Isoamyl alcohol

Isoamyl alcohol^[1]
Names
	Preferred IUPAC name 3-Methylbutan-1-ol
	Other names 3-Methyl-1-butanol; Isopentyl alcohol; Isopentanol; Isobutylcarbinol
Identifiers
CAS Number	123-51-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15837 ;
ChEMBL	ChEMBL372396 ;
ChemSpider	29000 ;
DrugBank	DB02296 ;
ECHA InfoCard	100.004.213
KEGG	C07328 ;
PubChem CID	31260;
CompTox Dashboard (EPA)	DTXSID3025469 ;
	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
Density	0.8104 g/cm3 at 20 °C
Melting point	−117 °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)
Magnetic susceptibility (χ)	-68.96·10−6 cm3/mol
Viscosity	3.692 mPa·s
Thermochemistry
Heat capacity (C)	2.382 J·g−1·K−1
Std enthalpy of; formation (ΔfH⦵298)	-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)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 100 ppm (360 mg/m3)
REL (Recommended)	TWA 100 ppm (360 mg/m3) ST 125 ppm (450 mg/m3)
IDLH (Immediate danger)	500 ppm
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Isoamyl alcohol (also known as isopentyl alcohol) is a colorless liquid with the formula (CH₃)₂CHCH₂CH₂OH. It is one of several isomers of amyl alcohol. It is an ingredient in the production of banana oil, an ester found in nature and also produced as a flavouring in industry. It is also an 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.^[7]

References

^ 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.
^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0348". National Institute for Occupational Safety and Health (NIOSH).
^ 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.
^ "Isoamyl alcohol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Zumbo, P. "Phenol-chloroform Extraction" (PDF). WEILL CORNELL MEDICAL COLLEGE P. ZUMBO LABORATORY OF CHRISTOPHER E. MASON, PH.D. Retrieved 19 June 2014.
^ Green, Michael; Sambrook, Joseph. "Purification of Nucleic Acids: Extraction with Phenol-Chloroform". Molecular Cloning: A Laboratory Manual. Cold Spring Harbor Laboratory Press. ISBN 1936113422.
^ Wilson, Calum & Davies, Noel & Corkrey, Ross & J. Wilson, Annabel & M. Mathews, Alison & C. Westmore, Guy. (2017). Receiver Operating Characteristic curve analysis determines association of individual potato foliage volatiles with onion thrips preference, cultivar and plant age. PLOS ONE. 12. e0181831. 10.1371/journal.pone.0181831.

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[hand-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.

[PGCH-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 or Health Concentrations (IDLH). 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.

[7] Wilson, Calum & Davies, Noel & Corkrey, Ross & J. Wilson, Annabel & M. Mathews, Alison & C. Westmore, Guy. (2017). Receiver Operating Characteristic curve analysis determines association of individual potato foliage volatiles with onion thrips preference, cultivar and plant age. PLOS ONE. 12. e0181831. 10.1371/journal.pone.0181831.

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