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Skeletal formula of 1-hexanol Spacefill formula of 1-hexanol
CAS number 111-27-3 YesY
PubChem 8103
ChemSpider 7812 YesY
EC number 203-852-3
UN number 2282
MeSH 1-Hexanol
RTECS number MQ4025000
Beilstein Reference 969167
Jmol-3D images Image 1
Molecular formula C6H14O
Molar mass 102.17 g mol−1
Density .8136 g cm−3
Melting point −53 to −41 °C; −64 to −42 °F; 220 to 232 K
Boiling point 155 to 159 °C; 311 to 318 °F; 428 to 432 K
Solubility in water 5.9 g/L (at 20 ºC)
log P 1.858
Vapor pressure 100 Pa (at 25.6 ºC)
Refractive index (nD) 1.4178 (at 20 ºC)
heat capacity
243.2 J K−1 mol−1
Std molar
287.4 J K−1 mol−1
Std enthalpy of
−377.5 kJ mol−1
Std enthalpy of
−3.98437 MJ mol−1
GHS signal word WARNING
GHS hazard statements H302
EU Index 603-059-00-6
EU classification Harmful Xn
R-phrases R22
S-phrases (S2), S24/25
NFPA 704
Flash point 59 °C (138 °F; 332 K)
Infobox references

1-Hexanol 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 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.


Hexanol is produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products.[2] An idealized synthesis is shown:

Al(C2H5)3 + 6C2H4 → Al(C6H13)3
Al(C6H13)3 + 1½O2 + 3H2O → 3HOC6H13 + Al(OH)3

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

Alternative methods[edit]

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.[2]

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[edit]

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.

See also[edit]

Cis-3-Hexenal, another volatile organic carbon biomolecule, is also considered responsible for the freshly mowed grass flavor.


  1. ^ "1-hexanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 8 October 2011. 
  2. ^ a b Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter (2005), "Alcohols, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a01_279 .

External links[edit]