934558-31-3

Basic information

• Product Name: 2-(4-Methoxyphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane, 4-(4,4,6-Trimethyl-1,3,2-dioxaborinan-2-yl)anisole
• Synonyms: 2-(4-Methoxyphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane, 4-(4,4,6-Trimethyl-1,3,2-dioxaborinan-2-yl)anisole;4-Methoxybenzeneboronic acid, hexylene glycol ester
• CAS NO: 934558-31-3
• Molecular Formula: C₁₃H₁₉BO₃
• Molecular Weight: 234.09916
• Mol File: 934558-31-3.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-Methoxyphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane, 4-(4,4,6-Trimethyl-1,3,2-dioxaborinan-2-yl)anisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Methoxyphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane, 4-(4,4,6-Trimethyl-1,3,2-dioxaborinan-2-yl)anisole(934558-31-3)
• EPA Substance Registry System: 2-(4-Methoxyphenyl)-4,4,6-trimethyl-1,3,2-dioxaborinane, 4-(4,4,6-Trimethyl-1,3,2-dioxaborinan-2-yl)anisole(934558-31-3)

Safety Data

• Hazardous Substances Data: 934558-31-3(Hazardous Substances Data)

Usage

Type

Different sources of media describe the Type of 934558-31-3 differently. You can refer to the following data:
1. Boronic ester
2. Boronic acid derivative

Usage

Different sources of media describe the Usage of 934558-31-3 differently. You can refer to the following data:
1. Suzuki-Miyaura coupling reactions
2. Cross-coupling reagent in organic synthesis

Applications

Building block in synthesis of pharmaceuticals, agrochemicals, and materials

Importance

Versatile reactivity and intermediate in chemical and pharmaceutical industries

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 10199-14-1 4,4,6-trimethyl-1,3,2-dioxaborinane 
• 230299-21-5 4,4,4',4',6,6'-hexamethyl-2,2'-bi(1,3,2-dioxaborinane)bis(hexyleneglycolato)diboron 
• 623-12-1 4-chloromethoxybenzene 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 696-62-8 para-iodoanisole 
• 701-56-4 4-methoxy-N,N-dimethylanilne 
• 104-94-9 4-methoxy-aniline 
• 107-41-5 2-methyl-2,4-pentanediol 

Downstream Products

• 53040-92-9 4-(4-tolyl)anisole 
• 58743-77-4 4'-methoxybiphenyl-4-carbonitrile 
• 2143-90-0 4-methoxy-4'-nitrobiphenyl 
• 834-14-0 p-benzylanizole 

Relevant articles and documents

Engaging Ag(0) single atoms in silver(I) salts-mediated C-B and C-S coupling under visible light irradiation

Silver(I) salts were found active in the borylation and sulfenylation of aryl iodides under visible light irradiation. The optimized borylation protocol using AgF did not need any additive, operated under very mild conditions, and well tolerated a broad scope of substrates and boron sources. Formation of Ag(0) single atoms (AgSAs) during the borylation reactions was examined using high-angle annular dark field aberration-corrected scanning transmission electron microscope (HAADF AC-STEM) and electron paramagnetic resonance (EPR). The activities of the silver(I) salts were affected by the anions and could be associated with their abilities in formation of AgSAs during the reactions. Kinetic studies showed that the deiodination rate was linearly correlated with the loading of AgSAs, and hence AgSAs were the true catalytic centers for the 1e?-reduction of the C-I moieties. The oxidation state of AgSAs kept 0 in both the resting and the working states. A “work-in-tandem” mechanism involving AgSAs as the catalytic centers and AgNPs as the light absorber to achieve the borylation of aryl iodides under visible light irradiation is proposed. The current approach not only provides an alternative system for borylation and sulfenylation of aryl iodides, but also reveals a new activity of silver(I) salts involving AgSAs under visible light irradiation.

Photocatalyzed borylation using water-soluble quantum dots

The synthesis of arylboronates by Sandmeyer-type reactions in the presence of water still remains a significant challenge. Herein, we report the use of water-soluble MPA-capped quantum dot (QD) photocatalysts for the borylation of diazonium salts in the presence of water. A biphasic system under mild acidic conditions remains critical to prevent decomposition and competitive disulphide bond formation. The present protocol offers a broader scope of substrates and borylating agents. Additionally, this catalytic system offers a significantly high turnover number (TON). The present methodology can effectively distinguish subtle reactivity differences between boronic acids and boronates. Mechanistic investigation suggests an excited-state electron transfer pathway.

Preparation method of aryl borate ester and allyl borate ester

The invention discloses a preparation method of aryl borate ester and allyl borate ester. The method comprises the following step: under the catalytic action of pyridine or a derivative thereof, carrying out 1) or 2) to obtain substituted boric acid ester shown as a formula I-1 or a formula I-2: 1) a reaction of a halide, bi-boric acid ester and alkoxide; 2) a reaction of a halide and a bi-boric acid ester-alkoxide complex. The method is an efficient preparation method of the aryl borate ester and the allyl borate ester. In the preparation method provided by the invention, the inexpensive pyridine or the derivative thereof is taken as a catalyst instead of a transition metal catalyst, the reaction conditions are mild, the reaction yield is high, residues of trace transition metal in a boronation product are avoided, and the cost of an aryl and allyl borate ester synthesis reaction is lowered.