2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine RC00170

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:  www.cnroyalchem.com

【  Providing a complete set of intermediates and impurities for  Tedizolid 】

【  Providing a complete set of intermediates and impurities for  Tedizolid 】

【  Providing a complete set of intermediates and impurities for  Tedizolid 】

Product Name:  2-(2-Methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 

CAS Registry Number:  1056039-83-8 

Synonyms: 5-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)-2-methyl-2H-tetrazole

2-Methyl-5-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]-2H-tetrazole

5-(Pyridin-2-yl)-2-methyl-2H-tetrazole-5-boronic acid pinacol ester

2-(2-Methyltetrazol-5-yl)-5-(pinacolboranyl)pyridine

(6-(2-Methyl-2H-tetrazol-5-yl)pyridin-3-yl)boronic acid pinacol ester

Molecular Formula:  C₁₇H₂₁BN₅O₂ 

Molecular Weight:  329.19 g/mol

Key Features

Boronic Ester (Pinacol Boronate):  Contains the stable, air-handleable  4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacol boronate ester)  protecting group at the pyridine 5-position. This protects the boronic acid functionality while enabling its use in transition metal-catalyzed cross-coupling reactions (e.g., Suzuki-Miyaura coupling).

Tetrazole Heterocycle:  Features a  2-methyl-2H-tetrazol-5-yl  substituent attached directly to the pyridine ring at the 2-position. Tetrazoles are important heterocycles in medicinal chemistry, often acting as bioisosteres for carboxylic acids or providing metabolic stability and enhancing binding affinity.

Bifunctional Molecule:  Combines the reactivity of an aryl boronic ester (for cross-coupling) with the distinct physicochemical and biological properties of a tetrazole moiety. This makes it a valuable  building block  for synthesizing more complex molecules, particularly in pharmaceutical research and agrochemical development.

Heteroaryl Building Block:  Belongs to a class of valuable heteroarylboronic esters used extensively in drug discovery and materials science.

Potential Applications

Pharmaceutical Intermediates:  Primarily used as a key synthetic intermediate for the preparation of Active Pharmaceutical Ingredients (APIs) or candidates, especially those incorporating both pyridine and tetrazole pharmacophores. Common targets include kinase inhibitors, receptor antagonists, and other biologically active heterocyclic compounds.

Suzuki-Miyaura Coupling:  The pinacol boronate group readily participates in palladium-catalyzed cross-coupling reactions with aryl or heteroaryl halides (or pseudohalides like triflates) to form new biaryl or heterobiaryl linkages. This allows for the efficient introduction of the 2-(2-methyltetrazol-5-yl)pyridin-5-yl scaffold onto more complex molecules.

Medicinal Chemistry Exploration:  Used as a building block for creating libraries of compounds for structure-activity relationship (SAR) studies targeting various therapeutic areas.

Agrochemical Synthesis:  Potential intermediate in the development of novel pesticides or herbicides.

Material Science:  Possible precursor for functional materials like organic semiconductors or metal-organic frameworks (MOFs), though less common than pharmaceutical uses.

Physical Properties (Typical/Expected)

Appearance:  White to off-white solid.

Solubility:  Soluble in common organic solvents such as Dichloromethane (DCM), Chloroform, Dimethylformamide (DMF), Dimethyl Sulfoxide (DMSO), Tetrahydrofuran (THF), and Acetonitrile. Generally insoluble in water.

Melting Point:  Specific value varies based on purity and polymorphic form; typically reported in the range of 120-180°C (exact value requires specification from the supplier/lot).

Stability:  The boronic ester is relatively stable to air and moisture compared to the free boronic acid, allowing for easier handling and storage under standard conditions. However, prolonged exposure to air/moisture or acidic/basic conditions should be avoided. Store under inert atmosphere (N₂ or Ar) at low temperatures (< -15°C or refrigerated) for long-term stability.  Light-sensitive.

Storage Recommendations

Store in a cool, dry place.

Keep container tightly sealed under an inert atmosphere (nitrogen or argon).

Recommended storage temperature:  -15°C to -20°C (Freezer)  or  2-8°C (Refrigerator)  for optimal long-term stability.

Protect from light and moisture.

Handling Precautions

Safety Data Sheet (SDS):  Consult the specific Safety Data Sheet (SDS) provided by the supplier before handling.

Personal Protective Equipment (PPE):  Wear appropriate PPE including safety glasses, gloves (chemical-resistant, e.g., nitrile), and a lab coat.

Handling:  Handle in a well-ventilated area, preferably within a fume hood. Avoid contact with skin, eyes, and clothing. Avoid breathing dust or vapors. Avoid ingestion.

Incompatibilities:  Avoid strong oxidizing agents, strong acids, and strong bases which may degrade the boronate ester or the tetrazole ring.