17821-93-1

Basic information

• Product Name: 5,6-Dichlorobenzo[c][1,2,5]thiadiazole
• Synonyms: 5,6-Dichlorobenzo[c][1,2,5]thiadiazole;5,6-Dichloro-2,1,3-benzothiadiazole
• CAS NO: 17821-93-1
• Molecular Formula: C6H2Cl2N2S
• Molecular Weight: 205.06448
• Mol File: 17821-93-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 288°Cat760mmHg
• Flash Point: 128°C
• Appearance: /
• Density: 1.662g/cm³
• Vapor Pressure: 0.00415mmHg at 25°C
• Refractive Index: 1.714
• Storage Temp.: Room temperature.
• CAS DataBase Reference: 5,6-Dichlorobenzo[c][1,2,5]thiadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Dichlorobenzo[c][1,2,5]thiadiazole(17821-93-1)
• EPA Substance Registry System: 5,6-Dichlorobenzo[c][1,2,5]thiadiazole(17821-93-1)

Safety Data

• Hazardous Substances Data: 17821-93-1(Hazardous Substances Data)

Usage

General Description

5,6-Dichlorobenzo[c][1,2,5]thiadiazole is a chemical compound with the molecular formula C6H2Cl2N2S. It is a benzothiadiazole derivative that contains two chlorine atoms attached to the benzene ring. 5,6-Dichlorobenzo[c][1,2,5]thiadiazole has been investigated for its potential use in organic electronics, specifically as a building block for conjugated polymers and organic semiconductors. Its unique structure and properties make it a promising candidate for applications in optoelectronic devices, such as solar cells, light-emitting diodes, and field-effect transistors. Additionally, it has been studied for its potential use in pharmaceuticals, agrochemicals, and materials science due to its versatile and tunable properties.

InChI:InChI=1/C6H2Cl2N2S/c7-3-1-5-6(2-4(3)8)10-11-9-5/h1-2H

Upstream product

• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 

Relevant articles and documents

Synthesis of novel halogenated heterocycles based on o‐phenylenediamine and their interactions with the catalytic subunit of protein kinase ck2

Protein kinase CK2 is a highly pleiotropic protein kinase capable of phosphorylating hundreds of protein substrates. It is involved in numerous cellular functions, including cell viability, apoptosis, cell proliferation and survival, angiogenesis, or ER‐stress response. As CK2 activity is found perturbed in many pathological states, including cancers, it becomes an attractive target for the pharma. A large number of low‐mass ATP‐competitive inhibitors have already been developed, the majority of them halogenated. We tested the binding of six series of halogenated heterocyclic ligands derived from the commercially available 4,5‐dihalo‐benzene‐1,2‐diamines. These ligand series were selected to enable the separation of the scaffold effect from the hydrophobic interactions attributed directly to the presence of halogen atoms. In silico molecular docking was initially applied to test the capability of each ligand for binding at the ATP‐binding site of CK2. HPLC‐derived ligand hydrophobicity data are compared with the binding affinity assessed by low‐volume differential scanning fluorimetry (nanoDSF). We identified three promising ligand scaffolds, two of which have not yet been described as CK2 inhibitors but may lead to potent CK2 kinase inhibitors. The inhibitory activity against CK2α and toxicity against four reference cell lines have been determined for eight compounds identified as the most promising in nanoDSF assay.

Formation and Rearrangement of Adducts from Benzyne and Substituted 2,1,3-Benzoselenadiazoles

A series of 5-(1,2-benzoselenazol-3-yl)pentadienonitrile derivatives (2) has been prepared by addition of benzyne to substituted 2,1,3-benzoselenadiazoles.Some of these adducts rearrange either thermally or photochemically to give 2-(2-pyridyl)phenyl selenocyanates (7), which are reduced to 2-phenylpyridine derivatives (6) or hydrolysed to give ultimately, diselenides (9).The crystal structure of one benzyne adduct (2b) is reported and the mechanism of its rearrangement discussed.