2,6-Dichloroquinone-4-chloroimide

Last updated
2,6-Dichloroquinone-4-chloroimide
Gibbs reagent.svg
Names
Preferred IUPAC name
2,6-Dichloro-4-(chloroimino)cyclohexa-2,5-dien-1-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.671 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-937-2
PubChem CID
UNII
  • InChI=1S/C6H2Cl3NO/c7-4-1-3(10-9)2-5(8)6(4)11/h1-2H
    Key: YHUMTHWQGWPJOQ-UHFFFAOYSA-N
  • C1=C(C(=O)C(=CC1=NCl)Cl)Cl
Properties
C6H2Cl3NO
Molar mass 210.44 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Warning
H242, H315, H319, H335
P210, P220, P234, P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P411, P420, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,6-Dichloroquinone-4-chloroimide (Gibbs reagent) is an organic compound used as an colorimetric indicator to detect phenolic compounds. [1] Upon reaction with phenol itself, 2,6-dichlorophenolindophenol is formed, [2] a chemical that is used as a redox indicator.

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Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", or arenes, are organic compounds containing one or more aromatic rings. The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were understood. The current definition of aromatic compounds does not have any relation to their odor. Aromatic compounds are now defined as cyclic compounds satisfying Hückel's Rule.

<span class="mw-page-title-main">Phenols</span> Chemical compounds in which hydroxyl group is attached directly to an aromatic ring

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (−OH) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, C
6
H
5
OH
. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.

<span class="mw-page-title-main">Alkylation</span> Transfer of an alkyl group from one molecule to another

Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene. Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents.

<span class="mw-page-title-main">Protecting group</span> Group of atoms introduced into a compound to prevent subsequent reactions

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In organic chemistry, an aryl halide is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. The haloarene are different from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications.

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<span class="mw-page-title-main">Trimethylsilyl group</span> Functional group

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

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<span class="mw-page-title-main">4,4'-Biphenol</span> Chemical compound

4,4′-Biphenol is an organic compound which is a phenolic derivative of biphenyl. It is a colorless solid.

<span class="mw-page-title-main">Boronic acid</span> Organic compound of the form R–B(OH)2

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<span class="mw-page-title-main">Folin–Ciocalteu reagent</span>

The Folin–Ciocâlteu reagent (FCR) or Folin's phenol reagent or Folin–Denis reagent, is a mixture of phosphomolybdate and phosphotungstate used for the colorimetric in vitro assay of phenolic and polyphenolic antioxidants, also called the gallic acid equivalence method (GAE). It is named after Otto Folin, Vintilă Ciocâlteu, and Willey Glover Denis. The Folin-Denis reagent is prepared by mixing sodium tungstate and phosphomolybdic acid in phosphoric acid. The Folin–Ciocalteu reagent is just a modification of the Folin-Denis reagent. The modification consisted of the addition of lithium sulfate and bromine to the phosphotungstic-phosphomolybdic reagent.

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

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. 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.

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2,6-Di-<i>tert</i>-butylpyridine Chemical compound

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2,4,6-Tri-<i>tert</i>-butylphenol Chemical compound

2,4,6-Tri-tert-butylphenol (2,4,6-TTBP) is a phenol symmetrically substituted with three tert-butyl groups and thus strongly sterically hindered. 2,4,6-TTBP is a readily oxidizable aromatic compound and a weak acid. It oxidizes to give the deep-blue 2,4,6-tri-tert-butylphenoxy radical. 2,4,6-TTBP is related to 2,6-di-tert-butylphenol, which is widely used as an antioxidant in industrial applications. These compounds are colorless solids.

References

  1. Arip, Mohamad Nasir Mat; Heng, Lee Yook; Ahmad, Musa; Aishah Hasbullah, Siti (2013). "Reaction of 2,6-dichloroquinone-4-chloroimide (Gibbs reagent) with permethrin – an optical sensor for rapid detection of permethrin in treated wood". Chem Cent J. 7: 122. doi: 10.1186/1752-153X-7-122 . PMC   3726330 . PMID   23867006.
  2. Svobodová, D.; Křenek, P.; Fraenkl, M.; Gasparič, J. (1977). "Colour Reaction of Phenols with the Gibbs Reagent. The Reaction Mechanism and Decomposition and Stabilisation of the Reagent". Microchim. Acta. 67 (3–4): 251–264. doi:10.1007/BF01213035. S2CID   93587492.