3-Fluoro-4-methylphenylboronic acid

Base Information

• Chemical Name: 3-Fluoro-4-methylphenylboronic acid
• CAS No.: 168267-99-0
• Molecular Formula: C7H8BFO2
• Molecular Weight: 153.949
• Hs Code.: 29163990
• European Community (EC) Number: 677-535-7
• DSSTox Substance ID: DTXSID30382205
• Nikkaji Number: J1.334.922C
• Wikidata: Q72474777
• ChEMBL ID: CHEMBL1824168
• Mol file: 168267-99-0.mol

Synonyms:3-Fluoro-4-methylphenylboronic acid;168267-99-0;3-Fluoro-4-methylbenzeneboronic Acid;(3-fluoro-4-methylphenyl)boronic acid;MFCD02683115;Boronic acid, (3-fluoro-4-methylphenyl)-;3-Fluoro-p-tolylboronic acid;3-Fluoro-4-methylbenzeneboronicacid;Boronic acid, B-(3-fluoro-4-methylphenyl)-;SCHEMBL177645;CHEMBL1824168;DTXSID30382205;WPVBHUUZDFUIJA-UHFFFAOYSA-N;4-methyl-3-fluorophenylboronic acid;(3-fluoro-4-methylphenyl)boranediol;2,5-Dichlorohydroquinonedimethylether;BBL103508;STL557318;3-fluoro-4-methyl-phenylboronic acid;3-fluoro-4-methylphenyl boronic acid;3-fluoro-4-methyl phenyl boronic acid;AKOS000285058;CS-W009262;PS-9624;3-fluoro-4-methyl-benzene boronic acid;AC-29842;SY007913;AM20050285;F0712;FT-0600750;EN300-117463;A810955;J-512499;Z381540952;(3-fluoro-4-methyl-phenyl)boronic acid;3-Fluoro-4-methylphenylboronic Acid

Chemical Property of 3-Fluoro-4-methylphenylboronic acid

Chemical Property:

• Appearance/Colour: Off-white cryst.
• Vapor Pressure: 0.00201mmHg at 25°C
• Melting Point: 232-237 °C(lit.)
• Refractive Index: 1.505
• Boiling Point: 278.7 °C at 760 mmHg
• PKA: 7.76±0.10(Predicted)
• Flash Point: 122.3 °C
• PSA: 40.46000
• Density: 1.2 g/cm³
• LogP: -0.18610
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 154.0601378
• Heavy Atom Count: 11
• Complexity: 132

Purity/Quality:

99% ^*data from raw suppliers

3-Fluoro-4-methylphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, T
• Hazard Codes: Xi,T
• Statements: 36/37/38-25
• Safety Statements: 26-36/37/39-45-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=C(C=C1)C)F)(O)O
• Chemical Composition and Structure: 3-Fluoro-4-methylphenylboronic acid is a boronic acid compound with a chemical structure containing a phenyl ring substituted with a fluorine atom and a methyl group, along with a boronic acid functional group.
• Uses: Chemical Synthesis: ; Used in palladium-catalyzed cross-couplings for the synthesis of liquid crystalline fluorobiphenylcyclohexenes and difluoroterphenyls.; ; Pharmaceutical Research: ; Utilized in the synthesis of o-phenylphenols, which exhibit potent leukotriene B4 receptor agonist activity.; ; Material Science: ; Applied in the preparation of lipophilic-tailed monocationic inhibitors of neuronal nitric oxide synthase.
• Mechanism of Action: The mechanism of action of 3-Fluoro-4-methylphenylboronic acid varies depending on its application. It is involved in palladium-catalyzed cross-couplings for the synthesis of liquid crystalline fluorobiphenylcyclohexenes and difluoroterphenyls. It also serves as a reactant in the synthesis of o-phenylphenols, which are potent leukotriene B4 receptor agonists.
• Analysis Method: Analytical methods for 3-Fluoro-4-methylphenylboronic acid may include techniques such as high-performance liquid chromatography (HPLC) and spectroscopic methods for characterization and quantification. Additionally, its biological activity may be assessed through bioassays such as bioluminescence inhibition assays.

Technology Process of 3-Fluoro-4-methylphenylboronic acid

There total 3 articles about 3-Fluoro-4-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: 91.0%

Trimethyl borate (121-43-7,63156-11-6) + 2-fluoro-4-bromotoluene (51436-99-8) → (3-fluoro-4-methylphenyl)boronic acid (168267-99-0)

Guidance literature:

2-fluoro-4-bromotoluene; With n-butyllithium; In tetrahydrofuran; hexane; at -50 ℃; for 0.5h;

Trimethyl borate; In tetrahydrofuran; hexane; at 20 ℃; for 12h;

With hydrogenchloride; In tetrahydrofuran; hexane;

DOI:10.1080/00304940009355929

Reference yield: 82.0%

2-fluoro-4-bromotoluene (51436-99-8) → (3-fluoro-4-methylphenyl)boronic acid (168267-99-0)

Guidance literature:

2-fluoro-4-bromotoluene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 10 ℃; Inert atmosphere;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.05.104

Reference yield: 50.0%

2-fluoro-4-iodotoluene (39998-81-7) → (3-fluoro-4-methylphenyl)boronic acid (168267-99-0)

Guidance literature:

2-fluoro-4-iodotoluene; With diisopropopylaminoborane; triethylamine; triphenylphosphine; palladium dichloride; In tetrahydrofuran; at 65 ℃; for 12h; Inert atmosphere;

With methanol; In tetrahydrofuran; at 0 ℃; Further stages; Inert atmosphere;

DOI:10.1016/j.tet.2010.11.065

upstream raw materials:

Trimethyl borate

2-fluoro-4-bromotoluene

2-fluoro-4-iodotoluene

Downstream raw materials:

C₁₃H₁₂FNO₂

C₁₃H₁₂FNO₂

C₁₄H₁₄FNO₂

C₂₀H₁₈FNO₄

Refernces

• 1、 White, James R.,Price, Gareth J.,Schiffers, Stefanie,Raithby, Paul R.,Plucinski, Pawel K.,Frost, Christopher G.. "A modular approach to catalytic synthesis using a dual-functional linker for Click and Suzuki coupling reactions". supporting information; experimental part. p. 3913 - 3917. Retrieved 2010/08/22.