S-(Fluoromethyl) Benzenesulfonothioate: Properties & Lab Guide

S-(Fluoromethyl) benzenesulfonothioate is a specialty organosulfur electrophilic reagent bearing a fluoromethyl thioester motif, employed in synthetic chemistry for the introduction of fluoromethyl or fluoromethylthio functionalities onto nucleophilic substrates.

Product Name

S-(Fluoromethyl) benzenesulfonothioate

SKU

B1530081

Compound Class

Organosulfur electrophilic fluoromethylation reagent

Key Functional Groups

Sulfonothioate (S–S(O)₂Ph) and fluoromethyl (–CH₂F) moieties

Typical Reaction Role

Electrophilic fluoromethylating or fluoromethylthiolating agent

Storage Recommendation

Store sealed under inert atmosphere at low temperature (2–8 °C recommended); protect from moisture

Chemical Identity and Structure

S-(Fluoromethyl) benzenesulfonothioate (Aladdin SKU B1530081) is an organosulfur compound featuring a sulfonothioate backbone in which a fluoromethyl group (–CH₂F) is appended at the sulfur atom of the thioester linkage. The molecule contains both a phenylsulfonyl (PhSO₂–) moiety and a thio-ether bridge to the fluoromethyl unit, combining electrophilic sulfur character with a fluorine substituent on the methylene carbon.

The coexistence of the strongly electron-withdrawing sulfonyl group and the electronegative fluorine atom renders the carbon–sulfur bond susceptible to nucleophilic displacement, underpinning the reagent's synthetic utility. Molecular formula verification and exact molecular weight should be confirmed against the certificate of analysis supplied with each lot.

Research Applications

S-(Fluoromethyl) benzenesulfonothioate serves as a versatile building block and transfer reagent in modern synthetic and medicinal chemistry. Its principal documented research uses include:

• Electrophilic fluoromethylation: The reagent can transfer a fluoromethyl group to sulfur-, oxygen-, or carbon-centered nucleophiles, providing access to –SCH₂F, –OCH₂F, and –CH₂F containing molecules that are of high interest in drug discovery due to the metabolic stability and lipophilicity modulation conferred by fluorine.
• Fluoromethylthiolation: By acting as an SCH₂F-transfer agent, it enables installation of the fluoromethylthio (–SCH₂F) pharmacophore, a bioisostere of trifluoromethylthio (–SCF₃) and methoxy (–OCH₃) groups widely explored in agrochemical and pharmaceutical lead optimization.
• Heterocycle functionalization: The compound may be used to introduce fluorine-containing sulfur substituents onto heterocyclic scaffolds under mild base or Lewis acid conditions, expanding chemical diversity for screening libraries.

Specific reaction conditions, yields, and substrate scope should be validated in-house; users are encouraged to consult the primary synthetic literature for protocols applicable to their target substrates.

Handling, Safety, and Storage Guidelines

Personal Protective Equipment (PPE): Always handle S-(Fluoromethyl) benzenesulfonothioate wearing chemically resistant gloves (nitrile or equivalent), a laboratory coat, and safety goggles. Perform all weighing and solution preparation in a well-ventilated fume hood.

Chemical hazards: As with most organosulfur reagents, this compound may be moisture-sensitive and could release sulfur-containing volatile species upon decomposition. Consult the Safety Data Sheet (SDS) provided with the product or request it from Aladdin Scientific prior to use. Avoid exposure to moisture, heat, and strong oxidizing agents.

Storage: Store in a tightly sealed container under an inert atmosphere (nitrogen or argon) at 2–8 °C away from light and moisture. Do not store with incompatible reagents such as strong bases, strong acids, or powerful oxidants. Check the expiry date on the label; degraded material may show reduced purity and altered reactivity.

Waste disposal: Dispose of residues and solutions in accordance with local institutional and regulatory guidelines for halogenated and sulfur-containing organic waste. Do not pour down the drain.

