1165936-03-7

Basic information

• Product Name: 2-Fluoro-4-methylphenylboronic acid pinacol ester
• Synonyms: 2-Fluoro-4-methylphenylboronic acid pinacol ester
• CAS NO: 1165936-03-7
• Molecular Formula: C₁₃H₁₈BFO₂
• Molecular Weight: 254.1055032
• Mol File: 1165936-03-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 58-60℃
• Boiling Point: 300.9±35.0 °C(Predicted)
• Appearance: /
• Density: 1.04±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2-Fluoro-4-methylphenylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoro-4-methylphenylboronic acid pinacol ester(1165936-03-7)
• EPA Substance Registry System: 2-Fluoro-4-methylphenylboronic acid pinacol ester(1165936-03-7)

Safety Data

• Hazardous Substances Data: 1165936-03-7(Hazardous Substances Data)

Upstream product

• 352-70-5 m-Fluorotoluene 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 33406-96-1 2-chloro-5-fluorotoluene 
• 170981-26-7 2-fluoro-4-methylphenylboronic acid 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 452-74-4 4-bromo-3-fluorotoluene 

Downstream Products

• 1029439-49-3 2-(4-(bromomethyl)-2-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

Undirected ortho-selectivity in C–H borylation of arenes catalyzed by NHC platinum(0) complexes

Borylation of arenes with bis(pinacolato)diboron catalyzed by sterically encumbered NHC platinum complexes proceeds predominantly at ortho-position even in the absence of a directing group (o: m: p ratio up to 10: 3: 1). The similar borylation with pinacolborane would proceed less selectively.

Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds

Boronic acids are centrally important functional motifs and synthetic precursors. Visible light-induced borylation may provide access to structurally diverse boronates, but a broadly efficient photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C-O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron-rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reaction exhibits excellent functional group tolerance, as demonstrated by the borylation of a range of structurally complex substrates. Remarkably, the reaction is catalyzed by phenothiazine, a simple organic photocatalyst with MW 200 that mediates the previously unachievable visible light-induced single electron reduction of phenol derivatives with reduction potentials as negative as approximately - 3 V versus SCE by a proton-coupled electron transfer mechanism. Mechanistic studies point to the crucial role of the photocatalyst-base interaction.

METHODS FOR PRODUCING BORYLATED ARENES

Methods for the selective borylation of arenes, including arenes substituted with an electron-withdrawing group (e.g., 1-chloro-3-fluoro-2-substituted benzenes) are provided. The methods can be used, in some embodiments, to efficiently and regioselectivel