Overview
5-Bromoindole is a brominated derivative of indole, a heterocyclic aromatic compound. It serves as a versatile intermediate in organic synthesis, particularly in the pharmaceutical and agrochemical industries. The bromine atom at the 5-position enhances its reactivity, making it valuable for cross-coupling reactions and further functionalization. This compound is typically synthesized through electrophilic bromination of indole. Its applications span from drug development to material science, where it contributes to the creation of complex molecules with biological activity.
Physical and Chemical Properties
5-Bromoindole appears as an off-white to pale yellow crystalline powder with a melting point around 90-94°C. It is soluble in common organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO), but has limited solubility in water. The bromine substituent on the indole ring increases its molecular weight to 196.05 g/mol and influences its electronic properties, making it more reactive toward nucleophilic and electrophilic reagents. This reactivity is exploited in various synthetic pathways to construct indole-based pharmaceuticals and agrochemicals.
Main Applications
5-Bromoindole is primarily used as a building block in the synthesis of pharmaceuticals, including serotonin receptor modulators and kinase inhibitors. Its bromine atom facilitates further chemical modifications, such as Suzuki-Miyaura cross-coupling reactions, to create more complex structures. In agrochemicals, it serves as an intermediate for producing compounds with herbicidal or insecticidal properties. Additionally, it is employed in academic and industrial research for developing new bioactive molecules and materials with tailored properties.
Safety and Storage
5-Bromoindole is classified as harmful if swallowed or inhaled and can cause skin and eye irritation. Proper personal protective equipment (PPE), including gloves, goggles, and lab coats, should be worn when handling this compound. Work should be conducted in a well-ventilated area or fume hood to minimize exposure. Storage conditions are critical to maintaining stability. The compound should be kept in a cool, dry place, away from light and moisture, in a tightly sealed container. Incompatible materials include strong oxidizing agents, which may cause hazardous reactions.
B2B Procurement Guide
When procuring 5-Bromoindole, buyers should verify the CAS number (10075-50-0) to ensure they are sourcing the correct compound. Purity levels, typically ranging from 95% to 99%, should be confirmed via certificates of analysis (COA). Reliable suppliers should provide safety data sheets (SDS) and comply with regulatory standards. Prices vary based on purity and quantity, with bulk purchases often offering cost advantages. Due to its hazardous nature, ensure proper shipping and handling protocols are followed to avoid safety risks.
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