t-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate

Base Information

• Chemical Name: t-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate
• CAS No.: 935278-73-2
• Molecular Formula: C₁₅H₂₄BNO₄
• Molecular Weight: 293.171
• Hs Code.: 2934999090
• Mol file: 935278-73-2.mol

Synonyms:1-BOC-Pyrrole-3-boronic acid, pinacol ester;t-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate;

Chemical Property of t-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate

Chemical Property:

• Melting Point: 76-77 °C
• Boiling Point: 381.3±34.0 °C(Predicted)
• PKA: -6.09±0.70(Predicted)
• PSA: 49.69000
• Density: 1.04±0.1 g/cm3(Predicted)
• LogP: 2.57050
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

97% ^*data from raw suppliers

1-BOC-pyrrole-3-boronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of t-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate

There total 3 articles about t-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate 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: 98.0%

N-tert-butyloxycarbonyl-pyrrole (5176-27-2) + bis(pinacol)diborane (73183-34-3) → tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate (935278-73-2)

Guidance literature:

bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tert-butyl methyl ether; Inert atmosphere;

N-tert-butyloxycarbonyl-pyrrole; In tert-butyl methyl ether; at 80 ℃; for 0.05h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/ol901306m

Reference yield: 90.0%

N-tert-butyloxycarbonyl-pyrrole (5176-27-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate (935278-73-2)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; at 55 ℃; for 13h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo901822b

Reference yield: 50.0%

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + 3-bromopyrrole-l-carboxylic acid tert-butyl ester (475561-75-2) → tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate (935278-73-2)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; triethylamine; dichloro bis(acetonitrile) palladium(II); In toluene; at 80 ℃; for 24h;

DOI:10.1021/ja068577p

upstream raw materials:

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

3-bromopyrrole-l-carboxylic acid tert-butyl ester

N-tert-butyloxycarbonyl-pyrrole

bis(pinacol)diborane