2-Methyl-1-butanol

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 biofuel, exploiting its hydrophobic (gasoline-like) and branched structure. It is chiral.[3]

2-Methyl-1-butanol[1][2]
Names
Preferred IUPAC name
2-Methylbutan-1-ol
Other names
2-Methyl-1-butanol
Active amyl alcohol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.809
UNII
  • InChI=1S/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3 checkY
    Key: QPRQEDXDYOZYLA-UHFFFAOYSA-N checkY
  • InChI=1/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3
    Key: QPRQEDXDYOZYLA-UHFFFAOYAW
  • OCC(C)CC
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
-356.6 kJ·mol−1 (liquid)
-301.4 kJ·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 their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Occurrence

2-Methyl-1-butanol is a component of many mixtures of commercial amyl alcohols. It is one of the many components of the aroma of various fungi and fruit, e.g., the summer truffle, tomato,[4] and cantaloupe.[5][6]

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.[7] It can be derived from fusel oil (because it occurs naturally in fruits such as grapes[8]) or manufactured by either the oxo process or via the halogenation of pentane.[2]

See also

References
  1. 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
  2. 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
  3. Xiong, Ren-Gen; You, Xiao-Zeng; Abrahams, Brendan F.; Xue, Ziling; Che, Chi-Ming (2001). "Enantioseparation of Racemic Organic Molecules by a Zeolite Analogue". 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.
  4. Buttery, Ron G.; Teranishi, Roy; Ling, Louisa C. (1987). "Fresh tomato aroma volatiles: A quantitative study". Journal of Agricultural and Food Chemistry. 35 (4): 540–544. doi:10.1021/jf00076a025.
  5. 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.
  6. Beaulieu, John C.; Grimm, Casey C. (2001). "Identification of Volatile Compounds in Cantaloupe at Various Developmental Stages Using Solid Phase Microextraction". Journal of Agricultural and Food Chemistry. 49 (3): 1345–1352. doi:10.1021/jf0005768. PMID 11312862.
  7. 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. S2CID 4413113.
  8. 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
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