Trichloroisocyanuric acid

Trichloroisocyanuric acid
	Symclosene
Names
	Preferred IUPAC name 1,3,5-Trichloro-1,3,5-triazinane-2,4,6-trione
	Other names Trichlor; Isocyanuric chloride; 1,3,5-Trichloro-1,3,5-triazine-2,4,6(1H,3H,5H)-trione; Chloreal; Symclosene; Trichloro-s-triazinetrione; TCICA; TCCA;
Identifiers
CAS Number	87-90-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	202022
ChEBI	CHEBI:33015 ;
ChEMBL	ChEMBL1698868;
ChemSpider	6643 ;
ECHA InfoCard	100.001.621
EC Number	201-782-8;
Gmelin Reference	240759
KEGG	D05985;
PubChem CID	6909;
RTECS number	XZ1925000;
UNII	RL3HK1I66B ;
UN number	2468
CompTox Dashboard (EPA)	DTXSID2026523 ;
	InChI InChI=1S/C3Cl3N3O3/c4-7-1(10)8(5)3(12)9(6)2(7)11 Key: YRIZYWQGELRKNT-UHFFFAOYSA-N ; InChI=1/C3Cl3N3O3/c4-7-1(10)8(5)3(12)9(6)2(7)11 Key: YRIZYWQGELRKNT-UHFFFAOYAR;
	SMILES ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O;
Properties
Chemical formula	C3Cl3N3O3
Molar mass	232.40 g·mol−1
Appearance	Colorless solid
Density	2.19 ± 0.1 g/cm3
Melting point	246 to 247 °C (475 to 477 °F; 519 to 520 K)
Boiling point	decomposes
Solubility in water	1.2%
Solubility in other solvents	Soluble in chlorocarbons, acetone, and acetonitrile
Structure
Coordination geometry	planar
Dipole moment	0 D
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	lung irritant
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H272, H302, H314, H319, H335, H410
Precautionary statements	P210, P220, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P351+P338, P316, P319, P321, P330, P337+P317, P363, P370+P378, P391, P403+P233, P405, P501
Flash point	NA
Related compounds
Related compounds	Cyanuric chloride; Dichloroisocyanuric acid; Tribromoisocyanuric acid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Trichloroisocyanuric acid is an organic compound with the formula (CONCl)₃. It is used as an industrial disinfectant, bleaching agent and a reagent in organic synthesis.^[1]^[2]^[3] This white crystalline powder, which has a strong "chlorine odour," is sometimes sold in tablet or granule form for domestic and industrial use.

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Trichloroisocyanuric acid is prepared from cyanuric acid via a reaction with chlorine gas and trisodium cyanurate.^[4]

The compound is a disinfectant, algicide and bactericide mainly for swimming pools and dyestuffs, and is also used as a bleaching agent in the textile industry. It is widely used in civil sanitation for pools and spas, preventing and curing diseases in animal husbandry and fisheries, fruit and vegetable preservation, wastewater treatment, as an algicide for recycled water in industry and air conditioning, in anti shrink treatment for woolens, for treating seeds and in organic chemical synthesis. It is used in chemical synthesis as an easy to store and transport chlorine gas source, it is not subject to hazardous gas shipping restrictions, and its reaction with hydrochloric acid produces relatively pure chlorine.^[5]

Trichloroisocyanuric acid as used in swimming pools is easier to handle than chlorine gas. It dissolves slowly in water, but as it reacts, cyanuric acid concentration in the pool will build-up. In large bodies of water, the TCCA is soluble and breaks down slowly, releasing chlorine in the water to sanitize contaminants. When TCCA instead comes in contact with or is wetted/moistened by a small amount of water and does not dissolve, it can experience a chemical reaction, generating heat and causing the decomposition of the chemical, which in turn produces toxic chlorine gas and can produce explosive nitrogen trichloride. ^[6]

[1]
Hiegel, G. A. (2001). "Trichloroisocyanuric Acid". Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/047084289X.rt209. ISBN 0471936235.
[2]
Barros, J. C. (2005). "Trichloroisocyanuric acid". Synlett. 2005 (13): 2115–2116. doi:10.1055/s-2005-872237.
[3]
Tilstam, Ulf; Weinmann, Hilmar (July 2002). "Trichloroisocyanuric Acid: A Safe and Efficient Oxidant". Organic Process Research & Development. 6 (4): 384–393. doi:10.1021/op010103h.
[4]
Chattaway, F. D.; Wadmore, J. Mello (1902). "XX.—The constitution of hydrocyanic, cyanic, and cyanuric acids". J. Chem. Soc., Trans. 81: 191–203. doi:10.1039/CT9028100191.
[5]
L. Lerner (2011). "Chlorine". Small-Scale Synthesis of Laboratory Reagents with Reaction Modeling. CRC Press. ISBN 9780367383046.
[6]
Trichloroisocyanuric Acid Reaction, Decomposition, and Toxic Gas Release at Bio-Lab, Inc., Westlake, LA, Incident Date: August 27, 2020, Report No. 2020-05-I-LA. U.S. Chemical Safety and Hazard Investigation Board. 2023.

[1] [1]
Hiegel, G. A. (2001). "Trichloroisocyanuric Acid". Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/047084289X.rt209. ISBN 0471936235.

[2] [2]
Barros, J. C. (2005). "Trichloroisocyanuric acid". Synlett. 2005 (13): 2115–2116. doi:10.1055/s-2005-872237.

[3] [3]
Tilstam, Ulf; Weinmann, Hilmar (July 2002). "Trichloroisocyanuric Acid: A Safe and Efficient Oxidant". Organic Process Research & Development. 6 (4): 384–393. doi:10.1021/op010103h.

[4] [4]
Chattaway, F. D.; Wadmore, J. Mello (1902). "XX.—The constitution of hydrocyanic, cyanic, and cyanuric acids". J. Chem. Soc., Trans. 81: 191–203. doi:10.1039/CT9028100191.

[5] [5]
L. Lerner (2011). "Chlorine". Small-Scale Synthesis of Laboratory Reagents with Reaction Modeling. CRC Press. ISBN 9780367383046.

[6] [6]
Trichloroisocyanuric Acid Reaction, Decomposition, and Toxic Gas Release at Bio-Lab, Inc., Westlake, LA, Incident Date: August 27, 2020, Report No. 2020-05-I-LA. U.S. Chemical Safety and Hazard Investigation Board. 2023.

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Trichloroisocyanuric acid

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