6-bromo-2,4-bis(4-methoxybenzyl)-1,2,4-triazine-3,5(2H,4H)-dione | CAS 2673410-43-8

INTRODUCTION

6‑bromo‑2,4‑bis(4‑methoxybenzyl)-1,2,4-triazine-3,5(2H,4H)-dione
CAS Number: 2673410‑43‑8
Molecular Formula: C₁₉H₁₈BrN₃O₄
Molecular Weight: 432.27 g/mol

6-bromo-2,4-bis(4-methoxybenzyl)-1,2,4-triazine-3,5(2H,4H)-dione | CAS 2673410-43-8  is a halogenated heterocyclic compound with a highly versatile triazine core. The molecule features a 1,2,4-triazine-3,5-dione ring substituted at the 6-position with bromine and at the 2 and 4 positions with 4-methoxybenzyl groups. This unique arrangement provides a balance of structural stability, reactivity, and lipophilicity, making it an important intermediate in chemical and pharmaceutical research.

CHEMICAL STRUCTURE & PROPERTIES

The compound’s key structural features include:

• 1,2,4-Triazine-3,5-dione core: Provides electron-deficient sites suitable for a variety of chemical transformations and potential hydrogen bonding interactions.

• 6-Bromo substituent: Offers a reactive site for nucleophilic substitution or cross-coupling reactions, enabling further derivatization.

• 4-Methoxybenzyl groups: Contribute to hydrophobicity and electronic modulation, enhancing the compound’s versatility in synthetic applications.

6-bromo-2,4-bis(4-methoxybenzyl)-1,2,4-triazine-3,5(2H,4H)-dione is typically a crystalline solid with high thermal stability. Its molecular structure and weight give it low volatility and favorable handling properties in laboratory environments.

SYNTHETIC UTILITY

This compound serves primarily as a specialty intermediate in organic synthesis and medicinal chemistry. Its applications include:

• Building block for analog synthesis: The bromine atom allows for substitution reactions and metal-catalyzed cross-couplings such as Suzuki, Heck, and Buchwald-Hartwig reactions.

• Precursor for bioactive derivatives: The triazine core can be modified to produce derivatives with potential biological activity, making it valuable for drug discovery and enzyme inhibition studies.

• Medicinal chemistry research: Its structure provides a scaffold for exploring structure-activity relationships (SAR), enabling optimization of binding properties, solubility, and metabolic stability in lead compounds.

The combination of reactive and stable functional groups makes this molecule suitable for multi-step synthetic protocols and high-throughput library generation.

CHEMICAL BEHAVIOR AND REACTIVITY

The compound’s reactivity is influenced by both its triazine core and substituents:

• The carbonyl groups in the triazine ring create electrophilic centers, allowing selective nucleophilic reactions.

• The 6-bromo substituent is reactive in nucleophilic aromatic substitution and cross-coupling reactions, enabling structural diversification.

• Methoxybenzyl groups are generally stable under mild conditions but can participate in oxidation or deprotection reactions when required.

This combination of reactive and stable sites allows chemists to design targeted synthetic strategies with precision.

APPLICATIONS IN RESEARCH & DEVELOPMENT

6-bromo-2,4-bis(4-methoxybenzyl)-1,2,4-triazine-3,5(2H,4H)-dione | CAS 2673410-43-8  finds use primarily in research and early-stage development:

• Academic research: Acts as a model compound for studying heterocyclic reactivity and halogen-mediated transformations.

• Pharmaceutical intermediates: Serves as a precursor to novel bioactive molecules for enzyme inhibition or receptor binding studies.

• Medicinal chemistry programs: Functions as a scaffold for generating analog libraries to investigate pharmacological and chemical properties.

Its structural complexity and modifiable bromine site make it particularly suitable for structure-activity relationship (SAR) studies, aiding researchers in optimizing molecular properties.

CONCLUSION

6-bromo-2,4-bis(4-methoxybenzyl)-1,2,4-triazine-3,5(2H,4H)-dione | CAS 2673410-43-8  is a highly versatile heterocyclic intermediate with significant value in chemical synthesis and medicinal research. Its combination of a reactive bromine site and stable triazine core makes it an ideal scaffold for generating diverse analogs, enabling exploration of new chemical space in drug discovery and organic methodology development. Researchers can leverage its unique structural properties to develop advanced molecules with tailored chemical and biological functionality.