Editing 1-Hexanol

{{Chembox
| Watchedfields  = changed
| verifiedrevid  = 477188181
| Name           = Hexyl Alcohol
| ImageFileL1    = Hexan-1-ol-2D-skeletal.png
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageNameL1    = Skeletal formula of 1-hexanol
| ImageFileR1    = Hexan-1-ol-3D-balls.png
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageNameR1    = Spacefill formula of 1-hexanol
| OtherNames     = amyl carbinol
| PIN            = Hexan-1-ol<ref>{{Cite web|title = 1-hexanol - Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8103&loc=ec_rcs|work = PubChem Compound|publisher = National Center for Biotechnology Information|access-date = 8 October 2011|location = USA|date = 26 March 2005|at = Identification and Related Records}}</ref>
| Section1       = {{Chembox Identifiers
| CASNo = 111-27-3
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 8103
| ChemSpiderID = 7812
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = 6CP2QER8GS
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 203-852-3
| UNNumber = 2282
| MeSHName = 1-Hexanol
| ChEBI = 87393
| ChEMBL = 14085
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = MQ4025000
| Beilstein = 969167
| SMILES = CCCCCCO
| StdInChI = 1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZSIAUFGUXNUGDI-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
| Section2       = {{Chembox Properties
| C=6 | H=14 | O=1
|Appearance = colorless liquid
| Density = 0.82 g cm<sup>−3</sup> (at 20 °C)<ref name=GESTIS>{{GESTIS|ZVG=22240}}</ref>
| MeltingPtC = -45
| MeltingPt_ref = <ref name=GESTIS/>
| BoilingPtC = 157
| BoilingPt_ref = <ref name=GESTIS/>
| Solubility = 5.9 g/L (at 20 °C)<ref name=GESTIS/>
| LogP = 1.858
| VaporPressure = 100 Pa (at 25.6 °C)
| RefractIndex = 1.4178 (at 20 °C)
}}
| Section3       = {{Chembox Thermochemistry
| DeltaHf = −377.5 kJ mol<sup>−1</sup>
| DeltaHc = −3.98437 MJ mol<sup>−1</sup>
| Entropy = 287.4 J K<sup>−1</sup> mol<sup>−1</sup>
| HeatCapacity = 243.2 J K<sup>−1</sup> mol<sup>−1</sup>
}}
| Section4       = {{Chembox Hazards
| ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics1084.htm ICSC 1084]
| GHSPictograms = {{GHS exclamation mark}}
| GHSSignalWord = '''WARNING'''
| HPhrases = {{H-phrases|302}}
| NFPA-H = 1
| NFPA-F = 2
| NFPA-R = 0
| FlashPtC = 59
| AutoignitionPtC = 293
}}
}}

'''1-Hexanol''' (IUPAC name hexan-1-ol) is an organic [[Alcohol (chemistry)|alcohol]] with a six-[[carbon]] chain and a condensed structural formula of CH<sub>3</sub>(CH<sub>2</sub>)<sub>5</sub>OH.  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|2-hexanol]] and [[3-hexanol]], exist, both of which differing by the location of the [[Hydroxy group|hydroxyl group.]]  Many isomeric alcohols have the formula C<sub>6</sub>H<sub>13</sub>OH. It is used in the [[perfume]] industry.

==Preparation==
Hexanol is produced industrially by the oligomerization of [[ethylene]] using [[triethylaluminium]] followed by oxidation of the [[organoaluminium|alkylaluminium products]].<ref name="Ullmann">{{Ullmann | first1 = Jürgen | last1 = Falbe | first2 = Helmut | last2 = Bahrmann | first3 = Wolfgang | last3 = Lipps | first4 = Dieter | last4 = Mayer | title = Alcohols, Aliphatic | doi =  10.1002/14356007.a01_279}}.</ref>  An idealized synthesis is shown:
:Al(C<sub>2</sub>H<sub>5</sub>)<sub>3</sub> + 6C<sub>2</sub>H<sub>4</sub> → Al(C<sub>6</sub>H<sub>13</sub>)<sub>3</sub>
:Al(C<sub>6</sub>H<sub>13</sub>)<sub>3</sub> + {{frac|1|1|2}}O<sub>2</sub> + 3H<sub>2</sub>O → 3HOC<sub>6</sub>H<sub>13</sub> + Al(OH)<sub>3</sub>
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 C<sub>6</sub>-alcohols, which are precursors to [[plasticizer]]s.<ref name="Ullmann"/>

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

[[Image:Hexene-hexanol.png|center]]
[[File:Hexan-1-ol.jpg|thumb|Hexan-1-ol]]

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 pheromone]]s emitted by the [[Koschevnikov gland]] of [[honey bee]]s contain 1-hexanol. It also is partly responsible for the fragrance of [[Strawberry|strawberries]].

==See also==

* [[Cis-3-Hexenal]], another [[volatile organic compound]], is also considered responsible for the freshly mowed grass odor.
== References ==

{{Reflist}}

==External links==
*{{ICSC|1084}}

{{Alcohols}}

{{DEFAULTSORT:Hexanol, 1-}}

[[Category:Flavors]]
[[Category:Hexanols]]
[[Category:Primary alcohols]]