C3H4O

Last updated

C3H4O 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:

NameCAS #NotesStructure
Oxetene, 2H-Oxete 287-25-2 Synthesized; [1] unstable. [2] Can be made by using light to cyclize acrolein. [3] C3H4Oisomer 12.png
2-Oxabicyclo[1.1.0]butane [4] 35553-05-0 C3H4Oisomer 13.png
Acrolein, 2-propenal 107-02-8 Forms from pollutants, burning, metabolism. [5] Cis and trans forms; cis form predominant. [5] C3H4Oisomer 01.png
Propa-1,2-dien-1-ol [6] 81788-96-7 Synthesized. [7] Tautomerizes "quantitatively" to acrolein above -50 °C. [7] C3H4Oisomer 04.png
Propargyl alcohol or 2-propyn-1-ol 107-19-7 "Mild, geranium odor" [8] Used in synthesis, as corrosion inhibitor, soil fumigant. [9] C3H4Oisomer 02.png
Methoxy ethyne, methoxyacetylene 6443-91-0 C3H4Oisomer 05.png
Prop-1-yn-1-ol, [10] 1-propynol [11] 6175-54-8 C3H4Oisomer 03.png
Methylketene or 1-propen-1-one [12] 6004-44-0 Synthesized. [13] Intermediate in acrolein pyrolysis. [14] Of astronomical interest. [13] C3H4Oisomer 06.png
Methylene oxirane, [15] allene oxide 40079-14-9 Synthesized; [16] predicted (1968) to isomerize "readily" to cyclopropanone. [16] [17] [ needs update ] C3H4Oisomer 07.png
Cyclopropanone 5009-27-8 Synthesized; unstable due to polymerization and ring-opening. [18] Derivatives used in synthesis, biology. [18]

Tautomer of 1-cyclopen-1-ol[ citation needed ]

 C3H4Oisomer 08.png
Cycloprop-1-en-1-ol, cyclopropene alcohol [19] 81788-95-6 Tautomer of cyclopropanone; Not synthesized[ citation needed ] C3H4Oisomer 09.png
2-Cyclopropenol or 1-hydroxy-2-cyclopropene[ dubious – discuss ] 81788-94-5 Not synthesized[ citation needed ] C3H4Oisomer 10.png
1,2-Epoxypropene or 2-methyloxirene [20] 2835-41-8 Synthesized; unstable. Product of ionized diazoacetone; isomerizes "rapidly" to methylketene, acrolein, methoxyethyne, and/or 1-propynol. [21] [22] C3H4Oisomer 11.png

