p-Tolylboronic acid

Base Information

• Chemical Name: p-Tolylboronic acid
• CAS No.: 5720-05-8
• Molecular Formula: C7H9BO2
• Molecular Weight: 135.958
• Hs Code.: 29319090
• NSC Number: 62870
• UNII: YJM4GM7K66
• DSSTox Substance ID: DTXSID00205836
• Nikkaji Number: J48.883F
• Wikipedia: 4-methylphenylboronic acid
• Wikidata: Q27294549
• ChEMBL ID: CHEMBL140780
• Mol file: 5720-05-8.mol

Synonyms:para-tolylboronic acid;tolylboronic acid

Chemical Property of p-Tolylboronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.976mmHg at 25°C
• Melting Point: 256-263 °C(lit.)
• Refractive Index: 1.505
• Boiling Point: 275.2 °C at 760 mmHg
• PKA: 8.84±0.10(Predicted)
• Flash Point: 120.2 °C
• PSA: 40.46000
• Density: 1.1 g/cm³
• LogP: -0.32520
• Storage Temp.: 0-6°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: It is soluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 136.0695597
• Heavy Atom Count: 10
• Complexity: 97.8

Purity/Quality:

99% ^*data from raw suppliers

4-Methylphenylboronic 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)C)(O)O
• Uses: suzuki reaction 4-Methylbenzeneboronic acid, is a commonly used chemical in Suzuki coupling reactions. It is also used as an intermediate in pharmaceutical industry Reagent used forPalladium (Pd)-catalyzed direct arylationDirect Palladium(II)-Catalyzed SynthesisPalladium-catalyzed arylation by Suzuki-Miyaura cross-coupling in waterCyclopalladationTandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequenceRuthenium catalyzed direct arylationRhodium-catalyzed asymmetric conjugate additionLigand-free copper-catalyzed cross-coupling reactionsRegioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactionsLigand-free Suzuki, Sonogashira, and Heck cross-coupling reactionsReagent used in Preparation ofCatalysts for Suzuki-Miyaura cross-coupling of aryl bromidesRecyclable Palladium nanoparticle catalysts immobilized by click ionic copolymers as for Suzuki-Miyaura cross-coupling reactions in water

Technology Process of p-Tolylboronic acid

There total 73 articles about p-Tolylboronic 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: 97.5%

Trimethyl borate (121-43-7,63156-11-6) + para-chlorotoluene (106-43-4) → 4-methylphenylboronic acid (5720-05-8)

Guidance literature:

With lithium; In tetrahydrofuran;

Reference yield: 94.0%

p-tolylboronic pinacol ester (195062-57-8) → 4-methylphenylboronic acid (5720-05-8)

Guidance literature:

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

DOI:10.1016/j.tetlet.2004.07.014

Reference yield: 91.0%

Triisopropyl borate (5419-55-6) + para-bromotoluene (106-38-7) → 4-methylphenylboronic acid (5720-05-8)

Guidance literature:

para-bromotoluene; With iodine; magnesium; In tetrahydrofuran; at 70 ℃; for 1h;

Triisopropyl borate; In tetrahydrofuran; at 0 ℃; for 1h; Temperature; Concentration; Time;

upstream raw materials:

dichloro-p-tolyl-borane

di(p-tolyl)borinic acid

triisobutyl borate

para-methylphenylmagnesium bromide

Downstream raw materials:

2,3-dihydro-2-(4-methylphenyl)benzo[d][1,3,2]diazaborinin-4(1H)-one

3,5-dimethyl-4-(4-methylphenyl)isoxazole

3-(4-methylphenyl)-4H-chromen-4-one

1,4-phenylenebis[(4-methylphenyl)methanone]

Refernces

• 1、 -. "Preparation method of trans-ketone intermediate". Paragraph 0086-0090; 0092. . Retrieved 2021/06/06.
• 2、 -. "Aryl boronic acid preparation method". Paragraph 0029-0030. . Retrieved 2020/01/25.