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CS-W001157 4
Total: USD 88.00

Pyridine-3-sulfonyl chloride

  • CAS No. 16133-25-8

  • Cat. No. CS-W008940
  • Molecule weight177.61
  • Purity≥98%
  • MDL No.MFCD03452747

*For research and further manufacturing use only, not for direct human use.

Pyridine-3-sulfonyl chloride|CS-W008940

Structure of 16133-25-8

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General Information

  • CAS No. 16133-25-8
  • Cat. No. CS-W008940
  • Purity ≥98%
  • MDL No. MFCD03452747
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄ClNO₂S
  • Molecular Weight 177.61
  • Synonym(s) None
  • SMILES O=S(C1=CC=CN=C1)(Cl)=O

Description

Pyridine-3-sulfonyl chloride delivers a reactive sulfonyl electrophile for C–H functionalization and heterocycle synthesis. This bench-stable reagent features a nitrogen-rich pyridine scaffold that enhances solubility in polar solvents and facilitates selective coupling with nucleophiles. The para-positioned sulfonyl group enables efficient incorporation into bioactive scaffolds, offering enhanced metabolic stability and improved pharmacokinetic profiles in medicinal chemistry applications.

Application

Pyridine-3-sulfonyl chloride serves as a versatile sulfonylating agent for the efficient introduction of the pyridine-3-sulfonyl group into organic molecules. It facilitates nucleophilic substitution reactions with amines and alcohols under mild conditions, enabling rapid access to sulfonamide and sulfonate derivatives. The compound exhibits good bench stability and ease of purification, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Karaman, Rafik; Blasko, Andrei; Almarsson, Oern; Arasasingham, Ramesh; Bruice, Thomas C. Journal of the American Chemical Society, 1992 , vol. 114, # 12 p. 4889 - 4898
  • Route2

    References

    • Journal of Organic Chemistry, , vol. 68, # 21 p. 8274 - 8276
  • Route3
    • Pyridine-3-thiol|CS-0265460
      16133-26-9
    • ~81%
    • In-stock
      Pyridine-3-sulfonyl chloride|CS-W008940
      16133-25-8

    References

    • Maslankiewicz, Andrzej; Marciniec, Krzysztof; Pawlowski, Maciej; Zajdel, Pawel Heterocycles, 2007 , vol. 71, # 9 p. 1975 - 1990

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3265
Class : 8
Packing Group : Ⅱ
Hazard Statements : H314
Precautionary Statements : P280-P301+P330+P331

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Computational Chemistry Data

  • TPSA   47.03
  • LogP   1.0091
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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