Phenylboronic acid

Base Information

• Chemical Name: Phenylboronic acid
• CAS No.: 98-80-6
• Deprecated CAS: 2055000-33-2
• Molecular Formula: C6H7BO2
• Molecular Weight: 121.931
• Hs Code.: 29310095
• European Community (EC) Number: 202-701-9
• NSC Number: 66487
• UNII: L12H7B02G5
• DSSTox Substance ID: DTXSID9059179
• Nikkaji Number: J119.652I
• Wikipedia: Phenylboronic acid
• Wikidata: Q408739
• Pharos Ligand ID: KR8SPQ67KDRA
• Metabolomics Workbench ID: 146424
• ChEMBL ID: CHEMBL21485
• Mol file: 98-80-6.mol

Synonyms:benzeneboronic acid;phenylboronate;phenylboronic acid

Chemical Property of Phenylboronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00446mmHg at 25°C
• Melting Point: 216-219 °C(lit.)
• Refractive Index: 1.534
• Boiling Point: 265.856 °C at 760 mmHg
• PKA: 8.83(at 25℃)
• Flash Point: 114.586 °C
• PSA: 40.46000
• Density: 1.139 g/cm³
• LogP: -0.63360
• Storage Temp.: 0-6°C
• Sensitive.: Hygroscopic
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 10 g/L (20 ºC)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 122.0539096
• Heavy Atom Count: 9
• Complexity: 79.1

Purity/Quality:

99% ^*data from raw suppliers

Phenylboronic Acid-d5 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,N
• Hazard Codes: Xn,Xi,N
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 22-24/25-36/37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Boron)
• Canonical SMILES: B(C1=CC=CC=C1)(O)O
• Description: Phenylboronic acid is an important organic compound known for its distinctive chemical properties and versatile applications. It exhibits fluorescence properties and chemical stability, making it suitable for stable labeling of target molecules in vivo for detection and localization purposes. As a fully synthetic polyhydroxy compound recognizer, it offers advantages such as cost-effectiveness, stability, and resistance to inactivation compared to enzyme-based substances. The preparation process of phenylboronic acid involves multiple steps, including synthesis, FITC labeling reaction, and purification, with precise control of reaction conditions and time being crucial for obtaining high-purity phenylboronic acid.
• Used in Drug Delivery Systems: Phenylboronic acid-based glucose-sensitive polymer carriers have emerged as promising platforms for diabetic therapy. These bioresponsive delivery systems mimic the physiological insulin secretion model of the pancreas, enabling precise regulation of hypoglycemic drug release to control blood sugar levels in diabetic patients. Phenylboronic acid derivatives exhibit reversible glucose responsiveness, offering stability, long-term storage capabilities, and enhanced drug release control, making them attractive candidates for advanced drug delivery systems aimed at managing diabetes effectively.^[1]
• Used in Biological Research: Phenylboronic acid finds widespread use in biological research, particularly in cell labeling and protein analysis applications. Its stable labeling capabilities make it valuable for visualizing and tracking target molecules in living systems, aiding in various research endeavors related to cell biology, molecular biology, and biochemistry.^[2]
• Used in Drug Synthesis: Phenylboronic acid serves as a key compound in the organic synthesis of various drugs and pharmaceutical intermediates. It is utilized in the preparation of Pincer nickel(II) complexes and palladium(II) pyridoxal hydrazone metal rings, which function as catalysts in Suzuki-Miyaura cross-coupling reactions. Additionally, phenylboronic acid is employed in the synthesis of N-type polymers for all-polymer solar cells and as a precursor for the production of efficient and selective mTOR kinase inhibitors, showcasing its significance in drug discovery and development.^[3]
• Used in Environmental Monitoring: Phenylboronic acid-based fluorescent probes have been developed for selective detection of mercury ions (Hg2+) and methylmercury ions (CH3Hg+) in groundwater and environmental samples. These probes offer high selectivity and sensitivity, enabling rapid and precise detection of trace mercury levels in real-world scenarios. The specific interaction between phenylboronic acid and mercury ions enables the development of cost-effective and efficient fluorescent probes for environmental monitoring applications, facilitating the identification and mitigation of mercury contamination hazards.^[4]
• References: [1] Bioresponsive Functional Phenylboronic Acid-Based Delivery System as an Emerging Platform for Diabetic Therapy; DOI 10.2147/IJN.S284357; [2] Blue light photocatalysis of carbazole-based conjugated microporous polymers: Aerobic hydroxylation of phenylboronic acids to phenols; DOI 10.1016/j.apcatb.2022.121210; [3] Phenylboronic Acid Modification Augments the Lysosome Escape and Antitumor Efficacy of a Cylindrical Polymer Brush-Based Prodrug; DOI 10.1021/jacs.1c09741; [4] A triphenylamine-based fluorescent probe with phenylboronic acid for highly selective detection of Hg2+ and CH3Hg+ in groundwater; DOI 10.1039/D3OB00183K

Technology Process of Phenylboronic acid

There total 168 articles about Phenylboronic 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: 99.0%

1-chloro-3,5-dimethylbenzene (556-97-8) → 3,5-dimethylbiphenyl (17057-88-4) + phenylboronic acid (98-80-6)

Guidance literature:

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

Reference yield: 88.0%

methanol (67-56-1) + bromobenzene (108-86-1,52753-63-6) + diisopropylamine borane (55124-35-1) → phenylboronic acid (98-80-6)

Guidance literature:

diisopropylamine borane; With magnesium; phenylmagnesium bromide; In tetrahydrofuran; at 20 ℃; for 0.166667h;

bromobenzene; In tetrahydrofuran; at 70 ℃;

methanol; Further stages;

DOI:10.1016/j.tet.2018.11.036

Reference yield: 82.7%

bromobenzene (108-86-1,52753-63-6) + triethyl borate (150-46-9) → phenylboronic acid (98-80-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

upstream raw materials:

diethyl ether

boric acid tributyl ester

diphenyl cadmium

Trimethyl borate

Downstream raw materials:

2-phenyl-1,3,2-benzodioxaborole

diethanolamine phenylboronic ester

dibutoxyphenylborane

4,5-dimethyl-2-phenyl-[1,3,2]dioxaborole

Refernces

• 1、 Yinghuai, Zhu,Chenyan, Koh,Ang, Thiam Peng,Emi,Monalisa, Winata,Louis, Loo Kui-Jin,Hosmane, Narayan S.,Maguire, John A.. "Catalytic phenylborylation reaction by iridium(0) nanoparticles produced from hydridoiridium carborane". . p. 5756 - 5761. Retrieved 2008.
• 2、 Gatin-Fraudet, Blaise,Ottenwelter, Roxane,Le Saux, Thomas,Norsikian, Stéphanie,Pucher, Mathilde,Lombès, Thomas,Baron, Aurélie,Durand, Philippe,Doisneau, Gilles,Bourdreux, Yann,Iorga, Bogdan I.,Erard, Marie,Jullien, Ludovic,Guianvarc’h, Dominique,Urban, Dominique,Vauzeilles, Boris. "Evaluation of borinic acids as new, fast hydrogen peroxide–responsive triggers". . . Retrieved 2021/12/23.
• 3、 Krempner, Clemens,Manankandayalage, Chamila P.,Unruh, Daniel K.. "Boronic, diboronic and boric acid esters of 1,8-naphthalenediol-synthesis, structure and formation of boronium salts". supporting information. p. 4834 - 4842. Retrieved 2020/04/27.