2-Methylbut-3-yn-2-ol
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Names | |
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Preferred IUPAC name 2-Methylbut-3-yn-2-ol | |
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ECHA InfoCard | 100.003.700 ![]() |
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UN number | 1987 |
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InChI
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Properties | |
Chemical formula | C5H8O |
Molar mass | 84.118 g·mol−1 |
Appearance | Colorless liquid |
Density | 0.8637 g/cm3 |
Melting point | 3 °C (37 °F; 276 K) |
Boiling point | 104 °C (219 °F; 377 K) |
Solubility in water | good |
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Danger | |
H225, H226, H302, H315, H318, H319, H335, H361 | |
P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501 | |
Flash point | 20 °C (68 °F; 293 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
Chemical compound
2-Methylbut-3-yn-2-ol is the organic compound with the formula HC2C(OH)Me2 (Me = CH3). A colorless liquid, it is classified as an alkynyl alcohol.
Preparation and use
It arises from the condensation of acetylene and acetone. The addition can be promoted with base[1] (Favorskii reaction) or with Lewis acid catalysts.[2] 2-Methylbut-3-yn-2-ol is produced on an industrial scale as a precursor to terpenes and terpenoids.
![](http://upload.wikimedia.org/wikipedia/commons/thumb/c/cb/IndustrialRouteGeranylAlc.png/424px-IndustrialRouteGeranylAlc.png)
2-Methylbut-3-yn-2-ol also is used as a monoprotected version of acetylene. For example, after arylation at carbon, the acetone can be removed with base:[4]
- HC2C(OH)Me2 + ArX + base → ArC2C(OH)Me2 + [Hbase]X
- ArC2C(OH)Me2 → ArC2H + OCMe2
In this regard, 2-methylbut-3-yn-2-ol is used similarly to trimethylsilylacetylene.
References
- ^ Donald D. Coffman (1940). "Dimethylethynylcarbinol". Org. Synth. 20: 40. doi:10.15227/orgsyn.020.0040.
- ^ Frantz, Doug E.; Fässler, Roger; Carreira, Erick M. (2000). "Facile Enantioselective Synthesis of Propargylic Alcohols by Direct Addition of Terminal Alkynes to Aldehydes". J. Am. Chem. Soc. 122 (8): 1806–1807. doi:10.1021/ja993838z.
- ^ Eberhard Breitmaier (2006). Terpenes: Flavors, Fragrances, Pharmaca, Pheromones. Wiley-VCH. doi:10.1002/9783527609949. ISBN 9783527609949.
- ^ Gordon, John (2001). "2-Methylbut-3-yn-2-ol". e-EROS Encyclopedia of Reagents for Organic Synthesis. pp. 1–2. doi:10.1002/047084289X.rm157. ISBN 0471936235.