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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Argentivorous Molecules with Chromophores in Side Arms: Silver Ion-Induced Turn on and Turn off of Fluorescence
Ju, Huiyeong,Taniguchi, Aya,Kikukawa, Kaoru,Horita, Hiroki,Ikeda, Mari,Kuwahara, Shunsuke,Habata, Yoichi
supporting information, p. 9141 - 9147 (2021/06/28)
The synthesis of argentivorous molecules (L1 and L2) having two chromophores (4-(anthracen-9-yl)benzyl or 4-(pyren-1-yl)benzyl groups) and two benzyl groups and the fluorescence properties of their silver complexes in a solution and the solid state are reported. A crystallographic approach for the Ag+ complexes with L1 and L2 revealed that the observed fluorescence changes stem from the excimer formation and extinction of fluorescent. Furthermore, binding stabilities of L1 and L2 toward Ag+ ions were estimated by the Ag+-induced UV-vis and PL spectral changes.
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.