Ethyl 2-amino-5-methylthiophene-3-carboxylate

Name: Ethyl 2-amino-5-methylthiophene-3-carboxylate
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CAS No. 4815-32-1
Cat. No. CS-W016945
Molecule weight185.24
Purity≥98%
MDL No.MFCD01922142

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Ethyl 2-amino-5-methylthiophene-3-carboxylate|CS-W016945

Structure of 4815-32-1

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General Information

CAS No. 4815-32-1
Cat. No. CS-W016945
Purity ≥98%
MDL No. MFCD01922142
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₁₁NO₂S
Molecular Weight 185.24
Synonym(s) 3-thiophenecarboxylic acid, 2-amino-5-methyl-, ethyl ester
SMILES O=C(C1=C(N)SC(C)=C1)OCC

Description

Ethyl 2-amino-5-methylthiophene-3-carboxylate features a fused thiophene core with complementary amino and methylthio substituents, enabling direct functionalization at the electron-rich C2 position. This bench-stable scaffold integrates readily into heterocyclic architectures, offering high reactivity in transition-metal-catalyzed couplings and serving as a key intermediate for bioactive molecule synthesis.

Application

Ethyl 2-amino-5-methylthiophene-3-carboxylate serves as a versatile heterocyclic building block for the synthesis of biologically relevant thieno[3,2-b]indoles and substituted thiophene derivatives. Its amino and ester functionalities enable sequential transformations—such as electrophilic substitution, palladium-catalyzed coupling, and cyclization—under mild conditions. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative medicinal chemistry campaigns and API intermediate development.

Synthesis

Route1
- 123-38-6
- 105-56-6
- ~86%
- In-stock
  
  4815-32-1
References
- Nihon Nohyaku Co., Ltd. Patent: EP1544202 A1, 2005 ; Location in patent: Page/Page column 53-54 ;
Route2
- 144918-37-6
- ~47%
- In-stock
  
  4815-32-1
References
- Iyengar, Rajesh R.; Judd, Andrew S.; Zhao, Gang; Kym, Philip R.; Sham, Hing L.; Gu, Yugui; Liu, Gang; Liu, Mei; Zhao, Hongyu; Clark, Richard F.; Frevert, Ernst U.; Cool, Barbara L.; Zhang, Tianyuan; Keyes, Robert F.; Hansen, Todd M.; Xin, Zhili Patent: US2005/38068 A1, 2005 ; Location in patent: Page/Page column 47 ; US 20050038068 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

Quality Control

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Computational Chemistry Data

TPSA 52.32
LogP 1.81542
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Thiophene compounds

Key Words

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Ethyl 2-amino-5-methylthiophene-3-carboxylate

CAS No. 4815-32-1

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