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Trichloroisocyanuric acid was used as a disinfection reagent in the transformation of benzophenone-3 in chlorinated water. It was also used in the synthesis of 2-halomethylene-3-oxoketoximes. It is used as a bleaching agent in the textile industry, a reagent in organic synthesis.
Ulf Tilstam and Hilmar Weinmann. Trichloroisocyanuric Acid:? A Safe and Efficient Oxidant. Org. Proc. Res. Dev. 2002, 6 (4), 384-393.
Ardeshir Khazaei; Mohammad Ali Zolfigol; Amin Rostami; Arash Ghorbani Choghamarani. Trichloroisocyanuric acid (TCCA) as a mild and efficient catalyst for the trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS) under heterogonous conditions. Catalysis Communications. 2007, 8 (3), 543-547.
Low-cost chlorinating and oxidizing agent; review: Org. Process Res. Dev., 6, 384 (2002). Aromatic compounds can be chlorinated either on the ring (ionic conditions) or on the side chain (free-radical conditions): J. Org. Chem., 35, 719 (1970). In the presence of BF3 etherate, ketones are ɑ-chlorinated at the more substituted position: Synth. Commun., 15, 385 (1985). In combination with pyridine, sulfides are selectively oxidized to sulfoxides: Synth. Commun., 31, 245 (2001), thiols to disulfides: Synth. Commun, 31, 1825 (2001), and secondary alcohols to ketones: Synth. Commun., 22, 1589 (1992). In the presence of methanol in acetonitrile, acetone or dichloromethane, the same reagent system converts aldehydes directly to methyl esters: Synth. Commun., 26, 2633 (1996). Effective co-oxidant for the TEMPO-catalyzed chemoselective oxidation of alcohols to aldehydes and ketones: Org. Lett., 3, 3041 (2001). In acetic acid, pyridines are converted to their N-oxides: Synth. Commun., 34, 247 (2004).
With NaNO2 and wet silica selective mononitration of phenols is accomplished under mild conditions: Synlett, 191 (2003). Effectively catalyzes both the protection and deprotection of alcohols as their tetrahydropyranyl ethers: Synth. Commun., 34, 3623 (2004).
For a brief feature on uses in synthesis, see: Synlett, 2265 (2005).
Note: Confusion with Cyanuric chloride, L03442, exists in some earlier Fieser references.
Hazard Statements: H272-H302-H319-H335
May intensify fire; oxidizer. Harmful if swallowed. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P220-P221-P261-P264b-P270-P271-P280-P301+P312-P304+P340-P305+P351+P338-P312-P330-P337+P313-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep/Store away from clothing/combustible materials. Take any precaution to avoid mixing with combustibles. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If eye irritation persists: Get medical advice/attention. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant