Back الکول ایزوآمیل AZB Izoamil-alkohol BS Isopentylalkohol Czech 3-Methyl-1-butanol German Izoamila alkoholo Esperanto الکل ایزوآمیل Persian 3-metyyli-1-butanoli Finnish 3-Méthylbutan-1-ol French Isoamil alkohol ID 3-metil-1-butanolo Italian

Isoamyl alcohol

Isoamyl alcohol[1]
Names
Preferred IUPAC name
3-Methylbutan-1-ol
Other names
3-Methyl-1-butanol
Isopentyl alcohol
Isopentanol
Isobutylcarbinol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.213 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3 checkY
    Key: PHTQWCKDNZKARW-UHFFFAOYSA-N checkY
  • InChI=1/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3
    Key: PHTQWCKDNZKARW-UHFFFAOYAW
  • OCCC(C)C
Properties
C5H12O
Molar mass 88.148 g/mol
Appearance Clear, colorless liquid
Odor Disagreeable odor in high concentrations
Density 0.8104 g/cm3 at 20 °C
Melting point −117[2][3] °C (−179 °F; 156 K)
Boiling point 131.1 °C (268.0 °F; 404.2 K)
Slightly soluble, 28 g/L
Solubility Very soluble in acetone, diethyl ether, ethanol
Vapor pressure 28 mmHg (20 °C)[3]
−68.96·10−6 cm3/mol
Viscosity 3.692 mPa·s
Thermochemistry
2.382 J/g·K
−356.4 kJ/mol (liquid)
−300.7 kJ/mol (gas)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable, moderately toxic
GHS labelling:
FlammableCorrosiveIrritant
Danger
H226, H302, H305, H315, H318, H332, H335
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Flash point 43 °C (109 °F; 316 K)
350 °C (662 °F; 623 K)
Explosive limits 1.2–9%
Lethal dose or concentration (LD, LC):
1453 mg/kg (rabbit, oral)
1300 mg/kg (rat, oral)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 100 ppm (360 mg/m3)[3]
REL (Recommended)
 TWA 100 ppm (360 mg/m3), ST 125 ppm (450 mg/m3)[3]
IDLH (Immediate danger)
 500 ppm[3]
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 ?)

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.[5]

Isoamyl alcohol is an ingredient in the production of banana oil, an ester found in nature and also produced as a flavouring in industry. It is a common fusel alcohol, produced as a major by-product of ethanol fermentation.

  1. ^ Lide, David R., ed. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 3–374, 5–42, 6–188, 8–102, 15–22. ISBN 0-8493-0487-3.
  2. ^ Straka, M.; van Genderen, A.; Růžička, K.; Růžička, V. Heat Capacities in the Solid and in the Liquid Phase of Isomeric Pentanols. J. Chem. Eng. Data 2007, 52, 794-802.
  3. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0348". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ "Isoamyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ Cite error: The named reference EB1911 was invoked but never defined (see the help page).
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