5720-06-9

Basic information

• Product Name: 2-Methoxyphenylboronic acid
• Synonyms: RARECHEM AH PB 0181;O-METHOXYPHENYLBORONIC ACID;AKOS BRN-0014;2-METHOXYPENYLBORONIC ACID;2-METHOXYPHENYLBORONIC ACID;2-METHOXYBENZENEBORONIC ACID;2-Boronoanisole;2-Methoxybenzeneboronicacid,97%
• CAS NO: 5720-06-9
• Molecular Formula: C₇H₉BO₃
• Molecular Weight: 151.96
• EINECS: 1312995-182-4
• Product Categories: Boronate Ester;Potassium Trifluoroborate;blocks;BoronicAcids;Boronic Acid series;Boron, Nitrile, Thio,& TM-Cpds;Substituted Boronic Acids;Boronic acids;Heterocyclic Compounds;Boronic Acid;Alkoxy;Aryl;Organoborons;B (Classes of Boron Compounds);CHIRAL CHEMICALS;organic or inorganic borate
• Mol File: 5720-06-9.mol

Chemical Properties

• Melting Point: 105-110 °C(lit.)
• Boiling Point: 319.3 °C at 760 mmHg
• Flash Point: 146.9 °C
• Appearance: Off-white/Crystals or Crystalline Powder
• Density: 1.17 g/cm³
• Vapor Pressure: 0.000142mmHg at 25°C
• Refractive Index: 1.524
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 8.55±0.58(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 3030981
• CAS DataBase Reference: 2-Methoxyphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxyphenylboronic acid(5720-06-9)
• EPA Substance Registry System: 2-Methoxyphenylboronic acid(5720-06-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• Hazardous Substances Data: 5720-06-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Methoxyphenylboronic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to form stable aryl structures makes it a valuable component in the development of new drugs and medications.
Used in Suzuki Reaction:
2-Methoxyphenylboronic acid is used as a reactant in the Suzuki reaction, an organic coupling reaction where a boronic acid with a halide is catalyzed by a palladium(0) complex. This reaction is crucial in the formation of carbon-carbon bonds and has been widely utilized in the synthesis of complex organic molecules, including those found in pharmaceuticals and advanced materials.
Used in Investigating Boron Function in Plants:
2-Methoxyphenylboronic acid is also used in scientific research to investigate the function of boron in plants. Understanding the role of boron in plant biology can lead to advancements in agricultural practices and the development of more efficient and sustainable crop production methods.
Used in Pesticide Industry:
In the pesticide industry, 2-Methoxyphenylboronic acid is used as a building block for the development of new and more effective pesticides. Its ability to form stable aryl structures allows for the creation of pesticides with improved performance and reduced environmental impact.
Used in Advanced Materials:
2-Methoxyphenylboronic acid is employed in the development of advanced materials, such as those used in electronics, optics, and energy storage. Its unique chemical properties make it a valuable component in the creation of innovative materials with enhanced performance characteristics.

Preparation

Under the protection of nitrogen, add magnesium (2.9 g, 1.2 times) and tetrahydrofuran (20 ml) and dibromoethane (1.9 g) to a 250 ml three-necked flask with a dropping funnel; then add 2-methoxybromobenzene (17.1 g, 0.1 mol), trimethyl borate (36.8 g, 3.5 times) and tetrahydrofuran (50 ml) as solvent to the dropping funnel. Heat to 40 ℃, activate the magnesium powder, and then slowly add the mixture in the dropping funnel dropwise, control the speed to the reaction temperature does not exceed 60 ℃, add the reaction after stirring until the magnesium basically disappeared, and then heat the reflux reaction for 6 hours. Stop heating, cool to room temperature, hydrolyze with 5% dilute hydrochloric acid to pH<2. Distillation to recover THF solvent, as the solvent is reduced, the product precipitated; cooling and filtration, recrystallization in methanol/water can be obtained 2-methoxyphenylboronic acid.

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

Upstream product

• 13195-76-1 triisobutyl borate 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 86487-17-4 2-tri-n-butylstannylanisole 
• 253280-01-2 C₉H₁₃BO₃ 
• 121-43-7 Trimethyl borate 
• 578-57-4 2-bromoanisole 
• 190788-60-4 pinacol 2-anisylboronate 
• 5419-55-6 Triisopropyl borate 
• 529-28-2 4-iodoanisol 
• 109-72-8 n-butyllithium 
• 10366-03-7 (2-methoxyphenyl)dichloroborane 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 766-51-8 2-Chloroanisole 
• 55124-35-1 diisopropylamine borane 

