Indophenol

Indophenol is an organic compound with the formula OC₆H₄NC₆H₄OH. It is deep blue dye that is the product of the Berthelot's reaction, a common test for ammonia.^[2] The indophenol group, with various substituents in place of OH and various ring substitutions, is found in many dyes used in hair coloring and textiles.^[3]

Indophenol

Names
IUPAC name 4-(4-hydroxyphenyl)iminocyclohexa-2,5-dien-1-one
Other names Benzenoneindophenol, phenolindophenol[1]
Identifiers
CAS Number	500-85-6 Y
3D model (JSmol)	Interactive image
ChemSpider	9951 Y
ECHA InfoCard	100.007.194
PubChem CID	10379
UNII	BW444H326B Y
CompTox Dashboard (EPA)	DTXSID2075425
InChI InChI=1S/C12H9NO2/c14-11-5-1-9(2-6-11)13-10-3-7-12(15)8-4-10/h1-8,14H Y Key: RSAZYXZUJROYKR-UHFFFAOYSA-N Y InChI=1/C12H9NO2/c14-11-5-1-9(2-6-11)13-10-3-7-12(15)8-4-10/h1-8,14H Key: RSAZYXZUJROYKR-UHFFFAOYAS
SMILES O=C/2/C=C\C(=N\c1ccc(O)cc1)\C=C\2
Properties
Chemical formula	C12H9NO2
Molar mass	199.209 g·mol−1
Appearance	Reddish-blue powder[1]
Melting point	above 300 °C[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Indophenol is used in hair dyes, lubricants, redox materials, liquid crystal displays, fuel cells and chemical-mechanical polishing. It is an environmental pollutant and is toxic to fish.^[1][4]

Berthelot test

In the Berthelot test (1859), a sample suspected of containing ammonia is treated with sodium hypochlorite and phenol. The formation of indophenol is used to determine ammonia and paracetamol by spectrophotometry.^[5] Other phenols can be used. Dichlorophenol-indophenol (DCPIP), a form of indophenol, is often used to determine the presence of vitamin C (ascorbic acid).^[6]

Related compounds

Indophenol blue is a different compound with systematic name N-(p-dimethylaminophenyl)-1,4-naphthoquinoneimine.^[7]

Indophenol blue