3,5-Difluorophenylboronic acid CAS 156545-07-2
3,5-Difluorophenylboronic acid Basic information
| Product Name: | 3,5-Difluorophenylboronic acid |
| Synonyms: | 3,5-DIFLUOROBENZENEBORONIC ACID;3,5-DIFLUOROPHENYLBORONIC ACID;AKOS BRN-0091;RARECHEM AH PB 0167;Boronic acid, (3,5-difluorophenyl)- (9CI);3,5-Difluorobenzeneboronic acid 98%;3,5-Difluorobenzeneboronicacid98%;3,5-DIFLUOROPHENYLBORONIC ACID 98% |
| CAS: | 156545-07-2 |
| MF: | C6H5BF2O2 |
| MW: | 157.91 |
| EINECS: | 605-060-7 |
| Product Categories: | Liquid crystal intermediates;Aryl Boronic Acids;Boronic Acids and Derivatives;Chemical Synthesis;Disubstituted Aryl Boronic Acids;Organometallic Reagents;Boronic Acids;Boronic Acids and Derivatives;B (Classes of Boron Compounds);Boronic Acids;Substituted Boronic Acids;Fluorin-contained phenyl boronic acid series;Boronic Acid;Aryl;Organoborons;HALIDE;blocks;BoronicAcids;FluoroCompounds;intermediate |
| Mol File: | 156545-07-2.mol |
3,5-Difluorophenylboronic acid Chemical Properties
| Melting point | 210-217 °C (lit.) |
| Boiling point | 266.9±50.0 °C(Predicted) |
| density | 1.35±0.1 g/cm3(Predicted) |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| form | powder |
| pka | 6.46±0.10(Predicted) |
| color | White to Orange to Green |
| BRN | 6800882 |
| InChI | InChI=1S/C6H5BF2O2/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,10-11H |
| InChIKey | QWQBQRYFWNIDOC-UHFFFAOYSA-N |
| SMILES | B(C1=CC(F)=CC(F)=C1)(O)O |
| CAS DataBase Reference | 156545-07-2(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi,Xn,F |
| Risk Statements | 36/37/38-20-19-11-22 |
| Safety Statements | 26-36-33-16-37/39 |
| WGK Germany | 3 |
| HazardClass | IRRITANT |
| HS Code | 29163990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Chemical Properties | White to beige-yellowish powder |
| Uses | Reactant involved in:• ;Synthesis of honokiol analogs as angiogenesis inhibitors1• ;Homo-coupling reactions2• ;Suzuki-Miyaura cross-coupling reactions3• ;Enantioselective borane reduction of trifluoroacetophenone4 |
| Uses | suzuki reaction |
| Uses | 3,5-Difluorophenylboronic Acid is used in the synthesis of N-thiazol-2-yl-benzamides as glucokinase (GK) activators for treatment of type 2 diabetes mellitus (T2DM). |
| Uses | Intermediates of Liquid Crystals |
| Synthesis | 121-43-7 461-96-1 156545-07-2 (1) A solution was prepared by dissolving 100 g of 3,5-difluorobromobenzene in 150 mL of tetrahydrofuran (THF) under nitrogen protection. The solution was slowly added dropwise to a mixture containing 13.85 g of magnesium shavings and 55 mL of THF at a controlled titration rate to keep the reaction system at mild reflux. (2) After the dropwise addition was completed, the reaction mixture was stirred at 40°C for 1 hour and subsequently cooled in an ice bath. (3) A solution prepared from 64.59 g of trimethyl borate dissolved in 130 mL of THF was slowly added dropwise under ice bath cooling. After completion of the dropwise addition, the ice bath was removed and the reaction mixture was continued to be stirred at room temperature for 1 hour. (4) 10% hydrochloric acid solution was added dropwise to the reaction system until the system became acidic, followed by stirring at room temperature for 30 minutes. (5) The organic layer was separated and the aqueous layer was extracted with hexane. The organic layer and hexane extract were combined and washed with saturated saline. (6) The washed organic layer was dried by adding anhydrous sodium sulfate, filtered and distilled under reduced pressure to remove the solvent to obtain 71.65 g of 3,5-difluorophenylboronic acid. |
| References | [1] Patent: US5521192, 1996, A [2] Patent: US6908914, 2005, B1 [3] Patent: EP2123623, 2009, A1. Location in patent: Page/Page column 43-44 [4] Patent: US2014/275577, 2014, A1. Location in patent: Paragraph 0094 |
3,5-Difluorophenylboronic acid Preparation Products And Raw materials
| Raw materials | Trimethyl borate-->1-Bromo-3,5-difluorobenzene-->Tetrahydrofuran-->Magnesium-->Hydrochloric acid |
| Preparation Products | 3-(3,5-DIFLUOROPHENYL)PICOLINALDEHYDE-->3,5-difluorobenzophenone-->4-(3,5-Difluorophenyl)benzonitrile-->3',5'-Difluoro-biphenyl-3-aMine-->3-BIPHENYL-3',5'-DIFLUORO-ACETIC ACID-->3-(3,5-DIFLUOROPHENYL)OXETANE |
