3876-05-9

Basic information

• Product Name: 2 3-DICHLORO-N-PHENYLMALEIMIDE
• Synonyms: Maleimide, 2,3-dichloro-N-phenyl-;3,4-dichloro-1-phenyl-pyrrol-2,5-dione;1-Phenyl-3,4-dichloro-3-pyrroline-2,5-dione;3,4-Dichloro-1-phenyl-1H-pyrrole-2,5-dione;N-Phenyl-2,3-dichloromaleimide;1H-Pyrrole-2,5-dione, 3,4-dichloro-1-phenyl-;3,4-dichloro-1-phenyl-3-pyrroline-2,5-quinone;3,4-dichloro-1-phenyl-pyrrole-2,5-dione
• CAS NO: 3876-05-9
• Molecular Formula: C₁₀H₅Cl₂NO₂
• Molecular Weight: 242.06
• Mol File: 3876-05-9.mol

Chemical Properties

• Melting Point: 198.5-204.5 °C(lit.)
• Boiling Point: 308.6°C at 760 mmHg
• Flash Point: 140.5°C
• Appearance: /
• Density: 1.57g/cm³
• Vapor Pressure: 0.000673mmHg at 25°C
• Refractive Index: 1.654
• PKA: -4.86±0.60(Predicted)
• CAS DataBase Reference: 2 3-DICHLORO-N-PHENYLMALEIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2 3-DICHLORO-N-PHENYLMALEIMIDE(3876-05-9)
• EPA Substance Registry System: 2 3-DICHLORO-N-PHENYLMALEIMIDE(3876-05-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 3876-05-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Dichloro-N-phenylmaleimide is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique structure allows for the creation of novel maleimide derivatives with potential therapeutic applications.
Used in Chemical Industry:
In the chemical industry, 2,3-dichlorro-N-phenylmaleimide is utilized as a building block for the synthesis of a range of maleimide-based compounds. These compounds can be used in various applications, such as in the production of specialty polymers, dyes, and other organic materials.
Used in Synthesis of Maleimide Derivatives:
2,3-Dichloro-N-phenylmaleimide is used as a starting material for the synthesis of several maleimide derivatives, including:
N-phenyl-2,3-di(thiophenyl)maleimide: 2 3-DICHLORO-N-PHENYLMALEIMIDE can be used in the development of new pharmaceutical agents or as a component in the synthesis of other organic compounds.
N-phenyl-2,3-dithiomaleimide: This derivative may have potential applications in the pharmaceutical industry or as an intermediate in the synthesis of other organic compounds.
2-chloro-3-cyclohexyl-N-phenylmaleimide: 2 3-DICHLORO-N-PHENYLMALEIMIDE can be used in the development of new pharmaceutical agents or as a building block for the synthesis of other organic materials.
2,3-dicyclohexyl-N-phenylmaleimide: This derivative may have potential applications in the pharmaceutical industry or as an intermediate in the synthesis of other organic compounds.
2-benzyl-3-chloro-N-phenylmaleimide: 2 3-DICHLORO-N-PHENYLMALEIMIDE can be used in the development of new pharmaceutical agents or as a component in the synthesis of other organic materials.
Overall, 2,3-dichlorro-N-phenylmaleimide is a versatile compound with a wide range of potential applications in both the pharmaceutical and chemical industries. Its ability to be used as a synthetic intermediate for various maleimide derivatives makes it a valuable asset in the development of new and innovative products.

InChI:InChI=1/C10H5Cl2NO2/c11-7-8(12)10(15)13(9(7)14)6-4-2-1-3-5-6/h1-5H

Upstream product

• 108-31-6 maleic anhydride 
• 62-53-3 aniline 
• 555-59-9 N-phenylmaleamic acid 
• 1122-17-4 dichloromaleic acid anhydride 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 941-69-5 N-phenyl-maleimide 
• 83-25-0 N-phenylmaleimide 
• 112080-62-3 C₁₀H₇Cl₂NO₃ 

Downstream Products

• 145621-90-5 3-Chlor-4-(R)-menthylamino-1-phenyl-pyrrolin-2,5-dion 
• 103056-35-5 3-chloro-1-(2,3-dichlorophenyl)-4-morpholino-1H-pyrrole-2,5-dione 
• 35740-47-7 3-chloro-4-(4-methoxyphenoxy)-1-phenyl-1H-pyrrole-2,5-dione 
• 959418-00-9 4-chloro-3-(1H-indol-3-yl)-1-phenyl-1H-pyrrole-2,5-dione 
• 959418-01-0 4-chloro-3-(5-bromo-1H-indol-3-yl)-1-phenyl-1H-pyrrole-2,5-dione 
• 1109273-47-3 2-phenyl-pyrrolo[3,4-b][1,4]benzoxazine-1,3(2H,9H)-dione 
• 1109273-70-2 2-phenyl-7-tert-butyl-pyrrolo[3,4-b][1,4]benzoxazine-1,3(2H,9H)-dione 
• 1109273-60-0 2-phenyl-7-chloro-pyrrolo[3,4-b][1,4]benzoxazine-1,3(2H,9H)-dione 
• 769140-77-4 4-(3-chloro-2,5-dioxo-4-piperidin-1-yl-2,5-dihydro-1H-pyrrol-1-yl)benzenesulphonyl chloride 

Relevant articles and documents

Application of maleimide compound as chitin synthase inhibitor

The invention discloses an application of a maleimide compound as shown in a formula I. In the formula I, R0 is phenyl, benzyl, phenethyl, phenylpropyl, p-fluorophenyl, p-chlorophenyl, p-bromophenyl,p-methoxyphenyl, p-methylphenyl or p-hydroxyphenyl, R1 is hydrogen, methyl, phenyl or chlorine; and R2 is hydrogen, methyl, phenyl or chlorine. The provided maleimide compound has a good inhibition effect on chitin synthase.

