4-Formylphenylboronic acid
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4-Formylphenylboronic acid

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Reagent used for: Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water ; Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides ; Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids ; Triethylamine-catalyzed three-component Hantzsch condensations ; Copper-catalyzed nitrations ; Oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta ; Palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides ; Palladium-catalyzed aerobic oxidative cross-coupling reactions Reagent used in Preparation of; Sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells; A novel protein synthesis inhibitor active against Gram-positive bacteria.

Category
Peptide Synthesis Reagents
Catalog number
BAT-006495
CAS number
87199-17-5
Molecular Formula
C7H7BO3
Molecular Weight
149.94
4-Formylphenylboronic acid
IUPAC Name
(4-formylphenyl)boronic acid
Synonyms
Boronic acid, (4-formylphenyl)-; 4-Boronobenzaldehyde; p-formylphenylboronic acid; MFCD00151823; 4-benzaldehyde boronic acid; 4-(Dihydroxyboryl)benzaldehyde; CHEMBL140254
Appearance
White to yellowish crystal powder
Purity
95 %
Density
1.240±0.10 g/cm3 (Predicted)
Melting Point
237-242 °C
Boiling Point
347.6±44.0 °C (Predicted)
Storage
2-8 °C
Solubility
Slightly Soluble in Water
InChI
InChI=1S/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H
InChI Key
VXWBQOJISHAKKM-UHFFFAOYSA-N
Canonical SMILES
B(C1=CC=C(C=C1)C=O)(O)O
1. Space-group revision for 4-formylphenylboronic acid
F R Fronczek, N N St Luce, R M Strongin Acta Crystallogr C. 2001 Dec;57(Pt 12):1423-5. doi: 10.1107/s0108270101015621. Epub 2001 Dec 6.
The space group of the title compound, C7H7BO3, previously reported to be P1, is properly Cc. There is no disorder of the formyl group or in the H atoms of the B(OH)2 group. Molecules lie on approximate twofold axes and are related by approximate centers, which relate all but the formyl O atom and boronic acid H atoms. The B-O distances are 1.363 (2) and 1.370 (2) A.
2. Facile synthesis of Fe₃O₄@polyethyleneimine modified with 4-formylphenylboronic acid for the highly selective extraction of major catecholamines from human urine
Qian Qin, Hua Li, Xianzhe Shi, Guowang Xu J Sep Sci. 2015 Aug;38(16):2857-64. doi: 10.1002/jssc.201500377. Epub 2015 Jun 30.
The levels of catecholamines, especially dopamine, epinephrine and norepinephrine in urine and plasma have been used to assist the diagnosis and treatment of psychosis. Due to their low endogenous concentrations, the determination of the three major catecholamines is very difficult. Boronate adsorbents are often employed to extract these cis-diol compounds from complex matrices. In this work, a novel type of magnetic nanoparticles modified with 4-formylphenylboronic named Fe3O4@PEI-FPBA was synthesized by a facile two-step approach. The abundant amino groups of polyethyleneimine provided the rich binding sites for boronate ligands. Herein, the adsorption capacity of Fe3O4@PEI-FPBA is greatly improved with a value of 3.45 mg/g towards epinephrine, which is much larger than that of analogous material without polyethyleneimine. The magnetic nanoparticles also exhibited high magnetization (72.25 emu/g) and specific selectivity towards the catecholamines. Finally, a liquid chromatography tandem mass spectrometry method based on Fe3O4@PEI-FPBA nanoparticles was successfully used to determine the three catecholamines from human urine samples. The linearity, limit of quantitation, recovery and precision of the method were satisfactory. Based on the method, it is found that the levels of dopamine, epinephrine and norepinephrine in depressive patients are higher than those in healthy controls.
3. 2,3-Difluoro-4-formylphenylboronic acid
Tomasz Klis, Sergiusz Lulinski, Janusz Serwatowski Acta Crystallogr C. 2007 Mar;63(Pt 3):o145-6. doi: 10.1107/S0108270107001576. Epub 2007 Feb 10.
The molecule of the title compound, 2,3-F(2)-4-(CHO)C(6)H(2)B(OH)(2) or C(7)H(5)BF(2)O(3), contains a formyl group coplanar with the benzene ring. The boronic acid group is twisted with respect to the benzene ring plane. The molecules are organized into infinite chains via intermolecular O-H...O hydrogen bonds. These chains are additionally connected via strong O-H...O hydrogen bonds, producing a folded layer structure perpendicular to the a axis. These layers are paired due to B...F interactions.
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