Identification | More | [Name]
9-Phenanthracenylboronic acid | [CAS]
68572-87-2 | [Synonyms]
9-PHENANTHRENEBORONIC ACID BORONIC ACID, 9-PHENANTHRENYL- PHENANTHREN-9-YLBORONIC ACID PHENANTHRENE-9-BORONIC ACID RARECHEM AH PB 0056 9-Phenanthreneboronic acid (contains varying amounts of anhydride) Phenanthreneboronicacid Phenanthrene-9-boronic acid 98% 9-Phenanthracenylboronic acid Phenanthracene-9-boronic acid | [EINECS(EC#)]
627-783-7 | [Molecular Formula]
C14H11BO2 | [MDL Number]
MFCD00143524 | [Molecular Weight]
222.05 | [MOL File]
68572-87-2.mol |
Chemical Properties | Back Directory | [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) |
Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust . S24/25:Avoid contact with skin and eyes . S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29319090 |
Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
9-Phenanthracenylboronic acid is used as an fluorescent analytical reagent in sensing systems for glucose-specific detection and in suzuki reaction.
| [Uses]
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 |
|
|