View source for C3H4O

{{DISPLAYTITLE:C<sub>3</sub>H<sub>4</sub>O}}'''C<sub>3</sub>H<sub>4</sub>O''' is a [[chemical formula]] that represents each of several actual and hypothetical compounds that differ in structure, but each consist of three atoms of carbon, four of hydrogen, and one of oxygen. The following compounds are among them:
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!Name
!CAS #
!Notes
!Structure
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|[[Oxetene]], 2H-Oxete
|{{CAS|287-25-2}}
|Synthesized;<ref>{{Cite journal |last1=Friedrich |first1=Louis E. |last2=Lam |first2=Patrick Yuk-Sun |date=1981-01-01 |title=Syntheses and reactions of 3-phenyloxete and the parent unsubstituted oxete |url=https://pubs.acs.org/doi/abs/10.1021/jo00315a016 |journal=The Journal of Organic Chemistry |volume=46 |issue=2 |pages=306–311 |doi=10.1021/jo00315a016 |issn=0022-3263|url-access=subscription }}</ref> unstable.<ref>{{Citation |last1=Ji Ram |first1=Vishnu |title=Chapter 4 - Four-Membered Heterocycles |date=2019-01-01 |work=The Chemistry of Heterocycles |pages=93–147 |editor-last=Ji Ram |editor-first=Vishnu |url=https://www.sciencedirect.com/science/article/abs/pii/B9780081010334000048 |access-date=2024-12-08 |publisher=Elsevier |isbn=978-0-08-101033-4 |last2=Sethi |first2=Arun |last3=Nath |first3=Mahendra |last4=Pratap |first4=Ramendra |editor2-last=Sethi |editor2-first=Arun |editor3-last=Nath |editor3-first=Mahendra |editor4-last=Pratap |editor4-first=Ramendra}}</ref> Can be made by [[Photochemistry|using light]] to cyclize acrolein.<ref name="2H-Azirines">{{cite journal |author=Kikuchi O. |date=1981 |title=A classification of the photochemical electrocyclic reactions of heteroatom conjugated systems |journal=Tetrahedron Lett. |volume=22 |issue=9 |pages=859–862 |doi=10.1016/0040-4039(81)80015-9}}</ref>
|[[File:C3H4Oisomer 12.png|frameless]]
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|2-Oxabicyclo[1.1.0]butane<ref>{{Cite PubChem|cid=18626665|title=2-Oxabicyclo[1.1.0]butane}}</ref>
|{{CAS|35553-05-0}}
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|[[File:C3H4Oisomer 13.png|frameless]]
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|[[Acrolein]], 2-propenal
|{{CAS|107-02-8}}
|Forms from pollutants, burning, metabolism.<ref name=":0">{{Cite journal |last1=Puzzarini |first1=Cristina |last2=Penocchio |first2=Emanuele |last3=Biczysko |first3=Malgorzata |last4=Barone |first4=Vincenzo |date=2014-08-21 |title=Molecular Structure and Spectroscopic Signatures of Acrolein: Theory Meets Experiment |url=https://pubs.acs.org/doi/10.1021/jp503672g |journal=The Journal of Physical Chemistry A |volume=118 |issue=33 |pages=6648–6656 |doi=10.1021/jp503672g |pmid=24842714 |bibcode=2014JPCA..118.6648P |issn=1089-5639|url-access=subscription }}</ref> ''Cis'' and ''trans'' forms; ''cis'' form predominant.<ref name=":0" />
|[[File:C3H4Oisomer 01.png|frameless]]
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|[[Propa-1,2-dien-1-ol]]<ref>{{Cite PubChem|cid=59964018|title=Propa-1,2-dien-1-ol}}</ref>
|{{Cas|81788-96-7}}
|Synthesized.<ref name=":3">{{Cite journal |last1=Hakiki |first1=Abdelhak |last2=Ripoll |first2=Jean-Louis |last3=Thuillier |first3=André |date=1984-01-01 |title=Retrodienic reactions XVI - flash thermolytic generation of reactive functional allenes |url=https://www.sciencedirect.com/science/article/abs/pii/S0040403901910469 |journal=Tetrahedron Letters |volume=25 |issue=32 |pages=3459–3460 |doi=10.1016/S0040-4039(01)91046-9 |issn=0040-4039|url-access=subscription }}</ref> Tautomerizes "quantitatively" to acrolein above -50&nbsp;°C.<ref name=":3" />
