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

Base Information

• Chemical Name: 3-BROMO-4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE
• CAS No.: 458532-92-8
• Molecular Formula: C₁₁H₁₅BBrNO₂
• Molecular Weight: 283.961
• Hs Code.: 2933399090
• Mol file: 458532-92-8.mol

Synonyms:3-Bromopyridine-4-boronic acid pinacol ester;3-Bromo-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;

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

Chemical Property:

• Vapor Pressure: 0.000168mmHg at 25°C
• Melting Point: 88-90ºC
• Refractive Index: 1.527
• Boiling Point: 340.6 °C at 760 mmHg
• Flash Point: 159.8 °C
• PSA: 31.35000
• Density: 1.34 g/cm³
• LogP: 2.14330
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

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

3-Bromopyridine-4-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 1 articles about 3-BROMO-4-(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: 48.0%

3-Bromopyridine (626-55-1,163928-56-1) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 3-bromo-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (458532-92-8)

Guidance literature:

3-Bromopyridine; With n-butyllithium; diisopropylamine; In diethyl ether; at -95 ℃; for 0.75h;

With Triisopropyl borate; In diethyl ether; at -95 - 10 ℃;

2,3-dimethyl-2,3-butane diol; With acetic acid; In diethyl ether; for 4h;

DOI:10.1016/S0040-4020(02)00416-7

Reference yield:

3-bromo-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (458532-92-8) → (2E)-N-{4-[(morpholin-4-yl)methyl]phenyl}-3-[4-(1,3-thiazol-5-yl)pyridin-3-yl]acrylamide

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 3 h / 130 °C

2: caesium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; C₃₇H₄₃ClNO₂PPd / 1,2-dimethoxyethane / 1 h / 130 °C / Microwave irradiation

3: 2 h / 20 °C

4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; C₃₇H₄₃ClNO₂PPd; palladium diacetate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,2-dimethoxyethane; N,N-dimethyl-formamide; 1: |Heck Reaction;

DOI:10.1016/j.bmc.2017.03.049

upstream raw materials:

3-Bromopyridine

2,3-dimethyl-2,3-butane diol

Refernces