2-Methyl-1-butanol

2-Methyl-1-butanol^[1]^[2]
Names
	Preferred IUPAC name 2-Methylbutan-1-ol
	Other names 2-Methyl-1-butanol; Active amyl alcohol
Identifiers
CAS Number	137-32-6 ; 1565-80-6 (S);
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:48945 ;
ChEMBL	ChEMBL451923 ;
ChemSpider	8398 ;
ECHA InfoCard	100.004.809
PubChem CID	8723;
UNII	7VTJ239ASU ;
CompTox Dashboard (EPA)	DTXSID5027069 ;
	InChI InChI=1S/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3 Key: QPRQEDXDYOZYLA-UHFFFAOYSA-N ; InChI=1/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3 Key: QPRQEDXDYOZYLA-UHFFFAOYAW;
	SMILES OCC(C)CC;
Properties
Chemical formula	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)
Solubility in water	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
Autoignition; temperature	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). verify (what is ?) Infobox references

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 various fungi and fruit, e.g., the summer truffle Tuber aestivum and cantaloupe Cucumis melo.^[4]^[5]

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.^[6] It can be derived from fusel oil (because it occurs naturally in fruits such as grapes^[7]) or manufactured by either the oxo process or via the halogenation of pentane.^[2]

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.
^ . doi:10.1021/jf0005768. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)
^ 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

[hand-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

[encyc-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 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] . doi:10.1021/jf0005768. {{cite journal}}: Cite journal requires |journal= (help); Missing or empty |title= (help)

[6] 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.

[hef-7] 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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Occurrence

Production and reactions

See also

References