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phenols wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 properties toggle properties subsection 1 1 acidity 1 2 condensation with aldehydes and ketones 1 3 c alkylation with alkenes 1 4 other reactions 2 synthesis 3 classification toggle classification subsection 3 1 drugs and bioactive natural products 4 analysis 5 references toggle the table of contents phenols 45 languages العربية беларуская тарашкевіца български bosanski català čeština dansk deutsch esperanto español eesti فارسی suomi français galego עברית hrvatski magyar հայերեն italiano 日本語 qaraqalpaqsha 한국어 lietuvių latviešu македонски norsk bokmål polski پنجابی português română русский srpskohrvatski српскохрватски slovenčina svenska тоҷикӣ türkçe татарча tatarça українська oʻzbekcha ўзбекча tiếng việt 吴语 文言 粵語 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical compounds in which hydroxyl group is attached directly to an aromatic ring this article is about the class of chemicals containing a phenol group for the molecule alone see phenol in organic chemistry phenols sometimes called phenolics are a class of chemical compounds consisting of one or more hydroxyl groups o h bonded directly to an aromatic hydrocarbon group 1 the simplest is phenol c 6 h 5 oh phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule phenol the simplest of the phenols chemical structure of salicylic acid the active metabolite of aspirin phenols are both synthesized industrially and produced by plants and microorganisms 2 properties edit acidity edit phenols are more acidic than typical alcohols the acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids their pk a is usually between 10 and 12 deprotonation of a phenol forms a corresponding negative phenolate ion or phenoxide ion and the corresponding salts are called phenolates or phenoxides aryloxides according to the iupac gold book citation needed condensation with aldehydes and ketones edit phenols are susceptible to electrophilic aromatic substitutions condensation with formaldehyde gives resinous materials famously bakelite citation needed another industrial scale electrophilic aromatic substitution is the production of bisphenol a which is produced by the condensation with acetone 3 c alkylation with alkenes edit phenol is readily alkylated at the ortho positions using alkenes in the presence of a lewis acid such as aluminium phenoxide citation needed ch 2 cr 2 c 6 h 5 oh r 2 chch 2 2 c 6 h 4 oh more than 100 000 tons of tert butyl phenols are produced annually year 2000 in this way using isobutylene ch 2 cme 2 as the alkylating agent especially important is 2 6 ditert butylphenol a versatile antioxidant 3 other reactions edit phenols undergo esterification phenol esters are active esters being prone to hydrolysis phenols are reactive species toward oxidation oxidative cleavage for instance cleavage of 1 2 dihydroxybenzene to the monomethylester of 2 4 hexadienedioic acid with oxygen copper chloride in pyridine 4 oxidative de aromatization to quinones also known as the teuber reaction oxidizing reagents are fremy s salt 5 and oxone 6 in reaction depicted below 3 4 5 trimethylphenol reacts with singlet oxygen generated from oxone sodium carbonate in an acetonitrile water mixture to a para peroxyquinole this hydroperoxide is reduced to the quinole with sodium thiosulfate phenols are oxidized to hydroquinones in the elbs persulfate oxidation reaction of naphtols and hydrazines and sodium bisulfite in the bucherer carbazole synthesis synthesis edit many phenols of commercial interest are prepared by elaboration of phenol or cresols they are typically produced by the alkylation of benzene toluene with propylene to form cumene then o 2 is added with h 2 so 4 to form phenol hock process in addition to the reactions above many other more specialized reactions produce phenols rearrangement of esters in the fries rearrangement 7 8 rearrangement of n phenylhydroxylamines in the bamberger rearrangement 9 10 dealkylation of phenolic ethers reduction of quinones replacement of an aromatic amine by an hydroxyl group with water and sodium bisulfide in the bucherer reaction 11 thermal decomposition of aryl diazonium salts the salts are converted to phenol 12 by the oxidation of aryl silanes an aromatic variation of the fleming tamao oxidation 13 catalytic synthesis from aryl bromides and iodides using nitrous oxide 14 classification edit the best selling drug in the u s acetaminophen also known as paracetamol is a phenol there are various classification schemes 15 2 a commonly used scheme is based on the number of carbons and was devised by jeffrey harborne and simmonds in 1964 and published in 1980 15 2 16 phenol the parent compound used as a disinfectant and for chemical synthesis bisphenol a and other bisphenols produced from ketones and phenol cresol bht butylated hydroxytoluene a fat soluble antioxidant and food additive 4 nonylphenol