13321-74-9

Basic information

• Product Name: 4-BROMO-2,5-DIMETHOXYTOLUENE
• Synonyms: 4-BROMO-2,5-DIMETHOXYTOLUENE;1-BROMO-2,5-DIMETHOXY-4-METHYLBENZENE;Benzene,1-broMo-2,5-diMethoxy-4-Methyl-
• CAS NO: 13321-74-9
• Molecular Formula: C₉H₁₁BrO₂
• Molecular Weight: 231.09
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives
• Mol File: 13321-74-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 77-78
• Boiling Point: 270.408 °C at 760 mmHg
• Flash Point: 114.151 °C
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 0.0114mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-BROMO-2,5-DIMETHOXYTOLUENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-2,5-DIMETHOXYTOLUENE(13321-74-9)
• EPA Substance Registry System: 4-BROMO-2,5-DIMETHOXYTOLUENE(13321-74-9)

Safety Data

• Hazard Codes: Xi
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g
• Hazardous Substances Data: 13321-74-9(Hazardous Substances Data)

Usage

General Description

4-Bromo-2,5-dimethoxytoluene is a chemical compound, usually found in crystal form. Characterized by its bromo, methoxy, and toluene functional groups, this organic compound is often used in chemical research and experimentation. Due to the specific nature of its functional groups, it exhibits unique chemical properties, such as a low boiling point and high solubility in various organic solvents. As an aromatic compound, it contains a stable ring of atoms, which also contributes to its distinct chemical behavior. Like other chemicals with similar structures, it requires careful handling due to potential hazards associated with its use.

InChI:InChI=1/C9H11BrO2/c1-6-4-9(12-3)7(10)5-8(6)11-2/h4-5H,1-3H3

Upstream product

• 67289-05-8 2-bromo-5-methylbenzene-1,4-diol 
• 77-78-1 dimethyl sulfate 
• 60732-17-4 2,5-dimethoxybenzyl bromide 
• 33524-31-1 2,5-dimethoxybenzyl alcohol 
• 31558-41-5 4-bromo-2,5-dimethoxybenzaldehyde 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 95-71-6 2-methylbenzene-1,4-diol 
• 24599-58-4 2,5-dimethoxy toluene 
• 74-88-4 methyl iodide 

Downstream Products

• 38439-76-8 2-(2,5-dimethoxy-4-methylphenyl)ethanol 
• 180578-98-7 2,5-dimethoxy-4-methylphenylmagnesium bromide 
• 13070-25-2 2-bromo-5-methyl-[1,4]benzoquinone 
• 78920-00-0 1-(2,5-dimethoxy-4-methylphenyl)ethyl diisopropylcarbamate 
• 68409-17-6 1-lithio-2,5-dimethoxy-4-methylbenzene 
• 100108-66-5 murrayaquinone A 
• 38844-23-4 1-(2,5-dimethoxy-4-methylphenyl)-2-propanol 
• 68409-21-2 2-(2,5-Dimethoxy-4-methylbenzoyl)-3-methoxybenzoesaeure-methylester 
• 68409-20-1 6-(2,5-Dimethoxy-4-methylbenzoyl)-2-methoxybenzoesaeure-methylester 

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.

Synthesis of murrayaquinone A and analogues via ring-closing C-H arylation

A compact synthesis of Murrayaquinone A is reported, based on sequential Buchwald-Hartwig amination/annulative C-H activation followed by oxidation of the intermediate carbazole. The methodology can be readily extended to other analogues with electron-rich quinone rings.

A short synthesis of bisabolane sesquiterpenes

A facile total synthesis of three members of the bisabolane sesquiterpene family, namely (±)-curcumene, (±)-xanthorrhizol and (±)-curcuhydroquinone had been achieved in high overall yield. The synthesis used bromobenzene derivatives as starting materials.