1-Bromo-2-methyl-3,4-dinitrobenzene: Properties & Lab FAQ

1-Bromo-2-methyl-3,4-dinitrobenzene is a halogenated polynitroaromatic compound widely used as a versatile electrophilic building block and synthetic intermediate in pharmaceutical, agrochemical, and materials research.

Chemical Name

1-Bromo-2-methyl-3,4-dinitrobenzene

SKU / Product Code

B728600

Molecular Formula

C7H5BrN2O4

Molecular Weight

261.03 g/mol

Key Functional Groups

Aryl bromide, two nitro groups, methyl substituent

Primary Application

Electrophilic aromatic intermediate for cross-coupling and nucleophilic substitution reactions

Supplier

Aladdin Scientific

Overview and Chemical Identity

1-Bromo-2-methyl-3,4-dinitrobenzene (SKU B728600) is an aromatic compound bearing three substituents on a benzene ring: a bromine atom at position 1, a methyl group at position 2, and two nitro groups at positions 3 and 4. Its molecular formula is C₇H₅BrN₂O₄ with a molecular weight of approximately 261.03 g/mol. The combination of electron-withdrawing nitro groups and an aryl bromide makes this compound highly reactive toward nucleophilic aromatic substitution (S_NAr) and transition-metal-catalysed cross-coupling reactions such as Suzuki–Miyaura and Buchwald–Hartwig couplings. The methyl substituent adjacent to the bromine introduces steric influences that can be exploited for regioselective transformations in complex molecule synthesis.

Handling, Safety, and Storage

As a polynitroaromatic compound, 1-Bromo-2-methyl-3,4-dinitrobenzene should be treated with appropriate caution in the laboratory. The following general guidelines apply:

• Personal Protective Equipment (PPE): Wear chemical-resistant gloves, safety goggles, and a lab coat at all times. Work in a well-ventilated fume hood to minimise inhalation of dust or vapours.
• Storage: Store in a cool, dry, well-ventilated area away from heat sources, open flames, and incompatible materials such as strong reducing agents and bases. Keep container tightly sealed.
• Disposal: Dispose of according to applicable local, regional, and national regulations for aromatic nitro compounds. Do not pour down the drain.
• First Aid: In case of skin or eye contact, flush immediately with copious water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air.

Always consult the product Safety Data Sheet (SDS) available from Aladdin Scientific before use. Specific hazard classifications and regulatory data should be verified from the SDS.

Synthetic Applications and Reactivity

1-Bromo-2-methyl-3,4-dinitrobenzene serves as a versatile building block in organic synthesis. Key applications include:

• Nucleophilic Aromatic Substitution (S_NAr): The two electron-withdrawing nitro groups strongly activate the ring toward S_NAr. Nucleophiles such as amines, alkoxides, and thiolates can displace the bromide or, under suitable conditions, a nitro group, enabling access to diversely substituted anilines, aryl ethers, and thioethers.
• Transition-Metal-Catalysed Cross-Coupling: The aryl C–Br bond participates readily in palladium-catalysed reactions including Suzuki–Miyaura (with arylboronic acids), Negishi, and Buchwald–Hartwig amination reactions, providing access to bi-aryl and aryl-amine scaffolds relevant to pharmaceutical lead optimisation.
• Nitro Group Reduction: Selective or complete reduction of nitro groups to amines (via catalytic hydrogenation or iron/acetic acid reduction) delivers aminobenzene derivatives that are key precursors for heterocyclic synthesis, dye chemistry, and bioactive compound libraries.
• Directed Metalation: The methyl group can be functionalised via benzylic oxidation or halogenation to introduce additional handles for further elaboration.

Researchers should optimise reaction conditions (solvent, temperature, catalyst loading) empirically, as the steric environment imposed by the 2-methyl group may influence reaction rates and regioselectivity.

