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

• 303779-66-0 3-bromo-1-naphthaldehyde 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 75-65-0 tert-butyl alcohol 
• 614-45-9 tert-Butyl peroxybenzoate 
• 64-19-7 acetic acid 
• 861331-93-3 4-chloro-2-methylnaphthalen-1-ol 
• 17735-17-0 2,3,4,4-tetrachloro-2-methyl-3,4-dihydro-2H-naphthalen-1-one 
• 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 
• 481-85-6 2-methyl-1,4-naphthohydroquinone 
• 7664-93-9 sulfuric acid 
• 861047-23-6 2,3-dibromo-2-methyl-2,3-dihydro-[1,4]naphthoquinone 
• 58-27-5 menadione 

Downstream Products

• 39055-47-5 2-bromo-3-methylnaphthohydroquinone 
• 1247849-69-9 2-(hydroxyphenyltellanyl)-3-methylnaphthoquinone 
• 483-55-6 phthiocol 
• 23912-79-0 pentacene-5,7,12,14-tetraone 
• 70691-68-8 3-methyl-2-(phenylthio)-1,4-naphthoquinone 
• 16354-53-3 7,12-dimethoxybenzo[a]anthracene 
• 2498-66-0 benz[a]anthracene-7,12-dione 
• 53772-33-1 2-bromo-3-methyl-1,4-dimethoxynaphthalene 
• 827347-02-4 2-(1,4-dimethoxy-3-methyl-2-naphthyl)benzaldehyde 
• 827347-03-5 2-(3-methyl-1,4-dioxo-1,4-dihydro-2-naphthalenyl)benzaldehyde 

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.

Synthesis and biochemical studies of novel organic selenides with increased selectivity for hepatocellular carcinoma and breast adenocarcinoma

Nineteen organoselenides were synthesized and tested for their intrinsic cytotoxicity in hepatocellular carcinoma (HepG2) and breast adenocarcinoma (MCF-7) cell lines and their corresponding selective cytotoxicity (SI) was estimated using normal lung fibroblast (WI-38) cells. Most of the organic selenides exhibited good anticancer activity, and this was more pronounced in HepG2 cells. Interestingly, the naphthoquinone- (5), thiazol- (12), and the azo-based (13) organic selenides demonstrated promising SI (up to 76). Furthermore, the amine 4c, naphthoquinone 5, and azo-based 13 and 15 organic selenides were able to down-regulate the expression of Bcl-2 and up-regulate the expression levels of IL-2, IL-6 and CD40 in HepG2 cells compared to untreated cells. Moreover, most of the synthesized candidates manifested good free radical-scavenging and GPx-like activities comparable to vitamin C and ebselen. The obtained results suggested that some of the presented organoselenium candidates have promising anti-HepG2 and antioxidant activities.