Downstream Products

• 93349-96-3 Methyl 5-(2-Methoxyphenyl)nicotinate 
• 118062-06-9 2-methoxy-5-(2'-methoxyphenyl)cyclohepta-2,4,6-trien-1-one 
• 130163-30-3 2-Methoxy-7-(2-methoxy-phenyl)-cyclohepta-2,4,6-trienone 
• 169774-67-8 (2S,3S)-N-benzoyl-2-methoxycarbonyl-3-tert-butoxycarbonylmethyl-4-(2-methoxyphenyl)-<4,5>-dehydropyrrolidine 
• 57455-06-8 3-iodobenzylalcohol 
• 208941-54-2 (2'-methoxybiphenyl-3-yl)methanol 
• 204571-88-0 methyl 3-(2-methoxy-5-{1-oxo-2-[3-(2-methoxyphenyl)phenyl]ethyl}phenyl)phenylacetate 
• 5957-89-1 2-(2-methoxy-phenyl)-pyridine 
• 92495-53-9 2-methoxy-4'-methylbiphenyl 
• 184040-64-0 N-[5-(2-methoxyphenyl)thiophene-2-sulfonyl]pyrrole 
• 5181-06-6 1-(2-methoxy-phenyl)piperidine 
• 65570-20-9 butyl-(2-methoxy-phenyl)amine 
• 22618-48-0 1-(cyclohexen-1-yl)-2-methoxybenzene 
• 5728-32-5 4-(2-methoxyphenyl)benzoic acid 

Relevant articles and documents

Aryl boronic acid preparation method

The invention belongs to the technical field of fine chemical engineering, and relates to an aryl boronic acid preparation method. In the prior art, aryl boronic acid as a novel safe and environmentally-friendly arylation reagent is widely used in scientific research and production of various fine chemicals containing aryl structures in the fields of medicines, pesticides, advanced materials and the like; and the aryl boronic acid compound preparation method reported in the disclosed literature has problems of harsh reaction conditions and high cost. A purpose of the invention is to provide amethod, wherein an aryl boron compound is formed by carrying out a reaction on a Grignard reagent and trialkyl borate under mild conditions, the composition of the aryl boron compound is converted from the main component diaryl borate into the main component aryl borate, and the aryl borate is hydrolyzed to obtain aryl boric acid, so that the preparation cost of the acyl aryl boric acid compound can be remarkably reduced, and the method has good practical application prospect.

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.).

Chemoselective Rhodium-Catalyzed Borylation of Bromoiodoarenes under Mild Conditions

A chemoselective rhodium-catalyzed borylation has been developed for the preparation of aryl boronate esters. The reaction proceeds under mild conditions with excellent selectivity for C-I bonds in bromoiodoarenes and exhibits broad functional group tolerance. This procedure can act as a complementary approach toward bifunctional arenes along with other metal-catalyzed borylations. Additionally, the reaction's utility in the preparation of monomers for metal-catalyzed cross-coupling polymerization is demonstrated.

Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water

A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.

Axially chiral tridentate isoquinoline derived ligands for diethylzinc addition to aldehydes

The synthesis and resolution of new tridentate isoquinoline-derived ligands has been developed. The key steps in the synthetic sequence include successive, chemo-selective Suzuki-Miyaura cross-couplings of 1,3-dichloroisoquinoline with suitable arylboronic acids. The new ligands prepared in this manner were resolved either via molecular complexation with N-benzylcinchonidinium chloride as with 1-[3-(2-hydroxyphenyl)isoquinolin-1-yl]naphthalen-2-ol or via chromatographic separation of its epimeric camphorsulfonates as for 1,3-bis-(2-hydroxynaphthalen-1-yl)isoquinoline. 4-tert-Butyl-2-chloro-6-[1-(2-hydroxymethylnaphthalen-1-yl)isoquinolin-3-yl]phenol was resolved by chiral semi-preparative HPLC. The application of these ligands in the diethylzinc addition to aldehydes was investigated. In certain cases, the desired secondary alcohols were obtained in high yield with excellent enantiomeric excess (ee > 99%) at low catalyst loading (1 mol%).

Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates

Organozinc pivalates, a recently developed air- and moisture-stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents and organozinc halides, is that the generation of multiorganylation byproducts such as borinic acids and trialkylboranes were completely suppressed. Additionally, the in situ generated boronates could be directly arranged into Suzuki-Miyaura type cross-coupling reactions to produce biaryls in high yields.

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.

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.

Evidence for Oxidative Decay of a Ru-Bound Ligand during Catalyzed Water Oxidation

In the evaluation of systems designed for catalytic water oxidation, ceric ammonium nitrate (CAN) is often used as a sacrificial electron acceptor. One of the sources of failure for such systems is oxidative decay of the catalyst in the presence of the st

Borinic Acids via Direct Arylation of Amine-Borane Complexes: An Air- and Water-Stable Boron Source

A synthesis of borinic acids and borinates was optimized using amine-borane complexes as a water and air insensitive borylating agent. The reaction operates under convenient conditions using a non-cryogenic temperature and with no flash chromatography, and it gives no boron impurities. The reaction proceeds through a tandem dehydrogenation-double addition mechanism.