196196-15-3

Basic information

• Product Name: benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazol-3-yl-phenyl-methanone
• Synonyms: benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazol-3-yl-phenyl-methanone
• CAS NO: 196196-15-3
• Molecular Weight: 279.322
• Mol File: 196196-15-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazol-3-yl-phenyl-methanone(CAS DataBase Reference)
• NIST Chemistry Reference: benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazol-3-yl-phenyl-methanone(196196-15-3)
• EPA Substance Registry System: benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazol-3-yl-phenyl-methanone(196196-15-3)

Safety Data

• Hazardous Substances Data: 196196-15-3(Hazardous Substances Data)

Upstream product

• 613-90-1 benzoyl cyanide 
• 85997-29-1 2-butylbenzimidazo<1,2-d><1,2,4>thiadiazol-3(2H)-one 

Downstream Products

• 134469-07-1 Benzimidazol-2-thiol 

Relevant articles and documents

Synthesis of 3-substituted bicyclic imidazo[1,2-d][1,2,4]thiadiazoles and tricyclic benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazoles

A versatile synthetic route to potentially useful fused-ring [1,2,4]thiadiazole scaffolds (e.g., 7a and 10b) via exchange reactions of the precursor [1,2,4]thiadiazol-3-(2H)one derivatives (e.g., 6 and 9) with appropriately substituted nitriles (e.g., cyanogen bromide or p-toluenesulfonyl cyanide) under mild conditions is described. For example, the tricyclic 3-bromo [1,2,4]THD derivative (7a) underwent SNAr substitution with a variety of nucleophiles, which included amines, malonate esters and alcohols. Likewise, the bicyclic 3-p-tosyl [1,2,4]THD (10b) was employed as a template in reaction with diamines, and the resulting substituted diamines (e.g., 12a or 12e) were further selectively derivatized at the N1 and/or N2 positions in a linear fashion. The X-ray crystal structure of the 3-methyl bicyclic [1,2,4]THD (21) was obtained, and selective methylation at the N1 position via a protection-alkylation-deprotection protocol, as illustrated in Scheme 6, was confirmed. Alternatively, a short convergent synthesis of N1-functionalized derivatives from the reaction of 10b with appropriately substituted secondary amines was also developed. Hence, these synthetic strategies were advantageously exploited to provide access to a variety of diversely derivatized 3-substituted fused-ring [1,2,4]thiadiazole derivatives.

Process for scavenging thiols

Thiols are trapped, and converted to disulfide compounds, by a process of reacting them with compounds containing a 1,2,4-thiadiazole ring structure carrying a substituent at position 3 of the thiadiazole ring, and being unsubstituted at position N-2. The process is useful pharmacologically, in inhibiting certain thiol-containing enzymes such as H+/K+-ATPase (the proton pump), and industrially, in selective removal of thiol compounds from gas or liquid mixtures.