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Revision as of 14:29, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 461829230 of page 1-Hexanol for the Chem/Drugbox validation project (updated: '').  Latest revision as of 23:21, 27 September 2023 edit Rai1i1inbow (talk | contribs)9 editsm →See also: most people dont eat fresh grass.Tag: Visual edit 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Chembox {{Chembox
| Verifiedfields = changed | Watchedfields = changed
⚫ | verifiedrevid = 477188181
| Watchedfields = changed
| Name = Hexyl Alcohol
⚫ | verifiedrevid = 457304985
| ImageFileL1 = Hexan-1-ol-2D-skeletal.png | ImageFileL1 = Hexan-1-ol-2D-skeletal.png
| ImageFileL1_Ref = {{chemboximage|correct|??}} | ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageNameL1 = Skeletal formula of 1-hexanol | ImageNameL1 = Skeletal formula of 1-hexanol
| ImageFileR1 = Hexan-1-ol-3D-vdW.png | ImageFileR1 = Hexan-1-ol-3D-balls.png
| ImageFileR1_Ref = {{chemboximage|correct|??}} | ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageNameR1 = Spacefill formula of 1-hexanol | ImageNameR1 = Spacefill formula of 1-hexanol
| OtherNames = amyl carbinol
| IUPACName = Hexan-1-ol<ref>{{Cite web|title = 1-hexanol - Compound Summary|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8103&loc=ec_rcs|work = PubChem Compound|publisher = National Center for Biotechnology Information|accessdate = 8 October 2011|location = USA|date = 26 March 2005|at = Identification and Related Records}}</ref> | 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 | Section1 = {{Chembox Identifiers
| CASNo = 111-27-3
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 111-27-3
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 8103 | PubChem = 8103
⚫ | ChemSpiderID = 7812
| PubChem_Ref = {{Pubchemcite|correct|pubchem}}
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 7812
⚫ | UNII = 6CP2QER8GS
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | UNII = 6CP2QER8GS
| EINECS = 203-852-3
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 203-852-3 | UNNumber = 2282
| UNNumber = 2282 | MeSHName = 1-Hexanol
| MeSHName = 1-Hexanol | ChEBI = 87393
| ChEMBL = 14085 | ChEMBL = 14085
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = MQ4025000 | RTECS = MQ4025000
| Beilstein = 969167 | Beilstein = 969167
| SMILES = CCCCCCO | SMILES = CCCCCCO
| StdInChI = 1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3 | StdInChI = 1S/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZSIAUFGUXNUGDI-UHFFFAOYSA-N | StdInChIKey = ZSIAUFGUXNUGDI-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C = 6 | C=6 | H=14 | O=1
|Appearance = colorless liquid
⚫ | H = 14
| Density = 0.82 g cm<sup>−3</sup> (at 20 °C)<ref name=GESTIS>{{GESTIS|ZVG=22240}}</ref>
⚫ | O = 1
| MeltingPtC = -45
| ExactMass = 102.104465070 g mol<sup>−1</sup>
| MeltingPt_ref = <ref name=GESTIS/>
| Density = 813.6 mg cm<sup>−3</sup>
| MeltingPtKL = 220 | BoilingPtC = 157
| BoilingPt_ref = <ref name=GESTIS/>
| MeltingPtKH = 232
| Solubility = 5.9 g/L (at 20 °C)<ref name=GESTIS/>
| BoilingPtKL = 428
| BoilingPtKH = 432 | LogP = 1.858
| Solubility = 5.9 g dm<sup>−3</sup> (at 20 ºC) | VaporPressure = 100 Pa (at 25.6 °C)
⚫ | RefractIndex = 1.4178 (at 20 °C)
| LogP = 1.858
| VaporPressure = 100 Pa (at 25.6 ºC)
⚫ | RefractIndex = 1.4178 (at 20 ºC)
}} }}
| Section3 = {{Chembox Thermochemistry | Section3 = {{Chembox Thermochemistry
| DeltaHf = −377.5 kJ mol<sup>−1</sup> | DeltaHf = −377.5 kJ mol<sup>−1</sup>
| DeltaHc = −3.98437 MJ mol<sup>−1</sup> | DeltaHc = −3.98437 MJ mol<sup>−1</sup>
| Entropy = 287.4 J K<sup>−1</sup> 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> | HeatCapacity = 243.2 J K<sup>−1</sup> mol<sup>−1</sup>
}} }}
| Section4 = {{Chembox Hazards | Section4 = {{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| GHSPictograms = {{GHS exclamation mark}} | GHSPictograms = {{GHS exclamation mark}}
| GHSSignalWord = '''WARNING''' | GHSSignalWord = '''WARNING'''
| HPhrases = {{H-phrases|302}} | HPhrases = {{H-phrases|302}}
⚫ | NFPA-H = 1
| EUIndex = 603-059-00-6
⚫ | NFPA-F = 2
| EUClass = {{Hazchem Xn}}
| RPhrases = {{R22}} | NFPA-R = 0
| FlashPtC = 59
| SPhrases = {{S2}}, {{S24/25}}
| NFPA-H = 1 | AutoignitionPtC = 293
| NFPA-F = 2
| NFPA-R = 0
| FlashPt = 59 °C
| Autoignition = 293 ºC
}} }}
}} }}

'''1-Hexanol''' (IUPAC name hexan-1-ol) is an organic ] with a six-] 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 ] with ] and ]. Two additional straight chain isomers of 1-hexanol, ] and ], exist, both of which differing by the location of the ] Many isomeric alcohols have the formula C<sub>6</sub>H<sub>13</sub>OH. It is used in the ] industry.

==Preparation==
Hexanol is produced industrially by the oligomerization of ] using ] followed by oxidation of the ].<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 ].

===Alternative methods===
Another method of preparation entails ] of ] followed by ] of the resulting aldehydes. This method is practiced in industry to produce mixtures of isomeric C<sub>6</sub>-alcohols, which are precursors to ]s.<ref name="Ullmann"/>

In principle, ] could be converted to 1-hexanol by ] (] in ] followed by treatment with ] and ]):

]
]

This method is instructive and useful in laboratory synthesis but of no practical relevance because of the commercial availability of inexpensive 1-hexanol from ].

==Occurrence in nature==
1-Hexanol is believed to be a component of the odour of freshly mown grass. ]s emitted by the ] of ]s contain 1-hexanol. It also is partly responsible for the fragrance of ].

==See also==

* ], another ], is also considered responsible for the freshly mowed grass odor.
== References ==

{{Reflist}}

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

{{Alcohols}}

{{DEFAULTSORT:Hexanol, 1-}}

]
]
]