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| | 2,6-Difluorophenylboronic acid Basic information |
| | 2,6-Difluorophenylboronic acid Chemical Properties |
| Melting point | 147-149 °C (lit.) | | Boiling point | 260.1±50.0 °C(Predicted) | | density | 1.35±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Soluble in methanol. | | form | solid | | pka | 8.12±0.58(Predicted) | | color | White to Almost white | | BRN | 8545931 | | InChI | InChI=1S/C6H5BF2O2/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3,10-11H | | InChIKey | DBZAICSEFBVFHL-UHFFFAOYSA-N | | SMILES | B(C1=C(F)C=CC=C1F)(O)O | | CAS DataBase Reference | 162101-25-9(CAS DataBase Reference) |
| Hazard Codes | Xi,Xn | | Risk Statements | 36/37/38-22 | | Safety Statements | 26-36-37/39 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29163990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 2,6-Difluorophenylboronic acid Usage And Synthesis |
| Chemical Properties | White to off-white crystalline powder | | Uses | suzuki reaction | | Uses | Intermediates of Liquid Crystals | | Uses | 2,6-Difluorophenylboronic acid can be used:
- As a substrate in the model reaction of Suzuki–Miyaura coupling with4-chloro-3-methylanisole.
- To prepare 4-bromo-2,3′,5′,6-tetrafluorobiphenyl, a key intermediate for the synthesis of 2,6-difluorinated oligophenyls applicable in organic semiconductors.
- To prepare ethyl 4-(2,6-difluorophenyl)nicotinate, a key intermediate for the synthesis of 4-phenyl pyridine based potent TGR5 agonists.
| | Synthesis | The general procedure for the synthesis of 2,6-difluorophenylboronic acid from trimethyl borate and 1,3-difluorobenzene was as follows: 22.8 g of 1,3-difluorobenzene (Compound I) and 150 mL of anhydrous ethyl ether were added to a 500 mL dry reaction flask under nitrogen protection and the system was cooled to -78 °C. Slowly 187 mL of 1.6 M n-butyllithium hexane solution was added dropwise to the mixture. After the dropwise addition was completed, the reaction was stirred at -60 to -70 °C for 2 hours. The system was again cooled to -78°C and 60 g of trimethyl borate was slowly added dropwise, and after the dropwise addition was completed, the reaction was stirred at a controlled temperature of -50 to -60°C for 2 hours. The reaction mixture was slowly warmed to room temperature, the reaction was quenched by the addition of 200 mL of water and acidified with 36% hydrochloric acid. After recovering the organic solvent by ascending distillation, the reaction mixture was stirred at 70 to 80 °C for 6 hours. Finally, the system was cooled to crystallization, filtered and washed with cold water to afford 27.0 g of 2,6-difluorophenylboronic acid (Compound II). | | References | [1] Patent: CN103819401, 2016, B. Location in patent: Paragraph 0023; 0066; 0067 |
| | 2,6-Difluorophenylboronic acid Preparation Products And Raw materials |
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