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.^[1] 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]

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.^[3]

References

^ Ettinger, M. B.; Ruchhoft, C. C. (1948-12-01). "Determination of Phenol and Structurally Related Compounds by Gibbs Method". Analytical Chemistry. 20 (12): 1191–1196. doi:10.1021/ac60024a018. ISSN 0003-2700.
^ 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] Ettinger, M. B.; Ruchhoft, C. C. (1948-12-01). "Determination of Phenol and Structurally Related Compounds by Gibbs Method". Analytical Chemistry. 20 (12): 1191–1196. doi:10.1021/ac60024a018. ISSN 0003-2700.

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

[3] 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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