2-Methyl-1-butanol
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| Names | |
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| Preferred IUPAC name
2-Methylbutan-1-ol | |
| Other names
2-Methyl-1-butanol
Active amyl alcohol | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.809 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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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 | 3 mm Hg |
| Viscosity | 4.453 mPa·s |
| Thermochemistry | |
Std enthalpy of
formation (ΔfH⦵298) |
-356.6 kJ·mol−1 (liquid) -301.4 kJ·mol−1 (gas) |
| Hazards | |
| 385 °C (725 °F; 658 K) | |
| Related compounds | |
Related compounds
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Amyl alcohol |
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-Methyl-1-butanol (IUPAC name, also called active amyl alcohol) is an organic compound with the formula CH3CH2CH(CH3)CH2OH. It is one of several isomers of amyl alcohol. A colorless liquid, it occurs naturally in trace amounts and has attracted some attention as a potential biofulel, exploiting its hydrophobic (gasoline-like) and branched structure. It is chiral.[3]
Occurrence
It is used as a solvent and an intermediate in the manufacture of other chemicals. 2-Methyl-1-butanol is a component of many mixtures of amyl alcohols sold industrially. It is one of the many components of the aroma of the summer truffle Tuber aestivum.[4]
Production and reactions
2-Methyl-1-butanol has been produced from glucose by genetically modified E. coli. 2-Keto-3-methylvalerate, a precursor to threonine, is converted to the target alcohol by the sequential action of 2-Keto acid decarboxylase and dehydrogenase.[5] It can be derived from fusel oil (because it occurs naturally in fruits such as grapes[6]) or manufactured by either the oxo process or via the halogenation of pentane.[2]
See also
References
- ^ Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3–374, 5–42, 6–188, 8–102, 16–22, ISBN 0-8493-0594-2
- ^ a b McKetta, John J.; Cunningham, William Aaron (1977), Encyclopedia of Chemical Processing and Design, vol. 3, Boca Raton, Florida: CRC Press, pp. 279–280, ISBN 978-0-8247-2480-1, retrieved 2009-12-14
- ^ Xiong, Ren-Gen; You, Xiao-Zeng; Abrahams, Brendan F.; Xue, Ziling; Che, Chi-Ming (2001). "Enantioseparation of Racemic Organic Molecules by a Zeolite Analogue This work was supported by the Major State Basic Research Development Program (Grant No. G2000077500), the National Natural Science Foundation of China, the Camille Dreyfus Teacher–Scholar Program, the National Science Foundation of the USA (CHE-9904338), and the University of Tennessee SARIF EPPE Fund". Angewandte Chemie International Edition. 40 (23): 4422–4425. doi:10.1002/1521-3773(20011203)40:23<4422::AID-ANIE4422>3.0.CO;2-G. PMID 12404434.
- ^ Dı́Az, P.; Ibáñez, E.; Señoráns, F.J; Reglero, G. (2003). "Truffle aroma characterization by headspace solid-phase microextraction". Journal of Chromatography A. 1017 (1–2): 207–214. doi:10.1016/j.chroma.2003.08.016. PMID 14584705.
- ^ Atsumi, Shota; Hanai, Taizo; Liao, James C. (2008). "Non-Fermentative Pathways for Synthesis of Branched-Chain Higher Alcohols as Biofuels". Nature. 451 (7174): 86–89. Bibcode:2008Natur.451...86A. doi:10.1038/nature06450. PMID 18172501.
- ^ Howard, Philip H. (1993), Handbook of Environmental Fate and Exposure Data for Organic Chemicals, vol. 4, Boca Raton, Florida: CRC Press, pp. 392–396, ISBN 978-0-87371-413-6, retrieved 2009-12-14