References

  1. ↑ Friedrich, Louis E.; Lam, Patrick Yuk-Sun (1981-01-01). "Syntheses and reactions of 3-phenyloxete and the parent unsubstituted oxete" . The Journal of Organic Chemistry. 46 (2): 306–311. doi:10.1021/jo00315a016. ISSN   0022-3263.
  2. ↑ Ji Ram, Vishnu; Sethi, Arun; Nath, Mahendra; Pratap, Ramendra (2019-01-01), Ji Ram, Vishnu; Sethi, Arun; Nath, Mahendra; Pratap, Ramendra (eds.), "Chapter 4 - Four-Membered Heterocycles", The Chemistry of Heterocycles, Elsevier, pp. 93–147, ISBN   978-0-08-101033-4 , retrieved 2024-12-08
  3. ↑ Kikuchi O. (1981). "A classification of the photochemical electrocyclic reactions of heteroatom conjugated systems". Tetrahedron Lett. 22 (9): 859–862. doi:10.1016/0040-4039(81)80015-9.
  4. ↑ "2-Oxabicyclo[1.1.0]butane". PubChem . National Center for Biotechnology Information.
  5. 1 2 Puzzarini, Cristina; Penocchio, Emanuele; Biczysko, Malgorzata; Barone, Vincenzo (2014-08-21). "Molecular Structure and Spectroscopic Signatures of Acrolein: Theory Meets Experiment" . The Journal of Physical Chemistry A. 118 (33): 6648–6656. Bibcode:2014JPCA..118.6648P. doi:10.1021/jp503672g. ISSN   1089-5639. PMID   24842714.
  6. ↑ "Propa-1,2-dien-1-ol". PubChem . National Center for Biotechnology Information.
  7. 1 2 Hakiki, Abdelhak; Ripoll, Jean-Louis; Thuillier, André (1984-01-01). "Retrodienic reactions XVI - flash thermolytic generation of reactive functional allenes" . Tetrahedron Letters. 25 (32): 3459–3460. doi:10.1016/S0040-4039(01)91046-9. ISSN   0040-4039.
  8. ↑ "Propargyl alcohol". NIOSH Pocket Guide to Safety and Hazards. National Institute for Occupational Safety and Health . Retrieved 2024-12-08.
  9. ↑ "Propargyl alcohol". PubChem . National Center for Biotechnology Information.
  10. ↑ "CID 141504292". PubChem . National Center for Biotechnology Information.
  11. ↑ "NIST Chemistry WebBook, SRD 69: 1-Propynol". NIST . Retrieved 8 December 2024.
  12. ↑ "Methylketene". PubChem . National Center for Biotechnology Information.
  13. 1 2 Derbali, Imene; Hrodmarsson, Helgi Rafn; Schwell, Martin; Bénilan, Yves; Poisson, Lionel; Hochlaf, Majdi; Alikhani, Mohammad Esmaïl; Guillemin, Jean-Claude; Zins, Emilie-Laure (2020-09-23). "Unimolecular decomposition of methyl ketene and its dimer in the gas phase: theory and experiment". Physical Chemistry Chemical Physics. 22 (36): 20394–20408. Bibcode:2020PCCP...2220394D. doi:10.1039/D0CP03921G. ISSN   1463-9084. PMID   32914152.
  14. ↑ Muzika, Michael; Genossar-Dan, Nadav; Fux, Dana; Har Lavan, Shani; Zamir, Uri; Rozenberg, Illya; Hemberger, Patrick; Baraban, Joshua H. (2024-04-01). "Radical intermediates and stable products in acrolein pyrolysis". Environmental Chemistry Letters. 22 (2): 491–497. doi:10.1007/s10311-023-01661-8. ISSN   1610-3661.
  15. ↑ "Methyleneoxirane". PubChem . National Center for Biotechnology Information.
  16. 1 2 Turecek, Frantisek; Drinkwater, Donald E.; McLafferty, Fred W. (1990-07-01). "The elusive methyleneoxirane: preparation and characterization by flash-vacuum pyrolysis and neutralization-reionization mass spectrometry" . Journal of the American Chemical Society. 112 (15): 5892–5893. Bibcode:1990JAChS.112.5892T. doi:10.1021/ja00171a046. ISSN   0002-7863.
  17. ↑ Hoffmann, Roald (March 1968). "Trimethylene and the addition of methylene to ethylene" . Journal of the American Chemical Society. 90 (6): 1475–1485. Bibcode:1968JAChS..90.1475H. doi:10.1021/ja01008a016. ISSN   0002-7863.
  18. 1 2 Wasserman, Harry H.; Berdahl, Donald R.; Lu, Ta-Jung (1987-10-28), Rappoport, Zvi (ed.), "The Chemistry of Cyclopropanones" , Cyclopropyl Group Volume 1 and Volume 2 (1987), Chichester, UK: John Wiley & Sons, Ltd, pp. 1455–1532, doi:10.1002/0470023449.ch23, ISBN   978-0-470-02344-0 , retrieved 2024-12-08
  19. ↑ "Cycloprop-1-en-1-ol". PubChem . National Center for Biotechnology Information.
  20. ↑ "2-Methyloxirene". PubChem . National Center for Biotechnology Information.
  21. ↑ Lewars, Errol G. (2008), Lewars, Errol G. (ed.), "Oxirene" , Modeling Marvels: Computational Anticipation of Novel Molecules, Dordrecht: Springer Netherlands, pp. 31–52, doi:10.1007/978-1-4020-6973-4_3, ISBN   978-1-4020-6973-4 , retrieved 2024-12-08
  22. ↑ Turecek, Frantisek; Drinkwater, Donald E.; McLafferty, Fred W. (1991-07-01). "Gas-phase formation and rearrangements of methyloxirene and its cation radical" . Journal of the American Chemical Society. 113 (16): 5958–5964. Bibcode:1991JAChS.113.5958T. doi:10.1021/ja00016a006. ISSN   0002-7863.


DAB list gray.svg
This set index page lists chemical structure articles associated with the same molecular formula.
If an internal link led you here, you may wish to change the link to point directly to the intended article.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.