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Cyanuric fluoride

Catalog No. A15666 Name Alfa Aesar
CAS Number 675-14-9 Website
M. F. C3F3N3 Telephone
M. W. 135.0474096 Fax
Purity 98% Email
Storage Chembase ID: 126782

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 Pictograms GHS05
GHS Pictograms GHS06
GHS Hazard statements H310-H330-H314-H318
European Hazard Symbols Highly toxic 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
Hazard Class 6.1
UN Number UN3389
Packing Group I

DETAILS

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).