5720-06-9 Usage
Description
2-Methoxyphenylboronic acid is an arylboronic acid, a white to light yellow crystal powder, that serves as a versatile compound in the field of organic chemistry. It is widely used as a safe and environmentally friendly aromatization reagent for the scientific research and production of various fine chemicals containing aryl structures, such as pharmaceuticals, pesticides, and advanced materials.
Uses
Used in Pharmaceutical Industry:
2-Methoxyphenylboronic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to form stable aryl structures makes it a valuable component in the development of new drugs and medications.
Used in Suzuki Reaction:
2-Methoxyphenylboronic acid is used as a reactant in the Suzuki reaction, an organic coupling reaction where a boronic acid with a halide is catalyzed by a palladium(0) complex. This reaction is crucial in the formation of carbon-carbon bonds and has been widely utilized in the synthesis of complex organic molecules, including those found in pharmaceuticals and advanced materials.
Used in Investigating Boron Function in Plants:
2-Methoxyphenylboronic acid is also used in scientific research to investigate the function of boron in plants. Understanding the role of boron in plant biology can lead to advancements in agricultural practices and the development of more efficient and sustainable crop production methods.
Used in Pesticide Industry:
In the pesticide industry, 2-Methoxyphenylboronic acid is used as a building block for the development of new and more effective pesticides. Its ability to form stable aryl structures allows for the creation of pesticides with improved performance and reduced environmental impact.
Used in Advanced Materials:
2-Methoxyphenylboronic acid is employed in the development of advanced materials, such as those used in electronics, optics, and energy storage. Its unique chemical properties make it a valuable component in the creation of innovative materials with enhanced performance characteristics.
Preparation
Under the protection of nitrogen, add magnesium (2.9 g, 1.2 times) and tetrahydrofuran (20 ml) and dibromoethane (1.9 g) to a 250 ml three-necked flask with a dropping funnel; then add 2-methoxybromobenzene (17.1 g, 0.1 mol), trimethyl borate (36.8 g, 3.5 times) and tetrahydrofuran (50 ml) as solvent to the dropping funnel. Heat to 40 ℃, activate the magnesium powder, and then slowly add the mixture in the dropping funnel dropwise, control the speed to the reaction temperature does not exceed 60 ℃, add the reaction after stirring until the magnesium basically disappeared, and then heat the reflux reaction for 6 hours. Stop heating, cool to room temperature, hydrolyze with 5% dilute hydrochloric acid to pH<2. Distillation to recover THF solvent, as the solvent is reduced, the product precipitated; cooling and filtration, recrystallization in methanol/water can be obtained 2-methoxyphenylboronic acid.
Check Digit Verification of cas no
The CAS Registry Mumber 5720-06-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,7,2 and 0 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 5720-06:
(6*5)+(5*7)+(4*2)+(3*0)+(2*0)+(1*6)=79
79 % 10 = 9
So 5720-06-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H9BO3/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5,9-10H,1H3
5720-06-9Relevant articles and documents
Asymmetric 1,4-Addition of Arylboronic Acids to β,γ-Unsaturated α-Ketoesters using Heterogeneous Chiral Metal Nanoparticle Systems
Miyamura, Hiroyuki,Yasukawa, Tomohiro,Zhu, Zhiyuan,Kobayashi, Shū
supporting information, p. 353 - 359 (2019/12/15)
Asymmetric 1,4-addition reactions with β,γ-unsaturated α-ketoesters are valuable because the resulting chiral ketoester compounds can be converted into various useful species that are often used as chiral building blocks in drug and natural product synthesis. However, β,γ-unsaturated α-ketoesters have two reactive points in terms of nucleophilic additions, which will lead to the 1,4-adduct, the 1,2-adduct and to the combined 1,4- and 1,2-adduct. Therefore, controlling this chemoselectivity is an important factor for the development of these transformations. Here, we developed an asymmetric 1,4-addition of aryl boronic acids to β,γ-unsaturated α-ketoesters by using heterogeneous chiral rhodium nanoparticle systems with a chiral diene ligand bearing a secondary amide moiety. The newly developed polydimethylsilane-immobilized rhodium nanoparticle catalysts showed high activity, high chemoselectivity, and excellent enantioselectivity, and this is the first heterogeneous catalytic system for this asymmetric reaction. Metal nanoparticle catalysts were recovered and reused without loss of activity or leaching of metal. (Figure presented.).
Chemoselective Rhodium-Catalyzed Borylation of Bromoiodoarenes under Mild Conditions
Varni, Anthony J.,Bautista, Michael V.,Noonan, Kevin J.T.
, p. 6770 - 6777 (2020/07/21)
A chemoselective rhodium-catalyzed borylation has been developed for the preparation of aryl boronate esters. The reaction proceeds under mild conditions with excellent selectivity for C-I bonds in bromoiodoarenes and exhibits broad functional group tolerance. This procedure can act as a complementary approach toward bifunctional arenes along with other metal-catalyzed borylations. Additionally, the reaction's utility in the preparation of monomers for metal-catalyzed cross-coupling polymerization is demonstrated.
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.