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Upstream product

• 7152-24-1 2-methylsulfanylbenzimidazole 
• 134469-07-1 Benzimidazol-2-thiol 

Downstream Products

• 112951-87-8 2-(1H-Benzimidazol-2-yl thio)-N,N-dimethyl benzenamine 
• 69104-73-0 2-<(2-aminophenyl)thio>-1H-benzimidazole 
• 1021915-05-8 C₁₆H₁₃N₃O₄S 
• 7152-24-1 2-methylsulfanylbenzimidazole 
• 57159-81-6 2-(methylsulfonyl)-1H-benzo[d]imidazole 
• 135430-20-5 {(S)-1-[2-(1H-Benzoimidazol-2-ylsulfanyl)-phenylcarbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester 
• 135430-23-8 {(S)-1-[2-(1H-Benzoimidazol-2-ylsulfanyl)-phenylcarbamoyl]-3-methyl-butyl}-carbamic acid benzyl ester 
• 135430-19-2 2-<(2-((benzyloxycarbonyl)glycylamino)phenyl)thio>-1H-benzimidazole 
• 135430-28-3 (S)-2-Amino-N-[2-(1H-benzoimidazol-2-ylsulfanyl)-phenyl]-3-phenyl-propionamide 
• 135430-57-8 2-<(2-(L-phenylalanylamino)phenyl)sulfinyl>-1H-benzimidazole 
• 135430-54-5 (S)-2-Amino-4-methyl-pentanoic acid [2-(1H-benzoimidazole-2-sulfinyl)-phenyl]-amide 
• 135430-31-8 (S)-2-Amino-4-methyl-pentanoic acid [2-(1H-benzoimidazol-2-ylsulfanyl)-phenyl]-amide 
• 135430-50-1 2-Amino-N-[2-(1H-benzoimidazole-2-sulfinyl)-phenyl]-acetamide 
• 135430-26-1 2-<(2-(glycylamino)phenyl)thio>-1H-benzimidazole 

Relevant academic research and scientific papers

An environmentally benign and selective electrochemical oxidation of sulfides and thiols in a continuous-flow microreactor

A practical and environmentally benign electrochemical oxidation of thioethers and thiols in a commercially-available continuous-flow microreactor is presented. Water is used as the source of oxygen to enable the oxidation process. The oxidation reaction utilizes the same reagents in all scenarios and the selectivity is solely governed by the applied potential. The procedure exhibits a broad scope and good functional group compatibility providing access to various sulfoxides (15 examples), sulfones (15 examples) and disulfides (6 examples). The use of continuous flow allows the optimal reaction parameters (e.g. residence time, applied voltage) to be rapidly assessed, to avoid mass- and heat-transfer limitations and to scale the electrochemistry.

Electrochemically Induced N-Alkylation of Chiral 2-(Methylsulfinyl) 1H-Benzimidazole

Galvanostatic electrolysis of chiral 2-(methylsulfinyl) 1H-benzimidazole in an acetonitrile/tetraethyl ammonium tetrafluoroborate system has been exploited to carry out the selective N-alkylation of the benzimidazole moiety with organohalides, thus obtain

Polyoxomolybdate-Calix[4]arene Hybrid: A Catalyst for Sulfoxidation Reactions with Hydrogen Peroxide

An easily accessible polyoxomolybdate-calix[4]arene hybrid 1 has been synthesized and applied as a heterogeneous catalyst in the sulfoxidation of thioethers to sulfoxides and to sulfones under strictly stoichiometric amounts of 30% H2O2 in CH3CN as the solvent. This study represents the first promising example of successful employment of calixarenes-polyoxometalate (POM) hybrid materials in the area of catalytic oxidations.

