2,6-Dibromoquinonechlorimide

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2,6-Dibromoquinonechlorimide
2,6-Dibromoquinonechlorimide.png
Names
Preferred IUPAC name
2,6-Dibromo-4-(chloroimino)cyclohexa-2,5-dien-1-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.881 Edit this at Wikidata
EC Number
  • 208-667-1
UNII
  • InChI=1S/C6H2Br2ClNO/c7-4-1-3(10-9)2-5(8)6(4)11/h1-2H
    Key: JYWKEVKEKOTYEX-UHFFFAOYSA-N
  • C1=C(C(=O)C(=CC1=NCl)Br)Br
Properties
C6H2Br2ClNO
Molar mass 299.35 g·mol−1
Appearance yellow powder
Hazards
GHS labelling:
GHS01: ExplosiveGHS07: Exclamation mark
Danger
H240, H312, H315, H319, H335
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 [77 °F], 100 kPa).

2,6-Dibromoquinonechlorimide is a chemical 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.[1]

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 a reaction of the chlorimide group (=NCl) with the phenol to produce an indophenol, with two rings joined via an =N- link.[2]

References[edit]

  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.