What Is 5-Bromo-1-methyl-1H-indole-3-carboxylic Acid?

5-Bromo-1-methyl-1H-indole-3-carboxylic acid is a halogenated indole derivative bearing three key structural features: a bromine substituent at the 5-position of the indole ring, an N-methyl group at position 1, and a carboxylic acid function at position 3. The indole scaffold is one of the most prevalent heteroaromatic systems in natural products and pharmaceutically active compounds, making substituted indole-3-carboxylic acids important intermediates in synthetic and medicinal chemistry.

The combination of the electron-withdrawing bromine and carboxylic acid groups with the electron-donating N-methyl group creates a molecule with well-balanced reactivity, suitable for further elaboration via cross-coupling reactions (e.g., Suzuki, Sonogashira), amide bond formation, esterification, and other transformations commonly employed in drug discovery programs.

Physical and Chemical Properties

5-Bromo-1-methyl-1H-indole-3-carboxylic acid is a solid organic compound at room temperature. Its molecular formula is C10H8BrNO2, giving a calculated molecular weight of approximately 254.08 g/mol (exact value should be confirmed against the certificate of analysis). The presence of a carboxylic acid group confers moderate acidity and hydrogen-bonding capability, influencing its solubility profile.

Solubility: The compound is generally sparingly soluble in water due to its aromatic, lipophilic character. It shows improved solubility in polar organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and methanol, which are commonly used to prepare stock solutions for biological or chemical assays. Solubility values should be experimentally verified for each application.

The aromatic bromine at the 5-position is well-suited for palladium-catalyzed cross-coupling reactions, while the carboxylic acid can be activated for coupling with amines or alcohols. The N-methyl group blocks the otherwise reactive N–H position, preventing unwanted N-alkylation and directing reactivity to the carbon framework.

Handling, Storage, and Safety Considerations

As with all research reagents, appropriate laboratory safety practices must be followed when handling 5-Bromo-1-methyl-1H-indole-3-carboxylic acid. Always consult the current Safety Data Sheet (SDS) provided by Aladdin Scientific before use. General precautions include wearing appropriate personal protective equipment (PPE) such as nitrile gloves, a laboratory coat, and safety goggles.

Storage: Store the compound in a tightly sealed container in a cool, dry, and well-ventilated location, away from moisture, heat sources, and incompatible reagents such as strong oxidizers and strong bases. Specific storage temperature recommendations should be confirmed on the product label and SDS. When not in use, ensure the container is properly resealed to prevent moisture uptake, which can lead to degradation.

Disposal: Dispose of the compound and any contaminated materials in accordance with applicable local, national, and institutional regulations. Do not pour chemical waste down the drain without authorization from your institution's environmental health and safety office.

Research and Synthetic Applications

5-Bromo-1-methyl-1H-indole-3-carboxylic acid serves primarily as a versatile building block in synthetic organic and medicinal chemistry. Its utility derives from two orthogonal reactive handles: the aryl bromide at C-5 and the carboxylic acid at C-3.

Cross-coupling chemistry: The C-5 aryl bromide is an excellent partner for palladium-catalyzed reactions including Suzuki–Miyaura (boronic acids), Sonogashira (terminal alkynes), Heck (alkenes), and Buchwald–Hartwig (amines) couplings. These transformations allow systematic introduction of diverse aryl, heteroaryl, alkynyl, and amino substituents, facilitating structure–activity relationship (SAR) exploration in drug discovery.

Amide and ester synthesis: The carboxylic acid can be converted to amides using standard coupling reagents (e.g., HATU, EDC/HOBt, T3P) or to esters under acidic or coupling conditions. Amide-containing indole derivatives represent a common pharmacophore in bioactive molecules targeting a variety of biological pathways.

The N-methyl group not only blocks N–H reactivity but also improves metabolic stability and membrane permeability compared to N–H indoles — properties that are advantageous in the design of drug candidates.

Purity, Quality, and Ordering Information

Aladdin Scientific supplies 5-Bromo-1-methyl-1H-indole-3-carboxylic acid under SKU B193218. Each lot is quality-controlled to ensure suitability for research applications. A Certificate of Analysis (CoA) is available for each batch and includes data such as purity (typically assessed by HPLC or NMR), appearance, and identity confirmation. Researchers are encouraged to request the CoA for their specific lot number to verify compliance with experimental requirements.

For bulk quantities, custom packaging, or specific purity grades, please contact Aladdin Scientific's technical sales team. Pricing and availability information can be found on the product page or obtained from your regional Aladdin Scientific representative. Orders may be placed online through the Aladdin Scientific website or via purchase order through established procurement channels.