Chemical Properties
LIGHT BROWN CRYSTALLINE POWDER
Uses
4-Chloro-3-nitrobenzenesulfonyl chloride can be used:
- In the preparation of functionalized 1H-indenes via copper-catalyzed arylative cyclization.
- As a precursor in the synthesis of N-arylsulfonyl-3-acylindole arylcarbonyl hydrazone derivatives that show potential nematicidal activity.
- As a key starting material in the synthesis of sulfonamide analogs of ferrostatin-1 (fer-1), which possess good ferroptosis inhibition property.
- In the synthesis of 4-chloro-3-nitrobenzene thiol.
Uses
4-Chloro-3-nitrobenzenesulfonyl Chloride is used in the synthesis of novel sulfonamide derivatives of tricyclic thieno[2,3-d]pyrimidin-4(3H)-ones which increases melanin synthesis in murine B16 cells.
Synthesis
Synthesis Example 2-2 Synthesis of 4-chloro-3-nitrobenzenesulfonyl chloride: to a reaction vial containing a mixture of 1280 g of potassium 4-chloro-3-nitrobenzenesulfonate, 1150 mL of acetonitrile, 250 mL of sulfoxide, and 30 mL of dimethylacetamide, 1240 mL of phosphinic acid chloride was added dropwise at a slow rate, while controlling the temperature within the reaction system to maintain a temperature of 60°C to 70°C. After the dropwise addition was completed, the reaction mixture was stirred at 73°C for 3 hours. Upon completion of the reaction, the reaction mixture was cooled with water, followed by the slow addition of 400 mL of water. The reaction mixture was poured into 5 L of ice water and the precipitated crystals were separated by filtration, washed with water and dried to give 1060 g of the target product 4-chloro-3-nitrobenzenesulfonyl chloride in 84% yield. The melting point of the product was 55 °C to 56 °C.
References
[1] Patent: US5221750, 1993, A
[2] Patent: US5071994, 1991, A
