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CS-W001157 4
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Methyl 2-aminothiophene-3-carboxylate

  • CAS No. 4651-81-4

  • Cat. No. CS-W007343
  • Purity≥97%
  • MDL No.MFCD00159547

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

Methyl 2-aminothiophene-3-carboxylate|CS-W007343

Structure of 4651-81-4

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General Information

  • CAS No. 4651-81-4
  • Cat. No. CS-W007343
  • Purity ≥97%
  • MDL No. MFCD00159547
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₇NO₂S
  • Molecular Weight 157.19
  • Synonym(s) Methyl2-aminothiophene-3-carboxylate
  • SMILES C1=CSC(=C1C(OC)=O)N

Description

Methyl 2-aminothiophene-3-carboxylate features a fused thiophene core with strategically positioned amino and ester groups, enabling direct integration into heterocyclic scaffolds. This bench-stable intermediate facilitates efficient coupling reactions and serves as a key building block in the synthesis of bioactive molecules and functional materials.

Application

Methyl 2-aminothiophene-3-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted thiophenes via palladium-catalyzed cross-coupling and electrophilic functionalization. The amino and ester groups provide orthogonal reactivity, facilitating sequential transformations. Bench-stable and readily purified by recrystallization, it functions effectively in multi-step sequences for API-relevant scaffolds.

Synthesis

  • Route1

    References

    • Hesse, Stephanie; Perspicace, Enrico; Kirsch, Gilbert Tetrahedron Letters, 2007 , vol. 48, # 30 p. 5261 - 5264
  • Route2
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      53982-98-2
    • ~%
    • In-stock
      Methyl 2-aminothiophene-3-carboxylate|CS-W007343
      4651-81-4

    References

    • Park, Chun-Ho; Lee, Chulho; Yang, Jee Sun; Joe, Bo-Young; Chun, Kwangwoo; Kim, Hyuntae; Kim, Hye Yun; Kang, Jong Soon; Lee, Jangik I.; Kim, Myung-Hwa; Han, Gyoonhee Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 12 p. 2655 - 2660
  • Route3

    References

    • Mugnaini, Claudia; Pedani, Valentina; Casu, Angelo; Lobina, Carla; Casti, Alberto; MacCioni, Paola; Porcu, Alessandra; Giunta, Daniela; Lamponi, Stefania; Solinas, Maurizio; Dragoni, Stefania; Valoti, Massimo; Colombo, Giancarlo; Castelli, Maria Paola; Gessa, Gian Luigi; Corelli, Federico Journal of Medicinal Chemistry, 2013 , vol. 56, # 9 p. 3620 - 3635

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

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Computational Chemistry Data

  • TPSA   52.32
  • LogP   1.1169
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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