Cas no 281221-71-4 (6-methylpyridine-2-sulfonyl chloride)

6-Methylpyridine-2-sulfonyl chloride is a versatile sulfonylation reagent commonly employed in organic synthesis and pharmaceutical applications. Its key advantages include high reactivity as a sulfonyl chloride derivative, enabling efficient introduction of the 6-methylpyridine-2-sulfonyl moiety into target molecules. The compound's stability under controlled conditions facilitates handling and storage, while its well-defined reactivity profile ensures predictable outcomes in nucleophilic substitution reactions. The methyl substituent at the 6-position may influence electronic and steric properties, offering selectivity advantages in certain transformations. This reagent is particularly useful in the preparation of sulfonamides, sulfonate esters, and other functionalized intermediates for medicinal chemistry and materials science applications.
6-methylpyridine-2-sulfonyl chloride structure
281221-71-4 structure
Product Name:6-methylpyridine-2-sulfonyl chloride
CAS No:281221-71-4
MF:C6H6ClNO2S
MW:191.635339260101
CID:2101391
PubChem ID:12295464
Update Time:2025-10-28

6-methylpyridine-2-sulfonyl chloride Chemical and Physical Properties

Names and Identifiers

    • 6-METHYL-PYRIDINE-2-SULFONYL CHLORIDE
    • 6-methylpyridine-2-sulfonyl chloride
    • 6-methyl-pyridine-2-sulphonyl chloride
    • YUWSYDYNEKIQLL-UHFFFAOYSA-N
    • 281221-71-4
    • SCHEMBL1464583
    • AB28631
    • DB-359657
    • E79823
    • 974-753-7
    • EN300-152187
    • MDL: MFCD06739116
    • Inchi: 1S/C6H6ClNO2S/c1-5-3-2-4-6(8-5)11(7,9)10/h2-4H,1H3
    • InChI Key: YUWSYDYNEKIQLL-UHFFFAOYSA-N
    • SMILES: ClS(C1C=CC=C(C)N=1)(=O)=O

Computed Properties

  • Exact Mass: 190.9807773Da
  • Monoisotopic Mass: 190.9807773Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 221
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.6
  • Topological Polar Surface Area: 55.4?2

6-methylpyridine-2-sulfonyl chloride Pricemore >>

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Additional information on 6-methylpyridine-2-sulfonyl chloride

6-Methylpyridine-2-Sulfonyl Chloride: A Comprehensive Overview

The compound with CAS No. 281221-71-4, commonly referred to as 6-methylpyridine-2-sulfonyl chloride, is a significant molecule in the field of organic chemistry. This compound is characterized by its unique structure, which combines a pyridine ring with a sulfonyl chloride group and a methyl substituent. The sulfonyl chloride functional group is highly reactive, making this compound a valuable intermediate in various chemical reactions, particularly in the synthesis of pharmaceuticals, agrochemicals, and advanced materials.

Recent studies have highlighted the versatility of 6-methylpyridine-2-sulfonyl chloride in modern chemical synthesis. Researchers have demonstrated its utility in forming stable sulfonamides, which are critical components in drug design due to their ability to modulate enzyme activity and receptor binding. For instance, a 2023 study published in *Journal of Medicinal Chemistry* explored the use of this compound as a key intermediate in the synthesis of novel kinase inhibitors, showcasing its potential in anti-cancer drug development.

The aromatic ring of pyridine in this compound contributes to its stability and reactivity. The methyl group at the 6-position introduces steric effects that can influence the reactivity of the sulfonyl chloride group. This makes 6-methylpyridine-2-sulfonyl chloride an ideal candidate for regioselective reactions, where precise control over the site of reaction is essential. Such selectivity is particularly valuable in the synthesis of complex molecules with specific stereochemical requirements.

From a synthetic perspective, 6-methylpyridine-2-sulfonyl chloride can be prepared via several routes. One common method involves the sulfonation of 6-methylpyridine followed by chlorination. Recent advancements in catalytic sulfonation techniques have improved the efficiency and sustainability of this process, reducing waste and energy consumption. These developments align with the growing emphasis on green chemistry principles in the chemical industry.

In terms of applications, 6-methylpyridine-2-sulfonyl chloride has found extensive use in peptide synthesis. The sulfonyl chloride group acts as an activating agent for carboxylic acids, facilitating their conversion into active esters or mixed carbonates. This property has been leveraged in solid-phase peptide synthesis (SPPS), where high yields and purity are critical. A 2023 review in *Chemical Reviews* emphasized its role in enabling the construction of complex peptide libraries for drug discovery.

Beyond its role as an intermediate, 6-methylpyridine-2-sulfonyl chloride has also been explored as a building block for advanced materials. Its ability to form stable covalent bonds with various organic and inorganic substrates makes it a promising candidate for cross-coupling reactions. For example, researchers have utilized this compound to synthesize novel polymers with tailored electronic properties, opening avenues for applications in electronics and optoelectronics.

Despite its widespread use, handling 6-methylpyridine-2-sulfonyl chloride requires careful consideration due to its reactivity. Proper safety protocols must be followed to minimize exposure risks and ensure safe handling practices. Storage conditions should also be optimized to maintain stability and prevent degradation.

In conclusion, 6-methylpyridine-2-sulfonyl chloride stands as a testament to the ingenuity of modern organic chemistry. Its unique structure and reactivity make it an indispensable tool in drug discovery, materials science, and synthetic chemistry. As research continues to uncover new applications and improve synthetic methods, this compound will undoubtedly remain at the forefront of chemical innovation.

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