192182-54-0 Usage
Description
3,5-Dimethoxyphenylboronic acid is an organic compound featuring a boron atom bonded to a phenyl ring with three methoxy groups attached at the 3,5-positions. It is a gray to white solid and is known for its reactivity in various chemical reactions, particularly in palladium-catalyzed coupling processes.
Uses
Used in Pharmaceutical Industry:
3,5-Dimethoxyphenylboronic acid is used as a reactant for the preparation of benzopyranone derivatives, which serve as positive GABAA receptor modulators. These modulators are crucial for the development of drugs targeting neurological disorders and conditions.
Used in Organic Synthesis:
3,5-Dimethoxyphenylboronic acid is used as a reactant for the preparation of aryl alkenes through a three-component coupling process catalyzed by palladium. This method is valuable for the synthesis of complex organic molecules and pharmaceutical intermediates.
Used in Biochemical Research:
3,5-Dimethoxyphenylboronic acid is used as a reactant for the preparation of bisphosphonate inhibitors of human farnesyl pyrophosphate synthase. These inhibitors are essential for studying enzyme activity and developing potential therapeutic agents for related diseases.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
3,5-Dimethoxyphenylboronic acid is used as a reagent in Suzuki-Miyaura cross-coupling reactions, a widely employed method for the formation of carbon-carbon bonds in organic synthesis. This reaction is crucial for the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
Used in Rhodium-Catalyzed Cyanation:
3,5-Dimethoxyphenylboronic acid is used in rhodium-catalyzed cyanation reactions with N-cyano-N-phenyl-p-methylbenzenesulfonamide. This process is significant for the synthesis of nitriles, which are valuable intermediates in the production of various organic compounds and pharmaceuticals.
Used in Suzuki Reaction:
3,5-Dimethoxyphenylboronic acid is used in the Suzuki reaction, a type of cross-coupling reaction that facilitates the formation of new carbon-carbon bonds. This reaction is widely used in the synthesis of complex organic molecules and is particularly valuable in the development of new pharmaceuticals and materials.
Check Digit Verification of cas no
The CAS Registry Mumber 192182-54-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,2,1,8 and 2 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 192182-54:
(8*1)+(7*9)+(6*2)+(5*1)+(4*8)+(3*2)+(2*5)+(1*4)=140
140 % 10 = 0
So 192182-54-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O2.BH3O2/c1-9-7-4-3-5-8(6-7)10-2;2-1-3/h3-6H,1-2H3;1-3H
192182-54-0Relevant articles and documents
Identification of a terphenyl derivative that blocks the cell cycle in the G0-G1 phase and induces differentiation in leukemia cells
Roberti, Marinella,Pizzirani, Daniela,Recanatini, Maurizio,Simoni, Daniele,Grimaudo, Stefania,Di Cristina, Antonietta,Abbadessa, Vincenzo,Gebbia, Nicola,Tolomeo, Manlio
, p. 3012 - 3018 (2006)
To further explore the SAR of resveratrol-related trans-stilbene derivatives, here we describe the synthesis of (a) a series of 3,5-dimethoxy analogues in which a variety of substituents were introduced at positions 2′, 3′, 4′, and 5′ of the stilbene scaf
Meso-substituted boron-dipyrromethene compounds: synthesis, tunable solid-state emission, and application in blue-driven LEDs
Liu, Hao,Su, Huan,Chen, Zhiyuan,Zhu, Senqiang,Liu, Rui,Zhu, Hongjun
, p. 1697 - 1705 (2021/07/10)
In this work, we depict the synthesis and characterization of a series of meso-substituted boron-dipyrromethene (BODIPY) compounds. Their optical and electrochemical properties were investigated systematically. All these compounds exhibited intense absorption bands in the ultraviolet (UV) and visible regions, which arise from the π–π* transitions based on their BODIPY core segments. By comparing electron-withdrawing substituents and electron-donating substituents, we found that these compounds exhibited some similar photophysical properties but exhibited different fluorescence in the solid state. All compounds were highly emissive in dichloromethane at room temperature (λem = 512–523 nm, ΦPL > 0.9). When these compounds were applied in blue-driven light-emitting diodes (LEDs) as light-emitting materials, the devices showed luminescence efficiency ranging from 1.09 to 34.13 lm/W. Their luminescence and electrochemical properties could be used for understanding the structure–property relationship of BODIPY compounds and developing functional fluorescent materials.
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.
