13070-25-2

Basic information

• Product Name: 2-BROMO-5-METHYL-1,4-BENZOQUINONE
• Synonyms: 2-BROMO-5-METHYL-1,4-BENZOQUINONE;2-BROMO-5-METHYL-P-QUINONE;5-BROMO-2-METHYL-1,4-BENZOQUINONE;5-BROMOTOLUQUINONE;2-BROMO-5-METHYL-1,4-BENZOQUINONE 98+%;2-Bromo-5-methyl-p-quinone 5-Bromotoluquinone;2-BroMo-5-Methylcyclohexa-2,5-diene-1,4-dione
• CAS NO: 13070-25-2
• Molecular Formula: C₇H₅BrO₂
• Molecular Weight: 201.02
• Product Categories: Anthraquinones, Hydroquinones and Quinones;Benzoquinones;Benzoquinones, etc. (Charge Transfer Complexes);Charge Transfer Complexes for Organic Metals;Functional Materials
• Mol File: 13070-25-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 106 °C
• Boiling Point: 238.5°C at 760 mmHg
• Flash Point: 95.9°C
• Appearance: /
• Density: 1.727g/cm³
• Vapor Pressure: 0.0423mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-BROMO-5-METHYL-1,4-BENZOQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-5-METHYL-1,4-BENZOQUINONE(13070-25-2)
• EPA Substance Registry System: 2-BROMO-5-METHYL-1,4-BENZOQUINONE(13070-25-2)

Safety Data

• Hazardous Substances Data: 13070-25-2(Hazardous Substances Data)

Usage

General Description

2-Bromo-5-methyl-1,4-benzoquinone is a chemical compound with the molecular formula C7H5BrO2. It is a derivative of benzoquinone, which is a type of organic compound known for its antiseptic and disinfectant properties. 2-Bromo-5-methyl-1,4-benzoquinone is a yellow crystalline solid that is soluble in organic solvents. It is commonly used in organic synthesis and as a building block for other chemical compounds. In addition, it has potential applications in the pharmaceutical and agrochemical industries. However, it is important to handle 2-Bromo-5-methyl-1,4-benzoquinone with caution as it is considered to be hazardous and can cause irritation to the skin, eyes, and respiratory system.

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 
• 67289-05-8 2-bromo-5-methylbenzene-1,4-diol 
• 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 
• 861315-10-8 2-bromo-5-methyl-4-nitroso-phenol 
• 36138-76-8 5-bromo-2-methylphenol 
• 24599-58-4 2,5-dimethoxy toluene 
• 13321-74-9 1-bromo-2,5-dimethoxy-4-methylbenzene 

Downstream Products

• 67289-05-8 2-bromo-5-methylbenzene-1,4-diol 
• 861315-10-8 2-bromo-5-methyl-4-nitroso-phenol 
• 187809-44-5 2-bromo-3-chloro-5-methyl-hydroquinone 
• 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 
• 1414286-80-8 2-(phenylselanyl)-5-methyl-1,4-benzoquinone 
• 1393101-70-6 6-(3,5-dimethoxybenzyl)-7-methylquinoline-5,8-dione 

Relevant articles and documents

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.

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.

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.