9-Phenanthrenylboronic acid (also named Phenanthrene-9-boronic acid) is an important aromatic boronic acid compound. It is widely used as a key building block in organic synthesis & Suzuki–Miyaura cross-coupling reactions. It also serves as a key precursor for the preparation of dibenzo[g,p]chrysene derivatives, which are essential building blocks for advanced organic light-emitting semiconductors and critical self-luminescent materials in OLED applications.
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📋Basic information:
- Chemical name: 9-phenanthrenylboronic acid
- CAS: 68572-87-2
- Molecular Formula: C14H11BO2
- Molecular Weight: 222.05
📌Specification:
| Appearance: | White to off-white powder |
| Melting point: | 165-170 °C |
| Boiling Point: | 479.5±28.0 °C |
| Solubility : | Soluble in DMSO. |
| Relative Density: | 1.26±0.1 g/cm3 |
| Storage: | Keep in dark place,Sealed in dry,Room Temperature |
📊Main Synthesis Route
The main synthesis route is using 9-bromophenanthrene as the starting material, it undergoes lithiation with n-butyllithium (-78°C), reacts with triisopropyl borate, and is hydrolyzed and acidified to obtain the product. Anhydrous and oxygen-free processes are commonly used in laboratory/pilot scale, achieving a purity of 97%–99.5%.
🧩Application of 9-phenanthrenylboronic acid CAS No.: 68572-87-2
1. Intermediate for Organic Synthesis
Mainly used in Suzuki-Miyaura cross-coupling reaction to construct C–C bonds efficiently. It is a critical raw material for preparing polycyclic aromatic hydrocarbons (PAHs), heterocyclic compounds, and conjugated organic molecules.
2. Optoelectronic Materials (OLED, OFET, OPV)
It can synthesize high-performance luminescent materials, organic semiconductors, and photovoltaic materials. It is widely applied in OLED light-emitting layers, organic field-effect transistors (OFETs), and organic photovoltaic devices (OPVs) to improve luminous efficiency, color purity, and carrier mobility.
3. Epoxy Resin Curing Agents
The primary amine groups undergo ring-opening reactions with epoxy groups, allowing BAMF to serve as a curing agent for epoxy resins. It is suitable for high-performance composites, electronic encapsulation, and adhesives, with the cured products offering both strength and temperature resistance.
4. Pharmaceutical and Biochemical Research
Served as a key intermediate for the synthesis of anti-inflammatory, anti-tumor, and antibacterial agents. It is used in the development of FLAP inhibitors, PARP-2 inhibitors, and β-lactamase inhibitors. It can also be used in fluorescent sensors and biological detection for specific recognition of sugar molecules.
5. Functional Materials and Catalysis
Used in the preparation of conjugated polymers, functional organic materials, and catalyst ligands, with good application prospects in material modification and catalytic synthesis.
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