3-Bromo-5-methylphenylboronic acid

Base Information

• Chemical Name: 3-Bromo-5-methylphenylboronic acid
• CAS No.: 849062-36-8
• Molecular Formula: C7H8BBrO2
• Molecular Weight: 214.854
• Hs Code.: 2931900090
• European Community (EC) Number: 898-215-5
• DSSTox Substance ID: DTXSID70584488
• Nikkaji Number: J3.123.827G
• Wikidata: Q82476155
• Mol file: 849062-36-8.mol

Synonyms:3-Bromo-5-methylphenylboronic acid;849062-36-8;(3-bromo-5-methylphenyl)boronic acid;MFCD06411355;3-Bromo-5-methylbenzeneboronic acid;(3-Bromo-5-methyl-phenyl)boronic acid;SCHEMBL3755288;DTXSID70584488;KKEPYOBFWSGWLQ-UHFFFAOYSA-N;AMY29939;ZIB06236;AKOS004114014;AB25255;CS-W000980;AS-18797;BP-11405;SY110024;F10514;EN300-7370373;A841003;Z3224142546

Chemical Property of 3-Bromo-5-methylphenylboronic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 278-283 °C
• Refractive Index: 1.585
• Boiling Point: 351.805 °C at 760 mmHg
• PKA: 7.65±0.10(Predicted)
• Flash Point: 166.566 °C
• PSA: 40.46000
• Density: 1.577 g/cm³
• LogP: 0.43730
• Storage Temp.: Keep Cold
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 213.98007
• Heavy Atom Count: 11
• Complexity: 132

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Bromo-5-methylphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC(=C1)Br)C)(O)O

Technology Process of 3-Bromo-5-methylphenylboronic acid

There total 2 articles about 3-Bromo-5-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: 90.7%

Triisopropyl borate (5419-55-6) + 3,5-dibromotoluene (1611-92-3) → (3-bromo-5-methylphenyl)boronic acid (849062-36-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 2.5h; Concentration; Inert atmosphere;

Reference yield: 65.0%

Trimethyl borate (121-43-7,63156-11-6) + 3,5-dibromotoluene (1611-92-3) → (3-bromo-5-methylphenyl)boronic acid (849062-36-8)

Guidance literature:

3,5-dibromotoluene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere; Schlenk technique;

Trimethyl borate; at 20 ℃; for 12h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c5dt02497h

Reference yield: 99.0%

(3-bromo-5-methylphenyl)boronic acid (849062-36-8) → 1-bromo-3-methyl-5-nitrobenzene (52488-28-5)

Guidance literature:

With nitric acid; In 1,2-dichloro-ethane; at 70 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.joc.1c00886

upstream raw materials:

Trimethyl borate

3,5-dibromotoluene

Triisopropyl borate

Downstream raw materials:

1-bromo-3-iodo-5-methylbenzene

3-bromo-5-methylphenol

3-bromo-5-methoxytoluene

Refernces

• 1、 Lo, Jerry C.Y.,So, Loi-Chi,Chan, Michael C.W.. "Synthesis and spectroscopic characterization of group 4 post-metallocenes bearing (σ-aryl)-2-phenolate-6-pyridyl and -isoquinolinyl auxiliaries". supporting information. p. 15905 - 15913. Retrieved 2015/09/15.