174577-69-6

Upstream product

• 124-38-9 carbon dioxide 
• 17534-15-5 Benzene-1,2-dithiol 

Downstream Products

• 1439141-35-1 N-phenyl-2,3-dimercaptobenzamide 
• 1403673-09-5 N-tert-butyl-2,3-dimercaptobenzamide 
• 1403673-08-4 N-tert-butyl-2,3-di(pivaloylthio)benzamide 
• 178626-89-6 C₁₈H₁₈O₄S₄ 
• 178626-91-0 CH₂CH₂(SC₆H₃(SH)CO₂H)2 
• 178626-86-3 2,3-dimercaptobenzoic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of Protected 3,4- And 2,3-Dimercaptophenylalanines as Building Blocks for Fmoc-Peptide Synthesis and Incorporation of the 3,4-Analogue in a Decapeptide Using Solid-Phase Synthesis

3,4-Dimercaptophenylalanines and 2,3-dimercaptophenylalanines have been synthesized for the first time by nucleophilic substitution of a protected aminomalonate on 3,4- and 2,3-dimercaptobenzyl bromide derivatives. The dithiol functions were protected as thioketals, and the key precursors, diphenylthioketal-protected dimercaptobenzyl bromides, were synthesized via two distinct routes from either dihydroxy benzoates or toluene-3,4-dithiol. Racemic mixtures of the fully protected amino acids were separated by chiral HPLC into the corresponding enantiomers. The absolute configuration of both 3,4- and 2,3-analogues could be assigned based on X-ray crystallography and VCD/DFT measurements. Thioketal groups were deprotected upon reaction with mercury oxide and aqueous tetrafluoroboric acid followed by treatment with H2S gas under an argon atmosphere to obtain the corresponding dimercapto amino acids. The optically pure l-Fmoc-protected 3,4-analogue (S- enantiomer) was successfully incorporated into a decapeptide using standard solid-phase peptide synthesis. Therefore, dithiolene-functionalized peptides are now accessible from a simple synthetic procedure, and this should afford new molecular tools for research into the catalysis, diagnostic, and nanotechnology fields.

Synthesis of water soluble fe and ru complexes novel thioether thiolate carboxylate substituents

In search of water soluble transition metal complexes with sulfur dominated coordination spheres that model key reactions of nitrogenases, the benzenedithiol derivatives 'CO2HS2'-H2 (I) and 'CO2Me-S2'-H2 (2) were synthesized as precursors for multidentate sulfur ligands. The template alkylation of 2 by C2H4Br2 at [Fe(CO)2] fragments yielded a mixture of two diastereomeric C2 symmetrical [Fe(CO)2('CO2Me-S4'}] complexes (4a and 4b), which were separated by crystallization. The hydrolysis of the mixture of the diastereomers 4a and 4b led to the isomerically pure tetradentate thioether thiol ligand 'CO2Me-S4'-H2 (5) proving the regioselectivity of the template alkylation ol the asymmetrical dithiol 2. The Q symmetrical [Fe{'CO2Me-S2')2]2~ anion is an intermediate of the template alkylation and was isolated as (AsPh4)2[Fe('CO2Me-S2'}2] (11). 4a, 5 and 11 were characterized by Xray structural analysis. Saponification of the methyl ester groups of 5 yielded 'CO2H-S4'-H2 (7). Treatment of 7 with FeCl2 · 4 H2O in the presence of CO and LiOMe gave a mixture of two C2 symmetrical and water soluble diastereomers of Li2SFe(CO)2('CO2-S4')] (8). Upon treatment with [RuCl2(PPh3)3], 7 yielded isomerically pure [Ru(PPh3)2-('CO2H-S4')] (9). 9 also exhibits C2 symmetry and could be reversibly deprotonated to form the water soluble complex K2[Ru(PPh3)2('CO2-S4')] (10). Treatment of (NBu4)2(CO2MeS2') with "Ru(NO)Cl3" led to isomerically pure (NBu4)[Ru(NO)('CO2Me-S2')2] (12). VCH Verlagsgesellschaft mbH, , 1996.

Synthese und Koordinationschemie von ortho-funktionalisiertem Dimercaptobenzol: Bausteine fuer tripodale Hexathiol-Liganden

Keywords: Chelatliganden; Molybdaenverbindungen; Thiole; Tripodliganden