6286-32-4

Usage

Uses

Used in Pesticide Industry:
2-Chloro-3,5-dinitro-thiophene is used as an insecticide and miticide for controlling insects and mites in agricultural settings. Its effectiveness in pest control makes it a valuable tool in protecting crops and maintaining yields.
Used in Dye Production:
2-Chloro-3,5-dinitro-thiophene is utilized as an intermediate in the production of dyes. Its chemical properties contribute to the development of various dye types, enhancing the color and quality of the final products.
Used in Pharmaceutical Industry:
2-Chloro-3,5-dinitro-thiophene is also employed in the manufacturing of pharmaceuticals. Its unique characteristics make it a useful component in the development of certain drugs, contributing to their efficacy and performance.
It is crucial to handle 2-Chloro-3,5-dinitro-thiophene with extreme caution due to its hazardous nature and potential health risks. Protective clothing and equipment should be used when working with this chemical to minimize exposure and prevent accidents.

InChI:InChI=1/C4HClN2O4S/c5-4-2(6(8)9)1-3(12-4)7(10)11/h1H

Upstream product

• 96-43-5 2-thienyl chloride 
• 5330-98-3 2-chloro-3-nitrothiophene 
• 13195-49-8 2-chloro-5-nitrothiophene 

Downstream Products

• 959-38-6 3,5-dinitro-2-phenylaminothiophene 
• 142-04-1 aniline hydrochloride 
• 30549-01-0 3,5-dinitro-2-phenoxy-thiophene 

Relevant academic research and scientific papers

Mechanism of action of 5-nitrothiophenes against mycobacterium tuberculosis

On using the streptomycin-starved 18b strain as a model for nonreplicating Mycobacterium tuberculosis, we identified a 5-nitrothiophene compound as highly active but not cytotoxic. Mutants resistant to 5-nitrothiophenes were found be cross-resistant to the nitroimidazole PA-824 and unable to produce the F420 cofactor. Furthermore, 5-nitrothiophenes were shown to be activated by the F420-dependent nitroreductase Ddn and to release nitric oxide, a mechanism of action identical to that described for nitroimidazoles. Copyright

Studies on the biological activity of some nitrothiophenes

The biological activity of nineteen substituted thiophenes (3) have been assessed by evaluating the minimum inhibitory concentration required to inhibit the growth of E. coli, M. luteus and A. niger. The series displays a wide range of activities with 2-chloro-3,5-dinitrothiophene (3a) or 2-bromo-3,5- dinitrothiophene (3c) showing the highest activity against all three organisms, while the simplest compound of the series, 2-nitrothiophene (3s) shows the smallest activity in each case. The mode of action of 3a and 3c is thought to involve nucleophilic attack by intracellular thiols at the 2-position of the heterocyclic ring leading to displacement of halogen, but other active derivatives, such as 2,4-dinitrothiophene (3h) and 5-nitrothiophene-2- carbaldehyde (3d) which have no displaceable halogen or leaving group are thought to act by forming Meisenheimer complexes. The Royal Society of Chemistry 2006.