768-35-4
3-Fluorophenylboronic acid
CAS: 768-35-4
Molecular Formula: C6H6BFO2
768-35-4 - Names and Identifiers
| Name | 3-Fluorophenylboronic acid |
| Synonyms | AKOS BRN-0105 AKOS BRN-0105 RARECHEM AH PB 0217 3-FLUOROPHENYLBORNIC ACID 3-FLUORO PHENYLBORIC ACID 3-Fluorophenylboroic acid M-FLUOROPHENYLBORONIC ACID 3-Fluorophenylboronic acid 3-FLUOROPHENYLBORONIC ACID 3-FLUOROBENZENEBORONIC ACID ethane-1,2-diylbis[bis(pentafluorophenyl)phosphane] |
| CAS | 768-35-4 |
| EINECS | 476-720-8 |
| InChI | InChI=1/C26H4F20P2/c27-3-7(31)15(39)23(16(40)8(3)32)47(24-17(41)9(33)4(28)10(34)18(24)42)1-2-48(25-19(43)11(35)5(29)12(36)20(25)44)26-21(45)13(37)6(30)14(38)22(26)46/h1-2H2 |
768-35-4 - Physico-chemical Properties
| Molecular Formula | C6H6BFO2 |
| Molar Mass | 139.92 |
| Density | 1.24±0.1 g/cm3(Predicted) |
| Melting Point | 214-218 °C (lit.) |
| Boling Point | 271.4±42.0 °C(Predicted) |
| Flash Point | 252.7°C |
| Water Solubility | 27.1g/L at 20℃ |
| Solubility | soluble in Methanol |
| Vapor Presure | 0Pa at 20℃ |
| Appearance | Crystalline powder |
| Color | White to off-white |
| BRN | 3030632 |
| pKa | 7.50±0.10(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| MDL | MFCD00236042 |
768-35-4 - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| TSCA | No |
| HS Code | 29163990 |
| Hazard Class | IRRITANT |
768-35-4 - Reference Information
| LogP | 2 at 23℃ |
| Application | 3-fluorobenzene boronic acid is a white solid, which is an important pharmaceutical and chemical intermediate, it is widely used in organic and pharmaceutical synthesis. In addition to its important application in Suzuki coupling reaction, there are other applications: for example, as a catalyst, catalyzing the condensation reaction of carboxylic acid and Amine, catalyzing the reduction of carboxylic acid to alcohol; And Alpha, the β-unsaturated compound undergoes a 1,4-conjugate addition reaction to synthesize a β-aryl substituted carbonyl compound and the like. |
| preparation | the material ratio of the feed of 3-fluorobromobenzene: magnesium: trimethyl borate was 1.0: 1.1: 1.5. The total mass amount of the solvent 2-methyltetrahydrofuran was 7 times the mass of 3-fluorobromobenzene. Add 2.6g(0.11mol) of magnesium turnings and 30g of iodine, 2-methyltetrahydrofuran to a 250mL four-necked bottle with a reflux condenser and a constant pressure dropping funnel, n2 protection at 40 ° C, a small amount of 3-fluorobromobenzene 17.5g(0.10mol) in 2-methyltetrahydrofuran (22.5g) was added dropwise, after stirring to initiate the reaction, the remaining 3-fluorobromobenzene solution was added dropwise. After completion of the dropwise addition, the mixture was reacted at this temperature for 3 hours to obtain a 2-methyltetrahydrofuran solution of 3-fluorophenylmagnesium bromide. Add 15.6g(0.153mol) of trimethyl borate and 90.0g of 2-tetrahydrofuran to a four-mouth vial, cool to -20 °c under N2 protection, and add Dropwise the above Grignard reagent solution, after completion of the dropwise addition, the reaction was maintained for 3 hours. At this temperature, add 8% hydrochloric acid 100ml, hydrolysis reaction for 2 hours, separate the organic phase, water layer with 2-methyltetrahydrofuran extraction, and then washed with saturated salt water to neutral, combined organic phase, dry with anhydrous sodium sulfate, The solvent was recovered under reduced pressure, and the crude product was recrystallized from 1, 2-dichloroethane to give 3-fluorobenzeneboronic acid 11.7g, white needle-like crystals in 83.7% yield and 99.6% HPLC purity, the melting point was 217.6-218.3 °c. |
Last Update：2024-04-10 22:29:15
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