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{{Chembox |
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{{Merge from|Rodinal|discuss=Talk:Rodinal|date=July 2014}} |
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|Watchedfields = changed |
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{{chembox |
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|verifiedrevid = 477220971 |
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| Watchedfields = changed |
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|ImageFileL1 = p-Aminophenol.svg |
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| verifiedrevid = 477220971 |
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|ImageSizeL1 = 70 |
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| ImageFileL1 = p-Aminophenol.svg |
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|ImageAltL1 = Skeletal formula of 4-aminophenol |
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| ImageSizeL1 = 70 |
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|ImageFileR1 = 4-Aminophenol3d.png |
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| ImageAltL1 = Skeletal formula of 4-aminophenol |
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|ImageSizeR1 = 120 |
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| ImageFileR1 = 4-Aminophenol3d.png |
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|ImageAltR1 = Space-filling model of the 4-aminophenol molecule |
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| ImageSizeR1 = 120 |
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|PIN = 4-Aminophenol<ref name="IUPAC2013_690">{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 690 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| ImageAltR1 = Space-filling model of the 4-aminophenol molecule |
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| OtherNames = {{Unbulleted list |
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| IUPACName = 4-Aminophenol |
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| ''p''-Aminophenol |
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| OtherNames = |
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| ''para''-Aminophenol |
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}} |
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|Section1={{Chembox Identifiers |
|Section1={{Chembox Identifiers |
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|Abbreviations = |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID = 392 |
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|PubChem = 403 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII = R7P8FRP05V |
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|InChIKey = PLIKAWJENQZMHA-UHFFFAOYAD |
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|SMILES1 = c1cc(ccc1N)O |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|ChEMBL = 1142 |
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|Gmelin = 2926 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|Beilstein = 385836 |
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| StdInChI = 1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 |
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|UNNumber = 2512 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = PLIKAWJENQZMHA-UHFFFAOYSA-N |
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|StdInChI = 1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo = 123-30-8 |
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|StdInChIKey = PLIKAWJENQZMHA-UHFFFAOYSA-N |
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| EINECS = |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| SMILES = Oc1ccc(N)cc1 |
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|CASNo = 123-30-8 |
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| InChI = 1/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 |
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|EINECS = 204-616-2 |
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| RTECS = |
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|SMILES = Oc1ccc(N)cc1 |
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| MeSHName = Aminophenols |
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|InChI = 1/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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|MeSHName = Aminophenols |
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| ChEBI = 17602 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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|ChEBI = 17602 |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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|KEGG = C02372 |
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}} |
}} |
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|Section2={{Chembox Properties |
|Section2={{Chembox Properties |
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|C=6 |
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| Formula = C<sub>6</sub>H<sub>7</sub>NO |
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|H=7 |
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| MolarMass = 109.126 g/mol |
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|N=1 |
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| Appearance = colorless to reddish-yellow crystals |
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|O=1 |
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| Density = 1.13 g/cm<sup>3</sup> |
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|Appearance = Colorless to reddish-yellow crystals |
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| MeltingPtC = 187.5 |
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|Density = 1.13 g/cm<sup>3</sup> |
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| MeltingPt_notes = |
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|MeltingPtC = 187.5 |
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| BoilingPtC = 284 |
