10365-98-7

Usage

Uses

Used in Suzuki Reaction:
3-Methoxyphenylboronic acid is used as a reagent in the Suzuki reaction, a widely employed cross-coupling reaction in organic synthesis. It facilitates the formation of carbon-carbon bonds between aryl and vinyl halides or triflates with boronic acids, leading to the synthesis of various biologically active compounds and pharmaceuticals.
Used in Investigating Boron Function in Plants:
3-Methoxyphenylboronic acid is used as a research tool to study the function of boron in plants. It helps in understanding the role of boron in plant growth, development, and stress responses, as well as its involvement in various metabolic processes.

InChI:InChI=1/C7H9BO3/c1-11-7-4-2-3-6(5-7)8(9)10/h2-5,9-10H,1H3

Upstream product

• 13195-76-1 triisobutyl borate 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 325142-84-5 3-methoxyphenylboronic acid pinacol ester 
• 2398-37-0 3-methoxyphenyl bromide 
• 5419-55-6 Triisopropyl borate 
• 100-66-3 methoxybenzene 
• 121-43-7 Trimethyl borate 
• 73183-34-3 bis(pinacol)diborane 
• 157670-38-7 C₉H₁₃BO₃ 
• 13675-18-8 tetrahydroxydiboron 
• 7732-18-5 water 

Downstream Products

• 79421-99-1 tris(3-methoxyphenyl)-1,3,5,2,4,6-trioxatriborinane 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 456-49-5 1-fluoro-3-methoxybenzene 
• 321-28-8 1-fluoro-2-methoxybenzene 
• 119100-84-4 2-(3-Methoxy-phenyl)-4-methyl-nicotinic acid ethyl ester 
• 160775-67-7 2,2-Dimethoxy-5-(3-methoxy-phenyl)-indan-1,3-dione 
• 169774-69-0 (2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(3-methoxyphenyl)-<4,5>-dehydropyrrolidine 
• 152609-46-6 1-(benzyloxy)-4-ethyl-2-(3-methoxyphenyl)-5-<(6-methyl-6-cyanoheptyl)oxy>benzene 
• 135018-84-7 4-(3-Methoxy-phenyl)-7-phenyl-5H-dibenzo[c,e]azepine 
• 172975-75-6 N-(3-Methoxy-[1,1';3',1'']terphenyl-2'-ylmethyl)-benzamide 
• 131575-58-1 4-(3-Methoxyphenyl)-2H-1-benzopyran-2-one 
• 192182-22-2 2-{2-[2-(3-Methoxy-phenyl)-1H-indol-3-yl]-ethyl}-isoindole-1,3-dione 
• 56231-51-7 3-(3-methoxyphenyl)cyclohex-2-en-1-one 
• 766-85-8 3-methoxy-1-iodobenzene 

Relevant academic research and scientific papers

Synthesis and guest recognition of molecular cleft consisting of terpyridine-Pt(II) acetylide complexes

The stable molecular clefts 1 consisting of inert Pt-acetylide moieties and a 1,1':30,100-terphenyl spacer were synthesized. Guest binding behavior of 1a was examined by 1H NMR spectroscopy to determine the association constants; naphthalene (Ka0M-1) an

Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source

In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.

Cationic platinum(II) complexes bearing aryl-BIAN ligands: Synthesis and structural and optoelectronic characterization

Five cationic platinum(II) complexes bearing a 2-(3′-substituted aryl)pyridine cyclometalating ligand (C^N) and a neutral Ar-BIAN ligand have been synthesized: [Pt(ppy)(PhBIAN)]PF6 (1), [Pt(3Fppy)(PhBIAN)]PF6 (2), [Pt(3MeOppy)(PhBIAN)]PF6 (3), [Pt(3MeOppy)(4-FPhBIAN)]PF6 (4), [Pt(ppy)(4-MeOPhBIAN)]PF6 (5). All complexes have been characterized by NMR spectroscopy and mass spectrometry. Complexes 2 and 3 have been characterized by X-ray crystallography. Structure-property relationships were established from UV-visible spectroscopy and cyclic voltammetry studies. Interestingly, we found that when both the C^N and the Aryl-BIAN ligands contained electron-donating MeO groups the absorption spectrum for the platinum complex extended out to 650 nm. The electrochemical studies of these complexes established that they are electronically compatible dye molecules for dye-sensitized solar cells.

