Isoamyl alcohol

Isoamyl alcohol^[1]

Names
IUPAC name 3-methyl-1-butanol
Other names Isopentyl alcohol, Isopentanol, Isobutylcarbinol
Identifiers
CAS Number	123-51-3
ChEBI	CHEBI:15837
ChEMBL	ChEMBL372396
ChemSpider	29000
DrugBank	DB02296
Jmol interactive 3D	Image
KEGG	C07328
PubChem	31260
InChI InChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3 Key: PHTQWCKDNZKARW-UHFFFAOYSA-N InChI=1/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3 Key: PHTQWCKDNZKARW-UHFFFAOYAW
SMILES OCCC(C)C
Properties
Chemical formula	C5H12O
Molar mass	88.148 g/mol
Appearance	Clear, colorless liquid
Odor	disagreeable[2]
Density	0.8104 g/cm^3 at 20 °C
Melting point	−117[3][2] °C (−179 °F; 156 K)
Boiling point	131.1 °C (268.0 °F; 404.2 K)
Solubility in water	slightly soluble, 28 g/L
Solubility	very soluble in acetone, diethyl ether, ethanol
Vapor pressure	28 mmHg (20°C)[2]
Viscosity	3.692 mPa·s
Thermochemistry
Specific heat capacity (C)	2.382 J·g^−1·K^−1
Std enthalpy of formation (ΔfH^o298)	-356.4 kJ·mol^−1 (liquid) -300.7 kJ·mol^−1 (gas)
Hazards
Flash point	43 °C (109 °F; 316 K)
Autoignition temperature	350 °C (662 °F; 623 K)
Explosive limits	1.2 – 9%
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	3438 mg/kg (rabbit, oral) 1300 mg/kg (rat, oral)[4]
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 100 ppm (360 mg/m^3)[2]
REL (Recommended)	TWA 100 ppm (360 mg/m^3) ST 125 ppm (450 mg/m^3)[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.

References

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. "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.