13070-25-2

Usage

Uses

Used in Organic Synthesis:
2-BROMO-5-METHYL-1,4-BENZOQUINONE is used as a building block for the synthesis of other chemical compounds, contributing to the development of new materials and products in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2-BROMO-5-METHYL-1,4-BENZOQUINONE is used as an intermediate in the production of drugs, leveraging its antiseptic and disinfectant properties for medicinal applications.
Used in Agrochemical Industry:
2-BROMO-5-METHYL-1,4-BENZOQUINONE is utilized as a component in the formulation of agrochemicals, potentially enhancing the effectiveness of pesticides and other agricultural chemicals.

InChI:InChI=1/C7H5BrO2/c1-4-2-7(10)5(8)3-6(4)9/h2-3H,1H3

Upstream product

• 64-17-5 ethanol 
• 13070-29-6 5,6-dibromo-2-methyl-cyclohex-2-ene-1,4-dione 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 13321-74-9 1-bromo-2,5-dimethoxy-4-methylbenzene 
• 95-71-6 2-methylbenzene-1,4-diol 
• 861619-66-1 5-bromo-2-methyl-4-nitroso-phenol 
• 39478-78-9 5-bromo-2-methylaniline 
• 36138-76-8 5-bromo-2-methylphenol 
• 67289-05-8 2-bromo-5-methylbenzene-1,4-diol 
• 861315-10-8 2-bromo-5-methyl-4-nitroso-phenol 
• 24599-58-4 2,5-dimethoxy toluene 

Downstream Products

• 98217-06-2 2-bromo-3-(N-allylamino)-5-methyl-1,4-benzoquinone 
• 98217-07-3 2-bromo-3,6-bis(N-allylamino)-6-methyl-1,4-benzoquinone 
• 98217-21-1 2-bromo-3-(N,N-diallylamino)-5-methyl-1,4-benzoquinone 
• 98217-22-2 2-Bromo-3-diallylamino-5-methyl-benzene-1,4-diol 
• 221108-38-9 9-Benzyl-4,5,6,7,8,9-hexahydro-3-methyl-1H-carbazole-1,4,5-trione 
• 495383-59-0 2-bromo-5-methyl-N,N'-diphenyl-1,4-phenylenediamine 
• 1402041-36-4 7-methyl-5,8-dioxo-6-(4-(trifluoromethyl)benzyl)-5,8-dihydronaphthalen-2-yl trifluoromethanesulfonate 
• 1402041-34-2 2-(4-bromobenzyl)-3,6,7-trimethylnaphthalene-1,4-dione 
• 1402041-26-2 3-(4-bromobenzyl)-2,5-dimethylnaphthalene-1,4-dione 
• 1402041-30-8 2-(4-bromobenzyl)-3,6-dimethylnaphthalene-1,4-dione 
• 1402041-33-1 2,6,7-trimethyl-3-(4-(trifluoromethyl)benzyl)naphthalene-1,4-dione 
• 1402041-25-1 2,5-dimethyl-3-(4-(trifluoromethyl)benzyl)naphthalene-1,4-dione 
• 1402041-29-5 3,6-dimethyl-2-(4-(trifluoromethyl)benzyl)naphthalene-1,4-dione 
• 46255-71-4 2,5-dimethylnaphthalene-1,4-dione 

Relevant academic research and scientific papers

Synthesis and antitumor activity evaluation of compounds based on toluquinol

Encouraged by the promising antitumoral, antiangiogenic, and antilymphangiogenic properties of toluquinol, a set of analogues of this natural product of marine origin was synthesized to explore and evaluate the effects of structural modifications on their cytotoxic activity. We decided to investigate the effects of the substitution of the methyl group by other groups, the introduction of a second substituent, the relative position of the substituents, and the oxidation state. A set of analogues of 2-substituted, 2,3-disubstituted, and 2,6-disubstituted derived from hydroquinone were synthesized. The results revealed that the cytotoxic activity of this family of compounds could rely on the hydroquinone/benzoquinone part of the molecule, whereas the substituents might modulate the interaction of the molecule with their targets, changing either its activity or its selectivity. The methyl group is relevant for the cytotoxicity of toluquinol, since its replacement by other groups resulted in a significant loss of activity, and in general the introduction of a second substituent, preferentially in the para position with respect to the methyl group, was well tolerated. These findings provide guidance for the design of new toluquinol analogues with potentially better pharmacological properties.

Palladium-Catalyzed Synthesis of Pyrayaquinones, Murrayaquinones, and Murrayafoline-B

We describe the total synthesis of murrayafoline-B and seven carbazole-1,4-quinone alkaloids. A palladium(II)-catalyzed oxidative cyclization is used to construct the carbazole skeleton. Pyran annulation and oxidation provide pyrayaquinone-A, -B, and -C. DIBAL-H-promoted reductive ring opening of pyrano[3,2-a]carbazole precursors leads to the prenylated and geranylated carbazole-1,4-quinone alkaloids murrayaquinone-B, -C, -D, and -E and to murrayafoline-B.

