325142-84-5

Basic information

• Product Name: 2-(3-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
• Synonyms: 2-(3-METHOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-(3-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;3-METHOXYPHENYLBORONIC ACID, PINACOL ESTER;2-(3-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-;2-(3-Methoxyloxyphenyl)-4;3-Methoxybenzeneboronic acid, pinacol ester;4,4,5,5-tetraMethyl-2-[3-(Methylperoxy)phenyl]-1,3,2-dioxaborolane;3-Methoxy-1-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzene
• CAS NO: 325142-84-5
• Molecular Formula: C₁₃H₁₉BO₃
• Molecular Weight: 234.1
• Mol File: 325142-84-5.mol
• Article Data: 118

Chemical Properties

• Boiling Point: 443.1°C at 760 mmHg
• Flash Point: >110℃
• Appearance: /
• Density: 1.028 g/mL at 25 °C
• Vapor Pressure: 1.25E-08mmHg at 25°C
• Refractive Index: n20/D1.502
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(3-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(325142-84-5)
• EPA Substance Registry System: 2-(3-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE(325142-84-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 325142-84-5(Hazardous Substances Data)

Usage

Description

2-(3-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE, also known as 3-Methoxyphenylboronic Acid Pinacol Ester, is an organic compound with the molecular formula C11H17BO3. It is a derivative of boronic acid and is characterized by its pinacol ester structure. 2-(3-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE is known for its potential applications in various fields due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
2-(3-METHOXYLOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE is used as a key intermediate compound for the synthesis of inhibitors targeting Transforming Growth Factor-beta 1 (TGF-β1) and Activin A signaling pathways. These inhibitors play a crucial role in regulating cellular processes such as cell proliferation, differentiation, and migration, which are often dysregulated in various diseases, including cancer. By modulating these signaling pathways, the compound can potentially be used in the development of therapeutic agents for treating diseases associated with abnormal TGF-β1 and Activin A signaling.

InChI:InChI=1/C9H13BO4S/c1-7(2)15(13,14)9-5-3-8(4-6-9)10(11)12/h3-7,11-12H,1-2H3

Upstream product

• 2845-89-8 1-chloro-3-methoxy-benzene 
• 73183-34-3 bis(pinacol)diborane 
• 100-66-3 methoxybenzene 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 2398-37-0 3-methoxyphenyl bromide 
• 766-85-8 3-methoxy-1-iodobenzene 
• 745783-97-5 triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 10365-98-7 3-methoxyphenylboronic acid 
• 1245824-47-8 4-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl N,N-diethylcarbamate 
• 85630-18-8 N,N-diethyl-O-(4-methoxyphenyl)carbamate 
• 36651-92-0 1-[2-(3-methoxyphenyl)diazen-1-yl]pyrrolidine 
• 536-90-3 m-Anisidine 
• 450412-22-3 1-bromo-2-iodo-3-methoxybenzene 

Downstream Products

• 10365-98-7 3-methoxyphenylboronic acid 
• 1011472-11-9 3-(3-methoxyphenyl)-N-phenylimidazo[1,2-a]pyrazin-8-amine 
• 1130489-32-5 C₂₂H₁₉N₃O 
• 1256781-58-4 2-(2-bromo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1256781-69-7 2-(2-iodo-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1256781-73-3 2-(2-chloro-5-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1272031-59-0 (R)-2-(1-(3-methoxyphenyl)-1-phenylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1333419-34-3 (Z)-methyl 3-(3-methoxyphenyl)-3-(2-oxopyrrolidin-1-yl)acrylate 
• 1333492-66-2 2-(3-methoxyphenyl)-4-(3-(pyridin-2-yl)-1-trityl-1H-pyrazol-4-yl)pyridine 
• 1613415-69-2 (R)-4-(3-methoxyphenyl)-4-methyl-1,2,3-oxathiazolidine 2,2-dioxide 
• 766-85-8 3-methoxy-1-iodobenzene 
• 16473-18-0 1-(methoxy)-3-(fluoromethyl)benzene 
• 1391925-48-6 2-(4-(3-methoxyphenyl)-6-morpholino-1,3,5-triazin-2-ylamino)acetic acid 
• 53906-83-5 3'-methoxyflavone 

Relevant articles and documents

Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands

Catalysts based on the combination of Pd(OAc)2 and the electron-deficient phosphatrioxa-adamantane ligands are described for borylation of aryl bromides and chlorides. Catalytic evaluation of a small library of phosphatrioxa-adamantane ligands provided some insights on the preferred ligand steric profile for borylation reactions. The corresponding aryl boronate esters were accessed under mild conditions (25–70 °C) and isolated in high yields (up to 96%).

Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation

Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.