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Methyl 5-(aminomethyl)thiophene-2-carboxylate

  • CAS No. 75985-18-1

  • Cat. No. CS-0289666
  • Purity≥97%
  • MDL No.None

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

Methyl 5-(aminomethyl)thiophene-2-carboxylate|CS-0289666

Structure of 75985-18-1

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General Information

  • CAS No. 75985-18-1
  • Cat. No. CS-0289666
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₉NO₂S
  • Molecular Weight 171.22
  • Synonym(s) 5-Methoxycarbonyl-2-thenylamine
  • SMILES O=C(C1=CC=C(CN)S1)OC

Description

Methyl 5-(aminomethyl)thiophene-2-carboxylate features a thiophene core functionalized with both a methyl ester and a pendant aminomethyl group, enabling direct incorporation into diverse synthetic scaffolds. This bifunctional architecture supports efficient derivatization in medicinal chemistry and materials science applications. The molecule exhibits excellent stability under standard conditions and facilitates straightforward downstream transformations.

Application

Methyl 5-(aminomethyl)thiophene-2-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to bioactive thiophene-based scaffolds. The pendant amine facilitates straightforward derivatization via alkylation, acylation, or reductive amination, while the ester group supports hydrolysis or coupling reactions. Its bench-stable nature and compatibility with standard reaction conditions make it ideal for medicinal chemistry campaigns and process development.

Synthesis

  • Route1
    • null|null
      503470-01-7
    • ~32%
    • In-stock
      Methyl 5-(aminomethyl)thiophene-2-carboxylate|CS-0289666
      75985-18-1

    References

    • Casagrande, Manolo; Barteselli, Anna; Basilico, Nicoletta; Parapini, Silvia; Taramelli, Donatella; Sparatore, Anna Bioorganic and Medicinal Chemistry, 2012 , vol. 20, # 19 p. 5965 - 5979
  • Route2

    References

    • Rueckle, Thomas; Biamonte, Marco; Grippi-Vallotton, Tania; Arkinstall, Steve; Cambet, Yves; Camps, Montserrat; Chabert, Christian; Church, Dennis J.; Halazy, Serge; Jiang, Xuliang; Martinou, Isabelle; Nichols, Anthony; Sauer, Wolfgang; Gotteland, Jean-Pierre Journal of Medicinal Chemistry, 2004 , vol. 47, # 27 p. 6921 - 6934
  • Route3

    References

    • Rueckle, Thomas; Biamonte, Marco; Grippi-Vallotton, Tania; Arkinstall, Steve; Cambet, Yves; Camps, Montserrat; Chabert, Christian; Church, Dennis J.; Halazy, Serge; Jiang, Xuliang; Martinou, Isabelle; Nichols, Anthony; Sauer, Wolfgang; Gotteland, Jean-Pierre Journal of Medicinal Chemistry, 2004 , vol. 47, # 27 p. 6921 - 6934

Safety Information

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GHS Pictogram : N/A
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UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

  • TPSA   52.32
  • LogP   0.9934
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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