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2/8/2017 PhenolWikipedia

Phenol
FromWikipedia,thefreeencyclopedia

Phenol,alsoknownascarbolicacid,isanaromaticorganic Phenol
compoundwiththemolecularformulaC6H5OH.Itisawhite
crystallinesolidthatisvolatile.Themoleculeconsistsofa
phenylgroup(C6H5)bondedtoahydroxylgroup(OH).Itis
mildlyacidicandrequirescarefulhandlingduetoitspropensity
tocausechemicalburns.

Phenolwasfirstextractedfromcoaltar,buttodayisproduced
onalargescale(about7billionkg/year)frompetroleum.Itisan
importantindustrialcommodityasaprecursortomanymaterials
andusefulcompounds.[7]Itisprimarilyusedtosynthesize
plasticsandrelatedmaterials.Phenolanditschemical
derivativesareessentialforproductionofpolycarbonates,
epoxies,Bakelite,nylon,detergents,herbicidessuchasphenoxy
herbicides,andnumerouspharmaceuticaldrugs.

Contents
1 Properties
1.1 Acidity
1.1.1 Phenoxideanion
1.1.2 Tautomerism
1.2 Reactions
2 Production
3 Uses
3.1 Nicheuses Names
4 History
4.1 SecondWorldWar PreferredIUPACname
5 Naturaloccurrences Phenol[1]
5.1 Occurrenceinwhisky Othernames
6 Biodegradation Benzenol
7 Toxicity
8 Phenols Carbolicacid
9 Seealso Phenylicacid
10 References Hydroxybenzene
11 Externallinks Phenicacid
Identifiers
CASNumber 108952(http://www.common
Properties chemistry.org/ChemicalDetail.a
spx?ref=108952)
Phenolisanorganiccompound.Phenolisappreciablysolublein
water,withabout84.2gdissolvingin1000mL(0.895M). 3Dmodel(Jmol) Interactiveimage(http://chema
Homogeneousmixturesofphenolandwateratphenoltowater pps.stolaf.edu/jmol/jmol.php?m
massratiosof~2.6andhigherarepossible.Thesodiumsaltof odel=c1ccc%28cc1%29O)
phenol,sodiumphenoxide,isfarmorewatersoluble. ChEBI CHEBI:15882(https://www.eb
https://en.wikipedia.org/wiki/Phenol 1/10
2/8/2017 PhenolWikipedia

Acidity i.ac.uk/chebi/searchId.do?chebi
Id=15882)
PhenolisweaklyacidicandathighpHsgivesthephenolate
ChEMBL ChEMBL14060(https://www.e
anionC6H5O(alsocalledphenoxide):[8] bi.ac.uk/chembldb/index.php/co
mpound/inspect/ChEMBL1406
PhOHPhO+H+(K=1010)
0)
Comparedtoaliphaticalcohols,phenolisabout1milliontimes ChemSpider 971(http://www.chemspider.co
moreacidic,althoughitisstillconsideredaweakacid.Itreacts m/ChemicalStructure.971.htm
completelywithaqueousNaOHtoloseH+,whereasmost l)
alcoholsreactonlypartially. DrugBank DB03255(https://www.drugba

Oneexplanationfortheincreasedacidityoveralcoholsis nk.ca/drugs/DB03255)
resonancestabilizationofthephenoxideanionbythearomatic ECHAInfoCard 100.003.303(https://echa.europ
ring.Inthisway,thenegativechargeonoxygenisdelocalized a.eu/substanceinformation//su
ontotheorthoandparacarbonatoms.[9]Inanotherexplanation, bstanceinfo/100.003.303)
increasedacidityistheresultoforbitaloverlapbetweenthe KEGG D06536(http://www.kegg.jp/en
oxygen'slonepairsandthearomaticsystem.[10]Inathird,the try/D06536)
dominanteffectistheinductionfromthesp2hybridisedcarbons PubChem 996(https://pubchem.ncbi.nlm.
thecomparativelymorepowerfulinductivewithdrawalof
nih.gov/compound/996)
electrondensitythatisprovidedbythesp2systemcomparedto
RTECSnumber SJ3325000
ansp3systemallowsforgreatstabilizationoftheoxyanion.
UNII 339NCG44TV(http://fdasis.nl
ThepKaoftheenolofacetoneis10.9,comparabletothatfor m.nih.gov/srs/srsdirect.jsp?regn

phenol.[11]Theaciditiesofphenolandacetoneenoldivergein o=339NCG44TV)

thegasphaseowingtotheeffectsofsolvation.About13ofthe InChI

increasedacidityofphenolisattributabletoinductiveeffects, SMILES
withresonanceaccountingfortheremainingdifference.[12] Properties
Chemicalformula C6H6O
Phenoxideanion
Molarmass 94.11gmol1
Thephenoxideanionhasasimilarnucleophilicitytofree Appearance Transparentcrystallinesolid
amines,withthefurtheradvantagethatitsconjugateacid Odor Sweetandtarry
(neutralphenol)doesnotbecomeentirelydeactivatedasa
Density 1.07g/cm3
nucleophileeveninmoderatelyacidicconditions.Phenolate
estersaremorestabletowardhydrolysisthanacidanhydrides Meltingpoint 40.5C(104.9F313.6K)
andacylhalidesbutaresufficientlyreactiveundermild Boilingpoint 181.7C(359.1F454.8K)
conditionstofacilitatetheformationofamidebonds. Solubilityinwater 8.3g/100mL(20C)
Vaporpressure 0.4mmHg(20C)[2]
Tautomerism
Acidity(pKa) 9.95(inwater),
Phenolexhibitsketoenoltautomerismwithitsunstableketo
tautomercyclohexadienone,butonlyatinyfractionofphenol 29.1(inacetonitrile)[3]
existsastheketoform.Theequilibriumconstantforenolisation
UVvis(max) 270.75nm[4]
isapproximately1013,meaningthatonlyoneineveryten
trillionmoleculesisintheketoformatanymoment.[13]The Dipolemoment 1.224D
smallamountofstabilisationgainedbyexchangingaC=Cbond Pharmacology

https://en.wikipedia.org/wiki/Phenol ATCcode 2/10