = 436 | year = 1955 | prep = cv3p0436}} 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.{{cite news |author=Queen Mary University of London |author-link=Queen Mary University of London |title=Astronomers find star material could be building block of life |url=https://www.eurekalert.org/pub_releases/2019-01/qmuo-afs012319.php |date=23 January 2019 |work=EurekAlert! |access-date=24 January 2019 }}