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| | 4-Formylphenylboronic acid Basic information |
| | 4-Formylphenylboronic acid Chemical Properties |
| Melting point | 237-242 °C (lit.) | | Boiling point | 347.6±44.0 °C(Predicted) | | density | 1.24±0.1 g/cm3(Predicted) | | vapor pressure | 0Pa at 25℃ | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | <10g/l | | form | Liquid | | pka | 7.34±0.10(Predicted) | | color | Clear colorless to yellow-orange | | PH | 5.5 (1g/l, H2O, 20℃) | | Water Solubility | Slightly Soluble in water. | | Sensitive | Air Sensitive | | BRN | 3030770 | | InChIKey | VXWBQOJISHAKKM-UHFFFAOYSA-N | | LogP | 1.36 at 20℃ | | CAS DataBase Reference | 87199-17-5(CAS DataBase Reference) | | EPA Substance Registry System | Boronic acid, (4-formylphenyl)- (87199-17-5) |
| | 4-Formylphenylboronic acid Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powder | | Uses | 4-Formylphenylboronic acid is a substrate for Suzuki cross-coupling reactions and it can be used as a reagent for:
- Palladium-catalyzed 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.
- The synthesis of sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells.
- The synthesis of a novel protein synthesis inhibitor active against Gram-positive bacteria.
- The Suzuki aryl-aryl coupling of the upper rim of hexahomotrioxacalix[3]arene.
- A rhodium-catalyzed cyclization, converting 1,5-enynes to cyclopentenes and spiro-cyclopentenes.
| | Uses | 4-Formylbenzeneboronic acid acts as a 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. It acts as a 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. | | Uses | suzuki reaction | | Flammability and Explosibility | Not classified | | Synthesis | Potassium phenyltrifluoroborate (184 mg, 1.00 mmol) was added to a solution of iron trichloride (185 mg, 1.10 mmol) in 3 mL of 1:1 THF/water. The mixture was stirred at room temperature for 30 min. The reaction mixture was then passed through a short column containing neutral absorption alumina. The alumina was then washed with a mixture of ethyl acetate/hexanes (2:1) to obtain 4-Formylphenylboronic acid (105 mg, 86%). [The boronic acid products can also be isolated by simple extraction techniques.] |
| | 4-Formylphenylboronic acid Preparation Products And Raw materials |
| Raw materials | Tetrahydrofuran-->Toluene-->n-Butyllithium-->p-Toluenesulfonic acid-->Ethylene glycol-->4-Bromobenzaldehyde | | Preparation Products | 3-THIOPHEN-2-YL-BENZALDEHYDE-->1,3,5-Tris(p-formylphenyl)benzene-->(2-(4-vinylphenyl)ethene-1,1,2-triyl)tribenzene-->3,4'-DIHYDROXYFLAVONE-->4-(2-Cyanophenyl)benzaldehyde-->4-AMINOMETHYLPHENYLBORONIC ACID, PINACOL ESTER, HCL-->4-((N-BOC-AMINO)METHYL)PHENYLBORONIC ACID-->4-(2-PHENYLETH-1-YNYL)BENZALDEHYDE-->Des-N-(methoxycarbonyl)-L-tert-leucine Bis-Boc Atazanavir-->URMC-099-->(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol |
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