3-CHLORO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE

Base Information

• Chemical Name: 3-CHLORO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE
• CAS No.: 865186-94-3
• Molecular Formula: C₁₁H₁₅BClNO₂
• Molecular Weight: 239.51
• Hs Code.: 2934999090
• Mol file: 865186-94-3.mol

Synonyms:3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Chemical Property of 3-CHLORO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE

Chemical Property:

• Vapor Pressure: 0.000384mmHg at 25°C
• Melting Point: 79-81℃
• Refractive Index: 1.505
• Boiling Point: 327.5 °C at 760 mmHg
• Flash Point: 151.9 °C
• PSA: 31.35000
• Density: 1.14 g/cm³
• LogP: 2.03420
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Chloropyridine-3-boronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-CHLORO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE

There total 3 articles about 3-CHLORO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE 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: 84.0%

3-Chloropyridine (626-60-8) + bis(pinacol)diborane (73183-34-3) → 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (865186-94-3)

Guidance literature:

bis(pinacol)diborane; With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C₅₁H₃₂N₈Zn; In para-xylene; at 20 ℃; for 0.5h; Schlenk technique;

3-Chloropyridine; In para-xylene; at 80 ℃; for 24h; regioselective reaction; Schlenk technique;

DOI:10.1002/anie.202101997

Reference yield:

3-bromo-5-chloropyridine (73583-39-8) + bis(pinacol)diborane (73183-34-3) → 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (865186-94-3)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 20 - 90 ℃; for 1.66667h;

Reference yield:

→ 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (865186-94-3)

Guidance literature:

upstream raw materials:

3-bromo-5-chloropyridine

bis(pinacol)diborane

3-Chloropyridine

Downstream raw materials:

3-chloro-5-nitropyridine

Refernces

• 1、 Al-Shehimy, Shaymaa,Gramage-Doria, Rafael,Roisnel, Thierry,Trouvé, Jonathan,Zardi, Paolo. "Enzyme-like Supramolecular Iridium Catalysis Enabling C?H Bond Borylation of Pyridines with meta-Selectivity". supporting information. p. 18006 - 18013. Retrieved 2021/05/07.
• 2、 Pei, Xiaocong,Zhou, Guan,Li, Xuejing,Xu, Yuchen,Panicker, Resmi C.,Srinivasan, Rajavel. "Sterically controlled C-H/C-H homocoupling of arenes: Via C-H borylation". supporting information. p. 5703 - 5707. Retrieved 2019/06/19.