149104-90-5 Usage
Description
4-Acetylphenylboronic acid is a boronate, a class of synthetic organic compounds characterized by their white to light yellow crystal powder appearance. It is known for its rapid reaction with peroxynitrite (ONOO(-)) to form stable hydroxy derivatives and is commonly utilized in various metal-catalyzed cross-coupling reaction studies.
Uses
Used in Chemical Synthesis:
4-Acetylphenylboronic acid is used as a reactant in several chemical reactions for the synthesis of complex organic molecules. Its ability to participate in cross-coupling reactions makes it a valuable compound in the field of organic chemistry.
Used in Suzuki Reaction:
In the field of chemical synthesis, 4-Acetylphenylboronic acid is used as a reactant in the Suzuki reaction, a widely employed palladium-catalyzed cross-coupling reaction that forms carbon-carbon bonds between an organoboronic acid and an organic halide or triflate.
Used in Palladium-catalyzed Decarboxylative Coupling:
4-Acetylphenylboronic acid is used as a reactant in palladium-catalyzed decarboxylative coupling, a reaction that involves the coupling of an organoboronic acid with a carboxylic acid, leading to the formation of a carbon-carbon bond and the release of carbon dioxide.
Used in Copper-catalyzed Hydroxylation:
4-Acetylphenylboronic acid is used as a reactant in copper-catalyzed hydroxylation, a reaction that introduces a hydroxyl group to an organic molecule, often resulting in the formation of alcohols or phenols.
Used in Palladium-catalyzed Suzuki-Miyaura Cross-coupling:
In the field of chemical synthesis, 4-Acetylphenylboronic acid is used as a reactant in palladium-catalyzed Suzuki-Miyaura cross-coupling, a reaction that forms carbon-carbon bonds between an organoboronic acid and an organic halide or triflate, facilitating the synthesis of complex organic molecules.
Used in Cross-coupling with α-Bromocarbonyl Compounds:
4-Acetylphenylboronic acid is used as a reactant in cross-coupling reactions with α-bromocarbonyl compounds, a process that involves the formation of carbon-carbon bonds and is essential for the synthesis of various organic compounds.
Used in Oxidation Catalyzed by Baeyer-Villiger Monooxygenases:
4-Acetylphenylboronic acid is used as a reactant in oxidation reactions catalyzed by Baeyer-Villiger monooxygenases, an enzyme class that catalyzes the oxidation of ketones to esters, providing a valuable synthetic route for the preparation of various organic compounds.
Used in 1,5-Substitution Reactions:
4-Acetylphenylboronic acid is used as a reactant in 1,5-substitution reactions, a type of organic reaction that involves the replacement of a functional group at the 1st and 5th positions of a molecule, leading to the formation of new organic compounds.
Used in Dendrimers Synthesis:
4-Acetylphenylboronic acid is used as a reactant in the synthesis of dendrimers, highly branched macromolecules with a well-defined structure, which have applications in various fields, including drug delivery, catalysis, and nanotechnology. It undergoes Suzuki coupling with 4-bromotriphenylamine catalyzed by dichlorobis(triphenylphosphine)Pd(II) during the synthesis process.
Check Digit Verification of cas no
The CAS Registry Mumber 149104-90-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,9,1,0 and 4 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 149104-90:
(8*1)+(7*4)+(6*9)+(5*1)+(4*0)+(3*4)+(2*9)+(1*0)=125
125 % 10 = 5
So 149104-90-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H9BO3/c1-6(10)7-2-4-8(5-3-7)9(11)12/h2-5,11-12H,1H3
149104-90-5Relevant articles and documents
Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source
Han, Min Su,Lim, Taeho,Ryoo, Jeong Yup
, p. 10966 - 10972 (2020/09/23)
In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.
Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water
Zernickel, Anna,Du, Weiyuan,Ghorpade, Seema A.,Sawant, Dinesh N.,Makki, Arwa A.,Sekar, Nagaiyan,Eppinger, J?rg
, p. 1842 - 1851 (2018/02/23)
A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.
Wacker-Type Oxidation Using an Iron Catalyst and Ambient Air: Application to Late-Stage Oxidation of Complex Molecules
Liu, Binbin,Jin, Fengli,Wang, Tianjiao,Yuan, Xiaorong,Han, Wei
supporting information, p. 12712 - 12717 (2017/09/11)
A practical and general iron-catalyzed Wacker-type oxidation of olefins to ketones is presented, and it uses ambient air as the sole oxidant. The mild oxidation conditions enable exceptional functional-group tolerance, which has not been demonstrated for any other Wacker-type reaction to date. The inexpensive and nontoxic reagents [iron(II) chloride, polymethylhydrosiloxane, and air] can, therefore, also be employed to oxidize complex natural-product-derived and polyfunctionalized molecules.
