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Cyanuric fluoride acts as a fluorinating agent used in the conversion of carboxylic acids into acyl fluorides. It is used as a precursor for fibre-reactive dyes. It is a specific reagent for tyrosine residues in enzyme. Further, it is involved in the preparation of cyanuric acid by hydrolysis
In combination with pyridine, converts carboxylic acids to acyl fluorides in high yields under mild conditions: Synthesis, 487 (1973). Similarly, protected (Fmoc) amino acids are converted in dichloromethane solution to amino acid fluorides. tert-Butyl ester and ether groups are also stable under these conditions. The resulting acyl fluorides are more stable to water than the corresponding acyl chlorides but are more reactive to amines, thus providing a useful peptide coupling method: J. Am. Chem. Soc., 112, 9651 (1990); Tetrahedron, 50, 5309 (1994); Appendix 6. For use of Fmoc amino acid fluorides in solid-phase peptide synthesis, see: Tetrahedron Lett., 32, 1303 (1991); J. Org. Chem., 59, 3275 (1994). For a review of peptide synthesis via amino acid halides, see: Acc. Chem. Res., 29, 268 (1996).
Carboxylic acids can be converted to alcohols under mild conditions via the acyl fluoride and reduction with NaBH4 in the presence of MeOH. The method can be carried out in one pot and is applicable to N-protected amino acids and peptides for which other reduction methods are unsuitable: J. Org. Chem., 61, 6994 (1996).
Reagent for deoxygenation of alkyl sulfoxides, cf Cyanuric chloride, L03442 : Synthesis, 221 (1980), and for dehydration, at room temperature in DMF, of Boc amino acid amides to nitriles: Tetrahedron. Lett., 38, 4221 (1997).
Prabhaharan, M.; Prabakaran, A. R.; Gunasekaran, S.; Srinivasan, S. DFT studies on vibrational spectra, HOMO-LUMO, NBO and thermodynamic function analysis of cyanuric fluoride. Spectrochim. Acta, Part A 2015, 136, 494-503.
Guo, W.; Pleixats, R.; Shafir, A.; Parella, T. Rhodium Nanoflowers Stabilized by a Nitrogen-Rich PEG-Tagged Substrate as Recyclable Catalyst for the Stereoselective Hydrosilylation of Internal Alkynes. Adv. Synth. Catal. 2015, 357 (1), 89-99.
Hazard Statements: H310-H314-H330-H335
Fatal in contact with skin. Causes severe skin burns and eye damage. Fatal if inhaled. May cause respiratory irritation.
Precautionary Statements: P260-P262-P264b-P270-P271-P280-P284-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Do not get in eyes, on skin, or on clothing. 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. Wear respiratory protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. 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. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant