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CS-W001157 4
Total: USD 88.00

4,4'-Disulfanediyldibenzoic acid

  • CAS No. 1155-51-7

  • Cat. No. CS-0132069
  • Purity≥97%
  • MDL No.MFCD00045857

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

4,4'-Disulfanediyldibenzoic acid|CS-0132069

Structure of 1155-51-7

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General Information

  • CAS No. 1155-51-7
  • Cat. No. CS-0132069
  • Purity ≥97%
  • MDL No. MFCD00045857
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₀O₄S₂
  • Molecular Weight 306.35
  • Synonym(s) 4-[(4-Carboxyphenyl)disulfanyl]benzoic acid
  • SMILES O=C(O)C1=CC=C(SSC2=CC=C(C=C2)C(=O)O)C=C1

Description

4,4'-Disulfanediyldibenzoic acid features a rigid aromatic backbone linked by a disulfide bridge, enabling robust conjugation in redox-active systems. The carboxylic acid groups facilitate derivatization and metal coordination, while the disulfide bond offers reversible cleavage under reducing conditions. This structure supports applications in responsive materials and bioconjugation.

Application

4,4'-Disulfanediyldibenzoic acid serves as a robust bifunctional building block for the construction of redox-active and conjugated architectures. Its dual carboxylic acid and disulfide functionalities enable reliable coupling in peptide and polymer synthesis, while the disulfide linkage offers reversible stability under physiological conditions. The molecule exhibits excellent bench stability, facilitates straightforward purification via recrystallization, and functions effectively in standard coupling protocols, making it a practical choice for advanced material and medicinal chemistry applications.

Synthesis

  • Route1

    References

    • FUJIFILM Corporation Patent: WO2007/37039 A1, 2007 ; Location in patent: Page/Page column 70-71 ;
  • Route2
    • 4-Aminobenzoic acid Conivaptan Impurity|CS-0213989
      150-13-0
    • ~15%
    • In-stock
      4,4'-Disulfanediyldibenzoic acid|CS-0132069
      1155-51-7

    References

    • Okamura, Taka-aki; Iwamura, Taku; Yamamoto, Hitoshi; Ueyama, Norikazu Journal of Organometallic Chemistry, 2007 , vol. 692, # 1-3 p. 248 - 256
  • Route3
    • 5-Methylfuro[2,3-d]pyrimidine-2,4-diamine|CS-0757005
      67194-84-7
    • In-stock
      4-Mercaptobenzoic acid|CS-W018038
      1074-36-8
    • ~0%
    • null|null
      1217309-62-0
    • In-stock
      4,4'-Disulfanediyldibenzoic acid|CS-0132069
      1155-51-7

    References

    • Gangjee, Aleem; Jain, Hiteshkumar D.; Phan, Jaclyn; Guo, Xin; Queener, Sherry F.; Kisliuk, Roy L. Bioorganic and Medicinal Chemistry, 2010 , vol. 18, # 2 p. 953 - 961

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+P364-P405-P501

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Computational Chemistry Data

  • TPSA   74.6
  • LogP   3.8824
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   5

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