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Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate

  • CAS No. 72752-81-9

  • Cat. No. CS-0037414
  • Purity≥97%
  • MDL No.MFCD09261169

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

Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate|CS-0037414

Structure of 72752-81-9

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General Information

  • CAS No. 72752-81-9
  • Cat. No. CS-0037414
  • Purity ≥97%
  • MDL No. MFCD09261169
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇NO₃S
  • Molecular Weight None
  • Synonym(s) methyl 2-sulfanylidene-3H-1,3-benzoxazole-6-carboxylate
  • SMILES COC(=O)C1=CC=C2C(=C1)OC(=S)N2

Description

Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate features a fused heterocyclic core with a thioether and ester functional group, enabling direct incorporation into bioactive molecule scaffolds. The mercapto moiety offers high reactivity in cross-coupling and metal coordination, while the methyl ester provides a handle for selective derivatization under mild conditions. This compound exhibits excellent stability under ambient storage and integrates seamlessly into synthetic sequences requiring sulfur-rich motifs.

Application

Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate serves as a versatile heterocyclic building block for medicinal chemistry and materials science applications. The thiol functionality enables efficient metal-catalyzed coupling reactions, while the ester group offers compatibility with standard transformations such as hydrolysis or reduction. Its bench-stable nature and orthogonal reactivity profile facilitate integration into complex synthetic sequences.

Synthesis

  • Route1
    • null|null
      140-89-6
    • In-stock
      Methyl 4-amino-3-hydroxybenzenecarboxylate|CS-W000706
      63435-16-5
    • ~79%
    • In-stock
      Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate|CS-0037414
      72752-81-9

    References

    • Jonckers, Tim H.M.; Rouan, Marie-Claude; Hache, Geerwin; Schepens, Wim; Hallenberger, Sabine; Baumeister, Judith; Sasaki, Jennifer C. Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 15 p. 4998 - 5002
  • Route2
    • null|null
      463-71-8
    • In-stock
      Methyl 4-amino-3-hydroxybenzenecarboxylate|CS-W000706
      63435-16-5
    • ~%
    • In-stock
      Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate|CS-0037414
      72752-81-9

    References

    • WO2010/56717 A1, ; Page/Page column 41; 42 ; WO 2010/056717 A1
  • Route3

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 22, # 15 p. 4998 - 5002

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   55.23
  • LogP   2.27699
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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