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CS-W001157 4
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Ethyl 5-chlorothiazole-4-carboxylate

  • CAS No. 425392-45-6

  • Cat. No. CS-W020679
  • Purity≥95%
  • MDL No.MFCD22494956

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

Ethyl 5-chlorothiazole-4-carboxylate|CS-W020679

Structure of 425392-45-6

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General Information

  • CAS No. 425392-45-6
  • Cat. No. CS-W020679
  • Purity ≥95%
  • MDL No. MFCD22494956
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆ClNO₂S
  • Molecular Weight 191.64
  • Synonym(s) Ethyl 5-chloro-1,3-thiazole-4-carboxylate
  • SMILES O=C(C1=C(Cl)SC=N1)OCC

Description

Ethyl 5-chlorothiazole-4-carboxylate features a chlorinated thiazole core that enables direct functionalization in heterocyclic synthesis. The ester group enhances solubility and reactivity, facilitating coupling reactions under mild conditions. This bench-stable compound serves as a key intermediate for pharmaceutical and agrochemical applications, offering predictable regioselectivity in cross-coupling and cyclization processes.

Application

Ethyl 5-chlorothiazole-4-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to thiazole-based scaffolds prevalent in medicinal chemistry. The electrophilic chlorine at the 5-position facilitates nucleophilic substitution reactions, while the ester group supports further functionalization via hydrolysis or coupling protocols. Its bench-stable nature and compatibility with standard reaction conditions make it well-suited for iterative synthetic strategies and API intermediate development.

Synthesis

  • Route1

    References

    • Hodgetts, Kevin J.; Kershaw, Mark T. Organic Letters, 2002 , vol. 4, # 8 p. 1363 - 1365
  • Route2

    References

    • Beijing Molecule Science and Technology Co., Ltd. Patent: EP2039686 A1, 2009 ; Location in patent: Page/Page column 24-25 ;
  • Route3

    References

    • ELI LILLY AND COMPANY Patent: WO2005/26177 A1, 2005 ; Location in patent: Page/Page column 33; 78-79 ; WO 2005/026177 A1

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   39.19
  • LogP   1.9732
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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