4-Methoxyphenylboronic acid

Base Information

• Chemical Name: 4-Methoxyphenylboronic acid
• CAS No.: 5720-07-0
• Molecular Formula: C7H9BO3
• Molecular Weight: 151.958
• Hs Code.: 29310095
• DSSTox Substance ID: DTXSID60205837
• Nikkaji Number: J54.864B
• Wikipedia: 4-boronoanisole
• Wikidata: Q72517513
• ChEMBL ID: CHEMBL21427
• Mol file: 5720-07-0.mol

Synonyms:4-methoxyphenylboronic acid

Chemical Property of 4-Methoxyphenylboronic acid

Chemical Property:

• Appearance/Colour: white to light beige crystalline powder
• Melting Point: 204-206 °C(lit.)
• Boiling Point: 306.8 °C at 760 mmHg
• PKA: 8.96±0.10(Predicted)
• Flash Point: 139.3 °C
• PSA: 49.69000
• Density: 1.17 g/cm³
• LogP: -0.62500
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: Soluble in dimethyl sulfoxide and methanol.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.0644743
• Heavy Atom Count: 11
• Complexity: 110

Purity/Quality:

99% ^*data from raw suppliers

4-Methoxylphenylboronic Acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)OC)(O)O
• Uses: 4-Methoxyphenylboronic acid can be used as a common organic reagent in Suzuki coupling reactions to study the N-arylation of imidazoles and amines catalyzed by copper exchange of calcium fluorophosphates.Reagent used in the preparation of various biological inhibitors. 4-Methoxyphenylboronic acid is a reagent used forSuzuki-Miyaura cross-coupling reactionsPd-catalyzed direct arylationHighly effective synthesis using palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in waterPalladium-catalyzed stereoselective Heck-type reactionTandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequenceCopper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides Ruthenium catalyzed direct arylationRh-catalyzed asymmetric conjugate addition 4-Methoxylphenylboronic Acid is a phenylboronic acid used to investigate boron function in plants. suzuki reaction

Technology Process of 4-Methoxyphenylboronic acid

There total 63 articles about 4-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: 99.0%

2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-79-7) → 4-methoxyphenylboronic acid (5720-07-0)

Guidance literature:

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

DOI:10.1016/j.tetlet.2004.07.014

Reference yield: 97.0%

1-bromo-4-methoxy-benzene (104-92-7) + Trimethyl borate (121-43-7,63156-11-6) → 4-methoxyphenylboronic acid (5720-07-0)

Guidance literature:

With Mg; In tetrahydrofuran; Mg (reflux), THF, B(OCH)3, bromobenzene-compound (-10°C) or n-butyllithium, B(OCH3)3, -78°C, THF;

DOI:10.1021/ja907882n

Reference yield: 96.0%

4-methoxyphenyl magnesium bromide (13139-86-1) → 4-methoxyphenylboronic acid (5720-07-0)

Guidance literature:

4-methoxyphenyl magnesium bromide; With Trimethyl borate; In tetrahydrofuran; at 20 ℃;

With acidic aq. solution;

DOI:10.1021/ja036808b

upstream raw materials:

4-CH₃OC₆H₄BCl₂

di-(4-methoxyphenyl)borinic acid

triisobutyl borate

4-methoxyphenyl magnesium bromide

Downstream raw materials:

2-methoxy-5-(4'-methoxyphenyl)cyclohepta-2,4,6-trien-1-one

2-methoxy-7-(4-methoxy-phenyl)-cycloheptatrienone

(1E)-3-(4-methoxyphenyl)-1-phenylpropene

1-(benzyloxy)-4-ethyl-2-(4-methoxyphenyl)-5-<(6-methyl-6-cyanoheptyl)oxy>benzene

Refernces

• 1、 Daud, Hina,Hoffman, David J.,Huang, Ning,Jezorek, Ryan L.,Malineni, Jagadeesh,McClure, Emily R.,Partridge, Benjamin E.,Percec, Virgil,Peterca, Mihai,Sahoo, Dipankar,Song, Se Lin,Sung, Paul D.,Wang, Shitao,Wang, Xuefeng,Zhang, Na. "An Accelerated Modular-Orthogonal Ni-Catalyzed Methodology to Symmetric and Nonsymmetric Constitutional Isomeric AB2to AB9Dendrons Exhibiting Unprecedented Self-Organizing Principles". supporting information. p. 17724 - 17743. Retrieved 2021/11/04.
• 2、 Igarashi, Takuya,Shimazumi, Ryoma,Tobisu, Mamoru. "Palladium-catalyzed B-diarylation of diethylaminoborane for the synthesis of diarylborinic acids". supporting information. p. 760 - 763. Retrieved 2020/07/10.