3-Pinacolateboryl-1H-pyrrole

Base Information

• Chemical Name: 3-Pinacolateboryl-1H-pyrrole
• CAS No.: 214360-77-7
• Molecular Formula: C₁₀H₁₆BNO₂
• Molecular Weight: 193.054
• Hs Code.: 2934999090
• Mol file: 214360-77-7.mol

Synonyms:3-PINACOLATEBORYL-1-TIPS-PYRROLE;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole;3-Pinacolateboryl-1H-pyrrole;Pyrrole-3-boronic acid, pinacol ester;1H-Pyrrole, 3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-

Chemical Property of 3-Pinacolateboryl-1H-pyrrole

Chemical Property:

• Melting Point: 77-79 °C
• Refractive Index: 1.489
• Boiling Point: 310.947 °C at 760 mmHg
• PKA: 17.01±0.50(Predicted)
• Flash Point: 141.856 °C
• PSA: 23.39000
• Density: 1.04g/cm³
• LogP: 4.81090
• Storage Temp.: Refrigerated.

Purity/Quality:

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

3-(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:

Technology Process of 3-Pinacolateboryl-1H-pyrrole

There total 7 articles about 3-Pinacolateboryl-1H-pyrrole 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: 91.0%

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole (214360-77-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/ja068577p

Reference yield: 80.0%

3-bromo-1H-pyrrole (87630-40-8) + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole (214360-77-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 153 ℃; for 12h; Inert atmosphere;

Reference yield: 80.0%

tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate (935278-73-2) → 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole (214360-77-7)

Guidance literature:

at 180 ℃; for 0.583333h;

DOI:10.1021/jo901822b

upstream raw materials:

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole

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

bis(pinacol)diborane

tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate

Downstream raw materials:

1-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole

Refernces

• 1、 Gilles, Philippe,Kashyap, Rudra S.,Freitas, Maria Jo?o,Ceusters, Sam,Van Asch, Koen,Janssens, Anke,De Jonghe, Steven,Persoons, Leentje,Cobbaut, Mathias,Daelemans, Dirk,Van Lint, Johan,Voet, Arnout R.D.,De Borggraeve, Wim M.. "Design, synthesis and biological evaluation of pyrazolo[3,4-d]pyrimidine-based protein kinase D inhibitors". supporting information. . Retrieved 2020/08/25.
• 2、 Cooper, Stephen P.,Booker-Milburn, Kevin I.. "A Palladium(II)-Catalyzed C-H Activation Cascade Sequence for Polyheterocycle Formation". supporting information. p. 6496 - 6500. Retrieved 2015/06/02.