2-Acetylphenylboronic acid

Base Information

• Chemical Name: 2-Acetylphenylboronic acid
• CAS No.: 308103-40-4
• Molecular Formula: C8H9BO3
• Molecular Weight: 163.969
• Hs Code.: 29310095
• DSSTox Substance ID: DTXSID50370200
• Nikkaji Number: J1.983.808K
• Wikidata: Q72435655
• Mol file: 308103-40-4.mol

Synonyms:2-acetylphenylboronic acid

Chemical Property of 2-Acetylphenylboronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.7E-05mmHg at 25°C
• Melting Point: 170 ºC (dec.)(lit.)
• Refractive Index: 1.535
• Boiling Point: 349.9 ºC at 760 mmHg
• PKA: 8.20±0.58(Predicted)
• Flash Point: 165.4 ºC
• PSA: 57.53000
• Density: 1.19 g/cm³
• LogP: -0.43100
• Storage Temp.: 0-6°C
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 164.0644743
• Heavy Atom Count: 12
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

2-Acetylphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,C
• Hazard Codes: Xi,C
• 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)C)(O)O
• Uses: 2-Acetylphenylboronic acid is a reactant used for a variety of coupling reactions, as well as synthesis and hydroxy masking, Suzuki-Miyaura cross-coupling reactions, rhodium-catalyzed annulation of ynamides, transient masking of hydroxy groups, cationic palladium complex-catalyzed diastereoselective tandem annulation, hydrogen peroxide mediated formation of heteroaryl ethers and copper-catalyzed transmetalation and homocoupling.

Technology Process of 2-Acetylphenylboronic acid

There total 16 articles about 2-Acetylphenylboronic 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-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one (325141-75-1) → (2-acetylphenyl)boronic acid (308103-40-4)

Guidance literature:

With polystyrene boronic acid; trifluoroacetic acid; In acetonitrile; for 18h; Heating;

DOI:10.1016/j.tetlet.2004.07.014

Reference yield: 90.0%

triethyl borate (150-46-9) + 2-bromophenyl methyl ketone (2142-69-0) → (2-acetylphenyl)boronic acid (308103-40-4)

Guidance literature:

2-bromophenyl methyl ketone; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

triethyl borate; In tetrahydrofuran; at 20 ℃; for 4h;

Reference yield:

C15H16BNO2 → benzylamine (100-46-9) + (2-acetylphenyl)boronic acid (308103-40-4)

Guidance literature:

With tris(2-carboxyethyl)phosphine; water; In aq. phosphate buffer; water-d2; for 0.0833333h; Reagent/catalyst;

DOI:10.1016/j.tetlet.2017.06.069

upstream raw materials:

1-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one

2-[(1',1'-ethylenedioxy)ethyl]benzeneboronic acid

2-(2-bromophenyl)-2-methyl-1,3-dioxolane

1-(2-chlorophenyl)ethanone

Downstream raw materials:

1-[2-(1,2-dimethyl-1H-indol-3-yl)phenyl]ethanone

1-[2-(5-methoxy-1,2-dimethyl-1H-indol-3-yl)phenyl]ethanone

1-(2-(phenylmethyl)phenyl)ethanone

1-[2-(1-benzyl-1H-pyrrol-2-yl)phenyl]ethanone