A Platform of Regioselective Methodologies to Access Polysubstituted 2-Methyl-1,4-naphthoquinone Derivatives: Scope and Limitations

A platform of synthetic methodologies has been established to access a focused library of polysubstituted 3-benzylmenadione derivatives functionalized on the aromatic ring of the naphthoquinone core. Two main routes were explored: 1) The naphthol route, starting from either an α-tetralone or a propiophenone, and 2) the regioselective Diels-Alder reaction, starting from various dienes and two 2-bromo-5(or 6)-methyl-1,4-benzoquinones. 6-Substituted 2-methylnaphthols were synthesized by using a xanthate-mediated free-radical addition/cyclization sequence for the construction of the 6-substituted menadione subunit. Furthermore, an efficient and simple new pathway that allows the formation of 6- or 7-substituted 3-(substituted-benzyl)menadione regioisomers from a common commercial scaffold has also been developed by the naphthol route, advantageous with regard to step economy. Our synthetic methodologies exemplified by 34 compounds have allowed structure-activity relationships to be deduced for use as the basis for the development of new antimalarial redox-active polysubstituted benzylmenadione derivatives.

Synthesis and biological evaluation of 1,4-naphthoquinones and quinoline-5,8-diones as antimalarial and schistosomicidal agents

Improving the solubility of polysubstituted 1,4-naphthoquinone derivatives was achieved by introducing nitrogen in two different positions of the naphthoquinone core, at C-5 and at C-8 of menadione through a two-step, straightforward synthesis based on the regioselective hetero-Diels-Alder reaction. The antimalarial and the antischistosomal activities of these polysubstituted aza-1,4-naphthoquinone derivatives were evaluated and led to the selection of distinct compounds for antimalarial versus antischistosomal action. The AgII-assisted oxidative radical decarboxylation of the phenyl acetic acids using AgNO3 and ammonium peroxodisulfate was modified to generate the 3-picolinyl-menadione with improved pharmacokinetic parameters, high antimalarial effects and capacity to inhibit the formation of β-hematin. The Royal Society of Chemistry 2012.

The aza-analogues of 1,4-naphthoquinones are potent substrates and inhibitors of plasmodial thioredoxin and glutathione reductases and of human erythrocyte glutathione reductase

Various aza-analogues of 1,4-naphthoquinone and menadione were prepared and tested as inhibitors and substrates of the plasmodial thioredoxin and glutathione reductases as well as the human glutathione reductase. The replacement of one to two carbons at the phenyl ring of the 1,4-naphthoquinone core by one to two nitrogen atoms led to an increased oxidant character of the molecules in accordance with both the redox potential values and the substrate efficiencies. Compared to the 1,4-naphthoquinone and menadione, the quinoline-5,8-dione 1 and both quinoxaline-5,8-diones 5 and 6 behaved as the most efficient subversive substrates of the three NADPH-dependent disulfide reductases tested. Modulation of these parameters was observed by alkylation of the aza-naphthoquinone core. The Royal Society of Chemistry.

Synthesis of quinones from hydroquinone dimethyl ethers. Oxidative demethylation with cobalt(III) fluoride

The oxidative demethylation of 1,4-dimethoxynaphthalene and 1,4- dimethoxybenzene derivatives with cobalt(III) fluoride proceeded in good to excellent yield to afford the corresponding naphthoquinone and benzoquinone derivatives.

Bromoquinone-enaminone annulations: Syntheses of murrayaquinone-A and (±)-bismurrayaquinone-A

A total synthesis of the carbazolequinone alkaloid, murrayaquinone-A was achieved by an initial annulation of the N-benzyl enamine 8 with 2-methyl-5-bromobenzoquinone 6. Shapiro deoxygenation-olefination followed by heating with DDQ resulted in the exclusive formation of N-benzylmurrayaquinone-A 16. Debenzylation proved very difficult but was finally achieved by heating briefly in trifluoroacetic acid with a catalytic quantity of trifluoromethanesulfonic acid. A single dimeric annulation side product was also formed in the annulation reaction. By using the same synthetic sequence as was employed in the synthesis of 1, the N,N-bis-p-methoxybenzyl dimer 13 was successfully converted to (±)-bismurrayaquinone-A 5.

Microwave induced selective bromination of 1,4-quinones and coumarins

Microwave irradiation accelerates the bromination of 1,4-quinones and coumarins with (i) bromide adsorbed on neutral alumina in 'dry media' and (ii) with iodine monobromide on acetic acid as compared to the reactions run at room temperature. Bromination takes place selectively at active quinonoid position in 1,4-quinones and at α,β-double bond in coumarins.