| |||
| Names | |||
|---|---|---|---|
| Preferred IUPAC name Hexan-1-ol[1] | |||
| Other names amyl carbinol | |||
| Identifiers | |||
| |||
3D model (JSmol) | |||
| 969167 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
| ||
| ECHA InfoCard | 100.003.503 | ||
| EC Number |
| ||
| MeSH | 1-Hexanol | ||
| RTECS number |
| ||
| UNII | |||
| UN number | 2282 | ||
| |||
| |||
| Properties | |||
| 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] | ||
| 5.9 g/L (at 20 °C)[2] | |||
| logP | 1.858 | ||
| Vapor pressure | 100 Pa (at 25.6 °C) | ||
Refractive index (nD) | 1.4178 (at 20 °C) | ||
| Thermochemistry | |||
| 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: | |||
 | |||
| Warning | |||
| H302 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 59 °C (138 °F; 332 K) | ||
| 293 °C (559 °F; 566 K) | |||
| Safety data sheet (SDS) | ICSC 1084 | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
1-Hexanol (IUPAC name hexan-1-ol) is an organicalcohol with a six-carbon chain and a condensed structural formula of CH3(CH2)5OH. This colorless liquid is slightly soluble in water, butmiscible withdiethyl ether andethanol. Two additional straight chain isomers of 1-hexanol,2-hexanol and3-hexanol, exist, both of which differing by the location of thehydroxyl group. Many isomeric alcohols have the formula C6H13OH. It is used in theperfume industry.
Hexanol is produced industrially by the oligomerization ofethylene usingtriethylaluminium followed by oxidation of thealkylaluminium products.[3] An idealized synthesis is shown:
The process generates a range of oligomers that are separated bydistillation.
Another method of preparation entailshydroformylation of1-pentene followed byhydrogenation of the resulting aldehydes. This method is practiced in industry to produce mixtures of isomeric C6-alcohols, which are precursors toplasticizers.[3]
In principle,1-hexene could be converted to 1-hexanol byhydroboration (diborane intetrahydrofuran followed by treatment withhydrogen peroxide andsodium hydroxide):
This method is instructive and useful in laboratory synthesis but of no practical relevance because of the commercial availability of inexpensive 1-hexanol fromethylene.
1-Hexanol is believed to be a component of the odour of freshly mown grass.Alarm pheromones emitted by theKoschevnikov gland ofhoney bees contain 1-hexanol. It also is partly responsible for the fragrance ofstrawberries.
