Cyanuric fluoride

• Catalog No.: A15666
• CAS Number: 675-14-9
• M. F.: C3F3N3
• M. W.: 135.0474096
• Purity: 98%

SYNONYMS

• Title: 三聚氟氰
• IUPAC name: trifluoro-1,3,5-triazine
• IUPAC Traditional name: cyanuric fluoride
• Synonyms: 2,4,6-Trifluoro-1,3,5-triazine

DATABASE IDS

• EC Number: 211-620-8
• MDL Number: MFCD00014597
• Beilstein Number: 124237
• CAS Number: 675-14-9

PROPERTIES

• Purity: 98%
• Boiling Point: 73-74°C
• Density: 1.574
• Melting Point: -38°C
• Refractive Index: 1.3840
• GHS Hazard statements: H310-H330-H314-H318
• European Hazard Symbols: Highly toxic (T+)
• GHS Precautionary statements: P260-P303+P361+P353-P304+P340-P305+P351+P338-P320-P361-P405-P501A
• Risk Statements: 24-26-35
• RTECS: XZ1750000
• Safety Statements: 20-26-27/28-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN3389
• Packing Group: I

REFERENCES

• 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).