6-bromo-1-isopropyl-2-methyl-1H-benzo[d]imidazole
[CAS# 1038408-36-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 6-bromo-1-isopropyl-2-methyl-1H-benzo[d]imidazole
• Molecular Formula: C₁₁H₁₃BrN₂
• Molecular Weight: 253.14
• CAS Registry Number: 1038408-36-4
• SMILES: CC1=NC2=C(N1C(C)C)C=C(C=C2)Br

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Boiling point: 353.9±15.0 ºC 760 mmHg (Calc.)^*
• Flash point: 167.8±20.4 ºC (Calc.)^*
• Index of refraction: 1.615 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

6-Bromo-1-isopropyl-2-methyl-1H-benzo[d]imidazole is a substituted benzimidazole derivative in which a bromine atom occupies the sixth position of the benzene ring, an isopropyl group is attached to the nitrogen at the first position, and a methyl group is located at the second position of the heterocyclic ring. Benzimidazole derivatives are important heterocyclic scaffolds widely studied for their biological activity and chemical versatility. The combination of halogenation and alkyl substitution modulates electronic properties and steric factors, making this compound a useful intermediate in medicinal and synthetic chemistry.

The synthesis of 6-bromo-1-isopropyl-2-methyl-1H-benzo[d]imidazole generally involves cyclization of appropriately substituted o-phenylenediamine derivatives with carboxylic acid or aldehyde precursors to form the benzimidazole ring, followed by N-alkylation to introduce the isopropyl group at the nitrogen. Bromination is typically performed selectively at the 6-position using controlled halogenation conditions to avoid polybromination or unwanted side reactions. Purification is achieved through recrystallization or chromatography to obtain a solid product with well-defined chemical and physical properties.

In organic synthesis, this compound serves as a versatile intermediate for the preparation of more complex benzimidazole derivatives. The bromine atom at the 6-position can undergo palladium-catalyzed cross-coupling reactions, such as Suzuki, Sonogashira, or Buchwald–Hartwig couplings, allowing the introduction of aryl, heteroaryl, or alkynyl substituents. The methyl and isopropyl groups influence both the steric environment and electronic characteristics of the benzimidazole ring, affecting regioselectivity and reactivity in subsequent transformations. These features enable construction of a variety of functionalized heterocycles with potential biological activity.

In medicinal chemistry, derivatives of 6-bromo-1-isopropyl-2-methyl-1H-benzo[d]imidazole have been explored as scaffolds for pharmacologically active molecules, including antimicrobial, antiviral, and anticancer agents. The benzimidazole core provides planarity and hydrogen-bonding capability, facilitating interactions with biological macromolecules such as enzymes, receptors, and nucleic acids. Substituents at the 1, 2, and 6 positions allow fine-tuning of lipophilicity, steric bulk, and electronic properties, which are critical for optimizing target binding, metabolic stability, and pharmacokinetic profiles.

The compound also finds utility in chemical methodology research and materials science. Its brominated position and N-alkylated heterocyclic framework make it a suitable substrate for exploring selective functionalization, coupling strategies, and heterocycle derivatization. In materials applications, benzimidazole derivatives have been studied for their optical, electronic, and coordination properties, and compounds like 6-bromo-1-isopropyl-2-methyl-1H-benzo[d]imidazole serve as intermediates for designing functional molecules with specific electronic or photophysical characteristics.

Physically, the compound is generally a crystalline solid with moderate solubility in polar organic solvents such as dimethylformamide, ethanol, and dichloromethane. It is stable under ambient conditions but should be protected from strong acids, bases, or oxidizing agents that could degrade the benzimidazole ring or alter the substituents. Proper storage ensures retention of chemical integrity and reactivity for synthetic or biological applications.

Overall, 6-bromo-1-isopropyl-2-methyl-1H-benzo[d]imidazole is a chemically versatile halogenated benzimidazole derivative. Its bromine, isopropyl, and methyl substituents provide multiple avenues for selective functionalization and derivatization, making it a valuable intermediate in the synthesis of bioactive molecules, heterocyclic scaffolds, and functional materials in both medicinal and synthetic chemistry.

References

2023. Aminopyrimidine and aminotriazine derivatives as myc protein modulators. WO Patent, 2024044757.

2022. Substituted heteroaryl derivative, and composition and use thereof. WO Patent, 2022166916.

2020. Polysubstituted anilinopyrimidine derivative and preparation method and application thereof. WO Patent, 2020135507.