214360-78-8

Basic information

• Product Name: 2,4,6-TRIMETHYLBENZENEBORONIC ACID NEOPENTYL GLYCOL CYCLIC ESTER
• Synonyms: 2,4,6-TRIMETHYLBENZENEBORONIC ACID NEOPENTYL GLYCOL CYCLIC ESTER;2,4,6-TRIMETHYLBENZENEBORONIC ACID NEOPENTYL GLYCOL ESTER;5,5-Dimethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborinane~Mesityleneboronic acid 2,2-dimethyltrimethylene cyclic ester;5,5-Dimethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborinane;Mesityleneboronicacid2,2-dimethyltrimethylenecyclicester;2,4,6-TRIMETHYLBENZENEBORONIC ACID NEOPENTYL GLYCOL ESTER, 9;2,4,6-Trimethylphenylboronic acidneopentylglycol ester;2-Mesityl-5,5-dimethyl-1,3,2-dioxaborinane
• CAS NO: 214360-78-8
• Molecular Formula: C₁₄H₂₁BO₂
• Molecular Weight: 232.13
• EINECS: -0
• Mol File: 214360-78-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 46-48°C
• Boiling Point: 339.91 °C at 760 mmHg
• Flash Point: 159.372 °C
• Appearance: /
• Density: 0.98 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.493
• BRN: 8689636
• CAS DataBase Reference: 2,4,6-TRIMETHYLBENZENEBORONIC ACID NEOPENTYL GLYCOL CYCLIC ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRIMETHYLBENZENEBORONIC ACID NEOPENTYL GLYCOL CYCLIC ESTER(214360-78-8)
• EPA Substance Registry System: 2,4,6-TRIMETHYLBENZENEBORONIC ACID NEOPENTYL GLYCOL CYCLIC ESTER(214360-78-8)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 214360-78-8(Hazardous Substances Data)

Usage

General Description

2,4,6-Trimethylbenzeneboronic acid neopentyl glycol cyclic ester is a boron-containing compound used in organic synthesis and catalysis. It is a cyclic boronic ester that contains a neopentyl glycol moiety, which makes it a useful reagent for the construction of various organic compounds. It is commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and materials. The compound's unique structure and reactivity make it a valuable tool in the development of new chemical processes and products.

InChI:InChI=1/C14H21BO2/c1-10-6-11(2)13(12(3)7-10)15-16-8-14(4,5)9-17-15/h6-7H,8-9H2,1-5H3

Upstream product

• 5980-97-2 mesitylboronic acid 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 23822-17-5 tris(2,4,6-trimethylphenyl)antimony 
• 69464-76-2 2,4,6-(trimethylphenyl)dichloroborane 

Downstream Products

• 23676-08-6 methyl 4-ethoxybenzoate 
• 121-98-2 methyl 4-methoxybenzoate 
• 502622-88-0 4′-(2,4,6-trimethylphenyl)-2,2′:6′,2″-terpyridine 
• 480-63-7 mesitylenecarboxylic acid 
• 137129-03-4 N,N-dibenzyl-2,4,6-trimethylaniline 
• 1421030-00-3 4-phenyl-3-(3,5-bis(2,4,6-trimethylphenyl)phenyldiazenyl)pyridine 

Relevant articles and documents

The steric aryl boric acid ester preparation method of the compound

The invention discloses a preparation method of a high-sterically-hindered arylborate compound. The preparation method includes following steps: in the presence of a catalyst of a catalyst tri(dibenzalacetone)dipalladium with a phosphine ligand (wherein the phosphine ligand is 3-diphenylphosphine-2-(2,6-dimethoxylphenyl)-N-methylindole), adding an aryl chloride, bis(neopentyl glycolato)diboron, and an additive ceseium acetate to a 1,4-dioxane solution; and carrying out a reaction at 100-130 DEG C for 12-48 hours to obtain the arylborate compound. In the invention, the employed substrate is stable, is low in cost and is easy to obtain and the catalyst is unique, is easy to prepare and is suitable for the reaction of the high-sterically-hindered aryl chloride. The system is compatible of existences of functional groups, such as an ester group, an aldehyde group, methoxyl and the like so that range of the substrate is greatly developed. The catalyst system is stable, is high in catalytic activity, is wide in suitable scope, is good in selectivity and is mild in reaction conditions. The high-sterically-hindered arylborate compound can be widely applied in cross coupling reaction catalyzed by transition metal, thereby preparing various compounds, such as biaromatic hydrocarbons. The preparation method has a great application potential in synthesis of natural medicines and drug intermediates.

Simple base-free Miyaura-type borylation of triarylantimony diacetates with tetra(alkoxo)diborons under aerobic conditions

The reaction of triarylantimony diacetates with tetra(alkoxo)diborons in the presence of PdCl2(PPh3)2 (1 mol%) catalyst resulted in the Miyaura-type B-arylation to form arylboronates in moderate to good yields under base-free conditions. In the present reaction, two of the three aryl groups of antimony reagent were transferred to the coupling products when the reaction was carried out under aerobic conditions, although only one of the three aryl group of the antimony reagent was involved under an argon atmosphere. The broad scope of the reaction was demonstrated by using a variety of triarylantimony diacetates with sterically hindered aryl groups and highly reactive p-bromo-functionalized aryl derivatives.

Beyond directed ortho metalation: Ruthenium-catalyzed amide-directed C Ar-N activation/C-C coupling reaction of anthranilamides with organoboronates

A new, catalytic, and general methodology for the synthesis of biaryls and heterobiaryls by the cross coupling of anthranilamide derivatives (o-NMe 2 benzamides) with aryl boroneopentylates is described. The reaction proceeds under catalytic RuH2(CO)(PPh3)3 conditions driven by the activation of the unreactive C-N bond by amide directing group (DG)-Ru catalyst chelation. High regioselectivity, orthogonality with the Suzuki-Miyaura reaction, operational simplicity, and convenient scale-up are features of these reactions which may lend themselves to industrial applications.