2699. Cyanuric Chloride

Nomenclature

CAS number: 108-77-0
2,4,6-Trichloro-1,3,5-triazine; trichloro-s-triazine.
C3Cl3N3; mol wt 184.41.
C 19.54%, Cl 57.68%, N 22.79%.

Description and references

Versatile coupling agent for proteins and nucleic acids; reagent in synthetic organic chemistry. Prepn: A. Gautier, Ann. 141, 122 (1867); H. Herlinger, Angew. Chem. 76, 437 (1964). Structural studies: A. W. Hofmann, Ber. 19, 2061 (1886); R. A. Pascal, Jr., D. M. Ho, Tetrahedron Lett. 33, 4707 (1992); S. J. Maginn et al., ibid. 34, 4349 (1993); V. Krishnakumar, R. Ramasamy, Spectrochim. Acta A 61, 3112 (2005). Polarographic determn in air: V. Stará et al., Anal. Chim. Acta 147, 371 (1983). Synthetic applications as a chlorinating reagent for alcohols: S. R. Sandler et al., J. Org. Chem. 35, 3967 (1970); for carboxylic acids: K. Venkataraman, D. R. Wagle, Tetrahedron Lett. 20, 3037 (1979); in macrocyclic lactonization: eidem, ibid. 21, 1893 (1980); as a Beckmann rearrangement catalyst: Y. Furuya et al., J. Am. Chem. Soc. 127, 11240 (2005); as a dehydrating agent: K. P. Haval et al., Tetrahedron 62, 937 (2006). Use as a linking agent in molecular biology applications: H.-D. Hunger et al., Anal. Biochem. 156, 286 (1986); idem et al., ibid. 165, 45 (1987); R. A. Abuknesha et al., J. Immunol. Methods 306, 211 (2005).

Chemical structure

Properties

Crystals from ether, mp 146°. bp 198°. Crystal density: 1.93 g/cm3.

Caution

Eye irritant; avoid skin contact and inhalation (Hunger, 1986).

Use

Intermediate in the synthesis of active dyes, agricultural products, and drug substances. Reagent in organic synthesis. Coupling agent for nucleic acids and proteins; cyanuric chloride-activated paper is used in capillary and electroblotting applications, dot tests, and hybridization protocols.