CAS 402-27-7
3-cyanobenzenesulfonyl fluoride
About This Compound
Sulfonyl fluorides are key building blocks in Sulfur(VI) Fluoride Exchange (SuFEx) click chemistry — one of the most robust click reactions introduced by Sharpless and colleagues. The SO₂F group reacts selectively with nucleophiles such as phenols, amines, and silyl ethers under mild conditions, forming stable sulfonate or sulfonamide linkages. These compounds are widely used in chemical biology for covalent protein labeling, activity-based protein profiling (ABPP), and the construction of molecular probes.
XHDHNTIGKYTAGT-UHFFFAOYSA-N
CAS Registry402-27-7
Literature Refs10 references
Synthesis Routes
Showing 3 of 9 available routes, sorted by yield.
Route 1
Route 2
BF4*C7H4N3
Route 3
CAS 402-27-7
C7H4FNO2S
CAS 98-80-6
C6H7BO2
Related Compounds
Other Sulfonyl Fluorides in our catalog:
Frequently Asked Questions
How should sulfonyl fluoride compounds be stored?
Store in a sealed container at room temperature, protected from moisture. Sulfonyl fluorides are generally stable to ambient humidity for weeks, but prolonged exposure to water can lead to hydrolysis of the SO₂F group. For long-term storage, keep under inert atmosphere (N₂ or Ar) at −20 °C.
What nucleophiles are compatible with SuFEx reactions?
SuFEx reactions selectively target silyl ethers, phenols, primary and secondary amines, and activated alcohols. Thiols and carboxylic acids generally do not react with sulfonyl fluorides under standard conditions, providing excellent chemoselectivity in complex biological environments.
What catalysts are commonly used for SuFEx?
Common SuFEx catalysts include BTMG (2-tert-butyl-1,1,3,3-tetramethylguanidine), BEMP, and 4-dimethylaminopyridine (DMAP). Base-catalyzed SuFEx typically proceeds at room temperature in organic solvents such as DMSO, DMF, or MeCN.
Are sulfonyl fluorides safe to handle in the lab?
Sulfonyl fluorides are generally safer and more stable than sulfonyl chlorides. However, standard PPE (gloves, goggles, fume hood) should be used. Avoid contact with strong bases and nucleophilic solvents. Small-molecule sulfonyl fluorides may have acute toxicity — always consult the SDS before use.
How do I purify sulfonyl fluoride products?
Most sulfonyl fluorides can be purified by silica gel column chromatography using hexane/ethyl acetate gradients. They are generally stable to standard chromatographic conditions. Alternatively, recrystallization from EtOAc/hexane works well for crystalline products.
Last updated: July 27, 2026