:Formyl cyanide
{{Short description|1=Organic compound (HC(O)C≡N)}}
{{chembox
| Watchedfields = changed
| verifiedrevid =
| Name = Formyl cyanide
| ImageFile = Formyl cyanide.svg
| ImageSize = 120px
| ImageName = Formyl cyanide
| PIN = Formyl cyanide
| SystematicName = Methanoyl cyanide
| OtherNames = Cyanoformaldehyde
Glyoxylonitrile
2-oxo-acetonitrile
oxo-acetonitrile
|Section1={{Chembox Identifiers
| SMILES = C(=O)C#N
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2HNO/c3-1-2-4/h2H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = TUHMQDODLHWPCC-UHFFFAOYSA-N
| CASNo = 4471-47-0
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3068544
| PubChem = 3843063
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|Section2={{Chembox Properties
| C=2 | H=1 | N=1 | O=1
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|Section4={{Chembox Thermochemistry
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|Section7={{Chembox Hazards
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Formyl cyanide is a simple organic compound with the formula HCOCN and structure {{chem2|HC(\dO)\sC\tN}}. It is simultaneously a nitrile ({{chem2|R\sC\tN}}) and an aldehyde ({{chem2|R\sCH\dO}}). Formyl cyanide is the simplest member of the acyl cyanide family. It is known to occur in space in the Sgr B2 molecular cloud.{{cite journal|last1=Gronowski|first1=Marcin|last2=Eluszkiewicz|first2=Piotr|last3=Custer|first3=Thomas Gage|title=Structure and Spectroscopy of C2HNO Isomers|journal=The Journal of Physical Chemistry A|volume=121|issue=17|pages=3263–3273|date=12 April 2017|doi=10.1021/acs.jpca.6b12609|pmid=28402122|bibcode=2017JPCA..121.3263G}}
Production
Formyl cyanide was first made through methoxyacetonitrile flash vacuum pyrolysis at 600 °C. The same technique with cinnamyloxyacetonitrile{{cite journal|last1=Lewis-Bevan|first1=Wyn|last2=Gaston|first2=Rick D.|last3=Tyrrell|first3=James|last4=Stork|first4=Wilmer D.|last5=Salmon|first5=Gary L.|title=Formyl cyanide: a stable species. Experimental and theoretical studies|journal=Journal of the American Chemical Society|date=March 1992|volume=114|issue=6|pages=1933–1938|doi=10.1021/ja00032a001|bibcode=1992JAChS.114.1933L }} or allyloxyacetonitrile also generates formyl cyanide.{{cite journal|last1=Bogey|first1=M.|last2=Destombes|first2=J.L.|last3=Vallee|first3=Y.|last4=Ripoll|first4=J.L.|title=Formyl cyanide: Efficient production from allyloxyacetonitrile and its millimeter-wave spectrum|journal=Chemical Physics Letters|date=May 1988|volume=146|issue=3–4|pages=227–229|doi=10.1016/0009-2614(88)87435-9|bibcode=1988CPL...146..227B}}{{cite journal|last1=Bogey|first1=M.|last2=Demuynck|first2=C.|last3=Destombes|first3=J.L.|last4=Vallee|first4=Y.|title=Millimeter-Wave Spectrum of Formyl Cyanide, HCOCN: Centrifugal Distortion and Hyperfine Structure Analysis|journal=Journal of Molecular Spectroscopy|date=August 1995|volume=172|issue=2|pages=344–351|doi=10.1006/jmsp.1995.1183|bibcode=1995JMoSp.172..344B}}
In molecular clouds, formation of formyl cyanide is speculated to result from formaldehyde and the cyanide radical:{{cite journal|last1=Remijan|first1=Anthony J.|last2=Hollis|first2=J. M.|last3=Lovas|first3=F. J.|last4=Stork|first4=Wilmer D.|last5=Jewell|first5=P. R.|last6=Meier|first6=D. S.|title=Detection of Interstellar Cyanoformaldehyde (CNCHO)|journal=The Astrophysical Journal|date=10 March 2008|volume=675|issue=2|pages=L85–L88|doi=10.1086/533529|bibcode=2008ApJ...675L..85R|s2cid=19005362 }}
:{{chem2 | CH2O + CN• -> HCOCN + H•}}
In Earth's atmosphere, the pollutant acrylonitrile reacts with hydroxyl radical forming formyl cyanide, hydroperoxyl and formaldehyde:{{cite journal|last1=Grosjean|first1=Daniel|title=Atmospheric Chemistry of Toxic Contaminants. 3. Unsaturated Aliphatics: Acrolein, Acrylonitrile, Maleic Anhydride|journal=Journal of the Air & Waste Management Association|date=December 1990|volume=40|issue=12|pages=1664–1669|doi=10.1080/10473289.1990.10466814|bibcode=1990JAWMA..40.1664G }}
:{{chem2 | CH2\dCHCN + HO• + }} {{fraction|3|2}} {{chem2 | O2 -> HOO• + HCOCN + CH2O }}
Reactions
Formyl cyanide reacts rapidly with trace quantities of water to form formic acid and hydrogen cyanide.
Related
By formally substituting the hydrogen atom, cyanoformyl chloride, ClC(O)CN, and cyanoformyl bromide, BrC(O)CN are obtained.{{cite journal|last1=Pasinszki|first1=Tibor|last2=Vass|first2=Gábor|last3=Klapstein|first3=Dieter|last4=Westwood|first4=Nicholas P. C.|title=Generation, Spectroscopy, and Structure of Cyanoformyl Chloride and Cyanoformyl Bromide, XC(O)CN|journal=The Journal of Physical Chemistry A|date=5 April 2012|volume=116|issue=13|pages=3396–3403|doi=10.1021/jp301528q|pmid=22409314|bibcode=2012JPCA..116.3396P}}