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|MeltingPt_notes = |
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| BoilingPt_notes = |
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|BoilingPtC = 284 |
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| Solubility = 1.5 g/100 mL (25 °C) |
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|BoilingPt_notes = |
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| SolubleOther = very soluble in [[dimethylsulfoxide]] <br> soluble in [[acetonitrile]] <br> [[ethyl acetate]] <br> [[acetone]] <br> slightly soluble in [[toluene]], [[diethyl ether]], [[ethanol]] <br> negligible in [[benzene]], [[chloroform]] |
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|Solubility = 1.5 g/100 mL |
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| pKa = 10.30 |
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|SolubleOther = {{bulletedlist|Very soluble in [[dimethylsulfoxide]]|Soluble in [[acetonitrile]], [[ethyl acetate]], and [[acetone]]|Slightly soluble in [[toluene]], [[diethyl ether]], and [[ethanol]]|Negligible solubility in [[benzene]] and [[chloroform]]}} |
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| pKb = |
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|pKa = {{Unbulleted list |
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| LambdaMax = |
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| 5.48 (amino; H<sub>2</sub>O) |
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| Absorbance = |
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| 10.30 (phenol; H<sub>2</sub>O)<ref name="CRC97">{{cite book | editor= Haynes, William M. | year = 2016 | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = [[CRC Press]] | isbn = 978-1498754286 | pages=5–89 | title-link = CRC Handbook of Chemistry and Physics }}</ref> |
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| RefractIndex = |
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}} |
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| Viscosity = |
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| Dipole = |
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| LogP = 0.04 |
| LogP = 0.04 |
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}} |
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|Section3={{Chembox Structure |
|Section3={{Chembox Structure |
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| CrystalStruct = orthorhombic |
| CrystalStruct = orthorhombic |
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}} |
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| Coordination = |
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| MolShape = |
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| Dipole = |
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}} |
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|Section4={{Chembox Thermochemistry |
|Section4={{Chembox Thermochemistry |
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| DeltaHf = -190.6 kJ/mol |
| DeltaHf = -190.6 kJ/mol |
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| DeltaHc = |
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| Entropy = |
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| HeatCapacity = |
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}} |
}} |
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|Section7={{Chembox Hazards |
|Section7={{Chembox Hazards |
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|ExternalSDS = |
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|NFPA-H = 2 |
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| EUClass = {{Carc2}}<br/>{{Muta2}}<br/>{{Repr3}}<br/>Toxic ('''T''') |
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|NFPA-F = 1 |
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|NFPA-R = 0 |
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|NFPA-S = - |
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|GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}} |
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| NFPA-S = - |
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|GHSSignalWord = Warning |
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| RPhrases = {{R20/21}}, {{R22}}, {{R40}}<br/>{{R52}}, {{Rlink|R54}}, {{R68}} |
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|HPhrases = {{H-phrases|302|332|341|410}} |
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| SPhrases = {{S28}}, {{S36}}, {{S37}}<br/>{{S60}}, {{S61}} |
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|PPhrases = {{P-phrases|201|202|261|264|270|271|273|281|301+312|304+312|304+340|308+313|312|330|391|405|501}} |
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| FlashPtC = 195 |
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|FlashPtC = 195 |
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| FlashPt_notes = (cc) |
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|FlashPt_notes = (cc) |
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| AutoignitionPt = |
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|LD50 = 671 mg/kg |
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| ExploLimits = |
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}} |
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| PEL = |
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| LD50 = 671 mg/kg |
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}} |
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|Section8={{Chembox Related |
|Section8={{Chembox Related |
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|OtherFunction = [[2-Aminophenol]]<br />[[3-Aminophenol]] |
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| OtherAnions = |
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|OtherFunction_label = aminophenols |
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| OtherCations = |
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|OtherCompounds = [[Aniline]]<br/>[[Phenol]] |
