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CS-W001157 4
Total: USD 88.00

2-Mercapto-N-methylbenzamide

  • CAS No. 20054-45-9

  • Cat. No. CS-0016511
  • Purity≥95%
  • MDL No.MFCD00136334

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

2-Mercapto-N-methylbenzamide|CS-0016511

Structure of 20054-45-9

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General Information

  • CAS No. 20054-45-9
  • Cat. No. CS-0016511
  • Purity ≥95%
  • MDL No. MFCD00136334
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₉NOS
  • Molecular Weight 167.23
  • Synonym(s) 1.2-mercapto-N-methylbenzamide
  • SMILES O=C(NC)C1=CC=CC=C1S

Description

2-Mercapto-N-methylbenzamide features a thiol group adjacent to an amide functionality, enabling direct conjugation in bioconjugation workflows. The N-methyl substitution enhances metabolic stability and reduces susceptibility to hydrolysis, while the sulfur-bearing moiety facilitates selective coupling under mild conditions. This compound serves as a robust anchor for cysteine-targeted labeling in peptide and protein modification.

Application

2-Mercapto-N-methylbenzamide serves as a versatile thiol-containing building block for heterocyclic synthesis, particularly in the construction of benzothiazole scaffolds. Its reactive thiol group enables efficient coupling with electrophiles, while the N-methyl amide functionality provides enhanced metabolic stability and favorable solubility. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for medicinal chemistry campaigns and process-scale applications.

Synthesis

  • Route1
    • 2,2'-Disulfanediylbis(N-methylbenzamide)|CS-0379459
      2527-58-4
    • ~90%
    • In-stock
      2-Mercapto-N-methylbenzamide|CS-0016511
      20054-45-9

    References

    • Sengar, Raghvendra S.; Miller, Jonathan J.; Basu, Partha Dalton Transactions, 2008 , # 19 p. 2569 - 2577
  • Route2
    • null|null
      593-51-1
    • In-stock
      Methyl 2-mercaptobenzoate|CS-W017801
      4892-02-8
    • ~77%
    • In-stock
      2-Mercapto-N-methylbenzamide|CS-0016511
      20054-45-9

    References

    • Correa, Arkaitz; Tellitu, Imanol; Dominguez, Esther; SanMartin, Raul Organic Letters, 2006 , vol. 8, # 21 p. 4811 - 4813
  • Route3
    • null|null
      54705-26-9
    • ~%
    • In-stock
      2-Mercapto-N-methylbenzamide|CS-0016511
      20054-45-9

    References

    • Tetrahedron Letters, , vol. 43, # 37 p. 6537 - 6540

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H317-H318
Precautionary Statements : P261-P272-P280-P302+P352-P362+P364-P501

Quality Control

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Computational Chemistry Data

  • TPSA   29.1
  • LogP   1.3349
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   1

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