DIMETHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE-2,6-DICARBOXYLATE

Base Information

• Chemical Name: DIMETHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE-2,6-DICARBOXYLATE
• CAS No.: 741709-66-0
• Molecular Formula: C15H20BNO6
• Molecular Weight: 321.13300
• Hs Code.: 2934999090
• Mol file: 741709-66-0.mol

Synonyms:4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-2,6-PYRIDINEDICARBOXYLIC ACID 2,6-DIMETHYL ESTER;

Chemical Property of DIMETHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE-2,6-DICARBOXYLATE

Chemical Property:

• Boiling Point: 453.1±45.0 °C(Predicted)
• PKA: -0.88±0.10(Predicted)
• PSA: 83.95000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 0.95400
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

2,6-Bis(methoxycarbonyl)pyridine-4-boronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of DIMETHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE-2,6-DICARBOXYLATE

There total 4 articles about DIMETHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE-2,6-DICARBOXYLATE 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: 98.0%

bis(pinacol)diborane (73183-34-3) + dimethyl 4-bromo-2,6-pyridinedicarboxylate (162102-79-6) → dimethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,6-dicarboxylate (741709-66-0)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; Inert atmosphere;

DOI:10.1039/d1dt00982f

Reference yield: 45.0%

4-iodo-2,6-pyridinedicarboxylic acid dimethyl ester (112776-84-8) + bis(pinacol)diborane (73183-34-3) → dimethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,6-dicarboxylate (741709-66-0)

Guidance literature:

With KCH₃COO; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 105°C;

DOI:10.1021/ic8012975

Reference yield:

dimethyl 4-hydroxypyridine-2,6-dicarboxylate (19872-91-4) → dimethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,6-dicarboxylate (741709-66-0)

Guidance literature:

Multi-step reaction with 2 steps

1: phosphorus pentabromide / methanol / 3 h / 95 °C

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; phosphorus pentabromide; In 1,4-dioxane; methanol; 2: |Miyaura Borylation Reaction;

DOI:10.1039/d1dt00982f

upstream raw materials:

4-iodo-2,6-pyridinedicarboxylic acid dimethyl ester

bis(pinacol)diborane

dimethyl 4-bromo-2,6-pyridinedicarboxylate

dimethyl 4-hydroxypyridine-2,6-dicarboxylate

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