|[[File:C3H4Oisomer 04.png|frameless]]
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|[[Propargyl alcohol]] or 2-propyn-1-ol
|{{CAS|107-19-7}}
|"Mild, geranium odor"<ref>{{Cite web |title=Propargyl alcohol |url=https://www.cdc.gov/niosh/npg/npgd0527.html |access-date=2024-12-08 |website=NIOSH Pocket Guide to Safety and Hazards |publisher=[[National Institute for Occupational Safety and Health]]}}</ref> Used in synthesis, as [[corrosion inhibitor]], [[soil fumigant]].<ref>{{Cite PubChem|cid=7859|title=Propargyl alcohol}}</ref>
|[[File:C3H4Oisomer 02.png|frameless]]
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|[[Methoxy ethyne]], methoxyacetylene
|{{CAS|6443-91-0}}
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|[[File:C3H4Oisomer 05.png|frameless]]
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|[[1-Propynol|Prop-1-yn-1-ol]],<ref>{{Cite PubChem|cid=141504292|title=CID 141504292}}</ref> 1-propynol<ref>{{Cite web |title=NIST Chemistry WebBook, SRD 69: 1-Propynol |url=https://webbook.nist.gov/cgi/inchi/InChI%3D1S/C3H4O/c1-2-3-4/h4H%2C1H3 |access-date=8 December 2024 |website=[[NIST]]}}</ref>
|{{CAS|6175-54-8}}
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|[[File:C3H4Oisomer 03.png|frameless]]
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|[[Methylketene]] or 1-propen-1-one<ref>{{Cite PubChem|cid=138641|title=Methylketene}}</ref>
|{{CAS|6004-44-0}}
|Synthesized.<ref name=":4">{{Cite journal |last1=Derbali |first1=Imene |last2=Hrodmarsson |first2=Helgi Rafn |last3=Schwell |first3=Martin |last4=Bénilan |first4=Yves |last5=Poisson |first5=Lionel |last6=Hochlaf |first6=Majdi |last7=Alikhani |first7=Mohammad Esmaïl |last8=Guillemin |first8=Jean-Claude |last9=Zins |first9=Emilie-Laure |date=2020-09-23 |title=Unimolecular decomposition of methyl ketene and its dimer in the gas phase: theory and experiment |url=https://pubs.rsc.org/en/content/articlelanding/2020/cp/d0cp03921g |journal=Physical Chemistry Chemical Physics |language=en |volume=22 |issue=36 |pages=20394–20408 |doi=10.1039/D0CP03921G |pmid=32914152 |bibcode=2020PCCP...2220394D |issn=1463-9084}}</ref> Intermediate in acrolein pyrolysis.<ref>{{Cite journal |last1=Muzika |first1=Michael |last2=Genossar-Dan |first2=Nadav |last3=Fux |first3=Dana |last4=Har Lavan |first4=Shani |last5=Zamir |first5=Uri |last6=Rozenberg |first6=Illya |last7=Hemberger |first7=Patrick |last8=Baraban |first8=Joshua H. |date=2024-04-01 |title=Radical intermediates and stable products in acrolein pyrolysis |url=https://link.springer.com/article/10.1007/s10311-023-01661-8 |journal=Environmental Chemistry Letters |language=en |volume=22 |issue=2 |pages=491–497 |doi=10.1007/s10311-023-01661-8 |issn=1610-3661|url-access=subscription }}</ref> Of astronomical interest.<ref name=":4" />
|[[File:C3H4Oisomer 06.png|frameless]]
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|[[Methylene oxirane]],<ref>{{Cite PubChem|cid=3029326|title=Methyleneoxirane}}</ref> allene oxide
|{{CAS|40079-14-9}}
