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Latest revision as of 22:26, 31 May 2023 edit Scyrme (talk | contribs)Extended confirmed users19,963 edits GHS omission rule |
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{{Chembox |
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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.}} |
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|Watchedfields = changed |
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{{chembox |
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| verifiedrevid = 443350497 |
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|verifiedrevid = 477220971 |
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| ImageFileL1 = p-Aminophenol.svg |
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|ImageFileL1 = p-Aminophenol.svg |
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| ImageSizeL1 = 80px |
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|ImageSizeL1 = 70 |
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|ImageAltL1 = Skeletal formula of 4-aminophenol |
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| ImageFileR1 = 4-Aminophenol3d.png |
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|ImageFileR1 = 4-Aminophenol3d.png |
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| IUPACName = 4-Aminophenol |
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| OtherNames = |
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|ImageSizeR1 = 120 |
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|ImageAltR1 = Space-filling model of the 4-aminophenol molecule |
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| Section1 = {{Chembox Identifiers |
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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 = ] | date = 2014 | location = Cambridge | page = 690 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| Abbreviations = |
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| OtherNames = {{Unbulleted list |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ''p''-Aminophenol |
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| ChemSpiderID = 392 |
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| ''para''-Aminophenol |
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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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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = PLIKAWJENQZMHA-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 123-30-8 |
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| EINECS = |
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| SMILES = Oc1ccc(N)cc1 |
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| InChI = 1/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 |
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| RTECS = |
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| MeSHName = Aminophenols |
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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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| ATCCode_prefix = |
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| ATCCode_suffix = |
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| ATC_Supplemental = |
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}} |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>6</sub>H<sub>7</sub>NO |
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| MolarMass = 109.13 g/mol |
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| Appearance = |
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| Density = 1.13 g/cm<sup>3</sup> |
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| MeltingPt = 188–190 °C |
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| Melting_notes = |
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| BoilingPt = 284 °C |
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| Boiling_notes = |
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| Solubility = 1.5 g/100 ml (25 °C) |
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| SolubleOther = |
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| Solvent = |
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| pKa = |
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| pKb = |
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| LambdaMax = |
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| Absorbance = |
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| RefractIndex = |
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| Viscosity = |
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| Dipole = |
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}} |
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| Section3 = {{Chembox Structure |
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| CrystalStruct = |
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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 |
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| DeltaHf = |
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| DeltaHc = |
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| Entropy = |
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| HeatCapacity = }} |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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| EUClass = {{Carc2}}<br/>{{Muta2}}<br/>{{Repr3}}<br/>Toxic ('''T''') |
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| EUIndex = 616-003-00-0 |
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| NFPA-H = 2 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| NFPA-O = |
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| RPhrases = {{R20/21}}, {{R22}}, {{R40}}<br/>{{R52}}, {{Rlink|R54}}, {{R68}} |
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| SPhrases = {{S28}}, {{S36}}, {{S37}}<br/>{{S60}}, {{S61}} |
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| FlashPt = 195 °C |
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| Autoignition = |
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| ExploLimits = |
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| PEL = |
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}} |
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| Section8 = {{Chembox Related |
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| OtherAnions = |
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| OtherCations = |
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| OtherFunctn = ]<br />] |
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| Function = aminophenols |
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| OtherCpds = ]<br/>] |
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}} |
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}} |
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}} |
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|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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|Beilstein = 385836 |
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|UNNumber = 2512 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI = 1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = PLIKAWJENQZMHA-UHFFFAOYSA-N |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|CASNo = 123-30-8 |
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|EINECS = 204-616-2 |
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|SMILES = Oc1ccc(N)cc1 |
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|InChI = 1/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 |
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|MeSHName = Aminophenols |
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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 |
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|C=6 |
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|H=7 |
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|N=1 |
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|O=1 |
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|Appearance = Colorless to reddish-yellow crystals |
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|Density = 1.13 g/cm<sup>3</sup> |
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|MeltingPtC = 187.5 |
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|MeltingPt_notes = |
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|BoilingPtC = 284 |
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|BoilingPt_notes = |
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|Solubility = 1.5 g/100 mL |
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|SolubleOther = {{bulletedlist|Very soluble in ]|Soluble in ], ], and ]|Slightly soluble in ], ], and ]|Negligible solubility in ] and ]}} |
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|pKa = {{Unbulleted list |
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| 5.48 (amino; H<sub>2</sub>O) |
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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 = ] | isbn = 978-1498754286 | pages=5–89 | title-link = CRC Handbook of Chemistry and Physics }}</ref> |
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}} |
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| LogP = 0.04 |
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}} |
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|Section3={{Chembox Structure |
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| CrystalStruct = orthorhombic |
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}} |
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|Section4={{Chembox Thermochemistry |
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| DeltaHf = -190.6 kJ/mol |
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}} |
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|Section7={{Chembox Hazards |
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|ExternalSDS = |
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|NFPA-H = 2 |
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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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|GHSSignalWord = Warning |
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|HPhrases = {{H-phrases|302|332|341|410}} |
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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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|FlashPt_notes = (cc) |
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|LD50 = 671 mg/kg |
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}} |
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|Section8={{Chembox Related |
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|OtherFunction = ]<br />] |
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|OtherFunction_label = aminophenols |
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|OtherCompounds = ]<br/>] |
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}} |
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}} |
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'''4-Aminophenol''' (or '''''para''-aminophenol''' or '''''p''-aminophenol''') is an ] with the ] H<sub>2</sub>NC<sub>6</sub>H<sub>4</sub>OH. Typically available as a white powder,<ref>] 65th Ed.</ref> it is commonly used as a ] for ], marketed under the name ]. |
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Reflecting its slightly hydrophilic character, the white powder is moderately soluble in alcohols and can be ] from hot water. In the presence of a base, it oxidizes readily. The ]ated ] ] and ] are of commercial value. |
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The compound is one of three ]ic aminophenols, the other two being ] and ]. |
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__TOC__ |
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== Preparation == |
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=== From phenol === |
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It is produced from ] by ] followed by reduction with iron. Alternatively, the partial ] of ] affords ], which rearranges primarily to 4-aminophenol (]).<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> + 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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=== From nitrobenzene === |
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It can be produced from nitrobenzene by electrolytic conversion to ], 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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] can be ] through a variety of methods, to yield 4-aminophenol. One method involves ] over a ] ]. A second method involves selective ] of the ] by ] in ] or ]. <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== |
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4-Aminophenol is a ] used in organic chemistry. Prominently, it is the final intermediate in the industrial synthesis of ]. Treating 4-aminophenol with ] 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 = }}</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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:] |
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It is a precursor to ], ], ], ], B-86810 & B-87836 (c.f. {{Cite patent|country=WO|number=2001042204}}). |
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4-Aminophenol converts readily to the ].<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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== References == |
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{{Reflist|2}} |
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{{DEFAULTSORT:Aminophenol, 4-}} |
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] |