TiCl4 hiocarbonyls and oxidation of sulfides in the presence of H2O2

H2O2 in combination with TiCl4 proved to be a highly reactive reagent system for the desulfurization of thioamide and thioketone derivatives in excellent yields and short reaction times with high purity. Sulfides were also found to undergo oxidation to sulfones under similar reaction conditions. In most cases, these reactions are highly selective, simple, and clean, affording products in high yields and purity.

Oxidation of polyfunctional sulfides with chlorine dioxide

3-Benzylsulfanyl-4,5-diphenyl-4H-1,2,4-triazole, 5-methylsulfanyl-1-phenyl- 1H-tetrazole, 2-methylsulfanyl-1H-benzimidazole, 2-benzylsulfanyl-1H- benzimidazole, and 1-butylsulfanyl-4-nitrobenzene were oxidized to the corresponding sulfoxides with chlorine

Discovery of small molecule benzimidazole antagonists of the chemokine receptor CXCR3

High-throughput screening identified a low molecular weight antagonist of CXCR3 displaying micromolar activity in a membrane filtration-binding assay. Systematic modification of the benzimidazole core and tethered acetophenone moiety established tractable SAR of analogs with improved physicochemical properties and sub-micromolar activity across both human and murine receptors.

Highly enantioselective oxidation of sulfides to sulfoxides by a new oxaziridinium salt

The new oxaziridinium salt 5 (R2 = TBDPS) is an effective reagent for the highly enantioselective oxidation of sulfides to sulfoxides with up to >99% ee and good yields. As such, it represents a new valuable nonmetallic alternative to the existing methods for asymmetric sulfoxidation.

Conversion of sulfides to sulfoxides and thiols to disulfides with o-xylylenebis(triphenylphosphonium tribromide)

o-Xylylenebis(triphenylphosphonium tribromide) (1) is an efficient reagent for the conversion of thiols to disulfides and sulfides to sulfoxides under neutral and anhydrous conditions in good to excellent yields. Selective oxidation of thiols in the presence of sulfides at room temperature is also observed with this reagent.

HIO3 in the presence of wet SiO2: A mild and efficient reagent for selective oxidation of sulfides to sulfoxides under solvent-free conditions

In the presence of wet SiO2, HIO3 is highly efficient for the selective oxidation of sulfides to sulfoxides. It may be applied to any type of dialkyl and alkyl aryl sulfides. It develops under solvent-free conditions, and gives high yield in the presence of different functional groups on the sulfide at room temperature.

Chemistry of covalent inhibition of the gastric (H+, K +)-ATPase by proton pump inhibitors

Proton pump inhibitors (PPIs), drugs that are widely used for treatment of acid related diseases, are either substituted pyridylmethylsulfinyl benzimidazole of imidazopyridine derivatives. They are all prodrugs that inhibit the acid-secreting gastric (H+, K+)-ATPase by acid activation to reactive thiophiles that form disulfide bonds with one or more cysteines accessible from the exoplasmic surface of the enzyme. This unique acid-catalysis mechanism had been ascribed to the nucleophilicity of the pyridine ring. However, the data obtained here show that their conversion to the reactive cationic thiophilic sulfenic acid or sulfenamide depends mainly not on pyridine protonation but on a second protonation of the imidazole component that increases the electrophilicity of the C-2 position on the imidazole. This protonation results in reaction of the C-2 with the unprotonated fraction of the pyridine ring to form the reactive derivatives. The relevant PPI pK a's were determined by UV spectroscopy of the benzimidazole or imidazopyridine sulfinylmethyl moieties at different medium pH. Synthesis of a relatively acid stable analogue, N1-methyl lansoprazole, (6b), allowed direct determination of both pKa values of this intact PPI allowing calculation of the two pKa values for all the PPIs. These values predict their relative acid stability and thus the rate of reaction with cysteines of the active proton pump at the pH of the secreting parietal cell. The PPI accumulates in the secretory canaliculus of the parietal cell due to pyridine protonation then binds to the pump and is activated by the second protonation on the surface of the protein to allow disulfide formation.