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

Last updated March 08, 2025

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. This colorless liquid 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]

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 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]

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
1 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
↑ 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.
↑ 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.
↑ 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.
↑ 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.
↑ 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.
↑ 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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[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] 1 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.

[hef-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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2-Methyl-1-butanol

Contents

Occurrence

Production and reactions

See also

References

Names

Preferred IUPAC name 2-Methylbutan-1-ol
Other names 2-Methyl-1-butanol Active amyl alcohol
Identifiers
CAS Number	137-32-6 ^Y 1565-80-6 (S)
3D model (JSmol)	Interactive image
ChEBI	CHEBI:48945 ^Y
ChEMBL	ChEMBL451923 ^Y
ChemSpider	8398 ^Y
ECHA InfoCard	100.004.809
PubChem CID	8723
UNII	7VTJ239ASU ^Y
CompTox Dashboard (EPA)	DTXSID5027069
InChI InChI=1S/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3^Y Key: QPRQEDXDYOZYLA-UHFFFAOYSA-N^Y 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 (Δ_fH^⦵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). Y verify (what is ^YN ?) Infobox references