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2,6-Dibromoquinonechlorimide

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2,6-Dibromoquinonechlorimide
Names
Preferred IUPAC name 2,6-Dibromo-4-(chloroimino)cyclohexa-2,5-dien-1-one
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.881 Edit this at Wikidata
EC Number
  • 208-667-1
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H2Br2ClNO/c7-4-1-3(10-9)2-5(8)6(4)11/h1-2HKey: JYWKEVKEKOTYEX-UHFFFAOYSA-N
SMILES
  • C1=C(C(=O)C(=CC1=NCl)Br)Br
Properties
Chemical formula C6H2Br2ClNO
Molar mass 299.35 g·mol
Appearance yellow powder
Hazards
GHS labelling:
Pictograms GHS01: ExplosiveGHS07: Exclamation mark
Signal word Danger
Hazard statements H240, H312, H315, H319, H335
Precautionary statements P210, P220, P234, P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P332+P313, P337+P313, P362, P363, P370+P378, P370+P380+P375, P403+P233, P403+P235, P405, P411, P420, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

2,6-Dibromoquinonechlorimide is used in chemical analysis and chromatography to detect phenolic chemicals. In the presence of phenolic substances it turns indigo in colour. In the presence of aflatoxin it turns green. 2,6-Dibromoquinonechlorimide explodes if heated above 120 °C and decomposes slowly over 60 °C.

2,6-Dibromoquinonechlorimide is used in a buffer solution around pH 9.4. It is very sensitive and can detect down to 0.05 parts per million of phenols. The mechanism is the chlorimide group (=NCl) reaction with the phenol to produce an indophenol, with two rings joined via an =N- link.

References

  1. Lewis, Robert A. (2016). Hawley's Condensed Chemical Dictionary. John Wiley & Sons. p. 441. ISBN 978-1-118-13515-0.
  2. Gibbs, H. D. (1 April 1927). "Phenol Tests. III. The Indophenol Test" (PDF). The Journal of Biological Chemistry. 72: 649–664. doi:10.1016/S0021-9258(18)84338-1. Retrieved 13 January 2020.
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