2-(1,3-DIOXOLAN-2-YL)PYRIDINE-5-BORONIC ACID

Base Information

• Chemical Name: 2-(1,3-DIOXOLAN-2-YL)PYRIDINE-5-BORONIC ACID
• CAS No.: 1072952-38-5
• Molecular Formula: C8H10BNO4
• Molecular Weight: 194.983
• Hs Code.: 2933399990
• Mol file: 1072952-38-5.mol

Synonyms:[6-(1,3-DIOXOLAN-2-YL)PYRIDIN-3-YL]BORONIC ACID;2-(1,3-DIOXOLAN-2-YL)PYRIDINE-5-BORONIC ACID

Chemical Property of 2-(1,3-DIOXOLAN-2-YL)PYRIDINE-5-BORONIC ACID

Chemical Property:

• Boiling Point: 409.1±55.0 °C(Predicted)
• PKA: 4.01±0.18(Predicted)
• PSA: 71.81000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: -1.19320
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

2-(1,3-Dioxolan-2-yl)pyridine-5-boronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(1,3-DIOXOLAN-2-YL)PYRIDINE-5-BORONIC ACID

There total 3 articles about 2-(1,3-DIOXOLAN-2-YL)PYRIDINE-5-BORONIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

5-bromo-2-(1,3-dioxolane-2-yl)pyridine (884495-16-3) + Triisopropyl borate (5419-55-6) + water (7732-18-5) → (6-(1,3-dioxolan-2-yl)pyridin-3-yl)boronic acid (1072952-38-5)

Guidance literature:

5-bromo-2-(1,3-dioxolane-2-yl)pyridine; Triisopropyl borate; With n-butyllithium; In tetrahydrofuran; toluene; at -40 ℃; for 0.75h; Inert atmosphere; Cooling with acetone-dry ice;

water; With hydrogenchloride; In tetrahydrofuran; toluene; at -20 - 20 ℃;

Reference yield: 74.0%

5-bromo-2-(1,3-dioxolane-2-yl)pyridine (884495-16-3) + Triisopropyl borate (5419-55-6) → (6-(1,3-dioxolan-2-yl)pyridin-3-yl)boronic acid (1072952-38-5)

Guidance literature:

5-bromo-2-(1,3-dioxolane-2-yl)pyridine; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -78 ℃; for 0.416667h; Inert atmosphere;

Triisopropyl borate; In tetrahydrofuran; hexane; toluene; at -78 - -20 ℃; for 0.5h; Inert atmosphere;

With sodium hydroxide; In tetrahydrofuran; hexane; water; toluene; at -20 - 20 ℃; for 0.25h; Inert atmosphere;

DOI:10.1021/jacs.6b02445

Reference yield:

5-bromo-pyridine-2-carbaldehyde (31181-90-5) → (6-(1,3-dioxolan-2-yl)pyridin-3-yl)boronic acid (1072952-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid / toluene / 135 °C / Dean-Stark

2.1: n-butyllithium / toluene; hexane; tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 - -20 °C / Inert atmosphere

2.3: 0.25 h / -20 - 20 °C / Inert atmosphere

With n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; toluene;

DOI:10.1021/jacs.6b02445

upstream raw materials:

5-bromo-pyridine-2-carbaldehyde

5-bromo-2-(1,3-dioxolane-2-yl)pyridine

Triisopropyl borate

water