Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate

Name: Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 1150566-27-0
Cat. No. CS-W022714
Purity≥97%
MDL No.MFCD11975600

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate|CS-W022714

Structure of 1150566-27-0

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General Information

CAS No. 1150566-27-0
Cat. No. CS-W022714
Purity ≥97%
MDL No. MFCD11975600
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₈ClN₃O₂
Molecular Weight 225.63
Synonym(s) Imidazo[1,2-b]pyridazine-3-carboxylic acid, 6-chloro-, ethyl ester
SMILES O=C(C1=CN=C2C=CC(Cl)=NN21)OCC

Description

Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate is a bench-stable heterocyclic ester featuring a chlorine atom at the 6-position of an imidazo[1,2-b]pyridazine core. This electron-deficient scaffold integrates readily into medicinal chemistry campaigns, enabling direct coupling or functionalization in late-stage diversification. Its moisture-tolerant nature simplifies handling under standard conditions.

Application

Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate serves as a versatile building block for constructing imidazopyridazine scaffolds in medicinal chemistry. The chlorine at the C6 position enables palladium-catalyzed cross-coupling reactions with diverse nucleophiles, facilitating rapid diversification. Its ethyl ester group supports subsequent transformations, including hydrolysis and amidation. The compound exhibits good bench stability and is readily purified by flash chromatography, making it well-suited for high-throughput synthesis and API precursor development.

Synthesis

Route1
- 1150566-26-9
- ~74%
- In-stock
  
  1150566-27-0
References
- CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO) Patent: WO2009/60197 A1, 2009 ; Location in patent: Page/Page column 59 ; WO 2009/060197 A1
Route2
- 35053-55-5
- ~%
- In-stock
  
  1150566-27-0
References
- IRM LLC Patent: US2012/65184 A1, 2012 ; US 20120065184 A1

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

Quality Control

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Computational Chemistry Data

TPSA 56.49
LogP 1.5594
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Key Words

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Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate

CAS No. 1150566-27-0

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