13380-67-1

Usage

Chemical Properties

Pale yellow crystalline powder

InChI:InChI=1/C10H6BrNO2/c11-7-1-3-8(4-2-7)12-9(13)5-6-10(12)14/h1-6H

Upstream product

• 108-31-6 maleic anhydride 
• 106-40-1 4-bromo-aniline 
• 59256-47-2 3-(4-bromophenylcarbamoyl)acrylic acid 
• 3052-50-4 monomethyl maleate 
• 59256-47-2 N-(p-bromophenyl)maleamic acid 
• 1022815-36-6 5-(4-Bromo-phenyl)-2,3-diphenyl-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 

Downstream Products

• 57703-47-6 2-(4-bromo-phenyl)-4,9-diphenyl-3a,4,9,9a-tetrahydro-4,9-epioxido-benzo[f]isoindole-1,3-dione 
• 73061-22-0 7-(4-bromo-phenyl)-(4ac,4bt,5at,8at,9at,9bc)-decahydro-5r,9c-etheno-[1,4]dioxino[2',3':3,4]cyclobuta[1,2-f]isoindole-6,8-dione 
• 54823-82-4 2-(4-bromo-phenyl)-7,7,9c-trimethyl-(3aξ,5ac,8ac,11aξ)-Δ^4a(10a)-dodecahydro-4r,11c-epioxido-azuleno[5,6-f]isoindole-1,3-dione 
• 134220-54-5 (4aR,5aR,8aS,8bR)-2-{Bis-[1-(4-bromo-phenyl)-2,5-dioxo-pyrrolidin-3-yl]-methyl}-7-(4-bromo-phenyl)-4a-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 
• 134220-47-6 (4aR,5aR,8aS,8bR)-2-{Bis-[1-(4-bromo-phenyl)-2,5-dioxo-pyrrolidin-3-yl]-methyl}-7-(4-bromo-phenyl)-3-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 
• 136119-03-4 N-(p-bromophenyl)-1,2,3,6,7-pentamethylbicyclo<2.2.1>hept-1-ene-4,5-dicarboximide 
• 93518-63-9 1-(4-Bromo-phenyl)-pyrrole-2,5-dione; compound with 1,2,3,4,5,6-hexamethyl-benzene 
• 140137-41-3 1,2,3,4-tetramethylbicyclo<2.2.1>hept-2-ene-5,6-dicarboxylic acid p-bromophenylimide 
• 80310-44-7 C₄₁H₂₈Br₂N₂O₅ 
• 80310-33-4 C₃₅H₂₄Br₂N₂O₄ 
• 80310-39-0 C₄₀H₂₆Br₂N₂O₄ 
• 78049-87-3 (2S,6R)-1,7,8,9,10,10-Hexabromo-4-(4-bromo-phenyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 
• 36829-89-7 C₃₉H₂₄BrNO₃ 
• 78049-93-1 (2S,6R)-1,7,8,9-Tetrabromo-4-(4-bromo-phenyl)-10,10-dimethoxy-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 

Relevant academic research and scientific papers

Improvement of thermal properties of poly(vinyl chloride) using chemical blending assisted ultrasonic technique

The thermal stabilization of poly(vinyl chloride) through blending techniques has been studied. Poly(vinyl chloride) was blended with modified polymer (cellulose acetate-diallyl amine) in different compositions to improve the thermal stability of poly(vinyl chloride). The thermal stability and morphology of the blend films were characterized by scanning electron microscope (SEM) and thermogravimetry. The results revealed that the presence of modified cellulose acetate improved the thermal stability of poly(vinyl chloride). This was attributed to the thermal stable diallylamine moieties among the cellulose acetate chains. The addition of traces of maleimide derivatives to poly(vinyl chloride) prior to the blend process led to an extra thermal stability of the blend film as shown from the values of the initial decomposition temperature (To) measured by thermogravimetry.

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.

