213596-33-9

Basic information

• Product Name: 2-(4-Methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborinane
• Synonyms: 2-(4-Methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborinane
• CAS NO: 213596-33-9
• Molecular Formula: C₁₂H₁₇BO₃
• Molecular Weight: 220.08
• Product Categories: Boronic Acids
• Mol File: 213596-33-9.mol
• Article Data: 66

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-Methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborinane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborinane(213596-33-9)
• EPA Substance Registry System: 2-(4-Methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborinane(213596-33-9)

Safety Data

• Hazardous Substances Data: 213596-33-9(Hazardous Substances Data)

Usage

General Description

2-(4-Methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborinane is a chemical compound with the molecular formula C11H17BO3. It is a boron-containing compound that belongs to the class of dioxaborinane compounds. 2-(4-Methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborinane is often used in organic synthesis as a reagent for the preparation of various organic compounds. It is commonly used in the formation of carbon-carbon and carbon-heteroatom bonds through various coupling reactions. Additionally, it is used as a building block in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. The presence of the methoxy and dimethyl groups in the compound makes it a versatile building block for the synthesis of a wide range of organic molecules.

Upstream product

• 53451-91-5 1-[(4-methoxyphenyl)thio]-4-(trifluoromethyl)benzene 
• 696-63-9 4-Methoxybenzenethiol 
• 696-62-8 para-iodoanisole 
• 100-66-3 methoxybenzene 
• 398126-90-4 1-methoxy-4-{[4-(trifluoromethyl)phenyl]sulfinyl}benzene 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 1774-36-3 bis(4-methoxyphenyl) sulfoxide 
• 623-12-1 4-chloromethoxybenzene 
• 701-53-1 p-methoxybenzoyl fluoride 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 78646-39-6 2-(4-methoxyphenoxy)pyridine 
• 701-56-4 4-methoxy-N,N-dimethylanilne 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 7294-69-1 4-CH₃OC₆H₄BCl₂ 

Downstream Products

• 20013-55-2 4'-methoxy-2-nitrobiphenyl 
• 53040-92-9 4-(4-tolyl)anisole 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 59115-45-6 2-(4-methoxyphenyl)naphthalene 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 
• 57479-35-3 8-(4-methoxyphenyl)quinoline 
• 1186126-51-1 5-(4-methoxyphenyl)isoquinoline 
• 1346262-17-6 1-(4'-methoxy-[1,1'-biphenyl]-4-yl)pyrrolidine-2,5-dione 
• 19617-68-6 methyl 4′-methoxy(1,1′-biphenyl)-3-carboxylate 
• 5958-02-1 3-(4-methoxyphenyl)pyridine 
• 17171-17-4 4'-methoxy-3-methylbiphenyl 
• 13021-18-6 1-(4'-methoxy-biphenyl-4-yl)-ethanone 
• 58743-77-4 4'-methoxybiphenyl-4-carbonitrile 
• 302924-67-0 tert-butyl 4-hydroxy-4-(4-methoxyphenyl)-1-piperidinecarboxylate 

Relevant articles and documents

A novel transmetallation of triarylstibanes into arylboronate: Boro-induced ipso-deantimonation and its theoretical calculation

Treatment of triarylstibanes with boron trichloride followed by derivatization with methanol and 1,3-propanediol afforded arylboronates in good yield with all three aryl groups on the antimony being utilized. Theoretical calculation of the reaction pathwa

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.

Visible-Light-Induced Ni-Catalyzed Radical Borylation of Chloroarenes

A highly selective and general photoinduced C-Cl borylation protocol that employs [Ni(IMes)2] (IMes = 1,3-dimesitylimidazoline-2-ylidene) for the radical borylation of chloroarenes is reported. This photoinduced system operates with visible light (400 nm) and achieves borylation of a wide range of chloroarenes with B2pin2 at room temperature in excellent yields and with high selectivity, thereby demonstrating its broad utility and functional group tolerance. Mechanistic investigations suggest that the borylation reactions proceed via a radical process. EPR studies demonstrate that [Ni(IMes)2] undergoes very fast chlorine atom abstraction from aryl chlorides to give [NiI(IMes)2Cl] and aryl radicals. Control experiments indicate that light promotes the reaction of [NiI(IMes)2Cl] with aryl chlorides generating additional aryl radicals and [NiII(IMes)2Cl2]. The aryl radicals react with an anionic sp2-sp3 diborane [B2pin2(OMe)]- formed from B2pin2 and KOMe to yield the corresponding borylation product and the [Bpin(OMe)]?- radical anion, which reduces [NiII(IMes)2Cl2] under irradiation to regenerate [NiI(IMes)2Cl] and [Ni(IMes)2] for the next catalytic cycle.