476004-79-2

Basic information

• Product Name: 2-Pinacolateborylpyrrole
• Synonyms: 2-PINACOLATEBORYLPYRROLE;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole;2-(((1H-pyrrol-2-yl)boryl)oxy)-3-hydroxy-2,3-dimethylbutanoate;(1H-PYRROL-2-YL)BORONIC ACID PINACOL ESTER
• CAS NO: 476004-79-2
• Molecular Formula: C10H15BNO4-
• Molecular Weight: 193.05
• Mol File: 476004-79-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 311 °C
• Flash Point: 142 °C
• Appearance: /
• Density: 1.04
• Vapor Pressure: 0.00106mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: 2-8°C
• PKA: 16.51±0.50(Predicted)
• CAS DataBase Reference: 2-Pinacolateborylpyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pinacolateborylpyrrole(476004-79-2)
• EPA Substance Registry System: 2-Pinacolateborylpyrrole(476004-79-2)

Safety Data

• Hazardous Substances Data: 476004-79-2(Hazardous Substances Data)

Usage

Uses

2-Pinacolateborylpyrrole is a useful reagent for organic reactions.

InChI:InChI=1/C10H16BNO2/c1-9(2)10(3,4)14-11(13-9)8-6-5-7-12-8/h5-7,12H,1-4H3

Upstream product

• 109-97-7 pyrrole 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 63202-71-1 2-(4′-nitrophenyl)pyrrole 
• 1459140-53-4 1-(3-cyano-4-(1H-pyrrol-2-yl)phenyl)-3-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)urea 

Relevant articles and documents

Impact of Five-membered Heterocyclic Rings on Photophysical Properties including Two-photon Absorption Character

A series of dipolar-type terphenyl derivatives 13 featuring an electron donor (p-NMe2C6H4 group) and acceptor (p-NO2C6H4 group) unit was synthesized and their photophysical properties were

Noncovalent Interactions in Ir-Catalyzed C-H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters

An efficient strategy for the para-selective borylation of aromatic esters is described. For achieving high para-selectivity, a new catalytic system has been developed modifying the core structure of the bipyridine. It has been proposed that the L-shaped ligand is essential to recognize the functionality of the oxygen atom of the ester carbonyl group via noncovalent interaction, which provides an unprecedented controlling factor for para-selective C-H activation/borylation.

Iridium-catalyzed C-H borylation of heterocycles using an overlooked 1,10-phenanthroline ligand: Reinventing the catalytic activity by understanding the solvent-assisted neutral to cationic switch

The preformed catalyst [Ir(Cl)(COD)(1,10-phenanthroline)] (2; COD = cyclooctadiene) was found to be highly effective in a model reaction for the borylation of N-Boc-indole at the 3-position with B2pin2 (pin = pinacolato) as the borylating agent to give consistently 99% yield with 0.5 mol % catalyst loading. The corresponding in situ formed catalyst from [Ir(Cl)(COD)]2 and 1,10-phenanthroline provided very inconsistent results for the same reaction (0-94% conversion). We propose this to be due to the competing formation of a catalytically inactive cationic complex, [Ir(COD)(1,10-phenanthroline)]+Cl- (1), in a noncoordinating solvent such as octane. Complexes 1 and 2 were characterized using solid-state NMR (13C and 35Cl) in conjunction with XPS to be cationic and neutral, respectively. The X-ray crystal structure of a pentavalent neutral Ir complex, [Ir(Cl)(COD)(2,2′-bipyridine)] (3), was also obtained for comparison purposes. Using catalyst 2, the total synthesis of Meridianin G was accomplished in 87% overall isolated yield in a one-pot, three-step process.