5-Bromo-2-methoxypyridin-4-ylboronic acid

Base Information

• Chemical Name: 5-Bromo-2-methoxypyridin-4-ylboronic acid
• CAS No.: 957060-94-5
• Molecular Formula: C₆H₇BBrNO₃
• Molecular Weight: 231.841
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID70475802
• Nikkaji Number: J1.909.712I
• Wikidata: Q82306579
• Mol file: 957060-94-5.mol

Synonyms:REF DUPL;

Chemical Property of 5-Bromo-2-methoxypyridin-4-ylboronic acid

Chemical Property:

• Melting Point: 130-134℃
• PSA: 62.58000
• LogP: -0.46750
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 230.97024
• Heavy Atom Count: 12
• Complexity: 149

Purity/Quality:

97% ^*data from raw suppliers

5-Bromo-2-methoxypyridine-4-boronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=NC=C1Br)OC)(O)O

Technology Process of 5-Bromo-2-methoxypyridin-4-ylboronic acid

There total 1 articles about 5-Bromo-2-methoxypyridin-4-ylboronic 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: 39.0%

2-methoxy-5-bromopyridine (13472-85-0,1199266-76-6) → (5-bromo-2-methoxy-4-pyridyl)boronic acid (957060-94-5)

Guidance literature:

2-methoxy-5-bromopyridine; With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 ℃; for 1h;

With Triisopropyl borate; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 ℃; for 1h;

DOI:10.1055/s-2003-39158

Reference yield:

(5-bromo-2-methoxy-4-pyridyl)boronic acid (957060-94-5) → 2-methoxy-4-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; 1,4-dioxane / 3 h / 60 °C / Inert atmosphere

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 80 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; sodium carbonate; In 1,4-dioxane; water; dimethyl sulfoxide;

Reference yield:

(5-bromo-2-methoxy-4-pyridyl)boronic acid (957060-94-5) → 2-(6-methoxy-4-phenylpyridin-3-yl)-5-phenyloxazole

Guidance literature:

Multi-step reaction with 3 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; 1,4-dioxane / 3 h / 60 °C / Inert atmosphere

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 80 °C

3: methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); caesium carbonate / water; 1,4-dioxane / 60 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); potassium acetate; sodium carbonate; caesium carbonate; In 1,4-dioxane; water; dimethyl sulfoxide;

upstream raw materials:

2-methoxy-5-bromopyridine