Ethyl 7-bromo-1H-indole-2-carboxylate

Name: Ethyl 7-bromo-1H-indole-2-carboxylate
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CAS No. 16732-69-7
Cat. No. CS-W004711
Purity≥96%
MDL No.MFCD04972046

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Ethyl 7-bromo-1H-indole-2-carboxylate|CS-W004711

Structure of 16732-69-7

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Description

Ethyl 7-bromo-1H-indole-2-carboxylate features a brominated indole core with a strategically positioned ester group, enabling direct functionalization in cross-coupling reactions. The electron-deficient indole ring enhances reactivity in palladium-catalyzed transformations, while the bench-stable ethyl ester facilitates handling and purification under standard conditions. This compound serves as a key intermediate for synthesizing biologically active indole derivatives.

Application

Ethyl 7-bromo-1H-indole-2-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling direct functionalization at the C7 position via palladium-catalyzed cross-coupling reactions. The bromo group exhibits high reactivity in Suzuki, Stille, and Negishi transformations, while the indole core supports electrophilic substitution at C3 and compatibility with standard protecting group strategies. Bench-stable and readily purified by flash chromatography, it facilitates efficient access to substituted indole scaffolds relevant to medicinal chemistry and materials science.

General Information

CAS No. 16732-69-7
Cat. No. CS-W004711
Purity ≥96%
MDL No. MFCD04972046
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₀BrNO₂
Molecular Weight 268.11
Synonym(s) ETHYL 7-BROMOINDOLE-2-CARBOXYLATE; Ethyl 7-bromo-1H-indole-2-carboxylate
SMILES O=C(C(N1)=CC2=C1C(Br)=CC=C2)OCC

Computational Chemistry Data

TPSA 42.09
LogP 3.1071
H_Acceptors 2
H_Donors 1
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-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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Ethyl 7-bromo-1H-indole-2-carboxylate

CAS No. 16732-69-7

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