1-Hexanol

Hexyl Alcohol

Names
Preferred IUPAC name Hexan-1-ol[1]
Other names amyl carbinol
Identifiers
CAS Number	111-27-3 Y
3D model (JSmol)	Interactive image
Beilstein Reference	969167
ChEBI	CHEBI:87393
ChEMBL	ChEMBL14085 Y
ChemSpider	7812 Y
ECHA InfoCard	100.003.503
EC Number	203-852-3
MeSH	1-Hexanol
PubChem CID	8103
RTECS number	MQ4025000
UNII	6CP2QER8GS Y
UN number	2282
CompTox Dashboard (EPA)	DTXSID8021931
InChI InChI=1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3 Y Key: ZSIAUFGUXNUGDI-UHFFFAOYSA-N Y
SMILES CCCCCCO
Properties
Chemical formula	C6H14O
Molar mass	102.177 g·mol−1
Appearance	colorless liquid
Density	0.82 g cm−3 (at 20 °C)[2]
Melting point	−45 °C (−49 °F; 228 K)[2]
Boiling point	157 °C (315 °F; 430 K)[2]
Solubility in water	5.9 g/L (at 20 °C)[2]
log P	1.858
Vapor pressure	100 Pa (at 25.6 °C)
Refractive index (nD)	1.4178 (at 20 °C)
Thermochemistry
Heat capacity (C)	243.2 J K−1 mol−1
Std molar entropy (S⦵298)	287.4 J K−1 mol−1
Std enthalpy of formation (ΔfH⦵298)	−377.5 kJ mol−1
Std enthalpy of combustion (ΔcH⦵298)	−3.98437 MJ mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
NFPA 704 (fire diamond)	1 2 0
Flash point	59 °C (138 °F; 332 K)
Autoignition temperature	293 °C (559 °F; 566 K)
Safety data sheet (SDS)	ICSC 1084
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

1-Hexanol (IUPAC name hexan-1-ol) is an organic alcohol with a six-carbon chain and a condensed structural formula of CH₃(CH₂)₅OH. This colorless liquid is slightly soluble in water, but miscible with diethyl ether and ethanol. Two additional straight chain isomers of 1-hexanol, 2-hexanol and 3-hexanol, exist, both of which differing by the location of the hydroxyl group. Many isomeric alcohols have the formula C₆H₁₃OH. It is used in the perfume industry.

Preparation

Hexanol is produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products.^[3] An idealized synthesis is shown:

Al(C₂H₅)₃ + 6C₂H₄ → Al(C₆H₁₃)₃

Al(C₆H₁₃)₃ + 1+1⁄2O₂ + 3H₂O → 3HOC₆H₁₃ + Al(OH)₃

The process generates a range of oligomers that are separated by distillation.

Alternative methods

Another method of preparation entails hydroformylation of 1-pentene followed by hydrogenation of the resulting aldehydes. This method is practiced in industry to produce mixtures of isomeric C₆-alcohols, which are precursors to plasticizers.^[3]

In principle, 1-hexene could be converted to 1-hexanol by hydroboration (diborane in tetrahydrofuran followed by treatment with hydrogen peroxide and sodium hydroxide):

This method is instructive and useful in laboratory synthesis but of no practical relevance because of the commercial availability of inexpensive 1-hexanol from ethylene.

Occurrence in nature

1-Hexanol is believed to be a component of the odour of freshly mown grass. Alarm pheromones emitted by the Koschevnikov gland of honey bees contain 1-hexanol. It also is partly responsible for the fragrance of strawberries.

See also

• Cis-3-Hexenal, another volatile organic compound, is also considered responsible for the freshly mowed grass odor.

References

External links

• International Chemical Safety Card 1084