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Description
TCI F0726 is Fluoro-N,N,N',N'-tetramethylformamidinium Hexafluorophosphate, a coupling reagent widely known by the abbreviation TFFH. Unlike uronium- or phosphonium-based coupling reagents that operate through active esters, this reagent converts a carboxylic acid group into an acyl fluoride in situ. The acyl fluoride is an activated species reactive enough to form an amide bond, yet far more resistant to hydrolysis than the corresponding acyl chloride. This makes handling at the bench considerably more forgiving and results easier to reproduce across runs.
The advantage that makes this reagent a preferred choice lies in its ability to overcome difficult couplings. The acyl fluoride is small in size, so steric hindrance is reduced, which makes it especially useful for amino acids bearing bulky side chains such as valine and isoleucine derivatives and quaternary amino acids. The reagent also does not generate guanidinylation side products on free amines, a problem that occasionally arises with uronium reagents. In addition, TFFH performs well with amino acids containing sensitive functional groups, including arginine, because activation proceeds rapidly and minimizes lactam formation.
In Indonesian laboratories, this reagent is typically used in peptide chemistry and chemical biology settings where amide bond formation is the central transformation. It suits academic research groups, pharmaceutical development laboratories, and synthesis facilities that prepare peptide sequences or small-molecule amides. Workers reach for it particularly when standard coupling conditions have already been attempted and a sterically demanding or side-reaction-prone residue requires a more robust activation route.
Laboratory Applications
- Solid-phase peptide synthesis: the in situ acyl fluoride route drives couplings to completion on resin-bound sequences where conventional active ester chemistry stalls or gives incomplete conversion.
- Coupling of sterically hindered amino acids: the compact acyl fluoride intermediate reduces steric congestion, making it effective for valine, isoleucine, and quaternary amino acid derivatives that resist standard reagents.
- Arginine-containing sequence assembly: rapid activation limits the residence time of the activated species and thereby minimizes lactam formation, a common side reaction with this residue.
- Synthesis involving free amine substrates: because the reagent produces no guanidinylation by-products on free amines, it avoids a side reaction that complicates purification when uronium reagents are used.
- General amide bond formation in chemical biology: the greater hydrolytic stability of acyl fluorides compared with acyl chlorides gives more forgiving handling and more reproducible yields between batches.
Specifications
- Brand: TCI
- CAS number: 164298-23-1
- Category: Chemistry > Chemical Biology > Peptide Chemistry
- Chemical name: Fluoro-N,N,N',N'-tetramethylformamidinium Hexafluorophosphate (TFFH)
- Pack sizes: available in standard TCI catalogue pack sizes; please confirm the required quantity when ordering
- Storage: keep in a tightly closed container under the conditions stated on the manufacturer label
Handling and Storage
Store the container tightly closed in a cool, dry place, away from moisture and from sources of heat or ignition, following the conditions given on the manufacturer label and safety data sheet. Because the reagent generates a moisture-sensitive activated species during use, keep the container sealed when not in use and weigh out portions promptly to limit exposure to humid air. Use the original manufacturer container or a compatible tightly sealed glass vessel, clearly labelled. Handle inside a fume hood with appropriate personal protective equipment, including safety glasses, gloves, and a laboratory coat, and avoid contact with skin, eyes, and inhalation of any dust. Keep it separate from incompatible materials and dispose of residues in accordance with local chemical waste regulations.
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