281221-71-4

Basic information

• Product Name: 6-METHYL-PYRIDINE-2-SULFONYL CHLORIDE
• Synonyms: 6-METHYL-PYRIDINE-2-SULFONYL CHLORIDE
• CAS NO: 281221-71-4
• Molecular Formula: C₆H₆ClNO₂S
• Molecular Weight: 191.64
• Mol File: 281221-71-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 294.0±28.0 °C(Predicted)
• Appearance: /
• Density: 1.413±0.06 g/cm3(Predicted)
• PKA: -4.41±0.19(Predicted)
• CAS DataBase Reference: 6-METHYL-PYRIDINE-2-SULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHYL-PYRIDINE-2-SULFONYL CHLORIDE(281221-71-4)
• EPA Substance Registry System: 6-METHYL-PYRIDINE-2-SULFONYL CHLORIDE(281221-71-4)

Safety Data

• Hazardous Substances Data: 281221-71-4(Hazardous Substances Data)

Upstream product

• 112498-22-3 2-(benzylsulfanyl)-6-methylpyridine 
• 18368-63-3 6-chloro-2-picoline 
• 18368-57-5 2-mercapto-6-methylpyridine 

Downstream Products

• 28369-92-8 2-methyl-6-phenoxypyridine 
• 1321517-90-1 4-(6-methylpyridin-2-yl)morpholine 
• 4385-63-1 2-(4-methoxyphenyl)-6-methyl-pyridine 
• 387827-69-2 2-(4-fluorophenyl)-6-methylpyridine 

Relevant articles and documents

Desulfonative Suzuki–Miyaura Coupling of Sulfonyl Fluorides

Sulfonyl fluorides have emerged as powerful “click” electrophiles to access sulfonylated derivatives. Yet, they are relatively inert towards C?C bond forming transformations, notably under transition-metal catalysis. Here, we describe conditions under which aryl sulfonyl fluorides act as electrophiles for the Pd-catalyzed Suzuki–Miyaura cross-coupling. This desulfonative cross-coupling occurs selectively in the absence of base and, unusually, even in the presence of strong acids. Divergent one-step syntheses of two analogues of bioactive compounds showcase the expanded reactivity of sulfonyl fluorides to encompass both S?Nu and C?C bond formation. Mechanistic experiments and DFT calculations suggest oxidative addition occurs at the C?S bond followed by desulfonation to form a Pd-F intermediate that facilitates transmetalation.

Transition-Metal-Catalyzed Transformation of Sulfonates via S-O Bond Cleavage: Synthesis of Alkyl Aryl Ether and Diaryl Ether

The catalytic conversion of sulfonates, a versatile class of pharmaceutical intermediates, is usually based on C-O bond cleavage. In this paper, however, we discover a rare transformation of sulfonates via S-O bond cleavage catalyzed by transition metal, through which alkyl sulfonates could undergo an intramolecular desulfitative C-O coupling to form aryl alkyl ethers in the presence of a nickel catalyst. Meanwhile, aryl sulfonates perform similarly to give diaryl ethers catalyzed by a palladium complex. This transformation could tolerate a wide range of functionalities. Controlled experiments reveal that the 2-pyridyl group is necessary to promote the reaction as designed. Crossover experiments proved that this transformation might proceed partly in an intermolecular pathway.

DERIVATIVES OF HETEROARYLSULFONAMIDES, THEIR PREPARATION AND THEIR APPLICATION IN HUMAN THERAPY

The present invention concerns derivatives of heteroarylsulfonamides, notably as blockers of Kv potassium channels, and more particularly of channels Kv1.5, Kv4.3 or Kv11.1, their application in clinical therapy and their preparation methods. These compounds correspond to the following general formula (I): where R1 represents one or more substituents of the phenyl core X such as: hydrogen, halogen, trifluoromethyl, trifluoromethoxy, linear or branched C1-C4 alkyl, or linear or branched C1-C4 alkoxy, A represents oxygen or sulphur, B represents nitrogen when n=1 or 2 and D represents —C(═O)—, or B represents CH when n=0 and D represents —CH2O— or when n=1 and D represents —O—, R2 represents a hydrogen, a methyl, a fluorine or chlorine atom or a methoxy, HetAr represents a pyridyl or quinolyl group, possibly substituted by a group such as a linear or branched C1-C4 alkyl, a linear or branched C1-C4 alkoxy, a halogen, or a trifluoromethyl, and to their pharmaceutically acceptable salts.