Design, synthesis and biochemical evaluation of novel ethanoanthracenes and related compounds to target burkitt’s lymphoma

Lymphomas (cancers of the lymphatic system) account for 12% of malignant diseases worldwide. Burkitt’s lymphoma (BL) is a rare form of non-Hodgkin’s lymphoma in which the cancer starts in the immune B-cells. We report the synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG- 75. Structural modifications were achieved by Diels-Alder reaction of the core 9-(2- nitrovinyl)anthracene with number of dienophiles including maleic anhydride, maleimides, acrylonitrile and benzyne. The antiproliferative activity of these compounds was evaluated in BL cell lines EBV? MUTU-1 and EBV+ DG-75 (chemoresistant). The most potent compounds 13j, 15, 16a, 16b, 16c, 16d and 19a displayed IC50 values in the range 0.17–0.38 μM against the BL cell line EBV? MUTU-1 and IC50 values in the range 0.45–0.78 μM against the chemoresistant BL cell line EBV+ DG- 75. Compounds 15, 16b and 16c demonstrated potent ROS dependent apoptotic effects on the BL cell lines which were superior to the control drug taxol and showed minimal cytotoxicity to peripheral blood mononuclear cells (PBMCs). The results suggest that this class of compounds merits further investigation as antiproliferative agents for BL.

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.

Nickel(II) Tetraphenylporphyrin as an Efficient Photocatalyst Featuring Visible Light Promoted Dual Redox Activities

Nickel(II) tetraphenylporphyrin (NiTPP) is presented as a robust, cost-effective and efficient visible light induced photoredox catalyst. The ground state electrochemical data (CV) and electronic absorption (UV-Vis) spectra reveal the excited state redox potentials for [NiTPP]*/[NiTPP].? and NiTPP].+/[NiTPP]* couples as +1.17 V and ?1.57 V vs SCE respectively. The potential values represent NiTPP as a more potent photocatalyst compare to the well-explored [Ru(bpy)3]2+. The non-precious photocatalyst exhibits excited state redox reactions in dual fashions, i. e., it is capable of undergoing both oxidative as well as reductive quenching pathways. Such versatility of a photocatalyst based on first-row transition metals is very scarce. This unique phenomenon allows one to perform diverse types of redox reactions by employing a single catalyst. Two different sets of chemical reactions have been performed to represent the synthetic utility. The catalyst showed superior efficiency in both carbon-carbon and carbon-heteroatom bond-forming reactions. Thus, we believe that NiTPP is a valuable addition to the photocatalyst library and this study will lead to more practical synthetic applications of earth-abundant-metal-based photoredox catalysts. (Figure presented.).

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.).

Alizarin red S-TiO2-catalyzed cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation

A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.

Solvent-free and room temperature visible light-induced C-H activation: CdS as a highly efficient photo-induced reusable nano-catalyst for the C-H functionalization cyclization of: T -amines and C-C double and triple bonds

Nano-sized CdS was successfully prepared, fully characterized and applied as a highly efficient reusable photocatalyst for the synthesis of pyrrolo[3,4-c]quinolone and pyrrolo[2,1-a]isoquinoline-8-carboxylate derivatives through a condensation reaction of N,N-dimethylanilines or alkyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetates with maleimides via a C-H activation approach under benign and eco-friendly conditions at room temperature without using any solvent and oxidant under visible light irradiation. Besides, the prepared photocatalyst has been successfully applied for the condensation reaction of N,N-dimethylanilines with alkyl but-2-ynedioates or phenyl acetylenes for the synthesis of novel 1,2-dihydroquinoline-3,4-dicarboxylate and aryl-1,2-dihydroquinoline derivatives for the first time. Using this method, all favourable products were obtained in good yields and relatively short reaction times under benign conditions with the application of visible light irradiation, a renewable energy source. The catalyst was easily recovered and reused several times without any loss of its activity.

Cp?Co(III)-Catalyzed C-H Alkylation with Maleimides Using Weakly Coordinating Carbonyl Directing Groups

A novel protocol for ortho-C-H alkylation of aromatic and heteroaromatic ketones and esters under Cp?Co(III) catalysis has been developed for the first time. The reaction proceeds through initial cyclometalation via weak chelation-assisted C-H bond activation, followed by coordination of activated alkene, insertion between Co-C, and protodemetalation.

Graphene Oxide as a Carbocatalyst for a Diels–Alder Reaction in an Aqueous Medium

The Diels–Alder (DA) reaction, a [4+2] cycloaddition reaction, is highly important in synthetic organic chemistry and is frequently used in the synthesis of natural products containing six-membered rings. Herein, we report an efficient protocol for the DA reaction between 9-hydroxymethylanthracene and N-substituted maleimides using two-dimensional graphene oxide (GO) as a heterogeneous carbocatalyst in an aqueous medium at room temperature. High yields, a wide substrate scope, low temperature, excellent functional group tolerance, atom economy, and water as a green solvent are noteworthy features of this protocol. The heterogeneous GO catalyst can be easily recovered and used multiple times without any significant loss in catalytic activity.