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5-chloro-3-iodo-1H-pyrazolo[4,3-b]pyridine
$400.00
CAS No.: 1357945-27-7
Catalog No.: 195651
Purity: 95%
MF: C6H3ClIN3
MW: 279.468
Storage: 2-8 degree Celsius
SMILES: ClC1=CC=C2C(=N1)C(=NN2)I
Catalog No.: 195651
Purity: 95%
MF: C6H3ClIN3
MW: 279.468
Storage: 2-8 degree Celsius
SMILES: ClC1=CC=C2C(=N1)C(=NN2)I
5-chloro-3-iodo-1H-pyrazolo[4,3-b]pyridine; CAS No.: 1357945-27-7; 5-chloro-3-iodo-1H-pyrazolo[4,3-b]pyridine. PROPERTIES: 5-Chloro-3-iodo-1H-pyrazolo[4,3-b]pyridine has molecular formula C8H4ClIN3, corresponding to a molecular weight of 312.5 g/mol. It appears as a dark yellow crystalline solid with a melting point between 185-188 C. The compound demonstrates moderate chemical stability under inert atmospheres but is sensitive to moisture and light. Recommended storage involves keeping it in nitrogen or argon atmosphere at -20 C. Safety precautions include using powder-free gloves and avoiding contact with water, as hydrolysis may release hydrochloric and hydriodic acids. The compound has a vapor pressure below 0.01 mmHg at 25 C and a density of approximately 2.0 g/mL. APPLICATIONS: This 5-chloro-3-iodo-1H-pyrazolo[4,3-b]pyridine is extensively used in modern pharmaceutical synthesis as a cross-coupling partner. The iodine substituent enables efficient Suzuki-Miyaura and Buchwald-Hartwig amination reactions to form complex polyaryl architectures common in kinase inhibitors. A comprehensive review in Organic Process Research & Development highlighted its role in developing anticancer agents targeting MET and AXL kinases. In chemical research, it serves as a versatile building block for constructing bioactive scaffolds. The chloro and iodo groups provide orthogonal reactivity for sequential coupling reactions. Additionally, the compound is utilized in the preparation of pyrazolopyridine-containing radiotracers. Research in Bioconjugate Chemistry demonstrated its utility in creating iodine-123 labeled imaging agents for visualizing neuroreceptor densities in psychiatric disorders. The chloro substituent offers a site for installing fluorescence tags for dual-modal imaging applications.
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