2-Methyl-1-butanol

Last updated
2-Methyl-1-butanol [1] [2]
2-Methyl-1-butanol.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3 Yes check.svgY
    Key: QPRQEDXDYOZYLA-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearancecolorless 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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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]

Contents

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]

See also

Related Research Articles

<span class="mw-page-title-main">Amyl alcohol</span> Chemical compound family

Amyl alcohols are alcohols with the formula C5H11OH. Eight are known. A mixture of amyl alcohols (also called amyl alcohol) can be obtained from fusel alcohol. Amyl alcohol is used as a solvent and in esterification, by which is produced amyl acetate and other products. The name amyl alcohol without further specification applies to the normal (straight-chain) form, 1-pentanol.

Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4H9OH, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a butyl or isobutyl group linked to a hydroxyl group (sometimes represented as BuOH, 1-BuOH, i-BuOH, and t-BuOH). These are 1-butanol, two stereoisomers of sec-butyl alcohol, isobutanol and tert-butyl alcohol. Butanol is primarily used as a solvent and as an intermediate in chemical synthesis, and may be used as a fuel. Biologically produced butanol is called biobutanol, which may be n-butanol or isobutanol.

1-Pentanol,, is an organic compound with the formula CH3CH2CH2CH2CH2OH and is classified as a primary alcohol. It is a colourless liquid with a distinctive aroma. It is one of 8 isomeric alcohols with the formula C5H11OH. It is used as a solvent, a biological drying agent and in the synthesis of some fragrance compounds. It is also a common component of fusel alcohols, the undesirable byproducts of alcoholic fermentation.

Fusel alcohols or fuselol, also sometimes called fusel oils in Europe, are mixtures of several higher alcohols produced as a by-product of alcoholic fermentation. The word Fusel is German for "bad liquor".

<span class="mw-page-title-main">Valeric acid</span> Carboxylic acid – CH3(CH2)3COOH

Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula CH3(CH2)3COOH. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. It is found in the perennial flowering plant Valeriana officinalis, from which it gets its name. Its primary use is in the synthesis of its esters. Salts and esters of valeric acid are known as valerates or pentanoates. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Several, including ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

Butan-2-ol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

<span class="mw-page-title-main">Acetone</span> Organic compound ((CH3)2CO); simplest ketone

Acetone is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colorless, highly volatile and flammable liquid with a characteristic pungent odor.

<span class="mw-page-title-main">Isobutanol</span> Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<span class="mw-page-title-main">Isoamyl alcohol</span> Chemical compound

Isoamyl alcohol is a colorless liquid with the formula C
5H
12O, specifically (H3C–)2CH–CH2–CH2–OH. It is one of several isomers of amyl alcohol (pentanol). It is also known as isopentyl alcohol, isopentanol, or (in the IUPAC recommended nomenclature) 3-methyl-butan-1-ol. An obsolete name for it was isobutyl carbinol.

<span class="mw-page-title-main">Silver carbonate</span> Chemical compound

Silver carbonate is the chemical compound with the formula Ag2CO3. This salt is yellow but typical samples are grayish due to the presence of elemental silver. It is poorly soluble in water, like most transition metal carbonates.

<span class="mw-page-title-main">1-Butanol</span> Chemical compound

1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.

<span class="mw-page-title-main">Magnesium bromide</span> Chemical compound

Magnesium bromide is a chemical compound of magnesium and bromine, with the chemical formula MgBr2. It is white and deliquescent crystalline solid. It is often used as a mild sedative and as an anticonvulsant for treatment of nervous disorders. It is water-soluble and somewhat soluble in alcohol. It can be found naturally in small amounts in some minerals such as: bischofite and carnallite, and in sea water, such as that of the Dead Sea.

Heptanal or heptanaldehyde is an alkyl aldehyde. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants.

<i>tert</i>-Amyl alcohol Chemical compound

tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol.

<span class="mw-page-title-main">3-Pentanol</span> Chemical compound

3-Pentanol is one of the eight isomers of amyl alcohol. It is found naturally and has a role as a pheromone.

<span class="mw-page-title-main">2-Pentanol</span> Chemical compound

2-Pentanol is an organic chemical compound. It is used as a solvent and an intermediate in the manufacturing of other chemicals. 2-Pentanol is a component of many mixtures of amyl alcohols sold industrially. 2-Pentanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-pentanol and (S)-(+)-2-pentanol.

<span class="mw-page-title-main">2-Methyl-2-pentanol</span> Chemical compound

2-Methyl-2-pentanol is an organic chemical compound. It can be added to a gas chromatograph to help distinguish between branched compounds, especially alcohols. Its presence in urine can be used to test for exposure to 2-methylpentane. As with many other short-chain alcohols, 2-methyl-2-pentanol can produce intoxication and sedative effects similar to those of ethanol, though it is more irritating to mucous membranes and generally more toxic to the body.

<span class="mw-page-title-main">2-Ethyl-1-butanol</span> Chemical compound

2-Ethyl-1-butanol is an organic chemical compound. It can be used to facilitate the separation of ethanol from water, which forms an azeotrope that otherwise limits the maximum ethanol concentration.

<span class="mw-page-title-main">Wine chemistry</span> Chemistry of wine

Wine is a complex mixture of chemical compounds in a hydro-alcoholic solution with a pH around 4. The chemistry of wine and its resultant quality depend on achieving a balance between three aspects of the berries used to make the wine: their sugar content, acidity and the presence of secondary compounds. Vines store sugar in grapes through photosynthesis, and acids break down as grapes ripen. Secondary compounds are also stored in the course of the season. Anthocyanins give grapes a red color and protection against ultraviolet light. Tannins add bitterness and astringency which acts to defend vines against pests and grazing animals.

3-Methyl-2-butanol is an organic chemical compound. It is used as a solvent and an intermediate in the manufacture of other chemicals.

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. 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.
  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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