Chemical Properties
white to light yellow crystal powder
Uses
3,4,5-Trichloronitrobenzene a reagent, used in the synthesis of INT131, a PPARγ molecule that regulates insulin sensitivity. Also is used in the synthesis of thyroid hormone receptor β selective ligands that are used in hormone treatments.
General Description
Pale-yellow crystals or yellow crystalline solid.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
This type of compound is incompatible with strong bases and strong oxidizing agents. .
Fire Hazard
Flash point data for 3,4,5-Trichloronitrobenzene are not available; however, 3,4,5-Trichloronitrobenzene is probably combustible.
Synthesis
General procedure for the synthesis of 1,2,3-trichloro-5-nitrobenzene from 2,6-dichloro-4-nitroaniline: 96 g of 98% concentrated sulphuric acid was added to the reaction flask at 20 °C, 7.2 g of sodium nitrite was added slowly with stirring, and then the temperature was raised to 70 °C. After the sodium nitrite was completely dissolved, the solution was cooled to 50°C. 20g of 2,6-dichloro-4-nitroaniline was added at once and the reaction was maintained at this temperature for 1 hour. After the reaction was completed, the mixture was cooled to 5 °C and 27.3 g of glacial acetic acid was slowly added dropwise. After the dropwise addition was completed, stirring was continued for 1 hour to obtain a 2,6-dichloro-4-nitroaniline diazonium salt solution. In another reaction flask, 18 g of cuprous chloride and 7.14 g of concentrated hydrochloric acid were added. The above diazonium salt solution was slowly added dropwise to this reaction flask under rapid stirring, keeping the temperature below 15 °C. After completion of the dropwise addition, the reaction was maintained for 1 hour, followed by raising the temperature to 70°C to continue the reaction for 1 hour. At the end of the reaction, the mixture was cooled to room temperature, poured into a 2L reaction flask, and 60 g of water was added under stirring. 0.5 h later, filtration was carried out to obtain 1,2,3-trichloro-5-nitrobenzene as a yellow solid with a dry weight of 21.5 g. The yield was 98.5%, and the purity was 98.3% by HPLC.
References
[1] Patent: CN104447597, 2018, B. Location in patent: Paragraph 0020; 0023; 0045-0047
[2] Patent: CN107746390, 2018, A. Location in patent: Paragraph 0021; 0022; 0023
[3] Journal of Medicinal Chemistry, 1980, vol. 23, # 10, p. 1083 - 1087
[4] Journal of the Chemical Society, 1926, p. 3044
[5] Patent: CN104098521, 2016, B. Location in patent: Paragraph 0038; 0039; 0040; 0041
