Methyl 3-cyano-1H-indole-5-carboxylate

Name: Methyl 3-cyano-1H-indole-5-carboxylate
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CAS No. 194490-33-0
Cat. No. CS-0654733
Molecule weight200.19
Purity≥98%
MDL No.None

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Methyl 3-cyano-1H-indole-5-carboxylate|CS-0654733

Structure of 194490-33-0

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General Information

CAS No. 194490-33-0
Cat. No. CS-0654733
Purity ≥98%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₈N₂O₂
Molecular Weight 200.19
Synonym(s) None
SMILES COC(=O)C1=CC2=C(C=C1)NC=C2C#N

Description

Methyl 3-cyano-1H-indole-5-carboxylate features a fused indole core with strategically positioned cyano and ester groups, enabling direct incorporation into heterocyclic scaffolds. The electron-deficient indole ring facilitates transition-metal-catalyzed couplings, while the methyl ester offers a handle for selective derivatization under mild conditions. This compound serves as a key intermediate in medicinal chemistry campaigns targeting kinase inhibitors and CNS-active agents.

Application

Methyl 3-cyano-1H-indole-5-carboxylate serves as a versatile building block for indole-based heterocycles, enabling efficient access to pharmaceutically relevant scaffolds. The ortho-positioned cyano and ester groups offer complementary reactivity for sequential functionalization, including nucleophilic addition, cyclization, and transition-metal-catalyzed coupling. Bench-stable and readily purified by column chromatography, it facilitates scalable synthesis of complex indole derivatives in medicinal chemistry and process development workflows.

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
Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P501

Quality Control

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Computational Chemistry Data

TPSA 65.88
LogP 1.82618
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Key Words

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Methyl 3-cyano-1H-indole-5-carboxylate

CAS No. 194490-33-0

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