6-Chloroimidazo[1,2-b]pyridazine-3-carbaldehyde 98% Purity Chlorinated Heterocyclic Aldehyde Building Block Drug Discovery and Organic Synthesis Key I

Product Overview

6-Chloroimidazo[1,2-b]pyridazine-3-carbaldehyde (CAS 154578-26-4) is a high‑purity chlorinated heterocyclic building block featuring an imidazo[1,2‑b]pyridazine core with a chlorine atom at the 6‑position and an aldehyde functionality at the 3‑position. The molecular formula is C₇H₄ClN₃O with a molecular weight of 181.58 g/mol. The aldehyde group serves as a versatile handle for reductive amination, Wittig reactions, Knoevenagel condensations, and other transformations. The chlorine atom provides an additional site for derivatization through SNAr or cross‑coupling reactions. Supplied at ≥98.0% purity.

Synthetic Process

The synthesis of 6‑chloroimidazo[1,2‑b]pyridazine‑3‑carbaldehyde typically involves the construction of the imidazopyridazine core followed by formylation at the 3‑position. A representative synthetic route is described below:

• Step 1 – Core Construction: An appropriately substituted aminopyridazine derivative is condensed with an α‑halo carbonyl compound to form the imidazo[1,2‑b]pyridazine ring system.

• Step 2 – Chlorination: The 6‑position is chlorinated using a suitable chlorinating agent.

• Step 3 – Formylation: The aldehyde group is introduced at the 3‑position through Vilsmeier‑Haack formylation or other formylation methods.

• Step 4 – Purification: The crude product is purified by recrystallization or column chromatography to achieve ≥98% purity.

• Quality Control: The final product is rigorously characterized by HPLC, ¹H‑NMR, ¹³C‑NMR, and mass spectrometry.

Mechanism of Action

As a synthetic building block, 6‑chloroimidazo[1,2‑b]pyridazine‑3‑carbaldehyde serves as a versatile precursor for:

• Reductive Amination: The aldehyde group can be reacted with amines in the presence of reducing agents to form secondary and tertiary amines.

• C‑C Bond Formation: The aldehyde enables Wittig, Knoevenagel, and aldol reactions for the introduction of diverse substituents.

• Heterocycle Synthesis: The aldehyde can be used for the construction of additional heterocyclic rings.

  Packaging & Shipping

  • Research quantities: Available in 1g, 5g, 10g, and 25g amber glass vials.

  • Bulk quantities: Available in 100g, 500g, and 1kg amber glass bottles.

  • Shipping conditions: This product is not classified as dangerous goods.

  • Storage conditions: Store at 2‑8°C, protected from light and moisture .

    Parameter	Specification	Details
    Product Name	6‑Chloroimidazo[1,2‑b]pyridazine‑3‑carbaldehyde	Chlorinated heterocyclic aldehyde
    CAS Number	154578‑26‑4	154578‑26‑4
    Molecular Formula	C₇H₄ClN₃O	7 carbons, 4 hydrogens, 1 chlorine, 3 nitrogens, 1 oxygen
    Molecular Weight	181.58 g/mol	—
    Appearance	Off‑white to pale yellow crystalline powder	Visual inspection
    Purity	≥98.0%	HPLC area normalization
    Storage Condition	2‑8°C, protected from light	Cool, dry place
    Shelf Life	24 months	From date of manufacture
    Packaging	1g, 5g, 10g, 25g, 100g, 500g, 1kg	Amber glass vials/bottles
    Grade	Research Grade, Reagent Grade	For laboratory and R&D use only