5467-74-3 Usage
Description
4-Bromophenylboronic acid is an organic compound that serves as a versatile reagent in various chemical reactions and synthesis processes. It is characterized by the presence of a boron atom bonded to a phenyl group with a bromine atom attached to the para position. This unique structure allows it to participate in a wide range of applications across different industries.
Uses
Used in Chemical Synthesis:
4-Bromophenylboronic acid is used as a reagent for palladium-catalyzed Suzuki-Miyaura cross-couplings, a widely employed method for the formation of carbon-carbon bonds. This reaction is crucial in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and advanced materials.
Used in Tandem Reactions:
4-Bromophenylboronic acid is utilized in tandem-type Pd(II)-catalyzed oxidative Heck reactions and intramolecular C-H amidation sequences. These reactions enable the efficient construction of complex molecular architectures, which are valuable in the development of new drugs and functional materials.
Used in Medicinal Chemistry:
4-Bromophenylboronic acid is employed in the preparation of protein modulators, enzymatic and kinase inhibitors, and gallate-based obovatol analogs with potential anti-tumor activity. These compounds are essential in the discovery and development of novel therapeutic agents for the treatment of various diseases.
Used in Fluoroalkylation Reactions:
4-Bromophenylboronic acid is used as a reagent for copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides. This reaction allows for the introduction of fluoroalkyl groups into organic molecules, which can improve their pharmacological properties, such as lipophilicity and metabolic stability.
Used in Cyclization Reactions:
4-Bromophenylboronic acid is utilized in Pd-catalyzed arylative cyclization of alkyne-tethered enals or enones via carbopalladation of alkynes. This reaction provides a convenient method for the synthesis of cyclic compounds, which are often found in biologically active natural products and pharmaceutical agents.
Used in Copper-Catalyzed Cross-Couplings:
4-Bromophenylboronic acid is employed in copper-catalyzed cross-couplings, which are useful for the formation of carbon-carbon and carbon-heteroatom bonds. These reactions contribute to the synthesis of diverse organic compounds, including those with potential applications in materials science and medicinal chemistry.
Used in Enzyme Inhibition:
Labelled 4-Bromophenylboronic acid (B686545) is used in the preparation of arylboronates as inhibitors of fatty acid amide hydrolase. These inhibitors can help researchers study the role of this enzyme in various biological processes and may lead to the development of new therapeutic agents for the treatment of related disorders.
Check Digit Verification of cas no
The CAS Registry Mumber 5467-74-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,4,6 and 7 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 5467-74:
(6*5)+(5*4)+(4*6)+(3*7)+(2*7)+(1*4)=113
113 % 10 = 3
So 5467-74-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H6BBrO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
5467-74-3Relevant articles and documents
Preparation method of monohalogenated phenylboronic acid
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Paragraph 0084-0087, (2020/09/20)
The invention relates to the technical field of chemical synthesis, and particularly discloses a preparation method of monohalogenated phenylboronic acid. The preparation method comprises the following steps of: by taking dihalogenated benzene as a raw material and a mixture of lithium salt and alkaline ionic liquid as a catalyst, carrying out Grignard exchange with R1MgCl to generate monohalogenated phenyl magnesium chloride, reacting with B (OR) 3 to generate monohalogenated phenyl borate, and hydrolyzing under acidic conditions to obtain monohalogenated phenylboronic acid. The HPLC (High Performance Liquid Chromatography) content of the monohalogenated phenylboronic acid prepared by the method is greater than 99.5%; the total yield of the product is greater than 80%, the contents of monohalogenated phenylboronic acid and phenyldiboronic acid impurities of another halogen are both less than 0.003%, the requirements of modern fine chemical synthesis are completely met, the raw materials are easily available, the operation is simple, the safety is high, and the industrial production of monohalogenated phenylboronic acid is realized.
An efficient method for the hydrolysis of potassium organotrifluoroborates promoted by montmorillonite K10
Silva, Renato L.,Santos, Cosme S.,Santos, Jonh A. M.,Oliveira, Roberta A.,Menezes, Paulo H.,Freitas, Juliano C. R.
, p. 1777 - 1785 (2018/09/04)
An efficient and non-expensive method for conversion of diverse potassium organotrifluoroborates to their corresponding boronic acids promoted by montmorillonite K10 using water as the reaction solvent is described. Further interconversion of potassium organotrifluoroborates to their corresponding boronic esters, via boronic acid intermediates was also successfully accomplished. The products were obtained in good yields, being the rate of hydrolysis influenced by the type of substituent present in the boronic acid.
Novel organic semiconductor compound and organic light emitting device using the same
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Paragraph 0169-0173, (2016/10/10)
The present invention relates to a novel organic semiconductor compound, and an organic electroluminescent device using the same. More particularly, the organic semiconductor compound according to the present invention is an azasiline derivative with a rigid structure having an electron doner and an electron acceptor in the molecule, and can embody excellent oxidation stability and light emitting characteristics. The organic electroluminescent device using the same has a high purity blue color having high quantum efficiency. The organic semiconductor compound is represented by chemical formula 1.