Synthesis of Tetrahydroisoindolinones via a Metal-Free Dehydrogenative Diels-Alder Reaction

A metal-free dehydrogenative Diels-Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields. (Figure presented.).

The coordination behavior of 2,3-bis(diphenylphosphino)maleic-: N -phenylimide towards copper, silver, gold and palladium

The bidentate phosphine bis(diphenylphosphino)-N-phenyl-maleimide (L1) is used to synthesize a series of complexes from coinage metals and palladium. Some of them are mononuclear species where one metal atom is coordinated by two phosphine ligands. Three of these complexes have been investigated in detail because they contain the initial ligand in an anionic, radical form (L1′) i.e. [Cu(L1L1′)] (1), [Ag(L1L1′)] (7), [Pd(L1′)2] (11). L1′ in 1, 7 and 11 shows significant differences in its bonding parameters compared to free or coordinating L1. By magnetic measurements the radical nature of these three compounds could be verified. Quantum chemical calculations prove the existence of either one (1 and 7) or two (11) unpaired electrons localized on the ligand. Furthermore these calculations can explain that 1 and 7 show an asymmetric structure in solid state where one can clearly differ L1 from L1′.

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.

Synthesis and biological evaluation of 3-chloro-4-(indol-3-yl)-2,5- pyrroledione derivatives as antitumor agents

A series of 3-chloro-4-(indol-3-yl)-2,5-pyrroledione derivatives were synthesized and evaluated for their cytotoxic activities in vitro against five human cancer cell lines (K562, A549, ECA-109, KB and SMMC-7721). Most compounds displayed potent cytotoxicity with IC50 values in low micromolar range. The results showed that the existence of the chlorine atom at 3-position on the pyrroledione ring was crucial for the activity. Compound 6a, the most potent one (IC50: 0.67～3.93 μM), would be a promising template for further development of novel antitumor agents.

Antifungal, cytotoxic and SAR studies of a series of N-alkyl, N-aryl and N-alkylphenyl-1,4-pyrrolediones and related compounds

The synthesis, in vitro evaluation and SAR studies of 67 maleimides and derivatives acting as antifungal agents are reported. A detailed SAR study supported by theoretical calculations led us to determine that: an intact maleimido ring appears to be necessary for a strong antifungal activity, dissimilarly affected by the substituents in positions 2 and 3. The best activities were shown by 2,3-nonsubstituted followed by 2,3 dichloro- and 2-methyl-substituted maleimides. They all were fungicide rather than fungistatic enhancing the importance of their antifungal activity. 2,3-Dimethyl and 2,3-diphenyl-maleimides possessed marginal or null activity. The presence of a flexible connecting chain in N-phenylalkyl maleimides appears not to be essential for antifungal activity, although its length shows a correlation with the antifungal behavior, displaying maleimides with alkyl chains of n = 3 and n = 4 the best antifungal activities in most fungi. Different substituents on the benzene ring did not have a clear influence on the activity. Values of chemical potential properties as well as of energy do not sufficiently discriminate between active and inactive compounds. Nevertheless, it was found that, although log P alone is not strong enough to properly predict the antifungal activity, the comparison of its values for compounds within the same sub-type, showed an enhancement of antifungal activity along with an increment of lipophilicity. In addition, the LUMO's electronic clouds of the highly active compounds showed to be concentrated on the imido ring, indicating that their carbon atoms are potential sites for nucleophilic attack. Same results were obtained from MEPs. Most of the active compounds did not show cytotoxic activity against human cancer cell lines and no one possessed hemolytic activity, indicating that their activity is selective to pathogenic fungi and that they are not toxic at MIC concentrations.

Synthesis of novel 1,4-benzoxazine-2,3-dicarboximides from maleic anhydride and substituted aromatic amines

A series of novel 1,4-benzoxazine-2,3-dicarboximides starting from maleic anhydride and substituted aromatic amines were synthesized. Copyright Taylor & Francis Group, LLC.

Synthesis and characterization of new compounds containing 1,4-dithiintetracarboxydiimide units

New compounds containing 1,4-dithiintetracarboxydiimide units were synthesized by the disubstitution reaction of N-substituted 2,3- dichloromaleimide with sodium sulflde nonahydrate or thiourea. IR, UV-vis and 1H-NMR spectroscopy, as well as elemental analysis, confirmed their structures. Thermal conversion of 1,4-dithiine ring to thiophene was monitored by differential calorimetry (DSC) and thermogravimetric (TGA) measurements.