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| | 4-Trifluoromethoxyphenylboronic acid Basic information |
| | 4-Trifluoromethoxyphenylboronic acid Chemical Properties |
| Melting point | 123-127 °C(lit.) | | Boiling point | 256.6±50.0 °C(Predicted) | | density | 1.41±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | pka | 8.29±0.10(Predicted) | | form | Crystalline Powder | | color | White to beige | | BRN | 8548201 | | InChI | InChI=1S/C7H6BF3O3/c9-7(10,11)14-6-3-1-5(2-4-6)8(12)13/h1-4,12-13H | | InChIKey | HUOFUOCSQCYFPW-UHFFFAOYSA-N | | SMILES | B(C1=CC=C(OC(F)(F)F)C=C1)(O)O | | CAS DataBase Reference | 139301-27-2(CAS DataBase Reference) |
| Hazard Codes | Xi,Xn | | Risk Statements | 36/37/38-20/21/22 | | Safety Statements | 37/39-26-36 | | WGK Germany | 3 | | Hazard Note | Irritant | | HS Code | 29319090 | | Storage Class | 11 - Combustible Solids |
| | 4-Trifluoromethoxyphenylboronic acid Usage And Synthesis |
| Chemical Properties | white to beige crystalline powder | | Uses | B-[4-(Trifluoromethoxy)phenyl]boronic Acid is a reagent used in the synthesis of orally bioavailable matrix metalloprotinase inhibitors. Also used in the preparation of chromen-4-one inhibitors used against DNA dependant protein kinases. | | Application | 4-Trifluoromethoxyphenylboronic acid can reactant involved in the synthesis of biologically active molecules including:
Lactate dehydrogenase inhibitors for use against cancer cell proliferation
Nitro-phenoxybenzoic acid derivatives for PAI-1 inhibition
PA-824 analogs for use as antituberculosis drugs
Modulators of survival motor neuron protein
Reactant involved in addition reactions and cross-coupling reactions including Suzuki-Miyaura cross-coupling | | Synthesis | Example 1E Synthesis of 4-(trifluoromethoxy)phenylboronic acid: 1-bromo-4-(trifluoromethoxy)benzene (1.69 kg) and triisopropyl borate (1.46 kg) were dissolved in THF (6.75 L) at -70 °C. A hexane solution (3.27 L) of 2.25 M butyllithium was slowly added to this solution over a period of 2.3 hours, followed by stirring for 10 minutes. Next, the reaction was quenched with 6 M HCl (1.52 L) and stirred at room temperature for 18 hours. The reaction mixture was poured into a mixture of heptane (8.43 L) and 20% (w/w) aqueous sodium chloride solution (8.44 kg) and stirred for 10 min to separate the aqueous and organic phases. The organic phase was concentrated to give a white paste. The paste was dried in vacuum (100 mmHg) at ambient temperature while nitrogen was passed for 2 days. Subsequently, it was further dried at 40-50 °C for 18 h to give 1.306 kg (90.4% yield) of the target product 4-(trifluoromethoxy)phenylboronic acid as a solid. The product was characterized by 1H NMR (CDCl3, 300 MHz): δ 7.24-7.19 (m, 2H), 8.14-8.10 (m, 2H) and additional absorption peaks were observed at δ 7.19-7.15 (m, 2H) and 8.04-8.00 (m, 2H), which corresponded to the cyclic boronic acid trimer. | | References | [1] Patent: US2002/19539, 2002, A1 |
| | 4-Trifluoromethoxyphenylboronic acid Preparation Products And Raw materials |
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