2-Methoxyphenylboronic acid

Base Information

• Chemical Name: 2-Methoxyphenylboronic acid
• CAS No.: 5720-06-9
• Molecular Formula: C7H9BO3
• Molecular Weight: 151.958
• Hs Code.: 29163990
• DSSTox Substance ID: DTXSID40370057
• Nikkaji Number: J331.438C
• Wikidata: Q72517510
• ChEMBL ID: CHEMBL348732
• Mol file: 5720-06-9.mol

Synonyms:2-Methoxyphenylboronic acid;5720-06-9;2-Methoxybenzeneboronic acid;(2-methoxyphenyl)boronic Acid;o-Methoxyphenylboronic acid;2-methoxyphenyl boronic acid;MFCD00236047;Boronic acid, (2-methoxyphenyl)-;2-methoxy phenylboronic acid;2-methoxybenzene boronic acid;2-Methoxylphenylboronic Acid (contains varying amounts of Anhydride);2-methoxyphenylboronicacid;2-Methoxybenzeneboronicacid;(2-methoxyphenyl)boranediol;o-methoxyphenyl boronic acid;2-methoxypbenylboronic acid;D01FLQ;2-methyoxyphenylboronic acid;2-methoxy-phenylboronic acid;2-methoxyphenyl-boronic acid;SCHEMBL23807;2-methoxy benzeneboronic acid;2-methoxy-benzeneboronic acid;2-methoxylphenyl boronic acid;2-methoxy phenyl boronic acid;2-methoxy-phenyl boronic acid;2-methoxy-phenyl-boronic acid;2-methoxyphenyl- boronic acid;2-methoxy benzene boronic acid;2-methoxy-benzene boronic acid;2-methoxy-benzene-boronic acid;(2-methoxyphenyl) boronic acid;CHEMBL348732;(2-methoxy-phenyl)-boronic acid;BDBM26138;DTXSID40370057;ROEQGIFOWRQYHD-UHFFFAOYSA-N;[2-(methyloxy)phenyl]boronic acid;[6-(methyloxy)phenyl]boronic acid;2-Methoxyphenylboronic acid, 95%;BCP26579;AKOS003585224;AB05344;AC-2769;AS-2331;CS-W002569;NCGC00249463-01;BP-12107;PD180533;SY002864;AM20061179;FT-0601801;EN300-79099;Q-102217;F0001-1493;Z381513020

Chemical Property of 2-Methoxyphenylboronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.000142mmHg at 25°C
• Melting Point: 105-110 °C(lit.)
• Refractive Index: 1.524
• Boiling Point: 319.3 °C at 760 mmHg
• PKA: 8.55±0.58(Predicted)
• Flash Point: 146.9 °C
• PSA: 49.69000
• Density: 1.17 g/cm³
• LogP: -0.62500
• Storage Temp.: 0-6°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.0644743
• Heavy Atom Count: 11
• Complexity: 118

Purity/Quality:

99% ^*data from raw suppliers

2-Methoxyphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1OC)(O)O
• 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.
• Uses: suzuki reaction 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.

Technology Process of 2-Methoxyphenylboronic acid

There total 31 articles about 2-Methoxyphenylboronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

pinacol 2-anisylboronate (190788-60-4) → 2-Methoxyphenylboronic acid (5720-06-9)

Guidance literature:

With hydrogenchloride; polystyrene boronic acid; In acetonitrile; at 20 ℃; for 18h;

DOI:10.1016/j.tetlet.2004.07.014

Reference yield: 87.0%

2-bromoanisole (578-57-4) → 2-Methoxyphenylboronic acid (5720-06-9)

Guidance literature:

2-bromoanisole; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃;

With Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;

DOI:10.1016/j.tet.2007.10.105

Reference yield: 85.0%

2-tri-n-butylstannylanisole (86487-17-4) → 2-Methoxyphenylboronic acid (5720-06-9)

Guidance literature:

With borane; water; In tetrahydrofuran; for 1h; Heating;

DOI:10.1016/S0022-328X(00)00536-2

upstream raw materials:

bis(o-methoxyphenyl)mercury

triisobutyl borate

4-methoxyphenyl magnesium bromide

2-bromoanisole

Downstream raw materials:

2-(2-methoxy-phenyl)-pyridine

2-(2-methoxyphenyl)-6-methylpyridine

N-[5-(2-methoxyphenyl)thiophene-2-sulfonyl]pyrrole

1-(2-methoxy-phenyl)piperidine

Refernces

• 1、 Varni, Anthony J.,Bautista, Michael V.,Noonan, Kevin J.T.. "Chemoselective Rhodium-Catalyzed Borylation of Bromoiodoarenes under Mild Conditions". . p. 6770 - 6777. Retrieved 2020/07/21.
• 2、 Fu, Ying,Gou, Bei-Lei,Shi, Chun-Zhao,Du, Zhengyin,Shen, Tong. "Copper-Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates". . p. 4253 - 4257. Retrieved 2018/09/18.