Methyl 3-amino-4-bromothiophene-2-carboxylate

Name: Methyl 3-amino-4-bromothiophene-2-carboxylate
Brand: ChemScene
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CAS No. 161833-42-7
Cat. No. CS-0041706
Molecule weight236.09
Purity≥95%
MDL No.MFCD09038329

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Methyl 3-amino-4-bromothiophene-2-carboxylate|CS-0041706

Structure of 161833-42-7

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General Information

CAS No. 161833-42-7
Cat. No. CS-0041706
Purity ≥95%
MDL No. MFCD09038329
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₆BrNO₂S
Molecular Weight 236.09
Synonym(s) None
SMILES O=C(C1=C(N)C(Br)=CS1)OC

Description

Methyl 3-amino-4-bromothiophene-2-carboxylate features a brominated thiophene core with complementary amino and ester functionalities, enabling direct integration into cross-coupling and heterocyclic synthesis. The electron-rich amine group facilitates nucleophilic transformations, while the bromine serves as a reliable coupling handle under palladium catalysis. This bench-stable scaffold supports rapid diversification in medicinal chemistry and materials development.

Application

Methyl 3-amino-4-bromothiophene-2-carboxylate serves as a versatile building block for heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its bromine handle. The amino and ester functionalities provide orthogonal reactivity, facilitating sequential transformations in medicinal chemistry and materials science. Bench-stable and readily purified by column chromatography, it supports efficient access to substituted thiophene scaffolds relevant to API development.

Synthesis

Route1
- In-stock
  
  22288-78-4
- ~33%
- In-stock
  
  161833-42-7
References
- LAILA NUTRACEUTICALS Patent: US2010/68178 A1, 2010 ; Location in patent: Page/Page column 12 ;

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 1.8794
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Thiophene compounds

Key Words

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Methyl 3-amino-4-bromothiophene-2-carboxylate

CAS No. 161833-42-7

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