Indophenol

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Indophenol
Indophenol.svg
Indophenol-3D-spacefill.png
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 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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<span class="mw-page-title-main">Titration</span> Laboratory method for determining the concentration of an analyte

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<span class="mw-page-title-main">Phthalic anhydride</span> Chemical compound

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<span class="mw-page-title-main">Resorcinol</span> Chemical compound

Resorcinol (or resorcin) is a phenolic compound. It is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or meta-isomer). Resorcinol crystallizes from benzene as colorless needles that are readily soluble in water, alcohol, and ether, but insoluble in chloroform and carbon disulfide.

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<span class="mw-page-title-main">Pyrogallol</span> Benzene-1,2,3-triol

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Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group [R−N+≡N]X where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent compound where R is hydrogen, is diazenylium.

In organic chemistry, an azo coupling is an reaction between a diazonium compound and another aromatic compound that produces an azo compound. In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the electrophile, and the activated carbon, serves as a nucleophile. Classical coupling agents are phenols and naphthols. Usually the diazonium reagent attacks at the para position of the coupling agent. When the para position is occupied, coupling occurs at a ortho position, albeit at a slower rate.

<span class="mw-page-title-main">Caffeic acid</span> Chemical compound

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<span class="mw-page-title-main">Rosocyanine</span> Chemical compound

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<span class="mw-page-title-main">Dichlorophenolindophenol</span> Chemical compound

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.

Polyphenol oxidase, an enzyme involved in fruit browning, is a tetramer that contains four atoms of copper per molecule.

Berthelot's reagent is an alkaline solution of phenol and hypochlorite, used in analytical chemistry. It is named after its inventor, Marcellin Berthelot. Ammonia reacts with Berthelot's reagent to form a blue product which is used in a colorimetric method for determining ammonia. The reagent can also be used for determining urea. In this case the enzyme urease is used to catalyze the hydrolysis of urea into carbon dioxide and ammonia. The ammonia is then determined with Berthelot's reagent.

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.