Ethyl 2-amino-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate

Name: Ethyl 2-amino-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate
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CAS No. 174072-89-0
Cat. No. CS-0099673
Purity≥98%
MDL No.None

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Ethyl 2-amino-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate|CS-0099673

Structure of 174072-89-0

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General Information

CAS No. 174072-89-0
Cat. No. CS-0099673
Purity ≥98%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₁₄N₂O₄S
Molecular Weight 306.34
Synonym(s) ETHYL 2-AMINO-4-METHYL-5-(4-NITRO-PHENYL)-THIOPHENE-3-CARBOXYLATE
SMILES O=C(C1=C(N)SC(C2=CC=C([N+]([O-])=O)C=C2)=C1C)OCC

Description

Ethyl 2-amino-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate features a fused thiophene core bearing a nitro-substituted aryl group and an aminoalkyl side chain, enabling direct incorporation into heterocyclic scaffolds. This electron-deficient, bench-stable building block facilitates transition-metal-catalyzed coupling reactions and serves as a key intermediate in the synthesis of bioactive thienyl compounds.

Application

Ethyl 2-amino-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate serves as a versatile building block in the synthesis of functionalized thiophene derivatives. The molecule combines a reactive amino group, a methyl substituent, and a nitroaryl moiety, enabling diverse transformations including Suzuki-Miyaura coupling, nucleophilic substitution, and reductive amination. Its bench-stable nature and compatibility with standard purification methods facilitate efficient incorporation into complex heterocyclic scaffolds relevant to medicinal chemistry and materials science.

Synthesis

Route1
- 5332-96-7
- 105-56-6
- ~69%
- In-stock
  
  174072-89-0
References
- Sasaki, Satoshi; Cho, Nobuo; Nara, Yoshi; Harada, Masataka; Endo, Satoshi; Suzuki, Nobuhiro; Furuya, Shuichi; Fujino, Masahiko Journal of Medicinal Chemistry, 2003 , vol. 46, # 1 p. 113 - 124
Route2
- 5332-96-7
- ~52%
- In-stock
  
  174072-89-0
References
- Takeda Chemical Industries, Ltd. Patent: US5817819 A1, 1998 ;

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 95.46
LogP 3.39062
H_Acceptors 6
H_Donors 1
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Thiophene compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Ethyl 2-amino-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate

CAS No. 174072-89-0

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