87199-17-5 Usage
Description
4-Formylphenylboronic 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 formyl group (aldehyde) attached to a phenyl ring, which is connected to a boronic acid moiety. This unique structure endows 4-Formylphenylboronic acid with a wide range of applications in organic synthesis, medicinal chemistry, and materials science.
Uses
Used in Organic Synthesis:
4-Formylphenylboronic acid is used as a reagent for various cross-coupling reactions, enabling the formation of carbon-carbon bonds and the synthesis of complex organic molecules. It is particularly useful in the following applications:
1. Palladium-catalyzed Suzuki-Miyaura cross-coupling in water: This reaction allows for the formation of aryl-aryl bonds in an aqueous medium, providing a greener and more sustainable approach to organic synthesis.
2. Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides: This process introduces fluoroalkyl groups to the arylboronic acid, expanding the scope of synthetically useful compounds.
3. Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids: This reaction facilitates the formation of aryl-nitro bonds, which are important structural motifs in various pharmaceuticals and agrochemicals.
4. Triethylamine-catalyzed three-component Hantzsch condensations: This condensation reaction leads to the formation of polyfunctionalized heterocycles, which are valuable building blocks in organic synthesis.
5. Copper-catalyzed nitrations: This reaction introduces a nitro group to the arylboronic acid, providing access to nitro-containing compounds for further functionalization.
6. Oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta: This enzymatic process selectively cleaves one of the carbon-carbon double bonds in a diene, offering a mild and environmentally friendly approach to olefin synthesis.
Used in Medicinal Chemistry:
4-Formylphenylboronic acid is used as a reagent in the synthesis of biologically active compounds, such as:
1. Sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells: These sensitizers are crucial for the development of next-generation solar energy technologies.
2. A novel protein synthesis inhibitor active against Gram-positive bacteria: 4-Formylphenylboronic acid has potential applications in the development of new antibiotics to combat drug-resistant bacterial infections.
Used in Materials Science:
4-Formylphenylboronic acid is used as a substrate for Suzuki cross-coupling reactions, which are essential for the synthesis of various functional materials, such as:
1. The Suzuki aryl-aryl coupling of the upper rim of hexahomotrioxacalix[3]arene: This process leads to the formation of novel calixarene-based materials with potential applications in molecular recognition and sensing.
2. A rhodium-catalyzed cyclization, converting 1,5-enynes to cyclopentenes and spiro-cyclopentenes: This reaction provides a route to the synthesis of cyclopentenes and spiro-cyclopentenes, which are important structural motifs in the development of new materials with unique properties.
Flammability and Explosibility
Notclassified
Check Digit Verification of cas no
The CAS Registry Mumber 87199-17-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,7,1,9 and 9 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 87199-17:
(7*8)+(6*7)+(5*1)+(4*9)+(3*9)+(2*1)+(1*7)=175
175 % 10 = 5
So 87199-17-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H
87199-17-5Relevant articles and documents
Space-group revision for 4-formylphenylboronic acid
Fronczek, Frank R.,St Luce, Nadia N.,Strongin, Robert M.
, (2001)
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Hydroxyl radical-mediated oxidative cleavage of CC bonds and further esterification reaction by heterogeneous semiconductor photocatalysis
Hong, Mei,Jia, Rui,Miao, Hongyan,Ni, Bangqing,Niu, Tengfei,Wang, Hui
, p. 6591 - 6597 (2021/09/10)
A hydroxyl radical-mediated aerobic cleavage of alkenes and further sequence esterification reaction for the preparation of carbonyl compounds have been developed by using tubular carbon nitride (TCN) as a general heterogeneous photocatalyst under an oxygen atmosphere with visible light irradiation. This protocol has an excellent substrate scope and gives the desired aldehydes, ketones and esters in moderate to high yields. Importantly, this metal-free procedure employed photogenerated hydroxyl radicals in situ as green oxidation active species, avoiding the present additional initiators. The reaction could be carried out under solar light irradiation and was applicable to large-scale reactions. Furthermore, the recyclable TCN catalyst could be used several times without a significant loss of activities.
Enantioselective Conjugate Addition of Aryl Halides and Triflates to Electron-Deficient Olefins via Nickel- And Rhodium-Catalyzed Sequential Relay Reactions
Fan, Chenrui,Wu, Qixu,Zhu, Chengfeng,Wu, Xiang,Li, Yougui,Luo, Yunfei,He, Jian-Bo
supporting information, p. 8888 - 8892 (2019/10/14)
Asymmetric conjugate addition of aryl halides or aryl triflates to electron-deficient olefins was realized by sequential Miyaura borylation and Hayashi-Miyaura conjugate addition in one pot. A nickel-catalyzed borylation of aryl halides or triflates and a rhodium-chiral diene complex catalyzed enantioselective conjugate addition was executed as a pair of relay reactions as a more efficient and greener protocol.