View source for 4-Aminophenol

{{chembox
| verifiedrevid = 300063540
| ImageFileL1 = p-Aminophenol.svg
| ImageSizeL1 = 80px
| ImageFileR1 = 4-Aminophenol3d.png
| IUPACName = 4-Aminophenol
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| Section1 = {{Chembox Identifiers
| Abbreviations = 
| CASNo_Ref = {{cascite}}
| CASNo = 123-30-8
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| MeSHName = Aminophenols
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| Section2 = {{Chembox Properties
| Formula = C<sub>6</sub>H<sub>7</sub>NO
| MolarMass = 109.13 g/mol
| Appearance =
| Density = 1.13 g/cm<sup>3</sup>
| MeltingPt = 188–190 °C
| Melting_notes =
| BoilingPt = 284 °C
| Boiling_notes = 
| Solubility = 1.5 g/100 ml (25 °C)
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| Section3 = {{Chembox Structure
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| Section4 = {{Chembox Thermochemistry
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| Section7 = {{Chembox Hazards
| ExternalMSDS = 
| EUClass = {{Carc2}}<br/>{{Muta2}}<br/>{{Repr3}}<br/>Toxic ('''T''')
| EUIndex = 616-003-00-0
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| NFPA-O = &nbsp;
| RPhrases = {{R20/21}}, {{R22}}, {{R40}}<br/>{{R52}}, {{Rlink|R54}}, {{R68}}
| SPhrases = {{S28}}, {{S36}}, {{S37}}<br/>{{S60}}, {{S61}}
| FlashPt = 195 °C
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| Section8 = {{Chembox Related
| OtherAnions = 
| OtherCations = 
| OtherFunctn = [[2-Aminophenol]]<br />[[3-Aminophenol]]
| Function = aminophenols
| OtherCpds = [[Aniline]]<br/>[[Phenol]]
  }}
}}
'''4-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]].

Reflecting its slight hydrophilic character, the white powder is moderately soluble in alcohols and can be [[Recrystallization (chemistry)|recrystallised]] from hot water.  In the presence of base, it oxidizes readily.  The ''N''-methyl and ''N'',''N''-dimethyl derivatives are of commercial value.

The compound is one of three [[isomer]]ic aminophenols, the other two being [[2-aminophenol]] and [[3-aminophenol]].

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== Preparation ==
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:<ref name=Mitchell_Waring>Mitchell, S.C. & Waring, R.H. “Aminophenols.” In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, {{DOI|10.1002/14356007.a02_099}}</ref>

: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

:C<sub>6</sub>H<sub>5</sub>NHOH   →  HOC<sub>6</sub>H<sub>4</sub>NH<sub>2</sub>

== Reactions ==
''p''-Aminophenol reacts with [[acetic anhydride]] to give [[paracetamol]].<ref>{{cite book |author=Ellis, Frank |title=Paracetamol: a curriculum resource |publisher=Royal Society of Chemistry |location=Cambridge |year=2002 |pages= |isbn=0-85404-375-6 |oclc= |doi= |accessdate=}}</ref>

:[[Image:Synthesis of paracetamol.png|400px]]

== References ==
{{Reflist}}

{{DEFAULTSORT:Aminophenol, 4-}}
[[Category:Phenols]]
[[Category:Aromatic amines]]

[[fr:4-aminophénol]]
[[pl:P-aminofenol]]
[[pt:4-Aminofenol]]
[[Category:2Fix]]