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CS-W001157 4
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4-(5-Methyl-3-phenylisoxazol-4-yl)benzene-1-sulfonyl chloride

  • CAS No. 509074-26-4

  • Cat. No. CS-0186875
  • Purity≥97%
  • MDL No.MFCD26385552

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

4-(5-Methyl-3-phenylisoxazol-4-yl)benzene-1-sulfonyl chloride|CS-0186875

Structure of 509074-26-4

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General Information

  • CAS No. 509074-26-4
  • Cat. No. CS-0186875
  • Purity ≥97%
  • MDL No. MFCD26385552
  • Storage 4°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₁₂ClNO₃S
  • Molecular Weight 333.79
  • Synonym(s) Benzenesulfonyl chloride, 4-(5-methyl-3-phenyl-4-isoxazolyl)-
  • SMILES CC1=C(C(C2=CC=CC=C2)=NO1)C3=CC=C(S(=O)(Cl)=O)C=C3

Description

This sulfonyl chloride features a 4-(5-methyl-3-phenylisoxazol-4-yl)benzene scaffold, combining a sterically hindered isoxazole ring with a reactive sulfonyl chloride group. The electron-deficient aryl moiety enables efficient coupling in synthetic transformations, while the phenyl-substituted isoxazole enhances stability and solubility under standard conditions.

Application

4-(5-Methyl-3-phenylisoxazol-4-yl)benzene-1-sulfonyl chloride serves as a versatile building block for constructing sulfonamide-containing heterocycles. The isoxazole moiety provides structural rigidity and metabolic stability, while the sulfonyl chloride group enables facile derivatization via nucleophilic substitution. Its bench-stable nature and compatibility with common protecting groups facilitate integration into multi-step synthetic sequences, particularly in medicinal chemistry campaigns targeting kinase inhibitors and other bioactive scaffolds.

Synthesis

  • Route1
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      897927-43-4
    • ~%
    • In-stock
      4-(5-Methyl-3-phenylisoxazol-4-yl)benzene-1-sulfonyl chloride|CS-0186875
      509074-26-4

    References

    • THAKASHINAMOORTHY, Chandiran; JESUDOSS, Mercy, Gnanadeepam; HARIHARASUBRAMANIAN, Meera; SEETHARAMAN, Subramanian, Sankara Patent: WO2005/85218 A1, 2005 ; Location in patent: Page/Page column 9 ;
  • Route2

    References

    • Reddy, Anumula Raghupathi; Goverdhan, Gilla; Sampath, Aalla; Mukkanti, Khagga; Reddy, Padi Pratap; Bandichhor, Rakeshwar Synthetic Communications, 2012 , vol. 42, # 5 p. 639 - 649
  • Route3
    • 4,5-Dihydro-5-methyl-3,4-diphenyl-5-isoxazolol|CS-0643180
      181696-73-1
    • ~%
    • In-stock
      4-(5-Methyl-3-phenylisoxazol-4-yl)benzene-1-sulfonyl chloride|CS-0186875
      509074-26-4

    References

    • Talley, John J.; Brown, David L.; Carter, Jeffery S.; Graneto, Matthew J.; Koboldt, Carol M.; Masferrer, Jaime L.; Perkins, William E.; Rogers, Roland S.; Shaffer, Alexander F.; Zhang, Yan Y.; Zweifel, Ben S.; Seibert, Karen Journal of Medicinal Chemistry, 2000 , vol. 43, # 5 p. 775 - 777

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3261
Class : 8
Packing Group : Ⅲ
Hazard Statements : H314
Precautionary Statements : P260-P264-P280-P301+P330+P331-P304+P340-P363-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   60.17
  • LogP   4.24452
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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