 | |
| Names | |
|---|---|
| Preferred IUPAC name 2-Methylbutan-1-ol | |
| Other names 2-Methyl-1-butanol Active amyl alcohol | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.004.809 |
| UNII | |
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| Properties | |
| C5H12O | |
| Molar mass | 88.148 g/mol |
| Appearance | colorless liquid |
| Density | 0.8152 g/cm3 |
| Melting point | −117.2 °C (−179.0 °F; 156.0 K) |
| Boiling point | 127.5 °C (261.5 °F; 400.6 K) |
| 31 g/L | |
| Solubility | organic solvents |
| Vapor pressure | 3mm Hg |
| Viscosity | 4.453 mPa·s |
| Thermochemistry | |
Std enthalpy of formation(ΔfH⦵298) | −356.6kJ·mol−1 (liquid) −301.4kJ·mol−1 (gas) |
| Hazards | |
| 385 °C (725 °F; 658 K) | |
| Related compounds | |
Related compounds | Amyl alcohol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
2-Methyl-1-butanol (IUPAC name, also calledactive amyl alcohol) is anorganic compound with the formula CH3CH2CH(CH3)CH2OH. It is one of severalisomers ofamyl alcohol. This colorless liquid occurs naturally in trace amounts and has attracted some attention as a potentialbiofuel, exploiting its hydrophobic (gasoline-like) and branched structure. It ischiral.[3]
2-Methyl-1-butanol is a component of many mixtures of commercialamyl alcohols.
2M1B also occurs naturally. For example,fusel alcohols like 2M1B are grain fermentation byproducts, and therefore trace amounts of 2M1B are present inmany alcoholic beverages. Also, it is one of the many components of the aroma of various fungi and fruit, e.g., the summertruffle, tomato,[4] andcantaloupe.[5][6]
2-Methyl-1-butanol has been produced from glucose by genetically modifiedE. coli. 2-Keto-3-methylvalerate, a precursor tothreonine, is converted to the target alcohol by the sequential action of 2-keto aciddecarboxylase anddehydrogenase.[7] It can be derived fromfusel oil (because it occurs naturally infruits such asgrapes[8]) or manufactured by either theoxo process or via thehalogenation ofpentane.[2]
