4-Fluoro-3-(trifluoromethylsulfonyl)benzenesulfonyl chloride
[CAS# 1027345-07-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Sulfonyl halide
• Name: 4-Fluoro-3-(trifluoromethylsulfonyl)benzenesulfonyl chloride
• Molecular Formula: C₇H₃ClF₄O₄S₂
• Molecular Weight: 326.67
• CAS Registry Number: 1027345-07-8
• SMILES: C1=CC(=C(C=C1S(=O)(=O)Cl)S(=O)(=O)C(F)(F)F)F

Safety Data

• Hazard Symbols: GHS07 Danger
• Hazard Statements: H314
• Precautionary Statements: P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310
• Transport Information: UN 3265

Discovory and Applicatios

4-Fluoro-3-(trifluoromethylsulfonyl)benzenesulfonyl chloride is a fluorinated aromatic sulfonyl chloride compound characterized by the presence of a fluorine atom at the para position and a trifluoromethylsulfonyl group at the meta position on the benzene ring, along with a sulfonyl chloride functional group. Its molecular formula is typically represented as C₇H₂ClF₄O₄S₂, reflecting the combination of fluorine and sulfonyl substituents on the aromatic core.

This compound was synthesized as part of research into fluorinated aromatic sulfonyl chlorides, which are valuable intermediates in the preparation of sulfonamide derivatives and other functionalized aromatic compounds. Its synthesis usually involves the chlorosulfonation of 4-fluoro-3-(trifluoromethylsulfonyl)benzene precursors, employing reagents such as chlorosulfonic acid or sulfuryl chloride under controlled conditions to introduce the sulfonyl chloride group selectively on the aromatic ring.

The presence of both strongly electron-withdrawing trifluoromethylsulfonyl and fluorine substituents significantly influences the reactivity and properties of this molecule. The trifluoromethylsulfonyl group imparts high thermal and chemical stability, while the sulfonyl chloride group serves as a highly reactive electrophilic site suitable for nucleophilic substitution reactions.

Applications of 4-fluoro-3-(trifluoromethylsulfonyl)benzenesulfonyl chloride are mainly found in organic synthesis, where it serves as a key intermediate for the preparation of sulfonamides, sulfonate esters, and other derivatives. These transformations often utilize the sulfonyl chloride group to react with amines, alcohols, or other nucleophiles, allowing the installation of the sulfonyl moiety onto various substrates. The fluorinated substituents on the aromatic ring enhance the chemical and biological properties of the resulting compounds, including increased metabolic stability, lipophilicity, and often improved bioavailability.

This compound is utilized in the development of pharmaceuticals, agrochemicals, and specialty chemicals where the incorporation of fluorinated groups is desirable for modifying activity and stability. In particular, sulfonamide derivatives derived from this compound are investigated for their potential biological activities, including antimicrobial and enzyme inhibitory properties.

The handling of 4-fluoro-3-(trifluoromethylsulfonyl)benzenesulfonyl chloride requires caution due to the reactivity of the sulfonyl chloride group, which can hydrolyze in the presence of moisture, releasing corrosive hydrogen chloride gas. Appropriate anhydrous conditions and protective equipment are essential during its storage and use.

Overall, 4-fluoro-3-(trifluoromethylsulfonyl)benzenesulfonyl chloride is a valuable fluorinated sulfonyl chloride intermediate. Its distinct electronic and steric features facilitate its application in synthesizing advanced fluorinated sulfonyl derivatives with relevance in pharmaceutical and agrochemical research.