2-(HYDROXYMETHYL)PYRIDINE-5-BORONIC ACID

Base Information

• Chemical Name: 2-(HYDROXYMETHYL)PYRIDINE-5-BORONIC ACID
• CAS No.: 913835-98-0
• Molecular Formula: C6H8BNO3
• Molecular Weight: 152.945
• Hs Code.: 2933399990
• Mol file: 913835-98-0.mol

Synonyms:Boronicacid, [6-(hydroxymethyl)-3-pyridinyl]- (9CI);[6-(Hydroxymethyl)pyridin-3-yl]boronic acid;

Chemical Property of 2-(HYDROXYMETHYL)PYRIDINE-5-BORONIC ACID

Chemical Property:

• Vapor Pressure: 1.39E-06mmHg at 25°C
• Refractive Index: 1.568
• Boiling Point: 384 °C at 760 mmHg
• PKA: 3.96±0.10(Predicted)
• Flash Point: 186.1 °C
• PSA: 73.58000
• Density: 1.34 g/cm³
• LogP: -1.74630
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

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

6-(Hydroxymethyl)pyridine-3-boronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-(Hydroxymethyl)pyridine-5-boronic acid is widely employed as intermediate in organic synthesis. It also acts as a laboratory reagent.

Technology Process of 2-(HYDROXYMETHYL)PYRIDINE-5-BORONIC ACID

There total 2 articles about 2-(HYDROXYMETHYL)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: 56.0%

(5-bromopyridin-2-yl)methanol (88139-91-7) + bis(pinacol)diborane (73183-34-3) → [6-(hydroxymethyl)pyridin-3-yl]boronic acid (913835-98-0)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In N,N-dimethyl-formamide; at 80 ℃; for 18h; Inert atmosphere;

Reference yield:

methyl 5-bromopicolinate (29682-15-3) → [6-(hydroxymethyl)pyridin-3-yl]boronic acid (913835-98-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate; ethanol / 0 - 20 °C

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / N,N-dimethyl-formamide / 18 h / 80 °C / Inert atmosphere

With sodium tetrahydroborate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; ethanol; potassium acetate; In N,N-dimethyl-formamide;

Reference yield: 62.0%

[6-(hydroxymethyl)pyridin-3-yl]boronic acid (913835-98-0) + C18H13BrF3N3O → 4-[6-(hydroxymethyl)pyridin-3-yl]-N-{-[3-(trifluoromethyl)benzyl]-1H-imidazol-4-yl}benzamide

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; water; at 100 ℃; for 3h; Inert atmosphere;

upstream raw materials:

(5-bromopyridin-2-yl)methanol

bis(pinacol)diborane

methyl 5-bromopicolinate

Downstream raw materials:

{5-[(3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl]pyridin-2-yl}methanol

2,2-dichloro-1-((4S,5R)-4-(fluoromethyl)-5-(4-(6-(hydroxymethyl)pyridin-3-yl)phenyl)-2,2-dimethyloxazolidin-3-yl)ethanone

2,2-dichloro-1-((4S,5R)-5-(4-(6-(chloromethyl)pyridin-3-yl)phenyl)-4 (fluoromethyl)-2,2-dimethyloxazolidin-3-yl)ethanone

2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(6-((methylsulfonyl)methyl)pyridin-3-yl)phenyl)propan-2-yl)acetamide

Refernces