Quality, Purity, and Analytical Verification

Aladdin Scientific supplies S-(Fluoromethyl) benzenesulfonothioate (B1530081) as a research-grade reagent. Each lot is accompanied by a Certificate of Analysis (CoA) specifying purity determined by HPLC or NMR, along with lot number, appearance, and recommended storage conditions.

Recommended in-house verification steps before use:

1. ¹H and ¹⁹F NMR: Confirm the characteristic doublet of the –CH₂F group in ¹H NMR (expected ~5.1–5.4 ppm, J ≈ 47 Hz) and the corresponding ¹⁹F NMR signal. Verify the aromatic signals consistent with a monosubstituted benzene ring.
2. HPLC purity check: A single dominant peak at the expected retention time (method-dependent) confirms absence of major impurities.
3. Melting point or appearance: Compare physical appearance (color, phase) against the CoA description to flag gross decomposition.

If analytical data deviate significantly from the CoA, contact Aladdin Scientific's technical support team for assistance or replacement under the applicable returns policy.

Ordering and Support

S-(Fluoromethyl) benzenesulfonothioate is available from Aladdin Scientific under SKU B1530081. To place an order or request a quotation, visit the Aladdin Scientific website or contact your regional sales representative. Bulk quantities and custom packaging may be available upon request.

For technical inquiries regarding applications, compatibility, or analytical data, Aladdin Scientific's scientific support team is available via email or phone. Please have the lot number and CoA available when contacting support to expedite assistance.

Related services including custom synthesis, contract research, and stability studies may be available through Aladdin Scientific's partner network. Inquire directly for current availability and lead times.

Frequently asked questions

What is S-(Fluoromethyl) benzenesulfonothioate used for in research?

It is primarily used as an electrophilic fluoromethylation or fluoromethylthiolation reagent in synthetic and medicinal chemistry. It transfers fluoromethyl (–CH₂F) or fluoromethylthio (–SCH₂F) groups to nucleophilic substrates, enabling access to fluorinated analogs with improved metabolic stability and tunable lipophilicity.

How should S-(Fluoromethyl) benzenesulfonothioate be stored to maintain stability?

Store the compound in a tightly sealed container under an inert atmosphere (nitrogen or argon) at 2–8 °C, protected from light and moisture. Avoid contact with strong acids, bases, and oxidizing agents. Always verify the purity against the Certificate of Analysis before use, especially after prolonged storage.

How can I confirm the identity and purity of S-(Fluoromethyl) benzenesulfonothioate upon receipt?

Identity can be confirmed by ¹H NMR (look for the –CH₂F doublet around 5.1–5.4 ppm with J ≈ 47 Hz) and ¹⁹F NMR. Purity is best assessed by HPLC. Compare all results against the Aladdin-supplied Certificate of Analysis (CoA) for the specific lot number received.

Is S-(Fluoromethyl) benzenesulfonothioate moisture-sensitive?

As an organosulfur reagent with an electrophilic thioester linkage, it is expected to be moisture-sensitive. All handling should be performed under anhydrous conditions in a fume hood, and solvents used in reactions should be dried appropriately. Refer to the product SDS and CoA for specific stability data.

What safety precautions are required when handling this compound?

Use chemical-resistant gloves, a laboratory coat, and safety goggles at all times. Conduct all operations in a well-ventilated fume hood. Consult the Safety Data Sheet before first use, and dispose of waste in accordance with local regulations for halogenated and sulfur-containing organic waste.

References

1. General reference for fluoromethylthiolation reagents and their synthetic applications in medicinal chemistry — specific primary literature to be identified and verified by editorial team.
2. Aladdin Scientific product page for S-(Fluoromethyl) benzenesulfonothioate, SKU B1530081. Aladdin Scientific, Shanghai.
3. Organofluorine Chemistry: Principles and Commercial Applications. R.E. Banks et al. (Eds.), Plenum Press — general textbook reference for fluorine-containing functional groups; specific edition and pages to be confirmed.

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