4-Cyanobenzenesulfonyl fluoride

• CAS: 33719-37-8
• Catalog Number: ACM33719378
• Category: Alkanes
• Molecular Weight: 185.18
• Molecular Formula: C₃₂H₆₂O₄Zn
• Appearance: solid or liquid (Conforms to requirements)
• Hazard Statements: H304
• RIDADR: UN 3261 8 / PGII
• Symbol: GHS08

Case Study

4-Cyanobenzenesulfonyl Fluoride for the Synthesis of Sulfonamide Compounds

Han, Brian, et al. Inorganic chemistry, 2022, 61(25), 9746-9755.

This study detailed the sulfur (VI)-fluoride ion exchange (SuFEx) mechanism involving sulfonyl fluoride and amine, facilitated by calcium bis(trifluorocarbonimide). For example, the synthesis of sulfonamide compound 24 utilized 4-cyanobenzenesulfonyl fluoride as the raw material.
Synthesis of Sulfonamide 24
· The reaction components including the amine substrate [1-(6-(trifluoromethyl)pyridin-2-yl)piperazine 3, 1.05 equiv], Ca(NTf2)2 (12.0 mg, 0.020 mmol, 0.1 equiv), DABCO (4.5 mg, 0.040 mmol, 0.2 equiv), and 1,1,3,3-tetramethyldisiloxane (TMDS) (53.7 mg, 71 μL, 0.400 mmol, 2 equiv.)were dissolved entirely in anhydrous THF at a concentration of 0.25 M in a 3.7 mL scintillating glass vial.
· To this reaction mixture, 4-cyanobenzenesulfonyl fluoride (37 mg, 0.200 mmol, 1.0 equiv) was added, and the mixture was stirred for 24 hours at 50 °C.
· Then diluted the reaction mixture with 20 mL ethyl acetate before washing the organic layer with saturated NH4Cl and subsequently with saturated brine. After drying the organic layer using anhydrous MgSO4 or Na2SO4 the sample was concentrated through reduced pressure before loading onto a flash chromatography column with silica gel cartridge and EtOAc/hexane mobile phase. The product fractions underwent TLC analysis before concentration under reduced pressure and high vacuum drying which produced 53 mg of the white powder product [4-((4-(6-(Trifluoromethyl)pyridin-2-yl)piperazin-1-yl)sulfonyl)benzonitrile 24, 0.330 mmol, 67% yield].

Custom Q&A

What is the molecular formula of 4-Cyanobenzenesulfonyl fluoride?

The molecular formula of 4-Cyanobenzenesulfonyl fluoride is C7H4FNO2S.

What is the molecular weight of 4-Cyanobenzenesulfonyl fluoride?

The molecular weight of 4-Cyanobenzenesulfonyl fluoride is 185.18 g/mol.

What is the IUPAC name of 4-Cyanobenzenesulfonyl fluoride?

The IUPAC name of 4-Cyanobenzenesulfonyl fluoride is 4-cyanobenzenesulfonyl fluoride.

What is the InChI of 4-Cyanobenzenesulfonyl fluoride?

The InChI of 4-Cyanobenzenesulfonyl fluoride is InChI=1S/C7H4FNO2S/c8-12(10,11)7-3-1-6(5-9)2-4-7/h1-4H.

What is the InChIKey of 4-Cyanobenzenesulfonyl fluoride?

The InChIKey of 4-Cyanobenzenesulfonyl fluoride is YKZXWWMBQGHLNP-UHFFFAOYSA-N.

What is the canonical SMILES representation of 4-Cyanobenzenesulfonyl fluoride?

The canonical SMILES representation of 4-Cyanobenzenesulfonyl fluoride is C1=CC(=CC=C1C#N)S(=O)(=O)F.

What is the CAS number of 4-Cyanobenzenesulfonyl fluoride?

The CAS number of 4-Cyanobenzenesulfonyl fluoride is 33719-37-8.

What is the XLogP3 value of 4-Cyanobenzenesulfonyl fluoride?

The XLogP3 value of 4-Cyanobenzenesulfonyl fluoride is 1.4.

How many hydrogen bond acceptors does 4-Cyanobenzenesulfonyl fluoride have?

4-Cyanobenzenesulfonyl fluoride has 4 hydrogen bond acceptors.

How many rotatable bonds does 4-Cyanobenzenesulfonyl fluoride have?

4-Cyanobenzenesulfonyl fluoride has 1 rotatable bond.