a breakdown product of detergents and nonoxynol 9 orthophenyl phenol a fungicide used for waxing citrus fruits picric acid trinitrophenol an explosive material phenolphthalein ph indicator xylenol used in antiseptics disinfectants drugs and bioactive natural products edit main article naturally occurring phenols more than 371 drugs approved by the fda between the years of 1951 and 2020 contain either a phenol or a phenolic ether a phenol with an alkyl with nearly every class of small molecule drugs being represented and natural products making up a large portion of this list 17 tyrosine one of the 20 standard amino acids l dopa dopamine prodrug used to treat parkinson s disease propofol short acting intravenous anesthetic agent vitamin k hydroquinone blood clotting agent that converts levothyroxine l thyroxine top selling drug to treat thyroid hormone deficiency amoxicillin top selling antibiotic estradiol the major female sex hormone analysis edit in chemical analysis phenols can be detected using 2 6 dibromoquinonechlorimide 18 it reacts with phenols to form indophenols resulting in a color change 19 references edit iupac compendium of chemical terminology 5th ed the gold book 2025 online version 2006 phenols doi 10 1351 goldbook p04539 hättenschwiler stephan vitousek peter m 2000 the role of polyphenols in terrestrial ecosystem nutrient cycling trends in ecology evolution 15 6 238 243 doi 10 1016 s0169 5347 00 01861 9 pmid 10802549 1 2 fiege h voges h w hamamoto t umemura s iwata t miki h fujita y buysch h j garbe d paulus w 2000 phenol derivatives ullmann s encyclopedia of industrial chemistry weinheim wiley vch doi 10 1002 14356007 a19_313 isbn 978 3 527 30673 2 2 4 hexadienedioic acid monomethyl ester z z organic syntheses coll vol 8 p 490 1993 vol 66 p 180 1988 article 2 5 cyclohexadiene 1 4 dione 2 3 5 trimethyl organic syntheses 52 83 1972 carreño m carmen gonzález lópez marcos urbano antonio 2006 oxidative de aromatization of para alkyl phenols into para peroxyquinols and para quinols mediated by oxone as a source of singlet oxygen angewandte chemie international edition 45 17 2737 2741 doi 10 1002 anie 200504605 pmid 16548026 fries k finck g 1908 über homologe des cumaranons und ihre abkömmlinge chemische berichte 41 3 4271 4284 doi 10 1002 cber 190804103146 fries k pfaffendorf w 1910 über ein kondensationsprodukt des cumaranons und seine umwandlung in oxindirubin chemische berichte 43 1 212 219 doi 10 1002 cber 19100430131 bamberger e 1894 ueber die reduction der nitroverbindungen chemische berichte 27 2 1347 1350 doi 10 1002 cber 18940270229 bamberger e 1894 über das phenylhydroxylamin chemische berichte 27 2 1548 1557 doi 10 1002 cber 18940270276 h bucherer 1904 über die einwirkung schwefligsaurer salze auf aromatische amido und hydroxylverbindungen j prakt chem in german 69 1 49 91 doi 10 1002 prac 19040690105 h e ungnade e f orwoll 1943 3 bromo 4 hydroxytoluene organic syntheses 23 11 doi 10 15227 orgsyn 023 0011 bracegirdle sonia anderson edward a 2010 arylsilane oxidation new routes to hydroxylated aromatics chem comm 46 20 3454 6 doi 10 1039 b924135c pmid 20582346 s2cid 31736757 le valliant franck mateos calbet ana gonzález pelayo silvia reijerse edward j ni shengyang busch julia cornella josep 2022 catalytic synthesis of phenols with nitrous oxide nature 604 7907 677 683 bibcode 2022natur 604 677l doi 10 1038 s41586 022 04516 4 pmc 9046086 pmid 35478236 1 2 wilfred vermerris and ralph nicholson phenolic compound biochemistry springer 2008 harborne j b 1980 plant phenolics in bell e a charlwood b v eds encyclopedia of plant physiology volume 8 secondary plant products berlin heidelberg new york springer verlag pp 329 395 scott kevin a cox philip b njardarson jon t 2022 05 26 phenols in pharmaceuticals analysis of a recurring motif journal of medicinal chemistry 65 10 7044 7072 doi 10 1021 acs jmedchem 2c00223 issn 0022 2623 pmid 35533692 s2cid 248667453 ettinger m b ruchhoft c c 1948 12 01 determination of phenol and structurally related compounds by gibbs method analytical chemistry 20 12 1191 1196 bibcode 1948anach 20 1191e doi 10 1021 ac60024a018 issn 0003 2700 gibbs h d 1 april 1927 phenol tests journal of biological chemistry 72 2 649 664 bibcode 1927jbich 72 649g doi 10 1016 s0021 9258 18 84338 1 authority control databases international gnd national united states france bnf data czech republic 2 israel other yale lux retrieved from https en wikipedia org w index php title phenols oldid 1367977351 categories phenols functional groups disinfectants hidden categories articles with short description short description matches wikidata all articles with unsourced statements articles with unsourced statements from july 2024 articles with unsourced statements from april 2024 cs1 german language sources de this page was last edited on 6 august 2026 at 08 41 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers 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