N-METHYLPYRROLE-2-BORONIC ACID, PINACOL ESTER

Base Information

• Chemical Name: N-METHYLPYRROLE-2-BORONIC ACID, PINACOL ESTER
• CAS No.: 850567-47-4
• Molecular Formula: C11H18BNO2
• Molecular Weight: 207.08
• Hs Code.: 2934999090
• Mol file: 850567-47-4.mol

Synonyms:1-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole;1-Methyl-1H-pyrrole-2-boronic acid, pinacol ester;N-Methylpyrrole-2-boronic acid, pinacol ester;

Chemical Property of N-METHYLPYRROLE-2-BORONIC ACID, PINACOL ESTER

Chemical Property:

• Vapor Pressure: 0.00246mmHg at 25°C
• Melting Point: 49-50 °C
• Refractive Index: 1.487
• Boiling Point: 296.9 °C at 760 mmHg
• Flash Point: 133.4 °C
• PSA: 23.39000
• Density: 0.99 g/cm³
• LogP: 1.32430
• Storage Temp.: Store below -20C

Purity/Quality:

97% ^*data from raw suppliers

1-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Reactant for:Cu assisted Suzuki-Miyaura coupling reactions

Technology Process of N-METHYLPYRROLE-2-BORONIC ACID, PINACOL ESTER

There total 14 articles about N-METHYLPYRROLE-2-BORONIC ACID, PINACOL ESTER 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: 93.3%

N-Methylpyrrole (96-54-8) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole and 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole (850567-47-4)

Guidance literature:

With 1-(trifluoroborato)-2-diethylaminobenzene; In neat (no solvent); at 80 ℃; for 2h; Reagent/catalyst; Solvent; Time; Temperature; regioselective reaction; Catalytic behavior; Inert atmosphere;

DOI:10.1021/jacs.7b08143

Reference yield: 77.0%

N-Methylpyrrole (96-54-8) + bis(pinacol)diborane (73183-34-3) → 1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole and 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole (850567-47-4)

Guidance literature:

With Pt(N,N′-dicyclohexylimidazol-2-ylidene)(divinyltetramethylsiloxane); In n-heptane; at 100 ℃; for 20h; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.5b07677

Reference yield: 39.0%

N-Methylpyrrole (96-54-8) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 1-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole (953040-54-5) + 1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole and 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole (850567-47-4)

Guidance literature:

N-Methylpyrrole; With aluminum (III) chloride; 2-chloro-1,3,2-benzodioxaborole; triethylamine; In dichloromethane; at 20 ℃; for 20h; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; In dichloromethane; for 1h; regioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201006196

upstream raw materials:

N-Methylpyrrole

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

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

2-chloro-1,3,2-benzodioxaborole

Downstream raw materials:

2-([1,1'-biphenyl]-4-yl)-1-methyl-1H-pyrrole

1-methyl-2-phenyl-1H-pyrrole

1-methyl-5-phenyl-1H- pyrrole-2-carboxaldehyde

Cyclohexyl-(1-methyl-1H-pyrrol-2-yl)-methanone

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