Methyl 5-bromo-1H-indole-2-carboxylate

Name: Methyl 5-bromo-1H-indole-2-carboxylate
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CAS No. 210345-56-5
Cat. No. CS-0036684
Purity≥97%
MDL No.MFCD01854034

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Methyl 5-bromo-1H-indole-2-carboxylate|CS-0036684

Structure of 210345-56-5

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Description

Methyl 5-bromo-1H-indole-2-carboxylate features a brominated indole core with a methyl ester at the 2-position, enabling direct functionalization in cross-coupling and heterocyclic synthesis. The electron-deficient aryl bromide facilitates palladium-catalyzed transformations, while the bench-stable ester group supports sequential derivatization under standard conditions.

Application

Methyl 5-bromo-1H-indole-2-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling direct functionalization at the C5 position via palladium-catalyzed cross-coupling reactions. The methyl ester group provides compatibility with standard deprotection and derivatization protocols, while the bromine substituent offers high reactivity in Suzuki, Stille, and Negishi couplings. Bench-stable and readily purified by flash chromatography, it functions effectively in the construction of complex indole-based scaffolds relevant to medicinal chemistry and materials science.

General Information

CAS No. 210345-56-5
Cat. No. CS-0036684
Purity ≥97%
MDL No. MFCD01854034
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₈BrNO₂
Molecular Weight 254.08
Synonym(s) Methyl 5-bromoindole-2-carboxyate
SMILES COC(=O)C1=CC2=C(C=CC(=C2)Br)N1

Computational Chemistry Data

TPSA 42.09
LogP 2.717
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Key Words

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Methyl 5-bromo-1H-indole-2-carboxylate

CAS No. 210345-56-5

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