74941-78-9

Upstream product

• 100-01-6 4-nitro-aniline 
• 61921-33-3 p-nitrocinnamoyl chloride 
• 619-89-6 p-nitrocinnamic acid 

Downstream Products

• 74941-75-6 1-(4-Nitrophenyl)-5-(4-nitrostyryl)tetrazole 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of substituted cinnamic acids and amide analogues: A new class of herbicides

In the present investigation, substituted cinnamic acids (3-hydroxy, 4-hydroxy, 2-nitro, 3-nitro, 4-nitro, 3-chloro, and 4-methoxy) and their amide analogues with four different types of substituted anilines have been synthesized. The synthesized compounds have been screened for their germination inhibition activity on radish (Raphanus sativus L. var. Japanese White) seeds at 50, 100, and 200 ppm concentrations, and the activity was compared with standard herbicide, metribuzin formulation (sencor). Significant activity was exhibited by all of the compounds. It was observed that with the increase in concentration of the test solution, the activity also increased. All of the compounds showed more than 70% inhibition at 100 ppm concentration except 4-hydroxy cinnamanilide. The compound, 2-chloro (4′-hydroxy) cinnamanilide was the best among the tested compounds, and it was found to be at par with the standard, metribuzin at all concentrations. Thus, it can be concluded that substituted cinnamic acids and their amide analogues may be developed as potential herbicides.

Nucleophilic substitution reactions of cinnamoyl chlorides with anilines in acetonitrile and acetonitrile-methanol mixtures

Kinetic studies on the solvolysis (in MeOH-MeCN mixtures) and aminolysis (with anilines in MeCN) of cinnamoyl chlorides have been carried out at 25.0 deg C.The relatively large negative values of ρY+ = -0.9 ca. -1.5 for the methanolysis are consistent with a dissociative SN2-like mechanism.For the aminolysis, the ρy values are positive (ρY = 0.52 ca. 1.64) and ρX values range from -1.68 to -2.51 in acetonitrile.The positive values of βX = 0.6-0.9 and ρXY = 0.88 in acetonitrile, and isotope effect data suggest that the aminolysis proceeds by a stepwise mechanism with rate-limiting breakdown of the tetrahedral intermediate, T+/-.It is noted that in the acyl-transfer reactions proceeding by rate-limiting departure of the leaving group from the tetrahedral intermediate the signs of both ρY and ρXY are positive and the reactivity-selectivity principle (RSP) is valid in general.