8-Chloro-6-(trifluoromethyl)imidazo-[1,2-a]pyridine-2-carboxylic acid

Name: 8-Chloro-6-(trifluoromethyl)imidazo-[1,2-a]pyridine-2-carboxylic acid
Brand: ChemScene
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CAS No. 353258-35-2
Cat. No. CS-0038251
Molecule weight264.59
Purity≥97%
MDL No.MFCD00831510

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8-Chloro-6-(trifluoromethyl)imidazo-[1,2-a]pyridine-2-carboxylic acid|CS-0038251

Structure of 353258-35-2

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General Information

CAS No. 353258-35-2
Cat. No. CS-0038251
Purity ≥97%
MDL No. MFCD00831510
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₄ClF₃N₂O₂
Molecular Weight 264.59
Synonym(s) 8-Chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid
SMILES C1=C(C2=NC(=CN2C=C1C(F)(F)F)C(=O)O)Cl

Description

8-Chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid features a rigid heterocyclic core combining electron-withdrawing chlorine and trifluoromethyl groups, enhancing its metabolic stability and binding affinity. This carboxylic acid moiety enables direct conjugation or salt formation for improved solubility in biological assays. The molecule’s defined electronic profile supports its use in medicinal chemistry campaigns targeting kinase inhibition and CNS-penetrant scaffolds.

Application

8-Chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid serves as a versatile heterocyclic building block for medicinal chemistry and catalytic research. Its fused imidazopyridine core exhibits enhanced metabolic stability and favorable pharmacokinetic properties. The carboxylic acid group enables direct derivatization via amide coupling or esterification, while the chloro and trifluoromethyl substituents provide orthogonal functional handles for cross-coupling reactions. This compound demonstrates excellent bench stability and compatibility with standard purification techniques, facilitating its use in high-throughput synthesis of bioactive molecules.

Synthesis

Route1
- In-stock
  
  353258-31-8
- ~82%
- In-stock
  
  353258-35-2
References
- EXELIXIS, INC.; CANNE BANNEN, Lynne; CHAN, Diva Sze-ming; GU, Xiao-hui; MAC, Morrison, B.; NG, Stephanie; WANG, Tie-lin; WANG, Yong; XU, Wei Patent: WO2010/65760 A1, 2010 ; Location in patent: Page/Page column 102 ; WO 2010/065760 A1

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-P280-P302+P352

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Computational Chemistry Data

TPSA 54.6
LogP 2.7047
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Key Words

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8-Chloro-6-(trifluoromethyl)imidazo-[1,2-a]pyridine-2-carboxylic acid

CAS No. 353258-35-2

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