1-Hexanol
IUPAC name	Hexan-1-ol
Other names	hexanol hexyl alcohol
Identifiers
CAS number	111-27-3 Y
PubChem	8103
EC-number	203-852-3
RTECS number	MQ4025000
SMILES	OCCCCCC
InChI	1/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3
InChI key	ZSIAUFGUXNUGDI-UHFFFAOYAO
ChemSpider ID	7812
Properties[1][2]
Molecular formula	C6H14O
Molar mass	102.17 g/mol
Density	0.8136 g/cm3 (20 ºC)
Melting point	−46.7 °C
Boiling point	158 °C
Solubility in water	0.59 g/100 ml (20 ºC)
log P	2.03
Refractive index (nD)	1.4178 (20 ºC)
Hazards[2]
MSDS	ICSC 1084
EU Index	603-059-00-6
EU classification	Harmful (Xn)
R-phrases	R22
S-phrases	(S2), S24/25
Flash point	63 °C (145 ºF)
Autoignition temperature	290 ºC (554 ºF)
Related compounds
Related primary alcohols	1-Pentanol 1-Heptanol
Related compounds	Hexanal Hexanoic acid
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 exist, 2-hexanol and 3-hexanol, both of which differ by the location of the hydroxyl group. Many isomeric alcohols have the formula C₆H₁₃OH. 1-hexanol is believed to be a component of the odour of freshly mowed grass. It is used in the perfume industry.

Contents 1 Preparation 1.1 Alternative methods 2 See also 3 References 4 External links

[edit] 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 + 1½O₂ + 3H₂O → 3HOC₆H₁₃ + Al(OH)₃

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

[edit] Alternative methods

Another method of preparation entails hydroformylation of 1-pentene followed by hydrogenation of the resulting aldehydes. This method is practiced industrially 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.

[edit] See also

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

[edit] References

[edit] External links

• International Chemical Safety Card 1084

v • d • e Alcohols (0°) Methanol Primary alcohols (1°) Ethanol · Propan-1-ol · Butanol/Isobutanol · 1-Pentanol · 1-Hexanol · 1-Heptanol Fatty alcohol: Octanol (C8) · 1-Nonanol (C9) · 1-Decanol (C10) · Undecanol (C11) · Dodecanol (C12) · 1-Tetradecanol (C14) · Cetyl alcohol (C16) · Stearyl alcohol (C18) · Arachidyl alcohol (C20) · Docosanol (C22) · Octanosol (C28) · Triacontanol (C30) Policosanol Secondary alcohols (2°) Isopropyl alcohol · 2-Butanol · 2-Hexanol · Cyclohexanol Tertiary alcohols (3°) tert-Butanol · 2-Methyl-2-butanol