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| OtherFunction_label = aminophenols |
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| OtherCompounds = [[Aniline]]<br/>[[Phenol]] |
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}} |
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}} |
}} |
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}} |
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'''4-Aminophenol''' (or para-aminophenol or ''p''-aminophenol) is the [[organic compound]] with the [[chemical formula|formula]] H<sub>2</sub>NC<sub>6</sub>H<sub>4</sub>OH. Typically available as a white powder,<ref name=crc>[[CRC Handbook of Chemistry and Physics]] 65th Ed.</ref> it is commonly used as a developer in [[black-and-white film]], marketed under the name [[Rodinal]]. |
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'''4-Aminophenol''' (or '''''para''-aminophenol''' or '''''p''-aminophenol''') is an [[organic compound]] with the [[chemical formula|formula]] H<sub>2</sub>NC<sub>6</sub>H<sub>4</sub>OH. Typically available as a white powder,<ref>[[CRC Handbook of Chemistry and Physics]] 65th Ed.</ref> it is commonly used as a [[photographic developer|developer]] for [[black-and-white film]], marketed under the name [[Rodinal]]. |
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Reflecting its |
Reflecting its slightly hydrophilic character, the white powder is moderately soluble in alcohols and can be [[recrystallization (chemistry)|recrystallized]] from hot water. In the presence ofa base, it oxidizes readily. The [[methyl]]ated [[derivative (chemistry)|derivatives]] [[N-methylaminophenol|''N''-methylaminophenol]] and [[4-Dimethylaminophenol|''N'',''N''-dimethylaminophenol]] are of commercial value. |
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The compound is one of three [[isomer]]ic aminophenols, the other two being [[ |
The compound is one of three [[isomer]]ic aminophenols, the other two being [[2-aminophenol]] and [[3-aminophenol]]. |
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__TOC__ |
__TOC__ |
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== Preparation == |
== Preparation == |
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=== From phenol === |
=== From phenol === |
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It is produced from [[phenol]] by [[nitration]] followed by reduction with iron. Alternatively, the partial [[hydrogenation]] of [[nitrobenzene]] affords [[phenylhydroxylamine]], which rearranges primarily to 4-aminophenol |
It is produced from [[phenol]] by [[nitration]] followed by reduction with iron. Alternatively, the partial [[hydrogenation]] of [[nitrobenzene]] affords [[phenylhydroxylamine]], which rearranges primarily to 4-aminophenol ([[Bamberger rearrangement]]).<ref>Mitchell, S.C. & Waring, R.H. "Aminophenols." In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, {{doi|10.1002/14356007.a02_099}}</ref> |
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:C<sub>6</sub>H<sub>5</sub>NO<sub>2</sub> |
:C<sub>6</sub>H<sub>5</sub>NO<sub>2</sub> + 2 H<sub>2</sub> → C<sub>6</sub>H<sub>5</sub>NHOH + H<sub>2</sub>O |
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:C<sub>6</sub>H<sub>5</sub>NHOH → HOC<sub>6</sub>H<sub>4</sub>NH<sub>2</sub> |
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:C<sub>6</sub>H<sub>5</sub>NHOH → HOC<sub>6</sub>H<sub>4</sub>NH<sub>2</sub> |
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=== From nitrobenzene === |
=== From nitrobenzene === |
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It can be produced from nitrobenzene by electrolytic conversion to [[phenylhydroxylamine]], which spontaneously rearranges to 4-aminophenol.<ref>{{citation|journal=Journal of Applied Electrochemistry|volume=32|pages=217–223|year=2002|publisher=Kluwer Academic Publishers|title=Electroreduction of nitrobenzene to p-aminophenol using voltammetric and semipilot scale preparative electrolysis techniques |first1=K. |last1=Polat |first2=M.L. |last2=Aksu |first3=A.T. |last3=Pekel |doi=10.1023/A:1014725116051 }}</ref> |
It can be produced from nitrobenzene by electrolytic conversion to [[phenylhydroxylamine]], which spontaneously rearranges to 4-aminophenol.<ref>{{citation|journal=Journal of Applied Electrochemistry|volume=32|pages=217–223|year=2002|publisher=Kluwer Academic Publishers|title=Electroreduction of nitrobenzene to p-aminophenol using voltammetric and semipilot scale preparative electrolysis techniques |first1=K. |last1=Polat |first2=M.L. |last2=Aksu |first3=A.T. |last3=Pekel |issue=2 |doi=10.1023/A:1014725116051|s2cid=54499902 }}</ref> |
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=== From 4-nitrophenol === |
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[[4-Nitrophenol|4-nitrophenol]] can be [[Redox|reduced]] through a variety of methods, to yield 4-aminophenol. One method involves [[hydrogenation]] over a [[Raney nickel|Raney Nickel]] [[Catalysis|catalyst]]. A second method involves selective [[Redox|reduction]] of the [[Nitro compound|nitro group]] by [[Tin(II) chloride|Tin(II) Chloride]] in [[Ethanol|anhydrous ethanol]] or [[Ethyl acetate|ethyl ethanoate]]. <ref>{{Cite patent|number=US2998450A|title=Process of preparing nu-acetyl-p-amino phenol|gdate=1961-08-29|invent1=Godfrey|invent2=De|inventor1-first=Wilbert|inventor2-first=Angelis John|url=https://patents.google.com/patent/US2998450A/en}}</ref><ref>{{Cite journal |last=Bellamy |first=F. D. |last2=Ou |first2=K. |date=1984-01-01 |title=Selective reduction of aromatic nitro compounds with stannous chloride in non acidic and non aqueous medium |url=https://www.sciencedirect.com/science/article/pii/S0040403901800411 |journal=Tetrahedron Letters |language=en |volume=25 |issue=8 |pages=839–842 |doi=10.1016/S0040-4039(01)80041-1 |issn=0040-4039}}</ref> |
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==Uses== |
==Uses== |
