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Revision as of 12:02, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 459312599 of page Phenethyl_alcohol for the Chem/Drugbox validation project (updated: '').  Latest revision as of 13:34, 9 June 2024 edit 2405:201:801d:a87f:5c09:16fe:2577:bf42 (talk) →Laboratory methods 
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{{Chembox
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
⚫ | Watchedfields = changed
{{chembox
⚫ | verifiedrevid = 464200140
⚫ | Verifiedfields = changed
⚫ | Name = Phenethyl alcohol
⚫ | verifiedrevid = 417792036
⚫ | Reference = <ref>{{Cite book|title=Merck Index|edition=11th|page=7185}}</ref>
⚫ | Name = Phenethyl alcohol
⚫ | ImageFile = Phenethyl alcohol.png
⚫ | Reference =<ref>''Merck Index'', 11th Edition, '''7185'''.</ref>
⚫ | ImageName = Skeletal formula
⚫ | ImageFile = Phenethyl alcohol.png
⚫ | ImageFile1 = Phenethyl-alcohol-3D-balls.png
| ImageSize = 200px
⚫ | ImageName1 = Ball-and-stick model
⚫ | ImageName = Skeletal formula
⚫ | IUPACName = 2-Phenylethanol
⚫ | ImageFile1 = Phenethyl-alcohol-3D-balls.png
| SystematicName =
⚫ | ImageName1 = Ball-and-stick model
⚫ | OtherNames = 2-Phenylethanol<br />Phenethyl alcohol<br />Benzyl carbinol<br />β-Hydroxyethylbenzene<br />Benzeneethanol
⚫ | IUPACName = 2-Phenylethanol
⚫ | OtherNames = Phenethyl alcohol<br />Benzyl carbinol<br />β-Hydroxyethylbenzene<br />Benzenethanol
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ML9LGA7468 | UNII = ML9LGA7468
| InChI = 1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2 | InChI = 1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
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| InChI1 = 1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2 | InChI1 = 1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
| CASNo = 60-12-8 | CASNo = 60-12-8
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB02192 | DrugBank = DB02192
| KEGG = D00192
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 49000 | ChEBI = 49000
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WRMNZCZEMHIOCP-UHFFFAOYSA-N | StdInChIKey = WRMNZCZEMHIOCP-UHFFFAOYSA-N
| SMILES = c1ccc(cc1)CCO | SMILES = c1ccc(cc1)CCO
| PubChem = 6054 | PubChem = 6054
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5830 | ChemSpiderID = 5830
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 448500 | ChEMBL = 448500
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
⚫ }}
| StdInChI=1S/C8H10O/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2
⚫ }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = C<sub>8</sub>H<sub>10</sub>O | Formula = {{chem2|C8H10O}}
| Odor = Soft, like roses
| MolarMass = 122.16 g/mol
| Density = 1.017 g/cm<sup>3</sup> | C=8|H=10|O=1
| Density = 1.017 g/cm<sup>3</sup>
| MeltingPtC = -27 | MeltingPtC = -27
| BoilingPt = 219-221 °C | BoilingPtC = 219 to 221
| LogP =1.36 <ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/60-12-8_509692.html|title=Phenylethyl alcohol_msds}}</ref>
}} }}
| Section3 =
| Section4 =
| Section5 =
| Section6 =
| Section7 = {{Chembox Hazards | Section7 = {{Chembox Hazards
| NFPA-H = 1 | NFPA-H = 1
| NFPA-F = 1 | NFPA-F = 1
| NFPA-R = 0 | NFPA-R = 0
| ExternalMSDS = | ExternalSDS =
}} }}
}} }}

'''Phenethyl alcohol''', or '''2-phenylethanol''', is an ] with the ] {{chem2|C6H5CH2CH2OH}}. It is a colourless liquid with a pleasant floral odor. It occurs widely in nature, being found in a variety of ]s. It is slightly soluble in water (2 ] per 100 ml of ]), but miscible with most ]. The molecule of phenethyl alcohol consists of a phenethyl group ({{chem2|C6H5CH2CH2\s}}) attached to a ] ({{chem2|\sOH}}).

== Synthesis ==
Phenethyl alcohol is prepared commercially via two routes. Most common is the ] reaction between ] and ] in the presence of ].
:{{chem2|C6H6 + CH2CH2O + AlCl3 → C6H5CH2CH2OAlCl2 + HCl}}
The reaction affords the aluminium alkoxide that is subsequently hydrolyzed to the desired product. The main side product is diphenylethane, which can be avoided by use of excess benzene. ] of ] also affords phenethyl alcohol.<ref name=Ullmann/>

===Laboratory methods===
Phenethyl alcohol can also be prepared by the reaction between ] and ]:
:{{chem2|C6H5MgBr + (CH2CH2)O → C6H5CH2CH2OMgBr}}
:{{chem2|C6H5CH2CH2OMgBr + ] → C6H5CH2CH2OH + MgBr+}}
Phenethyl alcohol can also be produced by ] from <small>L</small>-] using immobilized ] '']''.<ref>{{cite journal|vauthors=Eshkol N, Sendovski M, Bahalul M, Katz-Ezov T, Kashi Y, Fishman A|title=Production of 2-phenylethanol from L-phenylalanine by a stress tolerant Saccharomyces cerevisiae strain|journal=Journal of Applied Microbiology|year=2009|volume=106|pages=534–542|doi=10.1111/j.1365-2672.2008.04023.x|pmid=19200319|issue=2|doi-access=free}}</ref> It is also possible to produce phenethyl alcohol by the ] of ] using ] and ] in ]. <ref>{{cite journal|vauthors=Kanth JV, Periasamy M|title=Selective Reduction of Carboxylic Acids into Alcohols Using NaBH and I2|journal=Journal of Organic Chemistry|year=1991|volume=56|pages=5964–5965|doi=10.1021/jo00020a052}}</ref>

==Occurrence and uses==
Phenethyl alcohol is found in extract of ], ], ], ], ], ], ], ], and ]. It is also an ] produced by the fungus '']''.<ref>{{Cite journal|pmid=5762768|year=1969|last1=Lingappa|first1=BT|last2=Prasad|first2=M|last3=Lingappa|first3=Y|last4=Hunt|first4=DF|last5=Biemann|first5=K|title=Phenethyl alcohol and tryptophol: Autoantibiotics produced by the fungus Candida albicans|volume=163|issue=3863|pages=192–4|journal=Science |doi=10.1126/science.163.3863.192|bibcode=1969Sci...163..192L|s2cid=12430791}}</ref>

]s like phenethyl alcohol are grain fermentation byproducts, and therefore trace amounts of phenethyl alcohol are present in ].

It is therefore a common ingredient in flavors and perfumery, particularly when the odor of rose is desired.<ref name=Ullmann>{{cite book |doi=10.1002/14356007.a11_141 |chapter=Flavors and Fragrances |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2003 |last1=Fahlbusch |first1=Karl-Georg |last2=Hammerschmidt |first2=Franz-Josef |last3=Panten |first3=Johannes |last4=Pickenhagen |first4=Wilhelm |last5=Schatkowski |first5=Dietmar |last6=Bauer |first6=Kurt |last7=Garbe |first7=Dorothea |last8=Surburg |first8=Horst |isbn=978-3-527-30673-2}}</ref> It is used as an ]. It is also used as a ] in ]s due to its stability in ]. It is of interest due to its ] properties.

== See also ==
* ]
* ]
* ]
* ]

== References ==
{{reflist}}

{{Alcohols}}

]
]
]
]