16914-92-4Relevant academic research and scientific papers
Introduction of isothiuronium surfactant series: Synthesis, structure-dependent aggregation overview and biological activity
Valeeva,Karimova,Pavlov,Bakhtiyarov,Sapunova,Ivshin,Kataeva,Gaynanova,Syakaev,Voloshina,Galkina,Latypov, Sh.K.,Zakharova, L.Ya.
, (2020/11/20)
For a homologous series of isothiuronium surfactants (S-alkylisothiuronium bromides, CnSU, where n = 10, 12, 14, 16, 18), a synthesis procedure is described and aggregation properties are comprehensively characterized by a variety of techniques. Krafft temperature and critical micelle concentration (cmc) are obtained by methods of conductometry, tensiometry, spectrophotometry, fluorimetry. Using dynamic light scattering and NMR diffusometry, aggregate sizes in aqueous solutions were determined. The aggregation numbers of CnSU systems were estimated by alternative methods. An increase in the length of the alkyl tail from 10 to 16 carbon atoms leads to a decrease in cmc from 16 to 0.5 mM with a decrease in aggregation numbers. S-alkylisothiuronium bromides exhibit solubilization capacity toward a hydrophobic dye Orange OT which is 2–3 times higher than that of alkyltrimethylammonium analogues. Improved solubilization characteristics along with antimicrobial properties manifested at the concentrations of low hemolytic activity allow us to recommend these amphiphiles for the fabrication of soft nanocontainers for hydrophobic guests showing their own biological functionality.
Synthesis of difluoromethyl and deuterium-labeled difluoromethyl thioethers from aliphatic electrophiles
Ding, Tianqi,Jiang, Lvqi,Yi, Wenbin
, p. 3995 - 3998 (2020/04/17)
A one-pot difluoromethylthiolation of alkyl electrophiles with thiourea and diethyl bromodifluoromethylphosphonate is described. The transition-metal-free approach, readily available reagents, and mild conditions provide a practical way for the synthesis of difluoromethyl thioethers. By changing the "H" source to the most commonly used "D" sources CD3OD and D2O, this strategy enables efficient synthesis of SCF2D-substituted molecules in good yields with high levels of D incorporation.
Clean and economic synthesis of alkanesulfonyl chlorides from S-alkyl isothiourea salts via bleach oxidative chlorosulfonation
Yang, Zhanhui,Zhou, Bingnan,Xu, Jiaxi
, p. 225 - 229 (2014/03/21)
A simple procedure for clean and economic synthesis of alkanesulfonyl chlorides via bleach-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is disclosed. This procedure is environment- and worker-friendly with the advantages of readily accessible materials and reagents, simple and safe operations, easy purification without chromatography, and affords high yields of up to 99%.
Convenient and environment-friendly synthesis of sulfonyl chlorides from S -alkylisothiourea salts via N-chlorosuccinimide chlorosulfonation
Yang, Zhanhui,Xu, Jiaxi
, p. 1675 - 1682 (2013/07/27)
A convenient, practical, and environmentally friendly method for the synthesis of sulfonyl chlorides has been developed. Structurally diverse sulfonyl chlorides were synthesized in moderate to excellent yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea, via N-chlorosuccinimide chlorosulfonation. In large-scale syntheses, the byproduct succinimide from 'waste water' can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite (bleach) to make the method sustainable. Georg Thieme Verlag Stuttgart, New York.
Simple synthesis of sulfonyl chlorides from thiol precursors and derivatives by NaClO2-mediated oxidative chlorosulfonation
Yang, Zhanhui,Zheng, Yongpeng,Xu, Jiaxi
supporting information, p. 2165 - 2169 (2013/10/22)
A simple method to synthesize diverse sulfonyl chlorides through NaClO 2-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is presented. The approach features safe operation, environmental friendliness, convenient purification procedures, and delivers high yields of up to 96%. The procedure is also applicable to substrates such as thiols, disulfides, thioacetates, and xanthates. It is a versatile and convenient method for the synthesis of various sulfonyl chlorides from different thiol precursors and derivatives. Georg Thieme Verlag Stuttgart, New York.
