20138-79-8

Basic information

• Product Name: 2,1,3-Benzothiadiazole-4,7-dicarbonitrile
• CAS NO: 20138-79-8
• Molecular Weight: 186.197
• Mol File: 20138-79-8.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 2,1,3-Benzothiadiazole-4,7-dicarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2,1,3-Benzothiadiazole-4,7-dicarbonitrile(20138-79-8)
• EPA Substance Registry System: 2,1,3-Benzothiadiazole-4,7-dicarbonitrile(20138-79-8)

Safety Data

• Hazardous Substances Data: 20138-79-8(Hazardous Substances Data)

Usage

General Description

2,1,3-Benzothiadiazole-4,7-dicarbonitrile is a chemical compound with the molecular formula C10H2N4S. It is a heterocyclic compound containing both nitrogen and sulfur atoms in its structure. 2,1,3-Benzothiadiazole-4,7-dicarbonitrile is commonly used in the field of organic and materials chemistry as a building block for the synthesis of organic semiconducting materials. It possesses unique electronic properties due to its conjugated structure, making it useful in the development of organic electronic devices such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). Additionally, 2,1,3-Benzothiadiazole-4,7-dicarbonitrile has also been studied for its potential applications in the field of medicinal chemistry for the development of new pharmaceutical compounds.

Upstream product

• 23616-25-3 4,7-dibromobenzo[d][l,2,3]thiadiazole 
• 15155-41-6 4,7-dibromobenzo[c][1,2,5]thiadiazole 
• 557-21-1 zinc(II) cyanide 
• 273-13-2 benzo[1,2,5]thiadiazole 
• 95-54-5 1,2-diamino-benzene 
• 544-92-3 copper(I) cyanide 

Downstream Products

• 1377975-50-2 C₄₄H₅₃N₆O₇PS 
• 5170-41-2 2,1,3-benzothiadiazole-4,7-dicarboxylic acid 
• 79780-61-3 1,2-diamino-3,6-dicyanobenzene 

Relevant articles and documents

Two 3D Cd(II) Metal-Organic Frameworks Linked by Benzothiadiazole Dicarboxylates: Fantastic S@Cd6 Cage, Benzothiadiazole Antidimmer, and Dual Emission

On the basis of the same benzothiadiazole (BTD) ligand 2,1,3-benzothiadiazole-4,7-dicarboxylic acid (H2L), two new isomers of three-dimensional (3D) BTD-derived Cd(II) metal-organic frameworks 1-2 {[S@Cd6L6]·xH2O}n were obtained by the different solvothermal reactions, which were structurally similar. Surprisingly, structural analyses reveal that in 1 or 2, one free sulfur atom was fixed in a Cd(II) cluster cage by strong intermolecular interaction to form the secondary building unit (SBU) S@Cd6. Each SBU S@Cd6 is connected by six L2- ligands and further extended into the 3D porous framework. In this work, the BTD antidimmer was evidenced by structural analysis and photophysical study. Furthermore, either 1 or 2 showed the uncommon dual emission, while only one emission was observed in the solution of ligand H2L. The dual-emission mechanism was also realized by the structural analysis and photophysical study. Interestingly, although there is slight difference in structure (regular octahedral cage in 1 and slightly distorted octahedral cage in 2), the changes in N2 adsorption capability and photophysical performance between 1 and 2 are obvious, where 2 shows smaller Brunauer-Emmett-Teller surface area, broader absorption of antidimmer, and longer dual-emission lifetimes. Interestingly, either 1 or 2, the dual emission was clearly red-shifted by increasing the solvent polarity or the acidity of ambience, respectively.

Multi PCET in symmetrically substituted benzimidazoles

Proton-coupled electron transfer (PCET) reactions depend on the hydrogen-bond connectivity between sites of proton donors and acceptors. The 2-(2′-hydroxyphenyl) benzimidazole (BIP) based systems, which mimic the natural TyrZ-His190 pair of Photosystem II

The Photochemical Reduction of 2,1,3-Benzothiadiazole-4,7-dicarbonitrile in the Presence of Cationic Micelles, and Onward Electron-transfer Reactions

Photolysis of solutions containing 2,1,3-benzothiadiazole-4,7-dicarbonitrile (BTDN) ethylenediaminetetra-acetic acid disodium salt (EDTA) and cetyltrimethylammonium bromide (CTAB) micelles at pH 5.5 produces the radical anion, BTDN.-, with BTDN acting both as an electron acceptor and as a chromophore.Variations in the efficiency of this reaction with pH, and are interpreted in terms of the formation of a complex between EDTA and BTDN which is broken down by the micelles.Net electron transfer does not occur within the complex.Alternative electron donors such as triethanolamine (TEOA) or 4-morpholine-ethanesulphonic acid (MES) can be employed, but not ascorbic acid or sulphite ion.The use of BTDN.- to reduce anthraquinones in stoichiometric or catalytic (with continuous photolysis) reactions is described.This allows an estimate of the redox potential of BTDN/BTDN.- when incorporated into micelles.

Small Organic Molecule Based on Benzothiadiazole for Electrocatalytic Hydrogen Production

A small organic molecule 2,1,3-benzothiadiazole-4, 7-dicarbonitrile (BTDN) is assessed for electrocatalytic hydrogen evolution on glassy carbon electrode and shows a hydrogen production Faradaic efficiency of 82% in the presence of salicylic acid. The key catalytic intermediates of reduced species BTDN–? and protonated intermediates are characterized or hypothesized by using various spectroscopic methods and density functional theory (DFT)-based calculations. With the experimental and theoretical results, a catalytic mechanism of BTDN for electrocatalytic H2 evolution is proposed.

Direct Conversion of Benzothiadiazole to Benzimidazole: New Benzimidazole-Derived Metal–Organic Frameworks with Adjustable Honeycomb-Like Cavities

Up to now, the direct conversion of the thiadiazole ring to other heterocyclic rings has been a very challenging task. Herein, a CdII-mediated alcohol-substitution strategy for direct conversion from benzothiadiazole to benzimidazole is reported. Experimental and molecular modeling studies on the role of the chelated metal ion in this in situ alcohol-substitution reaction revealed that it serves as an all-rounder that is involved in the insertion of alcohol, activation of the thiadiazole ring by coordinative interaction, and the sulfur-extrusion process. Interestingly, the insertion of alcohol occurs much earlier than the sulfur-extrusion process, supported by a water-mediated proton-transfer process. This strategy also is suitable for constructing new benzimidazole-derived MOFs [Cd2(HMBIDC2?)2]?4 H2O (Cd-BID-MOF-1, HMBIDC2?=2-methyl-1H-benzimidazole-4,7-dicarboxylate) and [Cd2(HPBIDC2?)2]?1/3 H2O (Cd-BID-MOF-2, HPBIDC2?=2-(3-hydroxypropyl)-2H-benzimidazole-4,7-dicarboxylate). Because the terminal hydroxyl group on the imidazole ring protrudes into the circular channel in rhombohedral Cd-BID-MOF-2, the cavity is closer to hydrophilic than the honeycomb-like cavity in Cd-BID-MOF-1 with similar 3D structure. This rare observation will provide a new strategy to develop in situ ligand-reaction synthesis of functional MOFs and useful chelation-assisted catalytic reactions in heteroaromatic chemistry.