Methyl 3-iodo-1-methyl-1H-indazole-5-carboxylate

Name: Methyl 3-iodo-1-methyl-1H-indazole-5-carboxylate
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CAS No. 1234616-44-4
Cat. No. CS-0049081
Purity≥97%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
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Methyl 3-iodo-1-methyl-1H-indazole-5-carboxylate|CS-0049081

Structure of 1234616-44-4

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General Information

CAS No. 1234616-44-4
Cat. No. CS-0049081
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₉IN₂O₂
Molecular Weight 316.10
Synonym(s) 3-iodo-1-methyl-1H-indazole-5-carboxylic acid methyl ester
SMILES COC(=O)C1=CC=C2N(C)N=C(I)C2=C1

Description

Methyl 3-iodo-1-methyl-1H-indazole-5-carboxylate is a bench-stable, moisture-tolerant building block featuring a strategically positioned iodide for cross-coupling reactions. The electron-deficient indazole core integrates readily into complex heterocyclic architectures, enabling efficient access to bioactive scaffolds in medicinal chemistry and materials science.

Application

Methyl 3-iodo-1-methyl-1H-indazole-5-carboxylate serves as a versatile building block for transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl scaffolds. The iodide functionality facilitates palladium-catalyzed coupling with boronic acids, stannanes, and other nucleophiles under standard conditions. Its methylated indazole core provides enhanced stability and solubility, while the ester group offers a handle for further derivatization. This compound exhibits excellent bench stability and is compatible with common reaction protocols in medicinal chemistry and process R&D workflows.

Synthesis

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- In-stock
  
  1234616-44-4
References
- Padilla, Fernando; Bhagirath, Niala; Chen, Shaoqing; Chiao, Eric; Goldstein, David M.; Hermann, Johannes C.; Hsu, Jonathan; Kennedy-Smith, Joshua J.; Kuglstatter, Andreas; Liao, Cheng; Liu, Wenjian; Lowrie, Lee E.; Luk, Kin Chun; Lynch, Stephen M.; Menke, John; Niu, Linghao; Owens, Timothy D.; O-Yang, Counde; Railkar, Aruna; Schoenfeld, Ryan C.; Slade, Michelle; Steiner, Sandra; Tan, Yun-Chou; Villasenor, Armando G.; Wang, Ce; Wanner, Jutta; Xie, Wenwei; Xu, Daigen; Zhang, Xiaohu; Zhou, Mingyan; Lucas, Matthew C. Journal of Medicinal Chemistry, 2013 , vol. 56, # 4 p. 1677 - 1692

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-P405-P501

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Computational Chemistry Data

TPSA 44.12
LogP 1.9645
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Indazole compounds

Key Words

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Methyl 3-iodo-1-methyl-1H-indazole-5-carboxylate

CAS No. 1234616-44-4

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