Cas no 1934682-48-0 (4,5-Diamino-2-bromobenzonitrile)

4,5-Diamino-2-bromobenzonitrile is a brominated benzonitrile derivative featuring two amino substituents at the 4 and 5 positions. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of heterocyclic compounds and functionalized aromatic systems. The presence of both amino and bromo groups enhances its reactivity, enabling selective cross-coupling reactions, nucleophilic substitutions, and cyclization processes. Its high purity and stability make it suitable for pharmaceutical and agrochemical research, where precise functionalization is critical. The compound’s structural features also facilitate its use in materials science, particularly in the development of dyes and advanced polymers. Proper handling under inert conditions is recommended due to its sensitivity to oxidation.
4,5-Diamino-2-bromobenzonitrile structure
1934682-48-0 structure
Product Name:4,5-Diamino-2-bromobenzonitrile
CAS No:1934682-48-0
MF:C7H6BrN3
MW:212.046639919281
CID:4730518
PubChem ID:130665285
Update Time:2025-05-26

4,5-Diamino-2-bromobenzonitrile Chemical and Physical Properties

Names and Identifiers

    • 4,5-Diamino-2-bromobenzonitrile
    • Inchi: 1S/C7H6BrN3/c8-5-2-7(11)6(10)1-4(5)3-9/h1-2H,10-11H2
    • InChI Key: NOGOVJGNLNAETG-UHFFFAOYSA-N
    • SMILES: BrC1C(C#N)=CC(=C(C=1)N)N

Computed Properties

  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 185
  • XLogP3: 1
  • Topological Polar Surface Area: 75.8

4,5-Diamino-2-bromobenzonitrile Pricemore >>

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Additional information on 4,5-Diamino-2-bromobenzonitrile

Introduction to 4,5-Diamino-2-bromobenzonitrile (CAS No. 1934682-48-0)

4,5-Diamino-2-bromobenzonitrile, identified by its Chemical Abstracts Service (CAS) number 1934682-48-0, is a significant intermediate in the realm of organic synthesis and pharmaceutical development. This compound, featuring a brominated benzonitrile core with two amino substituents, has garnered attention due to its versatile reactivity and potential applications in medicinal chemistry. Its molecular structure, characterized by a conjugated system of nitrogen and carbon atoms, makes it a valuable building block for designing novel heterocyclic compounds and bioactive molecules.

The synthesis and application of 4,5-Diamino-2-bromobenzonitrile have been extensively explored in recent years, particularly in the context of drug discovery and material science. The presence of both amino and bromine functional groups provides multiple sites for chemical modification, enabling the construction of complex molecular architectures. This flexibility has made it a preferred choice for researchers aiming to develop small-molecule inhibitors, antimicrobial agents, and other therapeutic compounds.

In the pharmaceutical industry, 4,5-Diamino-2-bromobenzonitrile serves as a precursor for various pharmacophores. For instance, its bromine moiety can undergo cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings, facilitating the introduction of aryl or alkyl groups. These transformations are crucial for generating libraries of compounds with diverse biological activities. Additionally, the amino groups can be further functionalized through condensation reactions to form amides or ureas, expanding the synthetic possibilities.

Recent studies have highlighted the utility of 4,5-Diamino-2-bromobenzonitrile in the development of kinase inhibitors. Kinases are enzymes that play a pivotal role in signal transduction pathways and are often targeted in oncology and inflammatory diseases. By incorporating this compound into drug candidates, researchers have been able to design molecules that selectively inhibit aberrant kinase activity. The bromine atom's ability to participate in metal-catalyzed reactions has been particularly advantageous in optimizing binding affinities and selectivity.

The role of 4,5-Diamino-2-bromobenzonitrile extends beyond pharmaceutical applications. In material science, it has been utilized in the synthesis of organic semiconductors and conductive polymers. The conjugated system present in its structure contributes to its electronic properties, making it suitable for applications in optoelectronic devices such as organic light-emitting diodes (OLEDs) and photovoltaic cells. The ability to modify its molecular framework allows for fine-tuning of electronic characteristics, enhancing performance in these technologies.

From a synthetic chemistry perspective, 4,5-Diamino-2-bromobenzonitrile exemplifies the importance of multifunctional intermediates in streamlining drug discovery processes. Its compatibility with various reaction conditions and its amenability to iterative modifications make it an indispensable tool in medicinal chemistry laboratories. The ongoing development of new synthetic methodologies continues to expand its utility, ensuring its relevance in both academic research and industrial applications.

The chemical properties of 4,5-Diamino-2-bromobenzonitrile (CAS No. 1934682-48-0) also make it a valuable candidate for exploring novel chemical pathways. Researchers have leveraged its reactivity to develop innovative synthetic strategies that could be applied to other heterocyclic systems. For example, palladium-catalyzed reactions involving this compound have opened up avenues for constructing nitrogen-rich heterocycles, which are prevalent in biologically active molecules.

In conclusion,4,5-Diamino-2-bromobenzonitrile represents a cornerstone in modern synthetic chemistry and pharmaceutical research. Its unique structural features and broad applicability underscore its significance as a chemical intermediate. As advancements continue to emerge in drug discovery and materials science,4,5-Diamino-2-bromobenzonitrile is poised to remain at the forefront of innovation,CAS no 1934682-48-0 continues to inspire new possibilities.

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