1506-96-3

Upstream product

• 100-41-4 ethylbenzene 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 98-59-9 p-toluenesulfonyl chloride 
• 589-16-2 4-aminoethylbenzene 
• 5441-51-0 4-ethylcyclohexanone 
• 70-55-3 toluene-4-sulfonamide 

Downstream Products

• 1017280-90-8 C₁₅H₁₆FNO₂S 
• 108714-37-0 4-ethyl-N-(4-methoxyphenyl)aniline 
• 1620787-14-5 N-(4-ethyl-2-nitrophenyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Sulfapyridine-like benzenesulfonamide derivatives as inhibitors of carbonic anhydrase isoenzymes I, II and VI

The inhibition of two human cytosolic carbonic anhydrase (hCA, EC 4.2.1.1) isozymes I, II and human serum isozyme VI, with a series of tosylited aromatic amine derivatives was investigated. The KI ranges of compounds 1-14 and acetazolamide against hCA I ranged between 1.130 and- 448.2 μM, against hCA II between 0.103 and- 14.3 μM, and against hCA VI ranged between 0.340 and- 42.39 μM. Tosylited aromatic amine derivatives are thus interesting hCA I, II and VI inhibitors, and might be used as leads for generating enzyme inhibitors eventually targeting other isoforms which have not been assayed yet for their interactions with such agents.

Characteristic Hydrogen Bonding Observed in the Crystals of Aromatic Sulfonamides: 1D Chain Assembly of Molecules and Chiral Discrimination on Crystallization

N-Phenylbenzenesulfonamides exist preferentially in (+)- or (-)-synclinal conformations, which place the aromatic rings at both ends in the same direction with a twist. We have systematically analyzed the crystal structure of secondary aromatic sulfonamides bearing methyl, ethyl, and/or methoxy groups on the benzene rings. Intermolecular hydrogen bonding between the sulfonamide protons and sulfonyl oxygens was observed in 81 out of 85 crystals. The intermolecular hydrogen-bonding patterns could be classified into four types, i.e. Dimeric, Zigzag, Helical, and Straight patterns, with retention of the synclinal conformation of the sulfonamide moiety. We investigated the relationship between the hydrogen-bonding pattern and the proportion of the compounds that show chiral crystallization. On the basis of our classification of the intermolecular hydrogen bonds of aromatic sulfonamides, the crystals with Dimeric and Zigzag patterns, which both have enantiomeric synclinal conformers, intrinsically become achiral, except for kryptoracemates. In contrast, a high proportion of compounds with Helical or Straight patterns in the crystals showed chiral crystallization. Our classification is useful for discussion regarding the chirality of molecular assemblies, on the basis of the conformational chirality of the molecules in the crystal.

Palladium-catalyzed arylation of aryl sulfonamides with cyclohexanones

Pd-catalyzed intermolecular aerobic dehydrogenative aromatizations have been developed for the arylation of aryl sulfonamides with cyclohexanones. Various N-aryl sulfonamides were selectively obtained in good yields using molecular oxygen as oxidant. The reaction tolerated a wide range of functionalities.

Half-sandwich scorpionates as nitrene transfer catalysts

Scorpionate complexes of the middle to late 3d transition metals [(L)M(NCMe)3](BF4)n (M = Mn, Fe, Co, Ni: 1 M, L = tris(3,5-dimethylpyrazol-1-yl)methane, TpmMe,Me, n = 2; 2M, L = tris(3-phenylpyrazol-1-yl)methane, TpmPh, n = 2; 3M except 3Mn, L = hydrotris(3,5-dimethylpyrazol-1-yl) borate, [TpMe,Me]-, n = 1; 4M, L = hydrotris(3-phenyl-5-methylpyrazol-1-yl)borate, [TpPh,Me] -, n = 1) were examined as catalysts for styrene aziridination and THF amination using phenyl-N-tosyliodinane as a nitrene donor. [(Tpm Me,Me)Fe(NCMe)3](BF4)2 (1 Fe) was identified as the most active catalyst, giving nearly quantitative nitrene transfer yields at 5 mol % loadings. The reactivity of 1Fe with a wider range of organic substrates was also explored, and a striking observation was strong selectivity for aromatic rather than benzylic amination for alkylaromatic substrates.