2,4-Difluorophenylboronic acid CAS 144025-03-6
2,4-Difluorophenylboronic acid Basic information
| Product Name: | 2,4-Difluorophenylboronic acid |
| Synonyms: | 2,4-DIFLUOROBENZENEBORONIC ACID;2,4-DIFLUOROBENZENE BORONIC ACID;;B-(2,4-Difluorophenyl)boronic acid;RARECHEM AH PB 0168;2,4-DIFLUOROBENZENEBORONIC ACID;2,4-DIFLUOROPHENYLBORONIC ACID;2,4-FLUOROBENZENE BORONIC ACID;AKOS BRN-0089;2,4-Difluorophenylboric acid |
| CAS: | 144025-03-6 |
| MF: | C6H5BF2O2 |
| MW: | 157.91 |
| EINECS: | 604-390-9 |
| Product Categories: | 6;Substituted Boronic Acids;Fluorobenzene;Boronic Acid;Aryl;Halogenated;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic Acids;Boronic Acids and Derivatives;blocks;BoronicAcids;FluoroCompounds;Boric Acid;bc0001 |
| Mol File: | 144025-03-6.mol |
2,4-Difluorophenylboronic acid Chemical Properties
| Melting point | 247-250 °C (lit.) |
| Boiling point | 251.0±50.0 °C(Predicted) |
| density | 1.35±0.1 g/cm3(Predicted) |
| storage temp. | Keep in dark place,Inert atmosphere,2-8°C |
| solubility | Chloroform (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly) |
| form | Powder |
| pka | 8.47±0.58(Predicted) |
| color | Off-white to light beige or yellow |
| BRN | 8616257 |
| InChI | InChI=1S/C6H5BF2O2/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,10-11H |
| InChIKey | QQLRSCZSKQTFGY-UHFFFAOYSA-N |
| SMILES | B(C1=CC=C(F)C=C1F)(O)O |
| CAS DataBase Reference | 144025-03-6(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn,Xi |
| Risk Statements | 36/37/38-22 |
| Safety Statements | 37/39-26-36 |
| WGK Germany | 3 |
| Hazard Note | Irritant |
| HS Code | 29163990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Chemical Properties | off-white to light beige or yellow powder |
| Uses | suzuki reaction |
| Uses | 2,4-Difluorophenylboronic Acid is used as a reagent in suzuki-miyaura coupling reactions such as in the synthesis of enantiomerically pure 3,3''-bis-arylated BINOL derivatives. Also used in the synthesis of highly efficient phospherescent iridium (III) complexes which are used for light-emiiting diodes. |
| Synthesis | 121-43-7 144025-04-7 144025-03-6 (B) A solution of trimethyl borate (25.98 g, 0.25 mol, Fluka) and 2,4-difluorophenylmagnesium bromide (0.25 mol) in tetrahydrofuran (200 mL) was added dropwise simultaneously to a reactor containing tetrahydrofuran (125 mL) over a period of 1 h under nitrogen protection, maintaining the reaction temperature at -15 °C. The reaction was carried out by stirring the reaction mixture for 15 min. After the dropwise addition, the reaction mixture was continued to be stirred at -15°C for 15 minutes. Subsequently, the temperature of the reaction system was raised to 0 °C and water (17.5 mL) and 10% sulfuric acid solution (125 mL) were slowly added over 10 and 15 min, respectively. After the reaction was complete, water (250 mL) was added to ensure complete dissolution of the product, which was subsequently extracted with ether (3 x 150 mL). The organic phases were combined and concentrated to dryness under reduced pressure to afford the crude 2,4-difluorophenylboronic acid (36.98 g, 90% purity, 84.3% yield), which was used directly in the subsequent cross-coupling reaction without further purification. |
| References | [1] Patent: US5312975, 1994, A [2] Patent: EP494419, 1992, A2 [3] Patent: US5312975, 1994, A [4] Patent: EP494419, 1992, A2 [5] Patent: US2012/309971, 2012, A1. Location in patent: Page/Page column 2-3 |
2,4-Difluorophenylboronic acid Preparation Products And Raw materials
| Raw materials | 2,4-difluoro phenyl magnesium bromide-->Trimethyl borate-->1-Bromo-2,4-difluorobenzene-->2-Methoxyethanol-->Water-->Sulfuric acid-->Tetrahydrofuran |
| Preparation Products | 2,4-Difluoronitrobenzene-->2,4-Difluorobenzotrifluoride-->1,3-Difluorobenzene-->4-(2,4-Difluorophenyl)benzaldehyde-->6-(2,4-Difluorophenyl)-3-pyridinecarbaldehyde |
