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CS-W001157 4
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2-Amino-4-(trifluoromethyl)-5-(carbethoxy)thiazole

  • CAS No. 344-72-9

  • Cat. No. CS-0037014
  • Purity≥97%
  • MDL No.None

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

2-Amino-4-(trifluoromethyl)-5-(carbethoxy)thiazole|CS-0037014

Structure of 344-72-9

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General Information

  • CAS No. 344-72-9
  • Cat. No. CS-0037014
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₇F₃N₂O₂S
  • Molecular Weight 240.20
  • Synonym(s) Ethyl 2-amino-4-(trifluoromethyl)thiazole-5-carboxylate
  • SMILES O=C(C1=C(C(F)(F)F)N=C(N)S1)OCC

Description

2-Amino-4-(trifluoromethyl)-5-(carbethoxy)thiazole features a trifluoromethyl group enhancing electron-withdrawal and metabolic stability, while the carbethoxy moiety provides a handle for derivatization. This thiazole scaffold integrates into bioactive molecule design, offering robustness under standard bench conditions and compatibility with diverse synthetic transformations.

Application

2-Amino-4-(trifluoromethyl)-5-(carbethoxy)thiazole serves as a versatile building block in medicinal chemistry, enabling the synthesis of thiazole-based heterocycles with enhanced metabolic stability. The amino group facilitates nucleophilic substitution and coupling reactions, while the trifluoromethyl and carbethoxy functionalities offer favorable electronic effects and orthogonal reactivity. Its bench-stable nature and compatibility with standard synthetic protocols make it well-suited for iterative functionalization and API scaffold development.

Synthesis

  • Route1
    • In-stock
      Ethyl 2-chloro-4,4,4-trifluoroacetoacetate|CS-0121293
      363-58-6
    • null|null
      17356-08-0
    • ~85%
    • In-stock
      2-Amino-4-(trifluoromethyl)-5-(carbethoxy)thiazole|CS-0037014
      344-72-9

    References

    • SCHERING CORPORATION; TING, Pauline, C.; ASLANIAN, Robert, G.; CAPLEN, Mary Ann; CAO, Jianhua; KIM, David, Won-Shik; KIM, Hyunjin; KUANG, Rongze; LEE, Joe, F.; SCHWERDT, John, H.; WU, Heping; ZHOU, Gang; ZORN, Nicolas Patent: WO2010/59606 A2, 2010 ; Location in patent: Page/Page column 169 ;
  • Route2

    References

    • Ting, Pauline C.; Aslanian, Robert; Caplen, Mary Ann; Cao, Jianhua; Chan, Tin-Yau; Kim, David; Kim, Hyunjin; Kim, Jae-Hun; Kuang, Rongze; Lee, Joe F.; Schwerdt, John; Wu, Heping; Zorn, Nicolas Patent: US2011/224137 A1, 2011 ; US 20110224137 A1
  • Route3
    • Ethyl (Z)-3-amino-4,4,4-trifluorobut-2-enoate|CS-1720356
      141860-78-8
    • 4-Chloro-5H-1,2,3-dithiazol-5-one|CS-0529662
      65573-12-8
    • ~99%
    • In-stock
      2-Amino-4-(trifluoromethyl)-5-(carbethoxy)thiazole|CS-0037014
      344-72-9

    References

    • Park, Young Seok; Kim, Kyongtae Tetrahedron Letters, 1999 , vol. 40, # 35 p. 6439 - 6442

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   65.21
  • LogP   1.9208
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   2

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