N,N'-Diphenylguanidine monohydrobromide
[CAS# 93982-96-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Guanidine salt
• Name: N,N'-Diphenylguanidine monohydrobromide
• Synonyms: 1,2-Diphenylguanidine hydrobromide
• Molecular Formula: C₁₃H₁₃N₃.HBr
• Molecular Weight: 292.17
• CAS Registry Number: 93982-96-8
• EC Number: 301-283-6
• SMILES: C1=CC=C(C=C1)NC(=NC2=CC=CC=C2)N.Br

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317-H319
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

N,N'-Diphenylguanidine monohydrobromide is a chemical compound belonging to the class of guanidine derivatives. It is characterized by the presence of two phenyl groups attached to the guanidine structure, contributing to its unique properties. The discovery of N,N'-diphenylguanidine can be traced back to the early 20th century when researchers were exploring various guanidine derivatives for their potential applications in different fields, including rubber technology and pharmaceuticals.

The synthesis of N,N'-diphenylguanidine typically involves the reaction of diphenylurea with a strong base, leading to the formation of the guanidine derivative. Its monohydrobromide form is obtained by treating the base with hydrobromic acid, which enhances its solubility in aqueous solutions. This salt form is particularly useful in various applications, as it is more stable and easier to handle than the free base.

One of the primary applications of N,N'-diphenylguanidine monohydrobromide is in the rubber industry. It is widely used as a vulcanization accelerator in the production of rubber compounds. Its ability to promote cross-linking between rubber molecules significantly enhances the elasticity, durability, and heat resistance of rubber products. This property makes it essential for manufacturing tires, seals, and other rubber goods that require optimal performance under stress and temperature variations.

In addition to its role in rubber production, N,N'-diphenylguanidine monohydrobromide has found applications in the pharmaceutical industry. It is utilized as an intermediate in the synthesis of various pharmaceutical compounds, particularly those with therapeutic properties related to the central nervous system. Research has shown that guanidine derivatives can exhibit neuroprotective effects, making them potential candidates for the treatment of neurodegenerative diseases and other neurological disorders.

Moreover, N,N'-diphenylguanidine monohydrobromide has been studied for its antibacterial and antifungal properties. Its ability to inhibit the growth of certain pathogens has led to its investigation as a potential antimicrobial agent. This application is particularly relevant in the development of formulations for topical use, where effective antimicrobial action is crucial for preventing infections.

Despite its valuable applications, safety considerations are essential when handling N,N'-diphenylguanidine monohydrobromide. It is advisable to follow appropriate safety protocols, as exposure to the compound may cause skin and eye irritation. Proper protective equipment should be utilized when working with this chemical to minimize risks.

In summary, N,N'-diphenylguanidine monohydrobromide is a significant compound with diverse applications in the rubber and pharmaceutical industries. Its ability to act as a vulcanization accelerator and an intermediate in drug synthesis highlights its importance in industrial processes. Ongoing research into its properties and potential applications continues to uncover new opportunities for this versatile compound.

References

1998. Design, Synthesis, and Pharmacological Evaluation of Conformationally Constrained Analogues of N,N‘-Diaryl- and N-Aryl-N-aralkylguanidines as Potent Inhibitors of Neuronal Na+ Channels. Journal of Medicinal Chemistry, 41(14).
DOI: 10.1021/jm980124a