Cyanuric chloride

• Catalog No.: L03442
• CAS Number: 108-77-0
• M. F.: C3Cl3N3
• M. W.: 184.4112
• Purity: 98%

SYNONYMS

• Title: 三聚氯氰
• IUPAC name: trichloro-1,3,5-triazine
• IUPAC Traditional name: cyanuric chloride
• Synonyms: 2,4,6-Trichloro-1,3,5-triazine; TCT

DATABASE IDS

• EC Number: 203-614-9
• MDL Number: MFCD00006046
• CAS Number: 108-77-0
• Beilstein Number: 124246

PROPERTIES

• Purity: 98%
• Boiling Point: 192-194°C
• Density: 1.920
• Flash Point: >190°C(374°F)
• Melting Point: 145-149°C
• GHS Hazard statements: H330-H302-H317-H314
• European Hazard Symbols: Highly toxic (T+)
• GHS Precautionary statements: P260-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501A
• Risk Statements: 14-22-26-34-43
• RTECS: XZ1400000
• Safety Statements: 1/2-26-28-36/37/39-45-46-63
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN2670
• Packing Group: II

REFERENCES

• Effects deoxygenation of diaryl sulfoxides. Alkyl sulfoxides undergo ɑ-chlorination, which can be avoided by using cyanuric fluoride: Synthesis, 221 (1980).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 2156 (2006).
• In the presence of triethylamine, carboxylic acids are converted to their acid chlorides, allowing in situ formation of esters, amides and peptides: Tetrahedron Lett., 20, 3037 (1979). Similarly, sulfonic acids are converted to sulfonyl chlorides: Tetrahedron Lett., 44, 1499 (2003). ω-Hydroxy acids are converted to their lactones: Tetrahedron Lett., 21, 1893 (1980). Mild reagent in ?-lactam synthesis: Synthesis, 209 (1981). Carboxylic acids, including N-Boc, -Fmoc and -Cbz amino acids have been converted to alcohols in good yield by activation with cyanuric chloride and N-methylmorpholine (NMM), followed by reduction with aqueous NaBH₄: Tetrahedron Lett., 40, 4395 (1999). Hydroxamic acids can also be prepared in a simple one-flask method using hydroxylamine hydrochloride in the presennce of NMM and DMAP: Org. Lett., 5, 2715 (2003).
• For use, in combination with DMSO, in a mild and efficient alternative to the Swern oxidation of alcohols to aldehydes or ketones, see: J. Org. Chem., 66,7907 (2001).
• Reagent for dehydration of aldoximes: J. Chem. Soc., Chem. Commun., 1226 (1972), and primary carboxamides: Synthesis, 657 (1980) to nitriles. The Vilsmeier-type complex with DMF also converts aldoximes cleanly to nitriles; ketoximes undergo the Beckmann rearrangement at room temperature in high yield: J. Org. Chem., 67, 6272 (2002). The complex converts primary and secondary alcohols to alkyl chlorides in high yield; addition of NaBr affords mainly the alkyl bromide: Org. Lett., 4, 553 (2002); whereas with 4 eq. of LiF, primary alcohols are selectively formylated, providing a mild and convenient method for their protection: J. Org. Chem., 67, 5152 (2002).