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Amyl alcohol

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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.

Amyl alcohol isomers
Common name Structure Type IUPAC name Boiling point (°C)
1-pentanol
or normal amyl alcohol
primary Pentan-1-ol 138.5
2-methyl-1-butanol
or active amyl alcohol
primary 2-Methylbutan-1-ol 128.7
3-methyl-1-butanol
or isoamyl alcohol
or isopentyl alcohol
primary 3-Methylbutan-1-ol 131.2
2,2-dimethyl-1-propanol
or neopentyl alcohol
primary 2,2-Dimethylpropan-1-ol 113.1
2-pentanol
or sec-amyl alcohol
or methyl (n) propyl carbinol
secondary Pentan-2-ol 118.8
3-methyl-2-butanol
or sec-isoamyl alcohol
or methyl isopropyl carbinol
secondary 3-Methylbutan-2-ol 113.6
3-Pentanol secondary Pentan-3-ol 115.3
2-methyl-2-butanol
or tert-amyl alcohol
tertiary 2-Methylbutan-2-ol 102

Three of these alcohols, 2-methyl-1-butanol, 2-pentanol, and 3-methyl-2-butanol (methyl isopropyl carbinol), contain stereocenters, and are therefore chiral and optically active.

The most important amyl alcohol is isoamyl alcohol, the chief one generated by fermentation in the production of alcoholic beverages and a constituent of fusel oil. The other amyl alcohols may be obtained synthetically.

References

  1. Merriam-Webster's Collegiate Dictionary 11th Ed. 2004
  2. Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter (2000). "Alcohols, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_279. ISBN 3527306730.
  3. Calculated boiling points from ChemSpider.
Alcohols
By consumption
Alcohols found in
alcoholic drinks
Medical alcohol
Toxic alcohols
Primary
alcohols
(1°)
Methanol
Ethanol
Butanol
Straight-chain
saturated
C1 — C9
Straight-chain
saturated
C10 — C19
Straight-chain
saturated
C20 — C29
Straight-chain
saturated
C30 — C39
Straight-chain
saturated
C40 — C49
Secondary
alcohols (2°)
  • 1-Phenylethanol
  • 2-Butanol
  • 2-Deoxyerythritol
  • 2-Heptanol
  • 3-Heptanol
  • 2-Hexanol
  • 3-Hexanol
  • 3-Methyl-2-butanol
  • 2-Nonanol
  • 2-Octanol
  • 2-Pentanol
  • 3-Pentanol
  • Cyclohexanol
  • Cyclopentanol
  • Cyclopropanol
  • Diphenylmethanol
  • Isopropanol
  • Pinacolyl alcohol
  • Pirkle's alcohol
  • Propylene glycol methyl ether
  • Tertiary
    alcohols (3°)
    Hydric alcohols
    Monohydric alcohols
    Dihydric alcohols
    Trihydric alcohols
    Polyhydric alcohols (sugar alcohols)
    Amyl alcohols
    Aromatic alcohols
    Saturated
    fatty alcohols
    Branched and
    unsaturated
    fatty alcohols
    Sugar alcohols
    C1 — C7
    Deoxy sugar
    alcohols
    Cyclic sugar
    alcohols
    Glycylglycitols
    Terpene alcohols
    Monoterpene
    alcohols
    Sesquiterpene
    alcohols
    Diterpene
    alcohols
    Dialcohols
    Trialcohols
    Sterols
    Fluoroalcohols
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    Reactions
    GABAA receptor positive modulators
    Alcohols
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    Neuroactive steroids
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    Phenols
    Piperidinediones
    Pyrazolopyridines
    Quinazolinones
    Volatiles/gases
    Others/unsorted
    See also: Receptor/signaling modulatorsGABA receptor modulatorsGABA metabolism/transport modulators
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