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675-14-9 - Cyanuric fluoride, 98% - 2,4,6-Trifluoro-1,3,5-triazine - A15666 - Alfa Aesar

A15666 Cyanuric fluoride, 98%

CAS Number
675-14-9
Synonyms
2,4,6-Trifluoro-1,3,5-triazine

Size Price ($) Quantity Availability
5g 81.54
10g 143.10
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Cyanuric fluoride, 98%

MDL
MFCD00014597
EINECS
211-620-8

Chemical Properties

Formula
C3F3N3
Formula Weight
135.05
Melting point
-38°
Boiling Point
73-74°
Density
1.574
Refractive Index
1.3840
Sensitivity
Moisture Sensitive
Solubility
Miscible with chloroform, carbon tetrachloride,ether, dioxane and ketones.

Applications

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

Notes

May precipitate upon storage. Moisture sensitive. Incompatible strong oxidizing agents, strong bases and alcohols.

Literature 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).

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H310-H330-H314-H318

Fatal in contact with skin. Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P260-P284-P303+P361+P353-P304+P340-P305+P351+P338-P320-P361-P301+P330+P331-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear respiratory protection. 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. Specific treatment is urgent (see label). IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
124237
Hazard Class
6.1
Packing Group
I
Harmonized Tariff Code
2933.69
TSCA
Yes
RTECS
XZ1750000

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