Cyanuric Chloride

Title: Cyanuric Chloride
CAS Registry Number: 108-77-0
CAS Name: 2,4,6-Trichloro-1,3,5-triazine
Additional Names: trichloro-s-triazine
Molecular Formula: C3Cl3N3
Molecular Weight: 184.41
Percent Composition: C 19.54%, Cl 57.68%, N 22.79%
Literature 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).
Properties: Crystals from ether, mp 146°. bp 198°. Crystal density: 1.93 g/cm3.
Melting point: mp 146°
Boiling point: bp 198°
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.
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