1-Hexanol

1-Hexanol
IUPAC name Hexan-1-ol[1]
Identifiers
CAS number	111-27-3 Y
PubChem	8103
ChemSpider	7812 Y
UNII	6CP2QER8GS Y
EC number	203-852-3
UN number	2282
MeSH	1-Hexanol
ChEMBL	CHEMBL14085 N
RTECS number	MQ4025000
Beilstein Reference	969167
Jmol-3D images	Image 1
SMILES CCCCCCO
InChI InChI=1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3 N Key: ZSIAUFGUXNUGDI-UHFFFAOYSA-N N
Properties
Molecular formula	C6H14O
Molar mass	102.17 g mol−1
Exact mass	102.104465070 g mol−1
Density	813.6 mg cm−3
Melting point	-53--41 °C, 220-232 K, -64--42 °F
Boiling point	155-159 °C, 428-432 K, 311-318 °F
Solubility in water	5.9 g dm−3 (at 20 ºC)
log P	1.858
Vapor pressure	100 Pa (at 25.6 ºC)
Refractive index (nD)	1.4178 (at 20 ºC)
Thermochemistry
Std enthalpy of formation ΔfHo298	−377.5 kJ mol−1
Std enthalpy of combustion ΔcHo298	−3.98437 MJ mol−1
Standard molar entropy So298	287.4 J K−1 mol−1
Specific heat capacity, C	243.2 J K−1 mol−1
Hazards
MSDS	ICSC 1084
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H302
EU Index	603-059-00-6
EU classification	Xn
R-phrases	R22
S-phrases	(S2), S24/25
NFPA 704	2 1 0
Flash point	59 °C
Autoignition temperature	293 ºC
N (verify) (what is: Y/N?) 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. 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.^[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

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.^[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

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

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

References

1. ^ "1-hexanol - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8103&loc=ec_rcs. 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

• International Chemical Safety Card 1084