1111096-19-5

Basic information

• Product Name: 2-(2,6-Difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 1111096-19-5;2-(2,6-DIFLUORO-4-METHOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2,6-Difluoro-4-methoxyphenylboronic acid pinacol ester;SCHEMBL2524790;BXICLURBOWTZED-UHFFFAOYSA-N;DTXSID101149874;MFCD12405359;AKOS017550464;AT16083;BS-51083;CS-0088589;EN300-3256274;Z1336745230;2-(2,6-difluoro-4-methoxy-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 1111096-19-5
• Molecular Weight: 270.084
• Mol File: 1111096-19-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-(2,6-Difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,6-Difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1111096-19-5)
• EPA Substance Registry System: 2-(2,6-Difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1111096-19-5)

Safety Data

• Hazardous Substances Data: 1111096-19-5(Hazardous Substances Data)

Usage

Type of compound

boronic ester

Usage

building block for the construction of complex organic molecules in organic synthesis

Structural features

four methyl groups attached to a boron atom, a difluoromethoxyphenyl group

Steric hindrance

highly sterically hindered

Electron deficiency

electron-deficient

Common use in reactions

Suzuki-Miyaura cross-coupling reactions

Upstream product

• 325143-04-2 4,4,5,5-tetramethyl-2-(2,4,6-trifluorophenyl)-1,3,2-dioxaborolane 
• 7732-18-5 water 
• 406482-20-0 (2,6-difluoro-4-methoxyphenyl)boronic acid 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 93343-10-3 3,5-difluoroanisol 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 325142-81-2 4,4,5,5-tetramethyl-2-(2,3,4,5,6-pentafluorophenyl)-1,3,2-dioxaborolane 
• 1086111-09-2 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1,3-thiazole 
• 406482-20-0 (2,6-difluoro-4-methoxyphenyl)boronic acid 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Relevant articles and documents

Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis

The kinetics and mechanism of the base-catalyzed hydrolysis (ArB(OR)2→ ArB(OH)2) and protodeboronation (ArB(OR)2→ ArH) of a series of boronic esters, encompassing eight different polyols and 10 polyfluoroaryl and heteroaryl moieties, have been investigated by in situ and stopped-flow NMR spectroscopy (19F,1H, and11B), pH-rate dependence, isotope entrainment,2H KIEs, and KS-DFT computations. The study reveals the phenomenological stability of boronic esters under basic aqueous-organic conditions to be highly nuanced. In contrast to common assumption, esterification does not necessarily impart greater stability compared to the corresponding boronic acid. Moreover, hydrolysis of the ester to the boronic acid can be a dominant component of the overall protodeboronation process, augmented by self-, auto-, and oxidative (phenolic) catalysis when the pH is close to the pKaof the boronic acid/ester.

C-H Functionalization at Sterically Congested Positions by the Platinum-Catalyzed Borylation of Arenes

Despite significant progress in the area of C-H bond functionalization of arenes, no general method has been reported for the functionalization of C-H bonds at the sterically encumbered positions of simple arenes, such as mesitylene. Herein, we report the development of the first platinum-based catalyst for C-H borylation of arenes and heteroarenes. Notably, this method exhibited high tolerance toward steric hindrance and provided rapid access to a series of 2,6-disubstituted phenylboronic esters, valuable building blocks for further elaborations.