139911-27-6 Usage
Description
4-Fluoro-3-methylphenylboronic acid is an organic compound with the molecular formula C7H8BFO2. It is an off-white crystalline solid that is commonly used as a reagent in various chemical reactions and processes. Its structure features a boron atom bonded to a phenyl group, with a fluorine atom at the para position and a methyl group at the meta position.
Uses
Used in Suzuki Reaction:
4-Fluoro-3-methylphenylboronic acid is used as a reactant in the Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds, particularly in the synthesis of biaryl compounds. The reaction involves the cross-coupling of an organoboron compound with an organohalide in the presence of a palladium catalyst, leading to the formation of a new carbon-carbon bond.
Used in Pharmaceutical Industry:
4-Fluoro-3-methylphenylboronic acid is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly those targeting neuronal nitric oxide synthase. It serves as a reactant for the preparation of lipophilic-tailed monocationic inhibitors, which are essential in the development of drugs for neurological disorders.
Used in Stereoselective Synthesis:
In the field of organic chemistry, 4-Fluoro-3-methylphenylboronic acid is utilized as a reactant in stereoselective desymmetrizing rhodium-catalyzed allylic arylation reactions. This application is crucial for the synthesis of enantiomerically pure compounds, which are essential in the pharmaceutical industry for the development of chiral drugs with improved efficacy and reduced side effects.
Used in Solvent-free Catalytic C-H Functionalization Reactions:
4-Fluoro-3-methylphenylboronic acid is employed in solvent-free catalytic C-H functionalization reactions, which are environmentally friendly and cost-effective alternatives to traditional synthetic methods. These reactions involve the direct functionalization of C-H bonds without the need for pre-functionalization or the use of external solvents, leading to more sustainable and efficient synthetic processes.
Used in Homocoupling Reactions:
In the field of materials science, 4-Fluoro-3-methylphenylboronic acid is used as a reactant in homocoupling reactions, which involve the formation of a new carbon-carbon bond between two identical molecules. This process is essential for the synthesis of various materials, such as polymers and dendrimers, with potential applications in electronics, sensors, and drug delivery systems.
Used in Heck Reactions:
4-Fluoro-3-methylphenylboronic acid is also used in Heck reactions, which are palladium-catalyzed carbon-carbon bond-forming processes. These reactions are widely employed in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and advanced materials. The use of 4-Fluoro-3-methylphenylboronic acid in Heck reactions allows for the introduction of functional groups and the formation of complex molecular structures with high selectivity and efficiency.
Check Digit Verification of cas no
The CAS Registry Mumber 139911-27-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,9,9,1 and 1 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 139911-27:
(8*1)+(7*3)+(6*9)+(5*9)+(4*1)+(3*1)+(2*2)+(1*7)=146
146 % 10 = 6
So 139911-27-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H8BFO2/c1-5-4-6(8(10)11)2-3-7(5)9/h2-4,10-11H,1H3
139911-27-6Relevant articles and documents
Controlling Singlet–Triplet Energy Splitting for Deep-Blue Thermally Activated Delayed Fluorescence Emitters
Cui, Lin-Song,Nomura, Hiroko,Geng, Yan,Kim, Jong U.k.,Nakanotani, Hajime,Adachi, Chihaya
, p. 1571 - 1575 (2017)
The development of efficient metal-free organic emitters with thermally activated delayed fluorescence (TADF) properties for deep-blue emission is still challenging. A new family of deep-blue TADF emitters based on a donor–acceptor architecture has been developed. The electronic interaction between donor and acceptor plays a key role in the TADF mechanism. Deep-blue OLEDs fabricated with these TADF emitters achieved high external quantum efficiencies over 19.2 % with CIE coordinates of (0.148, 0.098).
