2-Methyl-1-butanol

Source: Wikipedia, the free encyclopedia.
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 Edit this at Wikidata
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
Std enthalpy of
formation
(ΔfH⦵298)
 -356.6
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).
checkY verify (what is checkY☒N ?)

2-Methyl-1-butanol (

chiral.[3]

Occurrence

2-Methyl-1-butanol is a component of many mixtures of commercial amyl alcohols.

2M1B also occurs naturally. For example, fusel alcohols like 2M1B are grain fermentation byproducts, and therefore trace amounts of 2M1B are present in many alcoholic beverages. Also, 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

oxo process or via the halogenation of pentane.[2]

See also

  • 2-Methyl-2-butanol

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. ^ 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
  3. PMID 12404434
    .
  4. doi:10.1021/jf00076a025
    .
  5. PMID 14584705
    .
  6. PMID 11312862
    .
  7. 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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