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
• Article Data: 48

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

Description

2-Methoxyphenylboronic acid is an arylboronic acid. Arylboronic acids can be widely used as safe and environmentally friendly new aromatization reagents for scientific research and production of various fine chemicals containing aryl structures, such as pharmaceuticals, pesticides, and advanced materials. The reactions of arylboronic acids with halogenates play a pivotal role in today's drug synthesis, and such reactions were pioneered by Japanese scientists Suzuki's team, which won the Nobel Prize in Chemistry in 2010.

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 5720-06-9 differently. You can refer to the following data:
1. suzuki reaction
2. 2-Methoxylphenylboronic acid is a phenylboronic acid used to investigate boron function in plants. It is used in Suzuki reaction, organic reaction that is classified as a coupling reaction where the coupling partners are a boronic acid with a halide catalyzed by a palladium(0) complex.

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 
• 578-57-4 2-bromoanisole 
• 121-43-7 Trimethyl borate 
• 109-72-8 n-butyllithium 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 766-51-8 2-Chloroanisole 
• 90-04-0 2-methoxy-phenylamine 
• 13675-18-8 tetrahydroxydiboron 
• 492-95-5 2-methoxyphenyldiazonium tetrafluoroborate 
• 5419-55-6 Triisopropyl borate 
• 529-28-2 4-iodoanisol 
• 73183-34-3 bis(pinacol)diborane 
• 7732-18-5 water 

Downstream Products

• 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 
• 139163-60-3 rac-2,2-dimethyl-1-<6-(2-methoxyphenyl)pyridin-2-yl>propanol 
• 131653-65-1 2,2-dimethyl-N-(4-(2-methoxyphenyl)-3-pyridyl)propanamide 
• 131653-71-9 N-[2-Methoxy-4-(2-methoxy-phenyl)-pyridin-3-yl]-2,2-dimethyl-propionamide 
• 93350-05-1 Methyl 5-(2-Methoxyphenyl)-6-methoxynicotinate 
• 142643-55-8 2-<4-(2-methoxyphenyl)-3-pivaloylamino>pyridyltriflate 
• 23982-29-8 7,8-Dimethoxy-4-(2-methoxyphenyl)-2H-1-benzopyran-2-one 
• 24050-68-8 5,7-Dimethoxy-4-(2-methoxyphenyl)-2H-1-benzopyran-2-one 
• 190188-43-3 1-(2-methoxyphenyl)-3-chloroisoquinoline 
• 1027535-02-9 4-(2-Methoxy-phenyl)-5-oxo-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester 
• 529-28-2 4-iodoanisol 
• 5957-89-1 2-(2-methoxy-phenyl)-pyridine 

Relevant articles and documents

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.

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.

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.