C3H4O

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!Name

!CAS #

!Notes

!Structure

|{{CAS|287-25-2}}

|Synthesized;{{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}} unstable.{{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}} Can be made by using light to cyclize acrolein.{{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}}

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|{{CAS|35553-05-0}}

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|{{CAS|107-02-8}}

|Forms from pollutants, burning, metabolism.{{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}} Cis and trans forms; cis form predominant.

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|{{Cas|81788-96-7}}

|Synthesized.{{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}} Tautomerizes "quantitatively" to acrolein above -50 °C.

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|{{CAS|107-19-7}}

|"Mild, geranium odor"{{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}} Used in synthesis, as corrosion inhibitor, soil fumigant.{{Cite PubChem|cid=7859|title=Propargyl alcohol}}

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|{{CAS|6443-91-0}}

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|{{CAS|6175-54-8}}

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|{{CAS|6004-44-0}}

|Synthesized.{{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}} Intermediate in acrolein pyrolysis.{{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}} Of astronomical interest.

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|{{CAS|40079-14-9}}

|Synthesized;{{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}} predicted (1968) to isomerize "readily" to cyclopropanone.{{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}}{{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}}

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|{{CAS|5009-27-8}}

|Synthesized; unstable due to polymerization and ring-opening.{{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}} Derivatives used in synthesis, biology.

Tautomer of 1-cyclopen-1-ol{{Citation needed|date=December 2024}}

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|{{CAS|81788-95-6}}

|Tautomer of cyclopropanone; Not synthesized{{Citation needed|date=December 2024}}

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|{{CAS|81788-94-5}}

|Not synthesized{{Citation needed|date=December 2024}}

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|{{CAS|2835-41-8}}

|Synthesized; unstable. Product of ionized diazoacetone; isomerizes "rapidly" to methylketene, acrolein, methoxyethyne, and/or 1-propynol.{{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}}{{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}}

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