Isoamyl alcohol

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Isoamyl alcohol[1]
Isoamyl alcohol.svg
Names
Preferred IUPAC name
3-Methylbutan-1-ol
Other names
3-Methyl-1-butanol
Isopentyl alcohol
Isopentanol
Isobutylcarbinol
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.004.213
KEGG
Properties
C5H12O
Molar mass 88.148 g/mol
Appearance Clear, colorless liquid
Odor disagreeable[2]
Density 0.8104 g/cm3 at 20 °C
Melting point −117[3][2] °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)[2]
-68.96·10−6 cm3/mol
Viscosity 3.692 mPa·s
Thermochemistry
2.382 J·g−1·K−1
-356.4 kJ·mol−1 (liquid)
-300.7 kJ·mol−1 (gas)
Hazards
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):
3438 mg/kg (rabbit, oral)
1300 mg/kg (rat, oral)[4]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 100 ppm (360 mg/m3)[2]
REL (Recommended)
TWA 100 ppm (360 mg/m3) ST 125 ppm (450 mg/m3)[2]
IDLH (Immediate danger)
500 ppm[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Isoamyl alcohol (also known as isopentyl alcohol) is a clear, colorless alcohol with the formula (CH3)2CHCH2CH2OH. It is one of several isomers of amyl alcohol. It is a main ingredient in the production of banana oil, an ester found in nature and also produced as a flavouring in industry. It is also the main ingredient of Kovac's reagent, used for the bacterial diagnostic indole test.

It is also used as an antifoaming agent in the Chloroform:Isomyl Alcohol reagent.[5]

Isoamyl alcohol is used in a phenol–chloroform extraction mixed with the chloroform to further inhibit RNase activity and prevent solubility of RNAs with long tracts of poly-adenine.[6]

It is one of the components of the aroma of Tuber melanosporum, the black truffle. It has been identified as a chemical in the pheromone used by hornets to attract other members of the hive to attack.[citation needed]

References[edit]

  1. ^ Lide, David R., ed. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, FL: CRC Press. pp. 3–374, 5–42, 6–188, 8–102, 15–22. ISBN 0-8493-0487-3. 
  2. ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0348". National Institute for Occupational Safety and Health (NIOSH). 
  3. ^ 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.
  4. ^ "Isoamyl alcohol". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH). 
  5. ^ Zumbo, P. "Phenol-chloroform Extraction" (PDF). WEILL CORNELL MEDICAL COLLEGE P. ZUMBO LABORATORY OF CHRISTOPHER E. MASON, PH.D. Retrieved 19 June 2014. 
  6. ^ Green, Michael; Sambrook, Joseph. "Purification of Nucleic Acids: Extraction with Phenol-Chloroform". Molecular Cloning: A Laboratory Manual. Cold Spring Harbor Laboratory Press. ISBN 1936113422.