214360-69-7

Basic information

• Product Name: 2,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER
• Synonyms: 2,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER;2-(2,4-DIMETHOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
• CAS NO: 214360-69-7
• Molecular Formula: C14H21BO4
• Molecular Weight: 264.13
• Mol File: 214360-69-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 367.9°Cat760mmHg
• Flash Point: 176.3°C
• Appearance: /
• Density: 1.05g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.491
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER(214360-69-7)
• EPA Substance Registry System: 2,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER(214360-69-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 214360-69-7(Hazardous Substances Data)

Usage

General Description

2,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER is a chemical compound commonly used in organic synthesis. It is a boronic acid derivative with two methoxy groups and a pinacol ester group attached to a phenyl ring. 2,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER is widely used as a reagent in cross-coupling reactions, particularly in the formation of carbon-carbon bonds. It is also used in the synthesis of various pharmaceuticals, agrochemicals, and materials. The 2,4-DIMETHOXYPHENYLBORONIC ACID, PINACOL ESTER is a versatile and important building block for the production of complex organic compounds.

InChI:InChI=1/C14H21BO4/c1-13(2)14(3,4)19-15(18-13)11-8-7-10(16-5)9-12(11)17-6/h7-9H,1-6H3

Upstream product

• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 151-10-0 1,3-Dimethoxybenzene 
• 20469-63-0 1-iodo-2,4-dimethoxybenzene 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 17715-69-4 1-Bromo-2,4-dimethoxybenzene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

Dibenzo[d, d ′]benzo[2,1- b:3,4- b ′]difurans with extended π-conjugated chains: Synthetic approaches and properties

Ru-catalysed cross-dimerisation of 3,8-di(hexyn-1-yl)dibenzo[d,d']benzo[2,1-b,3,4-b']difuran [3,8-di(hexyn-1-yl)-DBBDF] with 2 equivalents of methyl (E)-penta-2,4-dienoate produces 3,8-bis[(1E,3E,5E)-2-butyl-6-methoxycarbonylhexa-1,3,5-trien-1-yl]-DBBDF (9a), and the total yield of 9a obtained from 2,3-difluoro-1,4-diiodobenzene is 50% using the six-step reaction. A series of 3,8-bis(hexatrienyl)-DBBDF compounds and unsymmetrical 8-decyl-3-hexatrienyl-DBBDF compounds were also prepared using the same method. These compounds were evaluated using ultraviolet-visible (UV-vis) spectroscopy and cyclic voltammetry (CV). Time-dependent density-functional theory (TD-DFT) calculations indicate that efficient π-π? excitations occur using the conjugated trienyl side chain groups.

Amine-borane complexes: Air- and moisture-stable partners for palladium-catalyzed borylation of aryl bromides and chlorides

A method for using amine-borane complexes directly in palladium catalyzed borylation has been developed. The reaction proceeds through the sequential formation of a boronium species followed by deprotonation leading to the aminoborane. This reagent is then directly used in the borylation process leading, after work-up, to various boronic acid derivatives. The reaction was applied to (hetero)aryl triflates, iodides, bromides and chlorides.

Iridium complexes of CCC-pincer N-heterocyclic carbene ligands: Synthesis and catalytic C-H functionalization

A series of four meta-phenylene-bridged bis-benzimidazolium chlorides were synthesized as precursors to rigid, monoanionic, CCC-pincer N-heterocyclic carbene ligands. For ligands with mesityl, 3,5-xylyl, or 3,5-di-tert-butylphenyl side groups, reaction with [Ir(1,5-cyclooctadiene)Cl]2 in acetonitrile with either excess triethylamine or stoichiometric cesium fluoride as base gave neutral, iridium(III) pincer complexes of the formula Ir(CCC)HCl(MeCN), which were purified by chromatography on silica gel. Metalation failed under these conditions for a 2,6-diisopropylphenyl-substituted derivative. In combination with NaOtBu, these complexes form active catalysts for the acceptorless dehydrogenation of cyclooctane and for arene C-H borylation in neat arene solvent.