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| | 9-phenanthrenylboronic acid Basic information |
| | 9-phenanthrenylboronic acid Chemical Properties |
| Melting point | 165-170 °C | | Boiling point | 479.5±28.0 °C(Predicted) | | density | 1.26±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Soluble in DMSO. | | form | Solid | | pka | 8.53±0.30(Predicted) | | color | Pale Yellow | | InChI | InChI=1S/C14H11BO2/c16-15(17)14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9,16-17H | | InChIKey | JCDAUYWOHOLVMH-UHFFFAOYSA-N | | SMILES | B(C1=CC2C(C3C1=CC=CC=3)=CC=CC=2)(O)O | | CAS DataBase Reference | 68572-87-2(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 22-24/25-26 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29319090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 9-phenanthrenylboronic acid Usage And Synthesis |
| Chemical Properties | White solid | | Uses | 9-Phenanthreneboronic Acid is used as an fluorescent analytical reagent in sensing systems for glucose-specific detection. | | Uses | 9-Phenanthracenylboronic acid is used as an fluorescent analytical reagent in sensing systems for glucose-specific detection and in suzuki reaction. | | Synthesis | The general procedure for the synthesis of 9-phenanthrenylboronic acid from triisopropyl borate and 9-bromophenanthrene is as follows:
Step a: Preparation of 9-phenanthracenylboronic acid
Under argon protection, 9-bromophenanthrene (1 g, 3.9 mmol) and triisopropyl borate (1.35 ml, 1.1 g, 5.85 mmol) were dissolved in anhydrous THF (30 ml) and the solution was cooled to -78 °C. Subsequently, n-BuLi (1.6 M hexane solution, 2.9 ml, 4.68 mmol) was added slowly dropwise over 1 h. The reaction temperature was maintained at -78 °C and stirring was continued for 1 h. The reaction mixture was then cooled to -78 °C. The reaction temperature was then adjusted to -78 °C. After that, the reaction mixture was slowly warmed up to -20°C, 2M HCl (20 ml) was added, and the temperature was continued to 18°C and stirring was continued for 1 hour. After completion of the reaction, ether (300 ml) was added for extraction, the organic phase was dried with MgSO4, filtered and concentrated under reduced pressure to afford the crude product 9-phenanthrenylboronic acid (770 mg, 89% yield) as a white solid, which can be used in subsequent reactions without further purification. | | References | [1] Patent: WO2006/135973, 2006, A1. Location in patent: Page/Page column 31
[2] Patent: CN107652224, 2018, A. Location in patent: Paragraph 0086; 0089-0091
[3] Patent: CN107382748, 2017, A. Location in patent: Paragraph 0037; 0038; 0039; 0040 |
| | 9-phenanthrenylboronic acid Preparation Products And Raw materials |
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