2-Methylphenylboronic acid

Base Information

• Chemical Name: 2-Methylphenylboronic acid
• CAS No.: 16419-60-6
• Molecular Formula: C7H9BO2
• Molecular Weight: 135.958
• Hs Code.: 29163990
• DSSTox Substance ID: DTXSID40369820
• Nikkaji Number: J805.710I
• Wikidata: Q72509288
• Mol file: 16419-60-6.mol

Synonyms:para-tolylboronic acid;tolylboronic acid

Chemical Property of 2-Methylphenylboronic acid

Chemical Property:

• Appearance/Colour: beige crystalline powder
• Vapor Pressure: 8.13E-05mmHg at 25°C
• Melting Point: 162-164 °C(lit.)
• Refractive Index: 1.583
• Boiling Point: 283.4 °C at 760 mmHg
• PKA: 8.61±0.58(Predicted)
• Flash Point: 125.2 °C
• PSA: 40.46000
• Density: 1.1 g/cm³
• LogP: -0.32520
• Storage Temp.: 0-6°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Slightly 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: 106

Purity/Quality:

99% ^*data from raw suppliers

2-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=CC=C1C)(O)O
• Description: 2-Methylphenylboronic acid is an important organic boronic acid compound, which is widely used in Suzuki cross-coupling reaction and has important application value in the fields of organic synthesis and medicine and chemical industry.
• Physical properties: beige crystalline powder
• Uses: suzuki reaction 2-Methylbenzeneboronic acid is a reagent used for Pd-catalyzed arylation using Suzuki-Miyaura cross-coupling in water, Ruthenium catalyzed direct arylation reactions, Ligand-free copper-catalyzed coupling reactions, Rhodium-catalyzed asymmetric 1,4-addition reactions. Reagent used in Preparation of chiral monophosphorus ligands in asymmetric Suzuki-Miyaura coupling reaction, Human farnesyl pyrophosphate synthase inhibitors as antitumor agents for multiple myeloma cells

Technology Process of 2-Methylphenylboronic acid

There total 34 articles about 2-Methylphenylboronic 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: 100.0%

2-methylphenylboronic acid pinacol ester (195062-59-0) → 2-Methylphenylboronic acid (16419-60-6)

Guidance literature:

2-methylphenylboronic acid pinacol ester; With potassium hydrogen difluoride; In methanol; at 20 ℃; for 0.25h;

With chloro-trimethyl-silane; water; In acetonitrile; for 1h;

DOI:10.1016/j.tetlet.2005.09.101

Reference yield: 97.0%

2-methylchlorobenzene (95-49-8) → 2,2'-dimethyl-1,1'-biphenyl (605-39-0) + 2-Methylphenylboronic acid (16419-60-6)

Guidance literature:

With cesium fluoride; Pd(dba)2; In toluene;

Reference yield: 92.0%

2-methylphenyl bromide (95-46-5) → 2-Methylphenylboronic acid (16419-60-6)

Guidance literature:

2-methylphenyl bromide; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

With Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1039/b412932f

upstream raw materials:

ortho-tolylmagnesium bromide

triisobutyl borate

(2-methylphenyl)dichloroborane

Trimethyl borate

Downstream raw materials:

tri-o-tolylboroxine

2-bromomethylphenylboronic acid

(2-Br₂CHC₆H₄)B(OH)2

(2-CH₃-3.5-(NO₂)2C₆H₂)B(OH)2

Refernces

• 1、 Duan, Wei-Liang,Imazaki, Yusuke,Shintani, Ryo,Hayashi, Tamio. "Asymmetric construction of chiral C-N axes through rhodium-catalyzed 1,4-addition". . p. 8529 - 8536. Retrieved 2007.
• 2、 Lunazzi, Lodovico,Mazzanti, Andrea,Minzoni, Mirko,Edgar Anderson. "Structure, conformation, and dynamic processes of the stereolabile atropisomers of hindered terphenyl hydrocarbons". . p. 1291 - 1294. Retrieved 2005.
• 3、 -. "Method for synthesizing sodium 2-carboxyphenylborate". Paragraph 0020-0021. . Retrieved 2020/06/17.
• 4、 Yasukawa, Tomohiro,Kuremoto, Tatsuya,Miyamura, Hiroyuki,Kobayashi, Sh?. "Asymmetric Arylation of Imines Catalyzed by Heterogeneous Chiral Rhodium Nanoparticles". supporting information. p. 2716 - 2718. Retrieved 2016/06/15.