Mo–Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties

A catalytic domino reduction–imine formation–intramolecular cyclization–oxidation for the general synthesis of a wide variety of biologically relevant N-polyheterocycles, such as quinoxaline- and quinoline-fused derivatives, and phenanthridines, is reported. A simple, easily available, and environmentally friendly dioxomolybdenum(VI) complex has proven to be a highly efficient and versatile catalyst for transforming a broad range of starting nitroarenes involving several redox processes. Not only is this a sustainable, step-economical as well as air- and moisture-tolerant method, but also it is worth highlighting that the waste byproduct generated in the first step of the sequence is recycled and incorporated in the final target molecule, improving the overall synthetic efficiency. Moreover, selected indoloquinoxalines have been photophysically characterized in cyclohexane and toluene with exceptional fluorescence quantum yields above 0.7 for the alkyl derivatives.

Asymmetric 1,4-Addition of Arylboronic Acids to β,γ-Unsaturated α-Ketoesters using Heterogeneous Chiral Metal Nanoparticle Systems

Asymmetric 1,4-addition reactions with β,γ-unsaturated α-ketoesters are valuable because the resulting chiral ketoester compounds can be converted into various useful species that are often used as chiral building blocks in drug and natural product synthesis. However, β,γ-unsaturated α-ketoesters have two reactive points in terms of nucleophilic additions, which will lead to the 1,4-adduct, the 1,2-adduct and to the combined 1,4- and 1,2-adduct. Therefore, controlling this chemoselectivity is an important factor for the development of these transformations. Here, we developed an asymmetric 1,4-addition of aryl boronic acids to β,γ-unsaturated α-ketoesters by using heterogeneous chiral rhodium nanoparticle systems with a chiral diene ligand bearing a secondary amide moiety. The newly developed polydimethylsilane-immobilized rhodium nanoparticle catalysts showed high activity, high chemoselectivity, and excellent enantioselectivity, and this is the first heterogeneous catalytic system for this asymmetric reaction. Metal nanoparticle catalysts were recovered and reused without loss of activity or leaching of metal. (Figure presented.).

An efficient method for the hydrolysis of potassium organotrifluoroborates promoted by montmorillonite K10

An efficient and non-expensive method for conversion of diverse potassium organotrifluoroborates to their corresponding boronic acids promoted by montmorillonite K10 using water as the reaction solvent is described. Further interconversion of potassium organotrifluoroborates to their corresponding boronic esters, via boronic acid intermediates was also successfully accomplished. The products were obtained in good yields, being the rate of hydrolysis influenced by the type of substituent present in the boronic acid.

Boroquinol Complexes with Fused Extended Aromatic Backbones: Synthesis and Optical Properties

Boron-based dyes are attractive synthetic targets due to their large variability of absorption and emission wavelengths. Through Pictet–Spengler cyclizations, followed by oxidation, π-extended boroquinols have been synthesized. During optimization of the

Synthesis and evaluation of sulfonamide derivatives as potent Human Uric Acid Transporter 1 (hURAT1) inhibitors

This letter presents synthesis and structure-activity relationship study of sulfonamide derivatives as inhibitors of Human Uric Acid Transporter 1 (hURAT1). Among all tested sulfonamide derivatives, compounds 9b, 16i and 19b exhibited excellent inhibition activity with IC50 value of 10, 2, and 83?nM, respectively. In addition, compounds 9b and 19b demonstrated moderate PK profile in rats.

Importance of 5/6-aryl substitution on the pharmacological profile of 4?-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1?-biphenyl]-2-carboxylic acid derived PPARγ agonists

In this structure-activity relationship study, the influence of aryl substituents at position 5 or 6 on the pharmacological profile of the partial PPARγ agonist 4‘-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1‘-biphenyl]-2-carboxylic acid was investigated. This lead was previously identified as the essential part of telmisartan to induce PPARγ activation. Para-OCH3-phenyl substitution strongly increased potency and efficacy independent of the position. Both compounds represent full agonists because of strong hydrophobic contacts with the amino acid Phe363 in the ligand binding domain. Partial agonists with higher potency than telmisartan or the lead were obtained with OH or Cl substituents at the phenyl ring. Molecular modeling suggested additional hydrogen or halogen bonds with Phe360 located at helix 7. It is assumed that these interactions fix helix 7, thereby promoting a partial agonist conformation of the receptor. The theoretical considerations correlate very well with the results from the luciferase transactivation assay using hPPARγ-LBD as well as those from a time-resolved fluorescent resonance energy transfer (TR-FRET) assay in which the coactivator (TRAP220, PGC-1α) recruitment and corepressor (NCoR1) release pattern was investigated.

Scalable, Metal- and Additive-Free, Photoinduced Borylation of Haloarenes and Quaternary Arylammonium Salts

We report herein a simple, metal- and additive-free, photoinduced borylation of haloarenes, including electron-rich fluoroarenes, as well as arylammonium salts directly to boronic acids. This borylation method has a broad scope and functional group tolerance. We show that it can be further extended to boronic esters and carried out on gram scale as well as under flow conditions.