The Synthesis and Chemical Properties of 2-Amino-5-iodopyridine: An In-Depth Look
Understanding the synthesis and chemical properties of essential intermediates like 2-Amino-5-iodopyridine (CAS 20511-12-0) is fundamental for its effective application in diverse scientific and industrial sectors. Ningbo Inno Pharmchem Co., Ltd. offers an in-depth look at these critical aspects.
The synthesis of 2-Amino-5-iodopyridine typically involves the electrophilic iodination of 2-aminopyridine. Common methods include using iodine monochloride (ICl) or a combination of iodine and an oxidizing agent, such as hydrogen peroxide or nitric acid, in an acidic medium. Another prevalent approach utilizes iodine in the presence of a base or metal catalyst to achieve regioselective iodination at the 5-position of the pyridine ring. These methods are designed to yield the desired product with high purity and efficiency, minimizing side reactions and by-product formation.
Chemically, 2-Amino-5-iodopyridine exhibits properties characteristic of both an aromatic amine and an aryl halide. The electron-donating amino group activates the pyridine ring towards electrophilic substitution, while the iodine atom, being a relatively good leaving group, facilitates nucleophilic aromatic substitution and a variety of metal-catalyzed cross-coupling reactions. Its molecular weight is approximately 220.01 g/mol, and it typically appears as a light yellow crystalline solid or powder with a melting point generally in the range of 128-131°C.
The compound's solubility profile is also noteworthy. It tends to be sparingly soluble in water but soluble in various organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO). This solubility characteristic is important for selecting appropriate reaction media and for purification processes.
The reactivity of the iodine substituent is a cornerstone of its synthetic utility. For example, in Suzuki coupling reactions, it can react with boronic acids or boronate esters in the presence of a palladium catalyst to form new carbon-carbon bonds. Similarly, it can participate in Buchwald-Hartwig amination reactions to form carbon-nitrogen bonds. These transformations are critical for building complex heterocyclic structures commonly found in pharmaceuticals and advanced materials.
Ningbo Inno Pharmchem Co., Ltd. is dedicated to producing 2-Amino-5-iodopyridine of the highest quality, adhering to rigorous synthesis protocols and quality control measures. Our expertise ensures that the product supplied meets the precise specifications required for demanding research and industrial applications. When you choose to purchase 2-Amino-5-iodopyridine from us, you are assured of a reliable and high-purity intermediate.
In summary, the synthesis and chemical properties of 2-Amino-5-iodopyridine make it an exceptionally versatile intermediate. Its well-defined reaction pathways and functional group reactivity allow for its widespread use in creating diverse and complex molecules, underpinning its importance in modern chemical innovation.
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Silicon Analyst 88
“Our expertise ensures that the product supplied meets the precise specifications required for demanding research and industrial applications.”
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Bio Reader 7
“In summary, the synthesis and chemical properties of 2-Amino-5-iodopyridine make it an exceptionally versatile intermediate.”