Methyl 4-bromo-5-nitrothiophene-2-carboxylate

Name: Methyl 4-bromo-5-nitrothiophene-2-carboxylate
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CAS No. 31862-80-3
Cat. No. CS-0435112
Purity≥98%
MDL No.None

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Methyl 4-bromo-5-nitrothiophene-2-carboxylate|CS-0435112

Structure of 31862-80-3

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Description

Methyl 4-bromo-5-nitrothiophene-2-carboxylate features a thiophene core bearing bromine and nitro groups at adjacent positions, enabling selective functionalization via cross-coupling. The ester moiety provides solubility and reactivity in synthetic transformations. This electron-deficient heterocycle serves as a key intermediate for bioactive molecule synthesis.

Application

Methyl 4-bromo-5-nitrothiophene-2-carboxylate serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions due to its bromo group. The nitro and ester functionalities provide orthogonal reactivity for sequential transformations, including reduction, hydrolysis, or nucleophilic substitution. Its bench-stable nature and compatibility with standard reaction conditions facilitate efficient synthesis of substituted thiophenes and heterocyclic scaffolds relevant to medicinal chemistry and materials science.

General Information

CAS No. 31862-80-3
Cat. No. CS-0435112
Purity ≥98%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄BrNO₄S
Molecular Weight 266.07
Synonym(s) 2-Thiophenecarboxylic acid, 4-bromo-5-nitro-, methyl ester
SMILES O=C(C1=CC(Br)=C([N+]([O-])=O)S1)OC

Computational Chemistry Data

TPSA 69.44
LogP 2.2054
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 2

Safety Information

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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

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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 4-bromo-5-nitrothiophene-2-carboxylate

CAS No. 31862-80-3

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