2-Chloro-5-benzothiazolesulfonyl chloride
[CAS# 6608-49-7]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Thiazole, thiophene and pyridine
• Name: 2-Chloro-5-benzothiazolesulfonyl chloride
• Synonyms: 2-chloro-1,3-benzothiazole-5-sulfonyl chloride
• Molecular Formula: C₇H₃Cl₂NO₂S₂
• Molecular Weight: 268.14
• CAS Registry Number: 6608-49-7
• EC Number: 848-541-9
• SMILES: C1=CC2=C(C=C1S(=O)(=O)Cl)N=C(S2)Cl

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H314
• Safety Statements: P260-P264-P270-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P330-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

2-Chloro-5-benzothiazolesulfonyl chloride is a chemical compound belonging to the class of sulfonyl chlorides, characterized by a benzothiazole ring substituted with a chlorine atom at the 2-position and a sulfonyl chloride group attached at the 5-position. The benzothiazole core is a bicyclic heteroaromatic system composed of a benzene ring fused to a thiazole ring, which contains both sulfur and nitrogen atoms.

The compound was initially synthesized as part of research efforts focused on developing reactive sulfonyl chloride derivatives capable of serving as intermediates in organic synthesis, especially for the introduction of sulfonyl functional groups. Sulfonyl chlorides are widely used in organic chemistry due to their high reactivity with nucleophiles, enabling the formation of sulfonamides, sulfonate esters, and related derivatives.

2-Chloro-5-benzothiazolesulfonyl chloride exhibits specific reactivity stemming from the electron-withdrawing effects of the sulfonyl chloride moiety and the chlorine substituent on the benzothiazole ring. This combination influences its chemical behavior, including electrophilicity and stability, making it a valuable reagent for selective sulfonylation reactions.

In practical applications, this compound is primarily used as a sulfonylating agent to introduce the 2-chloro-5-benzothiazole sulfonyl group into target molecules. The resulting sulfonamide or sulfonate derivatives often display significant biological and pharmacological activity. Benzothiazole-containing sulfonyl derivatives are known for their roles in medicinal chemistry, where they can exhibit antimicrobial, anticancer, or enzyme inhibitory properties.

The introduction of the 2-chloro-5-benzothiazolesulfonyl group into pharmaceuticals or biologically active molecules can modulate their physicochemical properties, improve metabolic stability, or enhance target affinity. Due to these features, sulfonyl chlorides like this compound are valuable intermediates in the synthesis of bioactive compounds and drug candidates.

From a synthetic standpoint, 2-chloro-5-benzothiazolesulfonyl chloride can be prepared through chlorosulfonation of the corresponding benzothiazole derivative under controlled conditions. Its handling requires care due to the reactive sulfonyl chloride group, which readily hydrolyzes in the presence of moisture and reacts with nucleophiles, releasing hydrogen chloride gas.

In summary, 2-chloro-5-benzothiazolesulfonyl chloride is a specialized sulfonyl chloride reagent used primarily in organic synthesis to generate benzothiazole-containing sulfonamide and sulfonate derivatives. These derivatives are important in pharmaceutical chemistry and materials science for their bioactive properties and functional versatility. The compound’s unique structure and reactivity make it a useful building block in the preparation of compounds with potential therapeutic applications.

References

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