Indophenol

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Indophenol
Indophenol.svg
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Indophenol.jpg
Names
IUPAC name
4-(4-hydroxyphenyl)iminocyclohexa-2,5-dien-1-one
Other names
Benzenoneindophenol, phenolindophenol [1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.194 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C12H9NO2/c14-11-5-1-9(2-6-11)13-10-3-7-12(15)8-4-10/h1-8,14H Yes check.svgY
    Key: RSAZYXZUJROYKR-UHFFFAOYSA-N Yes check.svgY
  • 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
  • O=C/2/C=C\C(=N\c1ccc(O)cc1)\C=C\2
Properties
C12H9NO2
Molar mass 199.209 g·mol−1
AppearanceReddish-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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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 having 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]

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

Indophenol blue Indophenol Blue.svg
Indophenol blue

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2,6-Dichlorophenolindophenol is a chemical compound used as a redox dye. When oxidized, DCPIP is blue with a maximal absorption at 600 nm; when reduced, DCPIP is colorless.

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2-Naphthol Chemical compound

2-Naphthol, or β-naphthol, is a fluorescent colorless (or occasionally yellow) crystalline solid with the formula C10H7OH. It is an isomer of 1-naphthol, differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, but more reactive. Both isomers are soluble in simple alcohols, ethers, and chloroform. 2-Naphthol is a widely used intermediate for the production of dyes and other compounds.

References

  1. 1 2 3 4 Sabnis, R. W. (2007). Handbook of Acid-Base Indicators. CRC Press. p. 196. ISBN   978-0-8493-8219-2.
  2. Patton, Charles J.; Crouch, S. R. (1977). "Spectrophotometric and kinetics investigation of the Berthelot reaction for the determination of ammonia". Analytical Chemistry. 49 (3): 464–469. doi:10.1021/ac50011a034.
  3. Horst Berneth (2002). "Azine Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_213.pub2. ISBN   978-3527306732.
  4. "Indophenol I5763". 500-85-6. Retrieved 2020-06-11.
  5. Tsuboi, T.; Hirano, Y.; Shibata, Y.; Motomizu, S. (2002). "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". Analytical Sciences. 18 (10): 1141–4. PMID   12400662.
  6. Hughes, David Emlyn (1983). "Titrimetric Determination of Ascorbic Acid with 2,6-Dichlorophenol Indophenol in Commercial Liquid Diets". Journal of Pharmaceutical Sciences. 72 (2): 126–129. doi:10.1002/jps.2600720208.
  7. Graham, S. O. (1963). "Indophenol Blue as a Chromogenic Agent for Identification of Halogenated Aromatic Hydrocarbons". Science. 139 (3557): 835–836. Bibcode:1963Sci...139..835G. doi:10.1126/science.139.3557.835.