|Synthesized;<ref name=":2">{{Cite journal |last1=Turecek |first1=Frantisek |last2=Drinkwater |first2=Donald E. |last3=McLafferty |first3=Fred W. |date=1990-07-01 |title=The elusive methyleneoxirane: preparation and characterization by flash-vacuum pyrolysis and neutralization-reionization mass spectrometry |url=https://pubs.acs.org/doi/10.1021/ja00171a046 |journal=Journal of the American Chemical Society |volume=112 |issue=15 |pages=5892–5893 |doi=10.1021/ja00171a046 |bibcode=1990JAChS.112.5892T |issn=0002-7863|url-access=subscription }}</ref> predicted (1968) to isomerize "readily" to cyclopropanone.<ref name=":2" /><ref>{{Cite journal |last=Hoffmann |first=Roald |date=March 1968 |title=Trimethylene and the addition of methylene to ethylene |url=https://pubs.acs.org/doi/abs/10.1021/ja01008a016 |journal=Journal of the American Chemical Society |language=en |volume=90 |issue=6 |pages=1475–1485 |doi=10.1021/ja01008a016 |bibcode=1968JAChS..90.1475H |issn=0002-7863|url-access=subscription }}</ref>{{Needs update|date=December 2024|reason=The paper may describe what it actually decomposes to, but I do not have the technical knowledge to understand it}}
|[[File:C3H4Oisomer 07.png|frameless]]
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|[[Cyclopropanone]]
|{{CAS|5009-27-8}}
|Synthesized; unstable due to polymerization and ring-opening.<ref name=":1">{{Citation |last1=Wasserman |first1=Harry H. |title=The Chemistry of Cyclopropanones |date=1987-10-28 |work=Cyclopropyl Group Volume 1 and Volume 2 (1987) |pages=1455–1532 |editor-last=Rappoport |editor-first=Zvi |url=https://onlinelibrary.wiley.com/doi/10.1002/0470023449.ch23 |access-date=2024-12-08 |place=Chichester, UK |publisher=John Wiley & Sons, Ltd |language=en |doi=10.1002/0470023449.ch23 |isbn=978-0-470-02344-0 |last2=Berdahl |first2=Donald R. |last3=Lu |first3=Ta-Jung|url-access=subscription }}</ref> Derivatives used in synthesis, biology.<ref name=":1" /> 
Tautomer of 1-cyclopen-1-ol{{Citation needed|date=December 2024}}
|[[File:C3H4Oisomer 08.png|frameless]]
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|Cycloprop-1-en-1-ol, cyclopropene alcohol<ref>{{Cite PubChem|cid=57418002|title=Cycloprop-1-en-1-ol}}</ref>
|{{CAS|81788-95-6}}
|Tautomer of cyclopropanone; Not synthesized{{Citation needed|date=December 2024}}
|[[File:C3H4Oisomer 09.png|frameless]]
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|[[2-Cyclopropenol]] or 1-hydroxy-2-cyclopropene{{Dubious|date=November 2024}}
|{{CAS|81788-94-5}}
|Not synthesized{{Citation needed|date=December 2024}}
|[[File:C3H4Oisomer 10.png|frameless]]
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|[[1,2-Epoxypropene]] or 2-methyloxirene<ref>{{Cite PubChem|cid=15887307|title=2-Methyloxirene}}</ref>
|{{CAS|2835-41-8}}
|Synthesized; unstable. Product of ionized [[diazoacetone]]; isomerizes "rapidly" to methylketene, acrolein, methoxyethyne, and/or 1-propynol.<ref>{{Citation |last=Lewars |first=Errol G. |title=Oxirene |date=2008 |work=Modeling Marvels: Computational Anticipation of Novel Molecules |pages=31–52 |editor-last=Lewars |editor-first=Errol G. |url=https://link.springer.com/chapter/10.1007/978-1-4020-6973-4_3 |access-date=2024-12-08 |place=Dordrecht |publisher=Springer Netherlands |language=en |doi=10.1007/978-1-4020-6973-4_3 |isbn=978-1-4020-6973-4|url-access=subscription }}</ref><ref>{{Cite journal |last1=Turecek |first1=Frantisek |last2=Drinkwater |first2=Donald E. |last3=McLafferty |first3=Fred W. |date=1991-07-01 |title=Gas-phase formation and rearrangements of methyloxirene and its cation radical |url=https://pubs.acs.org/doi/10.1021/ja00016a006 |journal=Journal of the American Chemical Society |volume=113 |issue=16 |pages=5958–5964 |doi=10.1021/ja00016a006 |bibcode=1991JAChS.113.5958T |issn=0002-7863|url-access=subscription }}</ref>
|[[File:C3H4Oisomer 11.png|frameless]]
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== References ==
<references />


{{Molecular formula disambiguation}}