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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 [[isomer]]s 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]].<ref>{{cite journal |doi=10.1002/1521-3773(20011203)40:23<4422::AID-ANIE4422>3.0.CO;2-G|title=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|year=2001|last1=Xiong|first1=Ren-Gen|last2=You|first2=Xiao-Zeng|last3=Abrahams|first3=Brendan F.|last4=Xue|first4=Ziling|last5=Che|first5=Chi-Ming|journal=Angewandte Chemie International Edition|volume=40|issue=23|pages=4422–4425|pmid=12404434}}</ref>
'''2-Methyl-1-butanol''' ([[IUPAC]] name, also called '''active amyl alcohol''') is an [[organic chemistry|organic]] [[chemical compound]].


== Occurrence ==
It is one of the components of the aroma of ''[[Tuber melanosporum]]'', the black truffle.{{Citation needed|date=July 2017}}
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 alcohol]]s sold industrially. It is one of the many components of the aroma of the summer [[truffle]] ''[[Tuber aestivum]]''.<ref>{{cite journal |doi=10.1016/j.chroma.2003.08.016|title=Truffle aroma characterization by headspace solid-phase microextraction|year=2003|last1=Dı́Az|first1=P.|last2=Ibáñez|first2=E.|last3=Señoráns|first3=F.J|last4=Reglero|first4=G.|journal=Journal of Chromatography A|volume=1017|issue=1–2|pages=207–214|pmid=14584705}}</ref>

== Uses ==
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 alcohol]]s sold industrially.


==Production and reactions ==
==Production and reactions ==

Revision as of 12:59, 17 May 2021

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
-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).
checkY verify (what is checkY☒N ?)

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

  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. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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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