Methylcyclobutane
 | |
| Names | |
|---|---|
| Preferred IUPAC name
Methylcyclobutane | |
| Other names
1-Methylcyclobutane | |
| Identifiers | |
3D model (JSmol) |
|
| ChemSpider | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C5H10 | |
| Molar mass | 70.135 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 0.748 g/cm3 |
| Melting point | −135.7 °C (−212.3 °F; 137.5 K) |
| Boiling point | 36.3 °C (97.3 °F; 309.4 K) |
| insoluble | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
Methylcyclobutane is an organic compound with the chemical formula C5H10.[1] This is a cycloalkane consisting of a four-membered cyclobutane core substituted with a methyl group.[2] It is a colorless, volatile liquid at room temperature and is primarily of interest in fundamental organic chemistry research, particularly in studies of ring strain and reaction mechanisms.
Synthesis
- Wurtz-type coupling: Reaction of 1,3-dibromopropane with methylene iodide and sodium metal yields methylcyclobutane, though this method suffers from low yields due to competing elimination and polymerization.[3][4]
- Cycloaddition reactions: Photochemical cycloaddition of propene with ethylene or diazomethane-derived cyclopropanation followed by ring expansion can produce substituted cyclobutanes, including methylcyclobutane.[5]
Physical properties
Methylcyclobutane is a volatile, flammable liquid with a characteristic hydrocarbon odor. The compound is nonpolar and insoluble in water, but miscible with common organic solvents such as diethyl ether, ethanol, and benzene. Decomposes upon heating.[6]
The compound is toxic.[7]
References
- ↑ "Cyclobutane, methyl-". NIST. Retrieved 3 April 2026.
- ↑ "methylcyclobutane - SpringerMaterials". materials.springer.com. Retrieved 3 April 2026.
- ↑ Hiemstra, H., ed. (2009). "Product Class 3: Cyclobutanes". Category 6, Compounds with All-Carbon Functions (1 ed.). Thieme Verlag. p. 615. doi:10.1055/sos-SD-048-00343. ISBN 978-3-13-119021-5. Retrieved 6 April 2026.
- ↑ Connor, Daniel S.; Wilson, Eugene R. (1 January 1967). "Ring closures via the Wurtz reaction a convenient synthesis of cyclobutane". Tetrahedron Letters. 8 (49): 4925–4929. doi:10.1016/S0040-4039(01)89939-1. ISSN 0040-4039.
- ↑ Poplata, Saner; Tröster, Andreas; Zou, You-Quan; Bach, Thorsten (14 September 2016). "Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions". Chemical Reviews. 116 (17): 9748–9815. Bibcode:2016ChRv..116.9748P. doi:10.1021/acs.chemrev.5b00723. PMID 27018601.
- ↑ Thomas, Timothy F.; Conn, Paul J.; Swinehart, D. F. (December 1969). "Unimolecular Reactions of Methylcyclobutane at Low Pressures". Journal of the American Chemical Society. 91 (27): 7611–7616. Bibcode:1969JAChS..91.7611T. doi:10.1021/ja50001a014.
- ↑ "1-Methylcyclobutane - Hazardous Agents | Haz-Map". haz-map.com. Retrieved 6 April 2026.
Categories: