1,4,8,9-Tetramethylcarbazole

Updated: 2026-07-29

Overview

1,4,8,9-Tetramethylcarbazole is a carbazole derivative with a polycyclic aromatic structure, distinguished by four methyl groups attached to its central ring. This modification enhances its solubility in organic solvents and alters its electronic properties, making it valuable for specialized chemical synthesis. The compound is primarily utilized in industrial applications, including pharmaceuticals and advanced materials. First synthesized in the mid-20th century, it gained prominence as a building block for complex molecules. Its stability and reactivity balance make it a preferred intermediate in multi-step syntheses, particularly for nitrogen-containing heterocycles.

Physical and Chemical Properties

The compound appears as a white to pale yellow crystalline powder with a melting point of 150–155°C. Its molecular weight is 223.31 g/mol, and it exhibits moderate solubility in polar organic solvents like ethanol and acetone, while being insoluble in water. The methyl groups increase its lipophilicity compared to unsubstituted carbazole. Key chemical properties include resistance to hydrolysis under neutral conditions and susceptibility to electrophilic aromatic substitution. UV-Vis spectroscopy reveals absorption maxima typical for carbazoles, useful for analytical identification. Thermal stability allows handling at room temperature, though prolonged exposure to air may cause gradual oxidation.

Main Applications

1,4,8,9-Tetramethylcarbazole serves as a critical intermediate in pharmaceutical manufacturing, particularly for antipsychotic and anticancer agents. Its rigid structure facilitates binding to biological targets. In agrochemicals, it contributes to fungicides and herbicides by acting as a scaffold for bioactive molecules. The compound is also employed in optoelectronics, where its conjugated system enables use in organic light-emitting diodes (OLEDs) and photovoltaic materials. Additionally, it functions as a precursor for dyes, especially those requiring high thermal stability. Niche applications include corrosion inhibitors and polymer additives.

Safety and Storage

Handling requires precautions due to potential skin, eye, and respiratory irritation. Personal protective equipment (PPE) such as nitrile gloves and safety goggles is mandatory. Work should occur in a fume hood to minimize inhalation risks, and spills must be contained with inert absorbents. Storage demands include airtight containers in cool (below 25°C), dark environments, separate from strong oxidizers. Shelf life typically exceeds two years when stored properly. Safety Data Sheets (SDS) must be reviewed prior to use, and disposal should comply with local regulations for aromatic amines.

B2B Procurement Guide

Industrial buyers should prioritize suppliers with ISO 9001 certification and batch-specific Certificates of Analysis (CoA). Key specifications include purity (≥98%), residual solvent levels, and particle size if applicable. Bulk purchases (25+ kg) often reduce costs by 10–20%. Logistics considerations include temperature-controlled shipping for international orders and hazmat documentation for air freight. Sample testing is advised to confirm consistency. Emerging markets in Asia offer competitive pricing, but due diligence is required to avoid substandard material.