B-(10-Biphenyl-2-yl-9-anthracenyl)boronic Acid: Key FAQs
B-(10-Biphenyl-2-yl-9-anthracenyl)boronic Acid: Key FAQs
B-(10-[1,1'-Biphenyl]-2-yl-9-anthracenyl)boronic acid is a sterically hindered diarylanthracene-derived arylboronic acid valued as a versatile building block in Suzuki–Miyaura cross-coupling reactions and as a precursor for the synthesis of advanced organic semiconductor and OLED emitter materials.
- Chemical Name
- B-(10-[1,1'-Biphenyl]-2-yl-9-anthracenyl)boronic acid
- SKU
- B397999
- Functional Class
- Arylboronic acid; organoboron building block
- Primary Application
- Suzuki–Miyaura cross-coupling; OLED/organic semiconductor material synthesis
- Key Structural Feature
- Anthracen-9-yl core bearing a 2-biphenylyl group at C-10 and a boronic acid at C-9
- Supplier
- Aladdin Scientific
Chemical Identity and Structure
B-(10-[1,1'-Biphenyl]-2-yl-9-anthracenyl)boronic acid (Aladdin SKU: B397999) is an arylboronic acid built on an anthracene scaffold. The molecule features a biphenyl-2-yl substituent at the 10-position of the anthracene ring and a boronic acid (–B(OH)2) functional group at the 9-position. This structural arrangement results in a highly conjugated, sterically demanding molecule. The extended π-system of the anthracenyl–biphenyl framework contributes to the compound's utility in constructing organic π-conjugated architectures relevant to organic electronics and photonics. The boronic acid group serves as the reactive handle for palladium-catalyzed cross-coupling chemistry.
Applications in Synthetic Chemistry
The primary synthetic application of this compound is as a boronic acid coupling partner in Suzuki–Miyaura cross-coupling reactions. Under standard palladium catalysis (e.g., Pd(PPh3)4 or Pd(dppf)Cl2) with a mild base (e.g., K2CO3 or Cs2CO3) in aqueous-organic solvent mixtures, the boronic acid reacts with aryl or heteroaryl halides to form new C–C bonds. The resulting biaryl or oligoaryl products are of significant interest for the preparation of large acene-based molecules and extended polycyclic aromatic hydrocarbons (PAHs).
Beyond coupling chemistry, the compound serves as a precursor in the synthesis of anthracene-based organic semiconductors and emitters for organic light-emitting diodes (OLEDs). The biphenylanthracene unit is a recognized motif in blue-emitting OLED host and emitter materials due to its wide bandgap and favorable photophysical properties.
Handling, Storage, and Stability
As with most arylboronic acids, B-(10-[1,1'-Biphenyl]-2-yl-9-anthracenyl)boronic acid should be handled under inert atmosphere conditions when prolonged stability is required, as boronic acids can slowly undergo protodeboronation or oxidation upon extended exposure to moisture and air. For routine weighing and brief handling on the benchtop, standard laboratory precautions are sufficient.
Recommended storage: Store in a tightly sealed container, protected from light and moisture, at room temperature or under refrigeration (2–8 °C) under an inert gas (nitrogen or argon) blanket. Avoid exposure to strong oxidizing agents, strong acids, and strong bases. Always consult the product Safety Data Sheet (SDS) before use.
Users should verify specific purity, appearance, and stability data on the current certificate of analysis (CoA) provided with each lot.
Ordering and Technical Support
B-(10-[1,1'-Biphenyl]-2-yl-9-anthracenyl)boronic acid is available from Aladdin Scientific under SKU B397999. Researchers requiring technical documentation—including the Safety Data Sheet (SDS), Certificate of Analysis (CoA), or structural confirmation data—should contact Aladdin Scientific's technical support team or download documents directly from the product page on the Aladdin website.
For bulk quantities, custom packaging, or questions regarding pricing and lead times, please reach out to our sales or procurement team. Aladdin Scientific is committed to providing high-quality research reagents with full documentation to support reproducible science.
Frequently asked questions
What is B-(10-[1,1'-Biphenyl]-2-yl-9-anthracenyl)boronic acid used for?
This compound is primarily used as a boronic acid coupling partner in palladium-catalyzed Suzuki–Miyaura cross-coupling reactions to construct biaryl and extended polycyclic aromatic frameworks. It is also widely employed as a synthetic precursor for anthracene-based organic semiconductors and blue-emitting OLED host or emitter materials.
How should this boronic acid be stored to maintain its integrity?
Store B-(10-[1,1'-Biphenyl]-2-yl-9-anthracenyl)boronic acid in a tightly sealed container, protected from light and moisture, preferably under an inert gas atmosphere (nitrogen or argon) at room temperature or at 2–8 °C. Prolonged exposure to air and moisture can lead to slow degradation via protodeboronation or oxidation. Always refer to the current lot CoA and SDS for lot-specific guidance.
Is B-(10-[1,1'-Biphenyl]-2-yl-9-anthracenyl)boronic acid air-sensitive?
Arylboronic acids are generally moderately stable to brief air exposure, but prolonged contact with atmospheric moisture and oxygen can cause gradual protodeboronation or oxidative degradation. For best results, handle this compound under inert atmosphere conditions for weighing and solution preparation when long-term stability is critical, and store under nitrogen or argon.
What palladium catalysts are typically compatible with this boronic acid in Suzuki coupling?
Standard palladium catalysts commonly used with arylboronic acids—such as Pd(PPh3)4, Pd(dppf)Cl2, and Pd(OAc)2 with appropriate phosphine ligands—are generally compatible. Reaction conditions (solvent, base, temperature) should be optimized for the specific coupling partner. Users are encouraged to consult primary literature for substrate-specific protocols.
Where can I obtain the SDS and Certificate of Analysis for SKU B397999?
The Safety Data Sheet (SDS) and Certificate of Analysis (CoA) for B-(10-[1,1'-Biphenyl]-2-yl-9-anthracenyl)boronic acid (SKU B397999) are available for download on the Aladdin Scientific product page. If you require a lot-specific CoA or have additional technical questions, please contact Aladdin Scientific's customer service or technical support team directly.
References
- Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chemical Reviews 1995, 95 (7), 2457–2483. doi:10.1021/cr00039a007
- Hall, D. G. (Ed.) Boronic Acids: Preparation and Applications in Organic Synthesis, Medicine and Materials, 2nd ed.; Wiley-VCH: Weinheim, 2011.
- Shi, J.; Tang, C. W. Anthracene derivatives for stable blue-emitting organic electroluminescence devices. Applied Physics Letters 2002, 80 (17), 3201–3203. doi:10.1063/1.1475361
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