1204-35-9

Basic information

• Product Name: 1-(3-CHLORO-PHENYL)-PYRROLE-2,5-DIONE
• Synonyms: 1-(-3-CHLOROPHENYL)MALEIMIDE;1-(3-CHLOROPHENYL)-1H-PYRROLE-2,5-DIONE;1-(3-CHLORO-PHENYL)-PYRROLE-2,5-DIONE;AKOS B006724;AKOS MSC-0022;ART-CHEM-BB B006724;ASISCHEM D48958;AURORA 12546
• CAS NO: 1204-35-9
• Molecular Formula: C₁₀H₆ClNO₂
• Molecular Weight: 207.61
• Mol File: 1204-35-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 87-89.5 °C
• Boiling Point: 350.8 °C at 760 mmHg
• Flash Point: 165.9 °C
• Appearance: /
• Density: 1.459 g/cm³
• Vapor Pressure: 4.29E-05mmHg at 25°C
• Refractive Index: 1.639
• PKA: -1.95±0.20(Predicted)
• CAS DataBase Reference: 1-(3-CHLORO-PHENYL)-PYRROLE-2,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-CHLORO-PHENYL)-PYRROLE-2,5-DIONE(1204-35-9)
• EPA Substance Registry System: 1-(3-CHLORO-PHENYL)-PYRROLE-2,5-DIONE(1204-35-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 1204-35-9(Hazardous Substances Data)

Usage

General Description

1-(3-Chloro-phenyl)-pyrrole-2,5-dione, also known as 3-chlorophenylmaleimide, is a chemical compound with the molecular formula C10H6ClNO2. It is a crystalline solid that is commonly used as a building block in organic synthesis and in the production of various pharmaceuticals and agrochemicals. The compound is known for its reactive nature and ability to undergo various chemical reactions, making it a versatile and valuable intermediate in the manufacturing process of a wide range of products. It is also known for its potential as a starting material for the synthesis of organic compounds with potential biological activities. However, it is important to handle this compound with caution, as it is known to be toxic and harmful if ingested or inhaled.

InChI:InChI=1/C10H6ClNO2/c11-7-2-1-3-8(6-7)12-9(13)4-5-10(12)14/h1-6H

Upstream product

• 36847-88-8 C₁₀H₈ClNO₃ 
• 108-42-9 3-chloro-aniline 
• 108-31-6 maleic anhydride 
• 18196-80-0 (Z)-4-((3-chlorophenyl)amino)-4-oxobut-2-enoic acid 

Downstream Products

• 54819-72-6 2-(2-amino-4-oxo-4,5-dihydro-thiazol-5-yl)-N-(3-chloro-phenyl)-acetamide 
• 295345-23-2 (+/-)-(3R,3aS,6aR)-5-(3-chlorophenyl)-3-phenyl-3a,6a-dihydrospiro[1H-furo[3,4-c]pyrrole-1,2'-[2H]indene]-1',3',4,6(3H,5H)-tetrone 
• 295345-23-2 (+/-)-(3R,3aR,6aS)-5-(3-chlorophenyl)-3-phenyl-3a,6a-dihydrospiro[1H-furo[3,4-c]pyrrole-1,2'-[2H]indene]-1',3',4,6(3H,5H)-tetrone 
• 1004792-55-5 methyl (1S,3R,3aS,6aR)-4,6-dioxo-3-(1-naphthyl)-5-(m-chlorophenyl)-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate 
• 1233703-78-0 (S)-1-(3-chlorophenyl)-3-(2-oxopropyl)pyrrolidine-2,5-dione 
• 1255929-05-5 2-(1-(3-chlorophenyl)-2,5-dioxopyrrolidin-3-yl)-2-phenylpropanal 

Relevant articles and documents

Dual organic dyes as a pseudo-redox mediation system to promotion of tandem oxidation /[3+2] cycloaddition reactions under visible light

An atom- and step-economy protocol has been developed to synthesize some new biologically active pyrrolo[2,1-a]isoquinoline alkaloids via redox mediation system under visible light irradiation. A vast variety of double and triple bonds, as dipolarophiles, treated with in situ generated azomethine ylides to prepare corresponding products in good to excellent yields. This metal-free method effectively promoted oxidation/[3 + 2] cycloaddition/oxidative/aromatization domino reaction without further oxidant using dual organic dyes as pseudo-redox mediation system. Besides, for most of the products, product precipitate was readily separated from reaction media. To the best of our knowledge, this is the first report of dual dyes as a pseudo-redox mediation system.

The discovery, design and synthesis of potent agonists of adenylyl cyclase type 2 by virtual screening combining biological evaluation

Adenylate cyclases (ACs), play a critical role in the conversion of adenosine triphosphate (ATP) into the second messenger cyclic adenosine monophosphate (cAMP). Studies have indicated that adenylyl cyclase type 2 (AC2) is potential drug target for many diseases, however, up to now, there is no AC2-selective agonist reported. In this research, docking-based virtual screening with the combination of cell-based biological assays have been performed for discovering novel potent and selective AC2 agonists. Virtual screening disclosed a novel hit compound 8 as an AC2 agonist with EC50 value of 8.10 μM on recombinant human hAC2 + HEK293 cells. The SAR (structure activity relationship) based on the derivatives of compound 8 was further explored on recombinant AC2 cells and compound 73 was found to be the most active agonist with the EC50 of 90 nM, which is 160-fold more potent than the reported agonist Forskolin and could selectively activate AC2 to inhibit the expression of Interleukin-6. The discovery of a new class of AC2-selective agonists would provide a novel chemical probe to study the physiological function of AC2.

Iron(III) Chloride/Phenylsilane-Mediated Cascade Reaction of Allyl Alcohols with Maleimides: Synthesis of Poly-Substituted γ-Butyrolactones

A iron-catalyzed free radical cascade reaction of allyl alcohols with N-substituted maleimides for accessing poly-substituted γ-butyrolactones has been developed. In this protocol, various allyl alcohols can open N-substituted maleimide rings to form allyl ester intermediates, and the allyl ester intermediates can be converted into an allyl ester alkyl radicals and undergo intramolecular free radical addition cyclization to form a polysubstituted γ-butyrolactones. In this protocol, spiro γ-butyrolactone compounds can be also synthesized. Meanwhile, the strategy could be applied to further construct a fully substituted tetrahydrofuran. The reaction is not sensitive to oxygen or moisture and has been performed on gram-scale. (Figure presented.).