3129-39-3

Basic information

• Product Name: 2-Methyl-3-bromo-1,4-naphthoquinone
• Synonyms: 2-Bromo-3-methyl-1,4-naphthoquinone;2-Methyl-3-bromo-1,4-naphthoquinone;2-bromo-3-methylnaphthalene-1,4-dione
• CAS NO: 3129-39-3
• Molecular Formula: C₁₁H₇BrO₂
• Molecular Weight: 251.0761
• Mol File: 3129-39-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 152.8°C
• Boiling Point: 330.9°Cat760mmHg
• Flash Point: 115.8°C
• Appearance: /
• Density: 1.5480 (rough estimate)
• Vapor Pressure: 0.000162mmHg at 25°C
• Refractive Index: 1.5845 (estimate)
• CAS DataBase Reference: 2-Methyl-3-bromo-1,4-naphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-3-bromo-1,4-naphthoquinone(3129-39-3)
• EPA Substance Registry System: 2-Methyl-3-bromo-1,4-naphthoquinone(3129-39-3)

Safety Data

• Hazardous Substances Data: 3129-39-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H7BrO2/c1-6-9(12)11(14)8-5-3-2-4-7(8)10(6)13/h2-5H,1H3

Upstream product

• 861047-23-6 2,3-dibromo-2-methyl-2,3-dihydro-[1,4]naphthoquinone 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 58-27-5 menadione 
• 7726-95-6 bromine 
• 17735-17-0 2,3,4,4-tetrachloro-2-methyl-3,4-dihydro-2H-naphthalen-1-one 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 75-65-0 tert-butyl alcohol 
• 303779-66-0 3-bromo-1-naphthaldehyde 
• 614-45-9 tert-Butyl peroxybenzoate 
• 861331-93-3 4-chloro-2-methylnaphthalen-1-ol 
• 856197-80-3 2,6,7-tribromo-3-methyl-5,6,7,8-tetrahydro-naphthalene-1,4-diol 
• 3090-46-8 2-methyl-5,8-dihydro-1,4-naphthalenediol 
• 53772-19-3 1,4-dimethoxy-2-methylnaphthalene 

Downstream Products

• 39055-47-5 2-bromo-3-methylnaphthohydroquinone 
• 6325-58-2 3-(1,4-dihydro-2-methyl-1,4-dioxo-naphthalen-3-yl-thio)propionic acid 
• 134717-17-2 2-methyl-3-(phenylselanyl)naphthalene-1,4-dione 
• 586-76-5 4-Bromobenzoic acid 
• 130837-09-1 2-(Bromophenyl)-9,10-anthraquinone 
• 130837-08-0 1-(4-Bromobenzoyl)-2-(4-bromophenyl)-9,10-anthraquinone 
• 130837-07-9 2-(4-Bromobenzoyl)-3-(4-bromobenzoylmethylene)-2,3-dihydronaphtho<1,2-b>furan-5(4H)-one 
• 6485-97-8 2-Phenyl-anthrachinon 
• 130836-96-3 1-Benzoyl-2-phenyl-9,10-anthraquinone 
• 130836-98-5 2-Benzoyl-3-benzoylmethylene-2,3-dihydronaphtho<1,2-b>-furan-5-one 
• 65-85-0 benzoic acid 
• 88-14-2 2-furanoic acid 
• 130837-02-4 2-(2-Furyl)-3-(2-furoyl)-9,10-anthraquinone 
• 130836-99-6 2-(2-Furyl)-1-(2-furoyl)-9,10-anthraquinone 

Relevant articles and documents

Bismuth-catalyzed methylation and alkylation of quinone derivatives with tert-butyl peroxybenzoate as an oxidant

A bismuth-catalyzed methylation of quinones in the presence of tert-butyl peroxybenzoate (TBPB) was developed via a radical reaction mechanism. Particularly, TBPB was used not only as an efficient oxidant, but also as a green methyl source in such transformation. Moreover, this method could also be efficiently extended to the alkylation of quinones. This reaction tolerated a series of functional groups and prepared a series of derivatives of vitamin K3 and benzoquinone. Notably, antimalarial parvaquone was synthesized by the reaction.

Cytoprotective and antioxidant properties of organic selenides for the myelin-forming cells, oligodendrocytes

Here a new series of twenty-one organoselenides, of potential protective activity, were synthesized and tested for their intrinsic cytotoxicity, anti-apoptotic and antioxidant capacities in oligodendrocytes. Most of the organoselenides were able to decrease the ROS levels, revealing antioxidant properties. Compounds 5b and 7b showed a high glutathione peroxidase (GPx)-like activities, which were 1.5 folds more active than ebselen. Remarkably, compound 5a diminished the formation of the oligodendrocytes SubG1 peak in a concentration-dependent manner, indicating its anti-apoptotic properties. Furthermore, based on the SwissADME web interface, we performed an in-silico structure-activity relationship to explore the drug-likeness of these organoselenides, predicting the pharmacokinetic parameters for compounds of interest that could cross the blood-brain barrier. Collectively, we present new organoselenide compounds with cytoprotective and antioxidant properties that can be considered as promising drug candidates for myelin diseases.

The dimerisation of 2-methyl-1,4-naphthoquinone in acid solution

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Overcoming peri- and ortho-selectivity in C-H methylation of 1-naphthaldehydes by a tunable transient ligand strategy

Methyl groups widely exist in bioactive molecules, and site-specific methylation has become a valuable strategy for their structural functionalization. Aiming to introduce this smallest alkyl handle, a highly regioselective peri- and ortho-C-H methylation of 1-naphthaldehyde by using a transient ligand strategy has been developed. A series of methyl-substituted naphthalene frameworks have been prepared in moderate to excellent yields. Mechanistic studies demonstrate that peri-methylation is controlled by the higher electronic density of the peri-position of 1-naphthaldehyde as well as the formation of intermediary 5,6-fused bicyclic palladacycles, whereas experimental studies and theoretical calculations inferred that a 5-membered iridacycle at the ortho-position of 1-naphthaldehyde leads to energetically favorable ortho-methylation via an interconversion between the peri-iridacycle and ortho-iridacycle. Importantly, to demonstrate the synthetic utility of this method, we show that this strategy can serve as a platform for the synthesis of multi-substituted naphthalene-based bioactive molecules and natural products.

A Copper Halide Promoted Regioselective Halogenation of Coumarins Using N-Halosuccinimide as Halide Source

A safe, convenient, and regioselective synthesis of 3-halo coumarins using a metal halide (CuX 2 alone or with ZnX 2) promoted halogenation with N -halosuccinimide (NXS) as halide source is reported. The synthesis involved the steady in situ generation of highly reactive positive halogen (X +) by the coordination of copper or zinc with the N -halosuccinimide and subsequent electrophilic aromatic substitution of the electron-deficient coumarins. This procedure works well also for the halogenation of less electron-rich naphthoquinones, flavones, and methoxypsoralen in moderate to quantitative yields. This protocol features simple experimental conditions using readily available inexpensive reagents and provides a convenient approach to the chlorination or bromination of some useful heteroaromatic compounds.