3-Pyridinesulfonyl chloride
[CAS# 16133-25-8]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic acid halide
• Name: 3-Pyridinesulfonyl chloride
• Synonyms: m-Pyridinesulfonyl chloride
• Molecular Formula: C₅H₄ClNO₂S
• Molecular Weight: 177.61
• CAS Registry Number: 16133-25-8
• EC Number: 688-270-1
• SMILES: C1=CC(=CN=C1)S(=O)(=O)Cl

Properties

• Density: 1.488
• Boiling point: 284 °C
• Flash point: 126 °C

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314

Discovery and Applications

3-Pyridinesulfonyl chloride, also known as sulfonyl chloride of 3-pyridine, was first synthesized through organic synthesis methodologies aimed at functionalizing pyridine derivatives. The discovery of this compound can be traced back to the mid-20th century, as chemists sought to explore the reactivity and potential applications of various sulfonamide derivatives. By reacting pyridine with sulfuryl chloride (SO2Cl2), chemists successfully introduced a sulfonyl chloride group onto the pyridine ring, yielding 3-pyridinesulfonyl chloride. This compound's discovery laid the foundation for further investigations into its chemical properties and potential applications in organic synthesis and medicinal chemistry.

3-Pyridinesulfonyl chloride serves as a versatile building block in organic synthesis, enabling the introduction of the sulfonyl chloride functional group onto various organic molecules. Its reactivity allows for the selective modification of other functional groups, such as amines and alcohols, through nucleophilic substitution reactions, facilitating the synthesis of complex organic compounds. Sulfonyl chlorides, including 3-pyridinesulfonyl chloride, are commonly used as protecting groups in organic synthesis to temporarily mask reactive functional groups. By selectively blocking specific sites within a molecule, sulfonyl chloride groups prevent undesired reactions during synthetic transformations, enabling the controlled synthesis of target compounds.

3-Pyridinesulfonyl chloride derivatives serve as valuable intermediates in the synthesis of pharmaceutical compounds, particularly in the development of sulfa drugs and other therapeutic agents. The incorporation of sulfonyl chloride moieties into drug molecules can enhance their pharmacological properties, such as improving solubility, bioavailability, or target specificity. Sulfonyl chloride functional groups are utilized in bioconjugation chemistry for linking drugs or diagnostic agents to targeting molecules, such as antibodies or peptides. Conjugation via sulfonyl chloride chemistry enables the site-specific attachment of payloads to targeting vectors, facilitating the development of targeted drug delivery systems and molecular imaging probes.

Sulfonyl chloride groups are employed in surface modification strategies to functionalize materials and improve their properties. By covalently attaching sulfonyl chloride-containing molecules to surfaces, such as polymers or nanoparticles, researchers can tailor surface characteristics, such as wettability, adhesion, and biocompatibility, for specific applications in coatings, membranes, or biomedical devices. Sulfonyl chloride compounds, including 3-pyridinesulfonyl chloride derivatives, are utilized as crosslinking agents in polymer chemistry to form strong chemical bonds between polymer chains. This crosslinking imparts mechanical strength, thermal stability, and chemical resistance to polymer materials, making them suitable for applications in adhesives, sealants, and advanced composites.

Ongoing research focuses on exploring the chemical reactivity and synthetic applications of 3-pyridinesulfonyl chloride and its derivatives. Chemists investigate novel reaction pathways and catalyst systems to expand the scope and efficiency of sulfonyl chloride chemistry in organic synthesis. In medicinal chemistry, efforts are underway to develop new pharmaceutical agents incorporating 3-pyridinesulfonyl chloride scaffolds for various therapeutic indications, including cancer, inflammation, and infectious diseases. Rational drug design approaches utilize computational modeling and structure-activity relationship studies to optimize the pharmacological properties of sulfonyl chloride-based compounds.

References

1939. Derivate der Pyridin-3-sulfosäure. Monatshefte für Chemie und verwandte Teile anderer Wissenschaften, 70, 312-320.
DOI: 10.1007/bf02716118

2021. Recent advances in analysis of bisphenols and their derivatives in biological matrices. Analytical and Bioanalytical Chemistry, 413(24), 6005-6019.
DOI: 10.1007/s00216-021-03668-y

2014. Synthesis of Several Substituted Pyridine-3-Sulfonyl Chlorides, -Sulfonic Acids, and -Sulfonyl Amides. Chemistry of Heterocyclic Compounds, 50(8), 1123-1130.
DOI: 10.1007/s10593-014-1588-y