2,6-Dibromoquinonechlorimide

2,6-Dibromoquinonechlorimide
Names
	Preferred IUPAC name 2,6-Dibromo-4-(chloroimino)cyclohexa-2,5-dien-1-one
Identifiers
CAS Number	537-45-1;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3276933;
ChemSpider	10378;
ECHA InfoCard	100.007.881
EC Number	208-667-1;
PubChem CID	10835;
UNII	H750J4PI0N;
CompTox Dashboard (EPA)	DTXSID1060215 ;
	InChI InChI=1S/C6H2Br2ClNO/c7-4-1-3(10-9)2-5(8)6(4)11/h1-2H Key: JYWKEVKEKOTYEX-UHFFFAOYSA-N;
	SMILES C1=C(C(=O)C(=CC1=NCl)Br)Br;
Properties
Chemical formula	C6H2Br2ClNO
Molar mass	299.35 g·mol−1
Appearance	yellow powder
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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

References

^ Lewis, Robert A. (2016). Hawley's Condensed Chemical Dictionary. John Wiley & Sons. p. 441. ISBN 978-1-118-13515-0.
^ 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.

[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.

[1]

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