Production Method 1

60956-26-5

82420-34-6

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Acetonitrile ;  24 h, reflux; 48 h

Reference

Synthesis of mono-functionalized S-diazocines via intramolecular Baeyer-Mills reactions

Schehr, Miriam ; et al, Beilstein Journal of Organic Chemistry, 2018, 14, 2799-2804

Production Method 2

60956-26-5

82420-34-6

Reaction Conditions

1.1 Reagents: Bromine

Reference

A comparative study of the rearrangement of some 6- and 7-halo-substituted 3-amino-3,4-dihydro-1-hydroxycarbostyrils in concentrated hydrohalic acids

McCord, Tommy J.; et al, Journal of Heterocyclic Chemistry, 1982, 19(2), 401-6

Production Method 3

60956-26-5

82420-34-6

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride ;  10 h

Reference

A One-Pot-Three-Step Route to Triazolotriazepinoindazolones from Oxazolino-2H-indazoles

Conrad, Wayne E.; et al, Organic Letters, 2012, 14(15), 3870-3873

Production Method 4

82420-34-6

Reaction Conditions

1.1 Reagents: Sodium nitrite ,  Hydrogen bromide Solvents: Water ;  0 °C; < 2 °C; 45 min, 0 - 2 °C
1.2 Reagents: Copper bromide (CuBr) ,  Hydrogen bromide Solvents: Water ;  90 °C; 30 min, 90 °C
2.1 Reagents: N-Bromosuccinimide Catalysts: Azobisisobutyronitrile Solvents: Carbon tetrachloride ;  10 h

Reference

A One-Pot-Three-Step Route to Triazolotriazepinoindazolones from Oxazolino-2H-indazoles

Conrad, Wayne E.; et al, Organic Letters, 2012, 14(15), 3870-3873

4-Bromo-1-(bromomethyl)-2-nitrobenzene Raw materials

• 4-bromo-1-methyl-2-nitro-benzene

4-Bromo-1-(bromomethyl)-2-nitrobenzene Preparation Products

• 4-Bromo-1-(bromomethyl)-2-nitrobenzene (82420-34-6)

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Professional Introduction to 4-Bromo-1-(bromomethyl)-2-nitrobenzene (CAS No. 82420-34-6)

4-Bromo-1-(bromomethyl)-2-nitrobenzene, with the chemical identifier CAS No. 82420-34-6, is a significant intermediate in the realm of organic synthesis and pharmaceutical chemistry. This compound, characterized by its nitro and bromomethyl functional groups, has garnered attention due to its versatile reactivity and potential applications in the development of novel chemical entities.

The structural motif of 4-Bromo-1-(bromomethyl)-2-nitrobenzene consists of a benzene ring substituted with a nitro group at the 2-position and a bromomethyl group at the 1-position. This configuration imparts unique electronic and steric properties, making it a valuable building block for constructing more complex molecular architectures. The presence of both electron-withdrawing (nitro) and electron-donating (bromomethyl) groups allows for diverse chemical transformations, including nucleophilic substitution, metal-catalyzed cross-coupling reactions, and functional group interconversions.

In recent years, 4-Bromo-1-(bromomethyl)-2-nitrobenzene has found utility in the synthesis of pharmacologically active compounds. Its nitro group can be reduced to an amine, providing a pathway to introduce amine functionalities into the molecular framework. Additionally, the bromomethyl group serves as a versatile handle for further derivatization, enabling the construction of biaryl structures or the introduction of other nucleophiles. These attributes have made it a staple in medicinal chemistry libraries and a subject of interest for academic and industrial researchers alike.

One notable application of 4-Bromo-1-(bromomethyl)-2-nitrobenzene lies in the synthesis of kinase inhibitors. Kinases are enzymes that play crucial roles in cellular signaling pathways, making them attractive targets for therapeutic intervention. By leveraging the reactivity of the nitro and bromomethyl groups, researchers have been able to design and synthesize novel kinase inhibitors with improved potency and selectivity. For instance, modifications of this scaffold have led to the discovery of compounds that exhibit inhibitory activity against various kinases implicated in cancer and inflammatory diseases.

The pharmaceutical industry has also explored the use of 4-Bromo-1-(bromomethyl)-2-nitrobenzene in the development of antimicrobial agents. The nitro group, known for its ability to enhance bioavailability and metabolic stability, has been incorporated into molecules designed to combat resistant bacterial strains. Furthermore, the bromomethyl functionality allows for further functionalization, enabling the creation of compounds with enhanced binding affinity to bacterial targets. These efforts have resulted in promising candidates for new antibiotics targeting multidrug-resistant pathogens.

Beyond pharmaceutical applications, 4-Bromo-1-(bromomethyl)-2-nitrobenzene has been utilized in materials science research. Its ability to undergo cross-coupling reactions makes it a valuable precursor for synthesizing conjugated polymers and organic semiconductors. These materials are integral to advancements in optoelectronic devices such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). The incorporation of this compound into these systems has led to improved device performance, including higher charge carrier mobility and longer operational lifetimes.

The synthesis of 4-Bromo-1-(bromomethyl)-2-nitrobenzene itself is an area of active research. Recent advances in synthetic methodologies have enabled more efficient and scalable production methods. For example, catalytic bromination techniques have been employed to introduce the bromo substituent with high regioselectivity, minimizing side reactions. Additionally, green chemistry principles have been applied to reduce waste and improve atom economy during synthesis. These innovations not only enhance the accessibility of this compound but also align with global efforts toward sustainable chemical manufacturing.

In conclusion, 4-Bromo-1-(bromomethyl)-2-nitrobenzene (CAS No. 82420-34-6) represents a multifaceted compound with broad applications across multiple scientific disciplines. Its unique structural features make it an indispensable tool for synthetic chemists working on pharmaceuticals, materials science, and beyond. As research continues to uncover new methodologies and applications, this compound is poised to remain at the forefront of chemical innovation.

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