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4-Aminophenol is a [[building block (chemistry)|building block]] used in organic chemistry. Prominently, it is the final intermediate in the industrial synthesis of [[paracetamol]]. Treating 4-aminophenol with [[acetic anhydride]] gives paracetamol:<ref>{{cite book |author =Ellis, Frank |title=Paracetamol: a curriculum resource |publisher=Royal Society of Chemistry |location=Cambridge |year=2002 |isbn=0-85404-375-6 }}</ref><ref>{{cite book|author = Anthony S. Travis|year = 2007|chapter = Manufacture and uses of the anilines: A vast array of processes and products|editor = Zvi Rappoport|title = The chemistry of Anilines Part 1|url = https://archive.org/details/chemistryaniline01rapp_644|url-access = limited|publisher = Wiley|isbn = 978-0-470-87171-3|page = [https://archive.org/details/chemistryaniline01rapp_644/page/n784 764]}}</ref><ref>{{Ullmann | title = Analgesics and Antipyretics | author = Elmar Friderichs |author2=Thomas Christoph |author3=Helmut Buschmann | doi = 10.1002/14356007.a02_269.pub2}}</ref> |
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:[[ |
:[[File:Synthesis of paracetamol from phenol.png|500px|alt=]] |
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It is a precursor to [[amodiaquine]], [[mesalazine]], [[AM404]], [[parapropamol]], B-86810 & B-87836 (c.f. {{Cite patent|country=WO|number=2001042204}}). |
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Amidation with the acid chloride of [[ATRA]] gives [[Fenretinide]]. Another drug [[AM404]] can be made by acylating [[arachidonic acid]]. |
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4-Aminophenol converts readily to the [[diazonium salt]].<ref>{{cite journal |author=F. B. Dains, Floyd Eberly|doi=10.15227/orgsyn.015.0039|title=p-Iodophenol |journal=Organic Syntheses |year=1935 |volume=15 |page=39 }}</ref> |
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==See also== |
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* [[Metol]] is the N-methyl derivative of ''p''-aminophenol. In 1891 it replaced ''p''-aminophenol as a developing agent for black & white photography. |
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== References == |
== References == |
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{{DEFAULTSORT:Aminophenol, 4-}} |
{{DEFAULTSORT:Aminophenol, 4-}} |
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[[Category: |
[[Category:Aminophenols]] |
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[[Category:Anilines]] |
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Names | |||
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Preferred IUPAC name
4-Aminophenol[1] | |||
Other names
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Identifiers | |||
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3D model (JSmol) |
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385836 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider |
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ECHA InfoCard | 100.004.198 ![]() | ||
EC Number |
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2926 | |||
KEGG |
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MeSH | Aminophenols | ||
PubChem CID |
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UNII | |||
UN number | 2512 | ||
CompTox Dashboard (EPA) |
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Properties | |||
C6H7NO | |||
Molar mass | 109.128 g·mol−1 | ||
Appearance | Colorless to reddish-yellow crystals | ||
Density | 1.13 g/cm3 | ||
Melting point | 187.5 °C (369.5 °F; 460.6 K) | ||
Boiling point | 284 °C (543 °F; 557 K) | ||
1.5 g/100 mL | |||
Solubility |
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log P | 0.04 | ||
Acidity (pKa) |
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Structure | |||
orthorhombic | |||
Thermochemistry | |||
Std enthalpy of |
-190.6 kJ/mol | ||
Hazards | |||
GHS labelling: | |||
![]() ![]() ![]() | |||
Warning | |||
H302, H332, H341, H410 | |||
P201, P202, P261, P264, P270, P271, P273, P281, P301+P312, P304+P312, P304+P340, P308+P313, P312, P330, P391, P405, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | 195 °C (383 °F; 468 K) (cc) | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
671 mg/kg | ||
Related compounds | |||
Related aminophenols |
2-Aminophenol 3-Aminophenol | ||
Related compounds |
Aniline Phenol | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
4-Aminophenol (orpara-aminophenolorp-aminophenol) is an organic compound with the formulaH2NC6H4OH. Typically available as a white powder,[3] it is commonly used as a developer for black-and-white film, marketed under the name Rodinal.
Reflecting its slightly hydrophilic character, the white powder is moderately soluble in alcohols and can be recrystallized from hot water. In the presence of a base, it oxidizes readily. The methylated derivatives N-methylaminophenol and N,N-dimethylaminophenol are of commercial value.
The compound is one of three isomeric aminophenols, the other two being 2-aminophenol and 3-aminophenol.
It is produced from phenolbynitration followed by reduction with iron. Alternatively, the partial hydrogenationofnitrobenzene affords phenylhydroxylamine, which rearranges primarily to 4-aminophenol (Bamberger rearrangement).[4]
It can be produced from nitrobenzene by electrolytic conversion to phenylhydroxylamine, which spontaneously rearranges to 4-aminophenol.[5]
4-nitrophenol can be reduced through a variety of methods, to yield 4-aminophenol. One method involves hydrogenation over a Raney Nickel catalyst. A second method involves selective reduction of the nitro groupbyTin(II) Chlorideinanhydrous ethanolorethyl ethanoate. [6][7]
4-Aminophenol is a building block used in organic chemistry. Prominently, it is the final intermediate in the industrial synthesis of paracetamol. Treating 4-aminophenol with acetic anhydride gives paracetamol:[8][9][10]
It is a precursor to amodiaquine, mesalazine, AM404, parapropamol, B-86810 & B-87836 (c.f. WO 2001042204 ).
4-Aminophenol converts readily to the diazonium salt.[11]