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2-Fluoro-5-(methanesulfonyl)benzoic acid

  • CAS No. 247569-56-8

  • Cat. No. CS-M2064
  • Molecule weight218.20
  • Purity≥95%
  • MDL No.MFCD11179900

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

2-Fluoro-5-(methanesulfonyl)benzoic acid|CS-M2064

Structure of 247569-56-8

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General Information

  • CAS No. 247569-56-8
  • Cat. No. CS-M2064
  • Purity ≥95%
  • MDL No. MFCD11179900
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇FO₄S
  • Molecular Weight 218.20
  • Synonym(s) 2-Fluoro-5-(methylsulfonyl)benzoic acid; 2-Fluro-5-methanesulfonyl benzoic acid
  • SMILES OC(C1=CC(S(=O)(C)=O)=CC=C1F)=O

Description

It is employed as a reactant involved in synthesis of β-1,3-dicarbonyl aldehydes via oxidation, knoevenagel condensation using a lysine catalyst, and cycloisomerization for the synthesis of trisubstituted furans. It is also a reactant for the fluorination by HF and iodosylbenzene, intramolecular Michael addition reactions and synthesis of diols. Also applied in the synthesis of diols via reduction of aromatic and aliphatic ketos esters6 and cross-coupling reactions for stereo selective synthesis of unsymmetrical 1,4-enediones.

Application

2-Fluoro-5-(methanesulfonyl)benzoic acid serves as a versatile building block for medicinal chemistry and agrochemical synthesis, enabling direct incorporation of both fluorinated aromatic and sulfonate functionalities. The carboxylic acid group facilitates amide coupling and esterification, while the methanesulfonyl moiety provides excellent metabolic stability and modulates lipophilicity. Bench-stable and readily purified by recrystallization, it functions reliably in standard cross-coupling and electrophilic substitution workflows.

Synthesis

  • Route1

    References

    • Jolidon, Synese; Narquizian, Robert; Norcross, Roger David; Pinard, Emmanuel Patent: US2006/160788 A1, 2006 ; Location in patent: Page/Page column 12 ;
  • Route2
    • null|null
      79-11-8
    • In-stock
      5-(Chlorosulfonyl)-2-fluorobenzoic acid|CS-B0676
      37098-75-2
    • ~59%
    • In-stock
      2-Fluoro-5-(methanesulfonyl)benzoic acid|CS-M2064
      247569-56-8

    References

    • Pfleger, Christophe; Waldmeier, Pius; Wang, Shaoning Patent: US2008/221327 A1, 2008 ; Location in patent: Page/Page column 4-5 ;
  • Route3

    References

    • Pinard, Emmanuel; Alanine, Alexander; Alberati, Daniela; Bender, Markus; Borroni, Edilio; Bourdeaux, Patrick; Brom, Virginie; Burner, Serge; Fischer, Holger; Hainzl, Dominik; Halm, Remy; Hauser, Nicole; Jolidon, Synese; Lengyel, Judith; Marty, Hans-Peter; Meyer, Thierry; Moreau, Jean-Luc; Mory, Roland; Narquizian, Robert; Nettekoven, Mathias; Norcross, Roger D.; Puellmann, Bernd; Schmid, Philipp; Schmitt, Sebastien; Stalder, Henri; Wermuth, Roger; Wettstein, Joseph G.; Zimmerli, Daniel Journal of Medicinal Chemistry, 2010 , vol. 53, # 12 p. 4603 - 4614

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   71.44
  • LogP   0.9274
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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