Methyl 6-nitro-1H-indazole-4-carboxylate

Name: Methyl 6-nitro-1H-indazole-4-carboxylate
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CAS No. 885518-55-8
Cat. No. CS-0042030
Purity≥95%
MDL No.MFCD07781324

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Methyl 6-nitro-1H-indazole-4-carboxylate|CS-0042030

Structure of 885518-55-8

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General Information

CAS No. 885518-55-8
Cat. No. CS-0042030
Purity ≥95%
MDL No. MFCD07781324
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₇N₃O₄
Molecular Weight 221.17
Synonym(s) 6-NITRO-4-INDAZOLECARBOXYLIC ACID METHYL ESTER
SMILES O=C(C1=CC([N+]([O-])=O)=CC2=C1C=NN2)OC

Description

Methyl 6-nitro-1H-indazole-4-carboxylate features a fused bicyclic indazole core bearing a nitro group at the 6-position and a methyl ester at the 4-position. This electron-deficient heterocycle integrates readily into synthetic sequences requiring strong acceptor functionality, offering enhanced reactivity in transition metal-catalyzed couplings and enabling efficient access to complex nitrogen-rich architectures under standard conditions.

Application

Methyl 6-nitro-1H-indazole-4-carboxylate serves as a versatile building block for the synthesis of indazole-based pharmaceuticals and agrochemicals. The nitro group at C6 enables subsequent reduction and functionalization, while the ester moiety supports palladium-catalyzed cross-coupling reactions. Its bench-stable nature and compatibility with standard protecting group strategies facilitate efficient access to complex heterocyclic scaffolds in medicinal chemistry workflows.

Synthesis

Route1
- 146948-44-9
- ~%
- In-stock
  
  885518-55-8
References
- EP2226315 A1, ; Page/Page column 44-45 ;

Safety Information

Download SDS

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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Computational Chemistry Data

TPSA 98.12
LogP 1.2577
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Indazole compounds

Key Words

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Methyl 6-nitro-1H-indazole-4-carboxylate

CAS No. 885518-55-8

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