Trichloroisocyanuric acid

• Catalog No.: B23906
• CAS Number: 87-90-1
• M. F.: C3Cl3N3O3
• M. W.: 232.4094
• Purity: 97%

SYNONYMS

• Title: 三氯异三聚氰酸
• IUPAC name: trichloro-1,3,5-triazinane-2,4,6-trione
• IUPAC Traditional name: trichloroisocyanuric acid
• Synonyms: Isocyanuric chloride; Symclosene

DATABASE IDS

• Beilstein Number: 202022
• MDL Number: MFCD00006553
• CAS Number: 87-90-1
• Merck Index: 149641
• EC Number: 201-782-8

PROPERTIES

• Purity: 97%
• Density: 2.07
• Flash Point: >250°C(482°F)
• Melting Point: ca 245°C dec.
• GHS Hazard statements: H272-H400-H410-H302-H319-H335
• European Hazard Symbols: X
• European Hazard Symbols: Oxidising (O)
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P221-P210-P220-P305+P351+P338-P405-P501A
• Risk Statements: 8-22-31-36/37-50/53
• RTECS: XZ1925000
• Safety Statements: 8-26-41-60-61
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 5.1
• UN Number: UN2468
• Packing Group: II

REFERENCES

• Note: Confusion with Cyanuric chloride, L03442, exists in some earlier Fieser references.
• For a brief feature on uses in synthesis, see: Synlett, 2265 (2005).
• 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).