# Indophenol

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Indophenol
> Markdown URL: https://mediated.wiki/source/Indophenol.md
> Source: https://en.wikipedia.org/wiki/Indophenol
> Source revision: 1252435024
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{chembox
| verifiedrevid = 400118162
| ImageFile=Indophenol.svg
| ImageFile1 = Indophenol-3D-spacefill.png
| ImageAlt1 = Indophenol molecule
| ImageFile2 = Indophenol.jpg
| ImageSize=220
| IUPACName=4-(4-hydroxyphenyl)iminocyclohexa-2,5-dien-1-one
| OtherNames=Benzenoneindophenol, phenolindophenol<ref name=b1/>
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9951
| InChI = 1/C12H9NO2/c14-11-5-1-9(2-6-11)13-10-3-7-12(15)8-4-10/h1-8,14H
| InChIKey = RSAZYXZUJROYKR-UHFFFAOYAS
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H9NO2/c14-11-5-1-9(2-6-11)13-10-3-7-12(15)8-4-10/h1-8,14H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RSAZYXZUJROYKR-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=500-85-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BW444H326B
| PubChem=10379
| SMILES = O=C/2/C=C\C(=N\c1ccc(O)cc1)\C=C\2
}}
|Section2={{Chembox Properties
| C=12 | H=9 | N=1 | O=2
| Appearance=Reddish-blue powder<ref name=b1/>
| Density=
| MeltingPt= above 300 °C
| MeltingPt_ref =<ref name=b1>{{cite book|author=Sabnis, R. W. |title=Handbook of Acid-Base Indicators|url=https://books.google.com/books?id=EzDbTL9Oah0C&pg=PA196|date=2007|publisher=CRC Press|isbn=978-0-8493-8219-2|page=196}}</ref>
| BoilingPt=
| Solubility=
  }}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
  }}
}}

'''Indophenol''' is an [organic compound](/source/organic_compound) with the formula OC<sub>6</sub>H<sub>4</sub>NC<sub>6</sub>H<sub>4</sub>OH.  It is deep blue [dye](/source/dye) that is the product of the [Berthelot's reaction](/source/Berthelot's_reagent), a common test for ammonia.<ref>{{cite journal|doi=10.1021/ac50011a034|title=Spectrophotometric and kinetics investigation of the Berthelot reaction for the determination of ammonia|journal=Analytical Chemistry|volume=49|issue=3|pages=464–469|year=1977|last1=Patton|first1=Charles J.|last2=Crouch|first2=S. R.}}</ref>  The indophenol group, with various substituents in place of O''H'' and various ring substitutions, is found in many dyes used in [hair coloring](/source/hair_coloring) and textiles.<ref>{{cite encyclopedia|author=Horst Berneth|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2002|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a03_213.pub2|isbn=978-3527306732|chapter=Azine Dyes}}</ref>

Indophenol is used in hair dyes, lubricants, [redox](/source/redox) materials, [liquid crystal display](/source/liquid_crystal_display)s, [fuel cell](/source/fuel_cell)s and [chemical-mechanical polishing](/source/chemical-mechanical_polishing). It is an environmental pollutant and is toxic to fish.<ref name=b1/><ref>{{Cite web|title=Indophenol I5763|url=https://www.sigmaaldrich.com/catalog/product/sigma/i5763|access-date=2020-06-11|website=500-85-6}}</ref>

==Berthelot test==
In the [Berthelot test](/source/Berthelot_test) (1859), a sample suspected of containing ammonia is treated with [sodium hypochlorite](/source/sodium_hypochlorite) and [phenol](/source/Phenols). The formation of indophenol is used to determine [ammonia](/source/ammonia) and [paracetamol](/source/paracetamol) by [spectrophotometry](/source/spectrophotometry).<ref>{{cite journal|pmid=12400662|year=2002|last1=Tsuboi|first1=T.|title=Sensitivity improvement of ammonia determination based on flow-injection indophenol spectrophotometry with manganese(II) ion as a catalyst and analysis of exhaust gas of thermal power plant|journal=Analytical Sciences |volume=18|issue=10|pages=1141–4|last2=Hirano|first2=Y.|last3=Shibata|first3=Y.|last4=Motomizu|first4=S.}}</ref> Other phenols can be used. [Dichlorophenol-indophenol](/source/Dichlorophenolindophenol) (DCPIP), a form of indophenol, is often used to determine the presence of [vitamin C](/source/vitamin_C) ([ascorbic acid](/source/ascorbic_acid)).<ref>{{cite journal|doi=10.1002/jps.2600720208|title=Titrimetric Determination of Ascorbic Acid with 2,6-Dichlorophenol Indophenol in Commercial Liquid Diets|journal=Journal of Pharmaceutical Sciences|volume=72|issue=2|pages=126–129|year=1983|last1=Hughes|first1=David Emlyn}}</ref>

==Related compounds==
Indophenol blue is a different compound with [systematic name](/source/systematic_name) ''N-(p-dimethylaminophenyl)-1,4-naphthoquinoneimine''.<ref>{{cite journal|doi=10.1126/science.139.3557.835 |title=Indophenol Blue as a Chromogenic Agent for Identification of Halogenated Aromatic Hydrocarbons |journal=Science |volume=139 |issue=3557 |pages=835–836 |year=1963 |last1=Graham |first1=S. O. |bibcode=1963Sci...139..835G }}</ref>
thumb|left|Indophenol blue{{clear-left}}

==References==
{{Commons category|Indophenol}}
<references/>

Category:Indophenol dyes
Category:4-Hydroxyphenyl compounds

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Adapted from the Wikipedia article [Indophenol](https://en.wikipedia.org/wiki/Indophenol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Indophenol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.