5-Fluoro-2-mercaptobenzothiazole: Properties, Uses & FAQs

5-Fluoro-2-mercaptobenzothiazole is a fluorinated benzothiazole thiol building block widely used in medicinal chemistry and synthetic research as a versatile electrophilic and nucleophilic coupling partner.

Chemical Name

5-Fluoro-2-mercaptobenzothiazole

Molecular Formula

C7H4FNS2

Molecular Weight

185.24 g/mol

Aladdin SKU

F181751

Key Functional Groups

Thiol (–SH), Fluorine substituent, Benzothiazole ring

Typical Storage Condition

Store in a cool, dry, well-ventilated area away from light and moisture

What Is 5-Fluoro-2-mercaptobenzothiazole?

5-Fluoro-2-mercaptobenzothiazole is an organosulfur heterocyclic compound belonging to the benzothiazole family. Its structure consists of a benzothiazole bicyclic core bearing a fluorine atom at the 5-position and a free thiol (–SH) group at the 2-position. The combination of these two functional groups makes this molecule a highly reactive and versatile intermediate in organic synthesis.

The fluorine substituent imparts unique electronic and physicochemical properties, including enhanced metabolic stability and altered lipophilicity, characteristics that are particularly valued in drug discovery programs. The thiol group, meanwhile, enables a wide range of nucleophilic reactions, disulfide bond formation, and metal coordination chemistry.

Key Research Applications

5-Fluoro-2-mercaptobenzothiazole serves as a valuable building block and intermediate across several research domains:

• Medicinal Chemistry: Used as a scaffold for the synthesis of biologically active compounds, including potential antimicrobial, antifungal, and anticancer candidates. The fluorinated benzothiazole motif is a recognized pharmacophore in drug design.
• Heterocyclic Synthesis: The thiol group at position 2 can be alkylated, oxidized, or condensed with electrophiles to construct thioether, sulfonyl, or fused heterocyclic frameworks.
• Coordination Chemistry: The compound can act as a bidentate or bridging ligand for transition metals, enabling the preparation of metal complexes with potential catalytic or biological activity.
• Chemical Biology: Thiol-containing heterocycles are employed in bioconjugation strategies and as cysteine-reactive probes in proteomics research.

Handling, Safety, and Storage Guidelines

As with most thiol-containing compounds, 5-Fluoro-2-mercaptobenzothiazole requires careful handling in a research laboratory setting:

• Personal Protective Equipment (PPE): Always wear appropriate gloves, safety goggles, and a lab coat. Work in a well-ventilated fume hood to avoid inhalation of vapors or dust.
• Storage: Store in a tightly sealed container in a cool, dry, and well-ventilated location, away from direct sunlight, moisture, and incompatible materials such as strong oxidizers and strong bases.
• Stability: Thiol groups are susceptible to aerial oxidation over time, which can lead to disulfide formation and reduced purity. Use inert-atmosphere techniques (e.g., Schlenk or glovebox) when handling long-term stock solutions if high purity is critical.
• Disposal: Dispose of this compound and its solutions in accordance with local and institutional regulations governing organosulfur chemical waste.

Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use.

Purity, Specifications, and Quality Assurance

Aladdin Scientific supplies 5-Fluoro-2-mercaptobenzothiazole (SKU: F181751) as a research-grade reagent. Key specification considerations include:

• Purity: Lot-specific purity information is available on the Certificate of Analysis (CoA) accompanying each shipment. Researchers requiring high-purity material for sensitive applications should request the CoA prior to or at the time of purchase.
• Analytical Methods: Purity is typically confirmed by techniques such as HPLC, GC, or NMR spectroscopy. Structural identity is verified by mass spectrometry and/or NMR.
• Packaging: Available in multiple pack sizes to suit both small-scale exploratory research and larger synthetic programs. Contact Aladdin Scientific for bulk quantity inquiries.

For the most current and lot-specific specifications, always refer to the product page on the Aladdin Scientific website or contact our technical support team.

Frequently asked questions

What is the molecular formula and molecular weight of 5-Fluoro-2-mercaptobenzothiazole?

The molecular formula of 5-Fluoro-2-mercaptobenzothiazole is C7H4FNS2, and its molecular weight is approximately 185.24 g/mol. These values are consistent with its bicyclic benzothiazole core substituted with fluorine at position 5 and a thiol group at position 2.

How should 5-Fluoro-2-mercaptobenzothiazole be stored to maintain its purity?

This compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated location, away from light, moisture, and oxidizing agents. Because the free thiol group is susceptible to aerial oxidation leading to disulfide formation, storage under an inert atmosphere or with an oxygen scavenger is advisable for long-term preservation of purity.

What types of chemical reactions can 5-Fluoro-2-mercaptobenzothiazole participate in?

The thiol group at the 2-position allows this compound to undergo nucleophilic substitution (thioether formation), oxidative coupling (disulfide bond formation), and condensation reactions with carbonyl-containing electrophiles. The fluorine at the 5-position can participate in nucleophilic aromatic substitution (SNAr) under appropriate conditions. Together, these reactive sites make it a highly versatile synthetic intermediate.

Is 5-Fluoro-2-mercaptobenzothiazole suitable for use in biological assays?

This compound is primarily supplied as a research-grade synthetic building block and chemical intermediate. While fluorinated benzothiazole derivatives are studied for biological activity, any use in cell-based or in vivo assays should be preceded by appropriate purity verification (CoA review), solubility assessment, and cytotoxicity profiling. Researchers should consult relevant literature and institutional biosafety guidelines before biological application.

Where can I find the Safety Data Sheet (SDS) for 5-Fluoro-2-mercaptobenzothiazole (F181751)?

The Safety Data Sheet for 5-Fluoro-2-mercaptobenzothiazole (SKU: F181751) is available on the Aladdin Scientific product page for this compound. You may also contact Aladdin Scientific customer service or technical support to request the SDS directly. Always review the SDS before handling any chemical reagent.

References

1. Aladdin Scientific Product Page: 5-Fluoro-2-mercaptobenzothiazole, SKU F181751. Aladdin Scientific.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for thiol nucleophilic reactivity and SNAr reactions.
3. Gomtsyan, A. Heterocycles in drugs and drug discovery. Chemistry of Heterocyclic Compounds, 2012. General reference for benzothiazole pharmacophore significance.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.