6-Bromo-2-methyl-1,3-benzothiazole: Properties & Lab FAQ

6-Bromo-2-methyl-1,3-benzothiazole is a halogenated benzothiazole derivative widely used as a versatile building block in medicinal chemistry, agrochemical research, and heterocyclic synthesis.

CAS Number

7166-19-0

Molecular Formula

C8H6BrNS

Molecular Weight

228.11 g/mol

Appearance

Pale yellow to off-white solid

Key Functional Groups

Aryl bromide, benzothiazole ring, 2-methyl substituent

Aladdin SKU

B185010

Overview and Chemical Structure

6-Bromo-2-methyl-1,3-benzothiazole (CAS 7166-19-0) is a bicyclic heterocyclic compound consisting of a benzene ring fused with a thiazole ring bearing a bromine substituent at the 6-position and a methyl group at the 2-position. The benzothiazole scaffold is a privileged structure in drug discovery, known for its presence in a wide range of biologically active molecules. The 6-bromo substituent provides a reactive handle for palladium-catalyzed cross-coupling reactions such as Suzuki, Sonogashira, and Buchwald–Hartwig couplings, while the 2-methyl group can be further functionalized through oxidation or halogenation.

Physical Properties and Solubility

6-Bromo-2-methyl-1,3-benzothiazole is typically obtained as a pale yellow to off-white crystalline solid at room temperature. Its molecular weight is 228.11 g/mol (molecular formula C8H6BrNS). The compound is generally sparingly soluble in water due to its lipophilic aromatic character. It shows good solubility in common organic solvents including dichloromethane (DCM), dimethyl sulfoxide (DMSO), tetrahydrofuran (THF), acetonitrile, and ethyl acetate. For biological assay applications requiring aqueous media, dissolution in DMSO followed by dilution into aqueous buffer is the recommended approach. Researchers should verify solubility empirically at the concentrations required for their specific applications.

Storage and Handling

Store 6-Bromo-2-methyl-1,3-benzothiazole in a tightly sealed container away from light, heat, and moisture at room temperature or under refrigeration (2–8 °C) to maintain long-term stability. As with all organobromine compounds, standard laboratory safety precautions should be followed: use appropriate personal protective equipment (PPE) including gloves, lab coat, and eye protection. Handle in a well-ventilated area or fume hood. Consult the Safety Data Sheet (SDS) for complete hazard information before use. The compound should be kept away from strong oxidizing agents and strong bases.

Synthetic Applications and Reactivity

The primary synthetic utility of 6-Bromo-2-methyl-1,3-benzothiazole lies in its dual electrophilic reactivity. The aryl C–Br bond at the 6-position undergoes efficient palladium-catalyzed cross-coupling reactions, enabling the introduction of aryl, vinyl, alkynyl, and amino groups to elaborate the benzothiazole core. This makes it a valuable intermediate for constructing libraries of benzothiazole analogues in medicinal chemistry campaigns. The 2-methyl group offers orthogonal reactivity: it can be oxidized to a carboxylic acid, converted to a halomethyl group (e.g., bromomethyl), or deprotonated under strong base conditions to generate a stabilized benzylic carbanion for further C–C bond forming reactions. These combined handles make this compound a multi-functional scaffold in target-oriented and diversity-oriented synthesis.

Quality, Purity and Ordering Information

Aladdin Scientific supplies 6-Bromo-2-methyl-1,3-benzothiazole under SKU B185010. Purity is verified by standard analytical techniques including GC or HPLC analysis and NMR spectroscopy. Researchers requiring material for sensitive applications such as catalysis benchmarking or biological screening should request the Certificate of Analysis (CoA) for the specific lot number to confirm purity and analytical data. For bulk quantities or custom purity grades, please contact Aladdin Scientific's sales team. Product specification sheets and SDS documents are available on the product page.

Frequently asked questions

What is 6-Bromo-2-methyl-1,3-benzothiazole used for in organic synthesis?

It is primarily used as a bifunctional building block in medicinal and heterocyclic chemistry. The aryl bromide at C-6 enables palladium-catalyzed cross-coupling reactions (e.g., Suzuki, Sonogashira), while the 2-methyl group can be independently functionalized via oxidation or halogenation, allowing rapid diversification of the benzothiazole scaffold.

In which solvents does 6-Bromo-2-methyl-1,3-benzothiazole dissolve well?

The compound dissolves well in common organic solvents such as dichloromethane, DMSO, THF, acetonitrile, and ethyl acetate. It has poor solubility in water; for aqueous assay applications, dissolve first in DMSO and then dilute with the appropriate aqueous buffer.

What are the recommended storage conditions for 6-Bromo-2-methyl-1,3-benzothiazole?

Store the compound in a tightly closed container, protected from light and moisture, at room temperature or under refrigeration (2–8 °C). Keep away from strong oxidizing agents and strong bases. Always consult the SDS for full safety and storage guidance.

How can I confirm the purity of the batch I receive?

Request the Certificate of Analysis (CoA) corresponding to your specific lot number from Aladdin Scientific. The CoA provides analytical data including GC or HPLC purity values and other characterization data used for quality release. CoA documents can be requested via the product page or by contacting customer service.

Can the 2-methyl group of this compound be further functionalized?

Yes. The 2-methyl group on the benzothiazole ring can be oxidized to afford the corresponding carboxylic acid, subjected to radical or ionic halogenation to give bromomethyl or chloromethyl derivatives, or deprotonated under strong base conditions to generate a reactive benzylic carbanion suitable for C–C bond formation. These transformations allow the methyl group to serve as a versatile synthetic handle orthogonal to the aryl bromide.

References

1. Mtambo, S. et al. Benzothiazole: a privileged scaffold in medicinal chemistry. Review article (general textbook-level reference). Verification required.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley. General reference for cross-coupling reactions of aryl halides.
3. Aladdin Scientific Product Page: 6-Bromo-2-methyl-1,3-benzothiazole, SKU B185010. https://www.aladdin-e.com

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