2-Butyne
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| Names | |
|---|---|
| Preferred IUPAC name
But-2-yne | |
| Other names
Dimethylacetylene
Crotonylene | |
| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.239 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C4H6 | |
| Molar mass | 54.0904 g/mol |
| Density | 0.691 g/mL |
| Melting point | −32 °C (−26 °F; 241 K) |
| Boiling point | 27 °C (81 °F; 300 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Butyne (dimethylacetylene, crotonylene or but-2-yne) is an alkyne with chemical formula CH3C≡CCH3. Produced artificially, it is a colorless, volatile, pungent liquid at standard temperature and pressure.
2-Butyne (dimethylethin) forms with 5-decyne (dibutylethin), 4-octyne (dipropylethin) and 3-hexyne (diethylethin) a group of symmetric alkynes.
Synthesis
2-Butyne can be synthesized by the rearrangement of ethylacetylene in a solution of ethanolic potassium hydroxide.[3]
Applications
2-Butyne, along with propyne, is used to synthesize alkylated hydroquinones in the total synthesis of Vitamin E.[4]
See also
- 1-Butyne, a position isomer
References
- ^ 2-Butyne at Sigma-Aldrich
- ^ NIST Chemistry WebBook page for 2-butyne
- ^ Victor von Richter; Hans Meerwein (1916). Organic Chemistry: Chemistry of the aliphatic series Vol. I: Smith's 3rd American Ed. Philadelphia: P. Blakiston's Sons & Co. p. 89.
- ^ Reppe, Walter; Kutepow, N; Magin, A (1969). "Cyclization of Acetylenic Compounds". Angewandte Chemie International Edition in English. 8 (10): 727–733. doi:10.1002/anie.196907271. Retrieved 26 December 2013.
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