2,6-Dimethylphenylboronic acid

Base Information

• Chemical Name: 2,6-Dimethylphenylboronic acid
• CAS No.: 100379-00-8
• Molecular Formula: C8H11BO2
• Molecular Weight: 149.985
• Hs Code.: 29163990
• DSSTox Substance ID: DTXSID60342610
• Nikkaji Number: J1.072.041I
• Wikidata: Q72471231
• ChEMBL ID: CHEMBL3236888
• Mol file: 100379-00-8.mol

Synonyms:2,6-Dimethylphenylboronic acid;100379-00-8;(2,6-dimethylphenyl)boronic acid;2,6-Dimethylbenzeneboronic Acid;MFCD01009693;Boronic acid, (2,6-dimethylphenyl)-;2,6-Dimethyl-phenylboronic Acid;m-Xylene-2-boronic Acid;(2,6-Dimethlphenyl)borate;SCHEMBL61913;2,6-dimethlphenylboronic acid;2,6-dimethyphenylboronic acid;AKOS BRN-0223;(2,6-Dimethylphenyl)Boranediol;2,6-XYLENEBORONIC ACID;(2,6-dimethylphenyl)boronicacid;2,6-dimethyl phenylboronic acid;2,6-dimethylphenyl boronic acid;CHEMBL3236888;2,6-dimethylbenzene boronic acid;DTXSID60342610;2,6-Dimethylphenylboronic acid #;BCP22768;BBL103739;STL557549;AKOS000278423;AB07956;BCP9000266;CS-W002725;GS-6707;Boronic acid, B-(2,6-dimethylphenyl)-;AC-24790;SY015041;2,6-Dimethylphenylboronic acid, >=95.0%;AM20060968;D3633;FT-0642422;EN300-92955;Z336079988

Chemical Property of 2,6-Dimethylphenylboronic acid

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0.000838mmHg at 25°C
• Melting Point: 105 °C (dec.)(lit.)
• Refractive Index: 1.523
• Boiling Point: 299.9 °C at 760 mmHg
• PKA: 8.68±0.58(Predicted)
• Flash Point: 135.2 °C
• PSA: 40.46000
• Density: 1.07 g/cm³
• LogP: -0.01680
• Storage Temp.: 0-6°C
• Solubility.: Soluble in methanol.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 150.0852098
• Heavy Atom Count: 11
• Complexity: 117

Purity/Quality:

99% ^*data from raw suppliers

2,6-Dimethylphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=CC=C1C)C)(O)O
• Uses: suzuki reaction It is used as a reagent for palladium catalyzed Suzuki-Miyaura coupling reactions, Pd-catalyzed homocouplings, Rhodium(I)-catalyzed 1,4-addition reactions. It is used in the preparation of protein kinase inhibitors, G Protein-Coupled Receptor.

Technology Process of 2,6-Dimethylphenylboronic acid

There total 9 articles about 2,6-Dimethylphenylboronic 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%

water (7732-18-5) + potassium 2,6-dimethylphenyltrifluoroborate → 2,6-dimethylbenzene boronic acid (100379-00-8)

Guidance literature:

With montmorillonite K₁₀; at 25 ℃; for 0.333333h;

DOI:10.21577/0103-5053.20180126

Reference yield: 85.0%

Trimethyl borate (121-43-7,63156-11-6) + 2-Bromo-m-xylene (576-22-7) → 2,6-dimethylbenzene boronic acid (100379-00-8)

Guidance literature:

2-Bromo-m-xylene; With iodine; magnesium; In tetrahydrofuran; for 1h; Reflux;

Trimethyl borate; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1039/c9cp00553f

Reference yield: 81.0%

potassium 2,6-dimethylphenyltrifluoroborate → 2,6-dimethylbenzene boronic acid (100379-00-8)

Guidance literature:

With water; silica gel; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo901441u

upstream raw materials:

dimethoxy(2,6-dimethylphenyl)borone

2-Bromo-m-xylene

Trimethyl borate

(2,6-dimethylphenyl)magnesium bromide

Downstream raw materials:

7-(2,6-Dimethyl-phenyl)-benzo[1,2,4]triazin-3-ylamine

triphenyl(2,6-dimethylphenyl)bismuthonium tetrafluoroborate

Refernces

• 1、 Cho, Hye Jin,Kim, Sang Won,Kim, Sungjin,Lee, Sangback,Lee, Juhyen,Cho, Yeonchoo,Lee, Yunmi,Lee, Tae-Woo,Shin, Hyeon-Jin,Song, Changsik. "Suppressing π-π Stacking interactions for enhanced solid-state emission of flat aromatic molecules: Via edge functionalization with picket-fence-type groups". . p. 17289 - 17296. Retrieved 2020.
• 2、 -. "Aryl boronic acid preparation method". Paragraph 0033-0036; 0040. . Retrieved 2020/01/25.