4-Acetylphenylboronic acid

Base Information

• Chemical Name: 4-Acetylphenylboronic acid
• CAS No.: 149104-90-5
• Molecular Formula: C8H9BO3
• Molecular Weight: 163.969
• Hs Code.: 29310095
• European Community (EC) Number: 629-086-3
• DSSTox Substance ID: DTXSID90395250
• Nikkaji Number: J912.812C
• Wikidata: Q72435651
• ChEMBL ID: CHEMBL1209760
• Mol file: 149104-90-5.mol

Synonyms:4-Acetylphenylboronic acid;149104-90-5;(4-acetylphenyl)boronic Acid;4-Acetylbenzeneboronic Acid;p-acetylphenylboronic acid;MFCD01074667;BORONIC ACID, (4-ACETYLPHENYL)-;Boronic acid, B-(4-acetylphenyl)-;4-acetylphenyl boronic acid;1-[4-(Dihydroxyboranyl)Phenyl]Ethan-1-One;Boronicacid, B-(4-acetylphenyl)-;4acetylphenylboronic acid;4-actylphenylboronic acid;4acetylbenzeneboronic acid;p-acetylbenzeneboronic acid;4-acetyl phenylboronic acid;4-acetyl-phenylboronic acid;SCHEMBL9416;4-acetylbenzene boronic acid;4-(acetyl)phenylboronic acid;4-acetyl phenyl boronic acid;4-acetyl-phenyl boronic acid;4-acetyl benzene boronic acid;4-(acetyl)phenyl boronic acid;(4-Acetyl)-phenylboronic acid;CHEMBL1209760;DTXSID90395250;4-Acetylphenylboronic acid, 97%;OBQRODBYVNIZJU-UHFFFAOYSA-N;4-Acetylphenylboronic acid (contains varying amounts of Anhydride);CS-D1037;BBL100447;STL554241;AKOS004116069;AB08109;AS-3014;NCGC00249503-01;AM808105;SY014779;FT-0617405;EN300-103412;A801098;J-501346;Z1203161683

Chemical Property of 4-Acetylphenylboronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.25E-05mmHg at 25°C
• Melting Point: 240-244 °C(lit.)
• Refractive Index: 1.535
• Boiling Point: 354.2 °C at 760 mmHg
• PKA: 7.58±0.10(Predicted)
• Flash Point: 168 °C
• PSA: 57.53000
• Density: 1.19 g/cm³
• LogP: -0.43100
• Storage Temp.: Keep Cold
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 25 g/L
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 164.0644743
• Heavy Atom Count: 12
• Complexity: 162

Purity/Quality:

99% ^*data from raw suppliers

4-Acetylphenylboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)C(=O)C)(O)O
• Uses: suzuki reaction Reactant involved in:Palladium-catalyzed decarboxylative couplingCopper-catalyzed hydroxylationPalladium-catalyzed Suzuki-Miyaura cross-couplingCross-coupling with α-bromocarbonyl compoundsOxidation catalyzed by Baeyer-Villiger monooxygenases1,5-substitution reactions 4-Acetylphenylboronic acid4-Acetylphenylboronic Acid is used in several metal catalyzed cross-coupling reaction studies.

Technology Process of 4-Acetylphenylboronic acid

There total 19 articles about 4-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: 95.0%

potassium 4-acetylphenyltrifluoroborate → 4-acetylphenylboronic acid (149104-90-5)

Guidance literature:

With aluminum oxide; water; at 70 ℃; for 0.25h; Microwave irradiation;

DOI:10.1016/j.tetlet.2009.09.008

Reference yield: 94.0%

(4-(1-hydroxyethyl)phenyl)boronic acid (518336-20-4) → 4-acetylphenylboronic acid (149104-90-5)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1002/anie.200906710

Reference yield: 90.0%

4-Vinylphenylboronic acid (2156-04-9,593231-72-2) → 4-acetylphenylboronic acid (149104-90-5)

Guidance literature:

With iron(II) chloride; In ethanol; at 80 ℃; for 9h;

DOI:10.1002/anie.201707006

upstream raw materials:

4-Iodoacetophenone

1-bromo-4-(1,1-diethoxyethyl)benzene

para-bromoacetophenone

(4-(1-hydroxyethyl)phenyl)boronic acid

Downstream raw materials:

(4-acetylphenyl)(phenyl)methanol

4-acetylbenzophenone

1-(4-allylphenyl)ethanone

(E)-tert-butyl 3-(4-acetylphenyl)prop-2-enoate

Refernces

• 1、 Fan, Chenrui,Wu, Qixu,Zhu, Chengfeng,Wu, Xiang,Li, Yougui,Luo, Yunfei,He, Jian-Bo. "Enantioselective Conjugate Addition of Aryl Halides and Triflates to Electron-Deficient Olefins via Nickel- And Rhodium-Catalyzed Sequential Relay Reactions". supporting information. p. 8888 - 8892. Retrieved 2019/10/14.
• 2、 Liu, Binbin,Jin, Fengli,Wang, Tianjiao,Yuan, Xiaorong,Han, Wei. "Wacker-Type Oxidation Using an Iron Catalyst and Ambient Air: Application to Late-Stage Oxidation of Complex Molecules". supporting information. p. 12712 - 12717. Retrieved 2017/09/11.