Ordering, Purity, and Quality Specifications

Aladdin Scientific supplies 1-Bromo-2-methyl-3,4-dinitrobenzene under SKU B728600. When placing an order or evaluating the reagent, consider the following points:

• Purity: Check the Certificate of Analysis (CoA) provided with each lot for confirmed purity values determined by GC or HPLC. For sensitive synthetic applications, a purity of ≥97% is generally recommended; however, confirm the specification on the product page or CoA for the specific lot.
• Available Quantities: Contact Aladdin Scientific sales or visit the product page for current pack sizes and bulk pricing options.
• Lot-to-Lot Consistency: Each lot is accompanied by a CoA. Request the CoA before ordering if batch traceability is required for regulatory or publication purposes.
• Lead Time: Standard stock items typically ship within the timeframes listed on the Aladdin Scientific website. Contact customer service for estimated delivery if the item shows limited availability.

For procurement enquiries, volume discounts, or custom synthesis requests, contact Aladdin Scientific customer support directly.

Frequently Asked Questions at a Glance

This section summarises the most common researcher questions about 1-Bromo-2-methyl-3,4-dinitrobenzene. Detailed answers are provided in the FAQ section below. Topics covered include solubility, stability, typical reaction conditions, and compatibility with common laboratory solvents and reagents. If your question is not answered here, please contact Aladdin Scientific technical support for personalised assistance.

Frequently asked questions

What solvents are suitable for dissolving 1-Bromo-2-methyl-3,4-dinitrobenzene?

1-Bromo-2-methyl-3,4-dinitrobenzene is generally soluble in common polar aprotic organic solvents such as dichloromethane (DCM), dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), and ethyl acetate. It has limited solubility in water and aliphatic hydrocarbons. Always verify solubility experimentally for your specific application and concentration requirements.

How should 1-Bromo-2-methyl-3,4-dinitrobenzene be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated location away from heat, ignition sources, and incompatible materials including strong reducing agents and strong bases. Protection from prolonged exposure to light and moisture is recommended. Under appropriate storage conditions, the compound is expected to remain stable; however, always check the product CoA and SDS for lot-specific stability data.

Can 1-Bromo-2-methyl-3,4-dinitrobenzene be used directly in palladium-catalysed cross-coupling reactions?

Yes, the aryl C–Br bond in 1-Bromo-2-methyl-3,4-dinitrobenzene is a competent electrophilic partner in palladium-catalysed cross-coupling reactions such as Suzuki–Miyaura, Negishi, and Buchwald–Hartwig amination. The electron-withdrawing nitro groups can facilitate oxidative addition of the C–Br bond to palladium(0). Researchers should note that the ortho-methyl group introduces steric bulk near the reactive site, which may necessitate optimisation of the catalyst system and reaction temperature to achieve acceptable yields.

Is 1-Bromo-2-methyl-3,4-dinitrobenzene hazardous, and what precautions are required?

As a polynitroaromatic halide, this compound should be handled with care. Appropriate precautions include wearing chemical-resistant gloves, safety goggles, and a lab coat, and working in a well-ventilated fume hood. Avoid contact with strong reducing agents. Consult the Aladdin Scientific SDS for full GHS hazard classifications, first-aid measures, and disposal requirements before handling the compound.

What is the molecular weight and formula of 1-Bromo-2-methyl-3,4-dinitrobenzene?

The molecular formula of 1-Bromo-2-methyl-3,4-dinitrobenzene is C7H5BrN2O4, and its molecular weight is approximately 261.03 g/mol. These values are based on standard atomic weights and should be confirmed against the product CoA or SDS provided by Aladdin Scientific.

References

1. Aladdin Scientific product page: 1-Bromo-2-methyl-3,4-dinitrobenzene, SKU B728600. Aladdin Scientific.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 4th ed. Wiley-Interscience, 1992. (General reference for nucleophilic aromatic substitution and cross-coupling reactivity of aryl halides.)
3. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. 2nd ed. Oxford University Press, 2012. (General reference for aromatic substitution and functional group reactivity.)

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