29244-55-1

Basic information

• Product Name: 1-(4-Methylphenyl)-3,4-dichloro-3-pyrroline-2,5-dione
• Synonyms: 1-(4-Methylphenyl)-3,4-dichloro-3-pyrroline-2,5-dione;3,4-Dichloro-1-(4-methylphenyl)-1H-pyrrole-2,5-dione;N-(4-Methylphenyl)-2,3-dichloromaleimide;3,4-dichloro-1-(p-tolyl)-1H-pyrrole-2,5-dione
• CAS NO: 29244-55-1
• Molecular Formula: C₁₁H₇Cl₂NO₂
• Molecular Weight: 256.08
• Mol File: 29244-55-1.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(4-Methylphenyl)-3,4-dichloro-3-pyrroline-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Methylphenyl)-3,4-dichloro-3-pyrroline-2,5-dione(29244-55-1)
• EPA Substance Registry System: 1-(4-Methylphenyl)-3,4-dichloro-3-pyrroline-2,5-dione(29244-55-1)

Safety Data

• Hazardous Substances Data: 29244-55-1(Hazardous Substances Data)

Usage

General Description

1-(4-Methylphenyl)-3,4-dichloro-3-pyrroline-2,5-dione is a chemical compound that is characterized by its distinctive structure, which includes a pyrroline ring with two chlorine atoms attached and a 4-methylphenyl group. 1-(4-Methylphenyl)-3,4-dichloro-3-pyrroline-2,5-dione has been studied for its potential applications in pharmaceuticals and agrochemicals due to its unique properties. It is a yellow crystalline solid that is soluble in organic solvents and has been shown to exhibit biological activity in various assays. Further research into the potential uses and effects of 1-(4-Methylphenyl)-3,4-dichloro-3-pyrroline-2,5-dione is ongoing to fully understand its potential benefits and risks.

Upstream product

• 108-31-6 maleic anhydride 
• 106-49-0 p-toluidine 
• 24870-11-9 4-methylmaleanilic acid 
• 1631-28-3 N-p-tolylphenylmaleimide 
• 1122-17-4 dichloromaleic acid anhydride 

Downstream Products

• 916510-87-7 2,3-bis(diphenylphosphino)-N-p-tolylmaleimide 
• 1109273-51-9 2-(4-methylphenyl)-pyrrolo[3,4-b][1,4]benzoxazine-1,3(2H,9H)-dione 
• 1109273-74-6 2-(4-methylphenyl)-7-tert-butyl-pyrrolo[3,4-b][1,4]benzoxazine-1,3(2H,9H)-dione 
• 1109273-63-3 2-(4-methylphenyl)-7-chloro-pyrrolo[3,4-b][1,4]benzoxazine-1,3(2H,9H)-dione 
• 1373308-91-8 2,3-dichloro-N-(4-methylphenyl)bicyclo[2.2.2]oct-5-ene-2,3-dicarboximide 
• 329226-37-1 2-p-tolyl-6,7-dihydro-5H-9-thia-2,3b,8-triaza-cyclopenta[a]-s-indacene-1,3,4-trione 
• 804534-83-6 C₁₇H₂₀ClN₃O₂ 
• 303034-37-9 C₁₆H₁₈ClN₃O₂ 
• 94740-73-5 3-Chloro-4-morpholin-4-yl-1-p-tolyl-pyrrole-2,5-dione 
• 958732-65-5 C₂₃H₂₂ClN₃O₄ 
• 958729-31-2 C₂₂H₂₂ClN₃O₃ 

Relevant articles and documents

Sequential reaction of p-toluidine with 2,3-dichloromaleic anhydride: Synthesis and molecular structure of 2-chloro-3-p-toluidino-N-p-tolylmaleimide

The reaction of equimolar amounts of p-toluidine with 2,3-dichloromaleic anhydride in refluxing toluene affords 2,3-dichloro-N-p-tolylmaleimide (1) and 2-chloro-3-p-toluidino-N-p-tolylmaleimide (2), as the major and minor products, respectively. While increasing the amount of p-toluidine relative to 2,3-dichloromaleic anhydride yields the latter compound as the major product, the replacement of the chloro group in 2-chloro-3-p-toluidino-N-p-tolylmaleimide by added p-toluidine was not observed in refluxing toluene. Both 1 and 2 were isolated by column chromatography and characterized in solution by IR and NMR spectroscopies. The solid-state structure of 2-chloro-3-p-toluidino-N-p- tolylmaleimide was solved by X-ray crystallography. Further, 2-Chloro-3-p-toluidino-N-p-tolylmaleimide crystallizes in the monoclinic space group C2/c, a = 33.191(8) A, b = 4.037(1) A, c = 24.876(6) A, β = 107.050(4)°, V = 3187(1) A3, Z = 8, and d Calc = 1.362 mg/m3; R = 0.0561, Rw = 0.1246 for 2087 reflections with I > 2σ(I).

Anti-leishmanial and cytotoxic activities of a series of maleimides: Synthesis, biological evaluation and structure-activity relationship

In the present study, 45 maleimides have been synthesized and evaluated for anti-leishmanial activities against L. donovani in vitro and cytotoxicity toward THP1 cells. All compounds exhibited obvious anti-leishmanial activities. Among the tested compounds, there were 10 maleimides with superior anti-leishmanial activities to standard drug amphotericin B, and 32 maleimides with superior anti-leishmanial activities to standard drug pentamidine, especially compounds 16 (IC50 50 50 > 10 μg/mL). The anti-leishmanial activities of 16 and 42 were 10 times better than that of amphotericin B. The structure and activity relationship (SAR) studies revealed that 3,4-non-substituted maleimides displayed the strongest anti-leishmanial activities compared to those for 3-methyl-maleimides and 3,4-dichloro-maleimides. 3,4-dichloro-maleimides were the least cytotoxic compared to 3-methyl-maleimides and 3,4-non-substituted maleimides. The results show that several of the reported compounds are promising leads for potential anti-leishmanial drug development.

Color Tuning of the Aggregation-Induced Emission of Maleimide Dyes by Molecular Design and Morphology Control

Aggregation-induced emission (AIE)-active maleimide dyes, namely, 2-p-toluidino-N-p-tolylmaleimide, 3-phenyl-2-toluidino-N-p-tolylmaleimide, 2-p-thiocresyl-3-p-toluidino-N-p-tolylmaleimide, and 2,3-dithiocresyl-N-arylmaleimides, were synthesized by facile