Description

(9-Phenyl-9H-carbazol-2-yl)boronic acid (CAS: 1001911-63-2) is a high-purity boronic acid derivative featuring a carbazole-phenyl hybrid structure, with the molecular formula C₁₈H₁₄BNO₂. This compound is a valuable intermediate in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions, where it serves as a versatile boron-containing coupling partner for constructing complex aromatic systems. Its rigid carbazole core and phenyl substitution enhance its utility in materials science, enabling the development of advanced organic semiconductors, OLEDs, and photovoltaic materials. The boronic acid group offers excellent reactivity under mild conditions, ensuring high yields and selectivity. Supplied as a fine powder with ≥95% purity (HPLC), it is rigorously tested for moisture-sensitive applications and stored under inert conditions to ensure stability. Ideal for researchers in pharmaceutical, agrochemical, and optoelectronic industries seeking to innovate in heterocyclic and conjugated molecular architectures.

Properties

• CAS Number: 1001911-63-2
• Complexity: 385
• IUPAC Name: (9-phenylcarbazol-2-yl)boronic acid
• InChI: InChI=1S/C18H14BNO2/c21-19(22)13-10-11-16-15-8-4-5-9-17(15)20(18(16)12-13)14-6-2-1-3-7-14/h1-12,21-22H
• InChI Key: XSAOVBUSKVZIBE-UHFFFAOYSA-N
• Exact Mass: 287.1117589
• Molecular Formula: C18H14BNO2
• Molecular Weight: 287.1
• SMILES: B(C1=CC2=C(C=C1)C3=CC=CC=C3N2C4=CC=CC=C4)(O)O
• Topological: 45.4
• Monoisotopic Mass: 287.1117589
• Synonyms: (9-Phenyl-9H-carbazol-2-yl)boronic acid, 1001911-63-2, DTXSID10736782, DTXCID90687526, 808-209-6, (9-phenylcarbazol-2-yl)boronic acid, 9-Phenylcarbazole-2-boronic Acid, Boronic acid, B-(9-phenyl-9H-carbazol-2-yl)-, MFCD22207050, 9-Phenyl-9H-carbazol-2-ylboronic acid, (9-Phenyl)carbazole-2-boronic acid, 2-BAPC, SCHEMBL2127336, 9-Phenyl-9H-carbazol-2-ylboronicacid, 9-Phenylcarbazole-2-boronic acid (contains varying amounts of Anhydride), AKOS016008924, CS-W021124, DS-4925, SB66611, (9-Phenyl-9H-carbazol-2-yl)boronicacid, AC-28763, SY037131, DB-362254, P2169

Application

(9-Phenyl-9H-carbazol-2-yl)boronic acid is widely used in palladium-catalyzed cross-coupling reactions to synthesize extended π-conjugated systems for organic electronics. It serves as a key building block in the development of high-efficiency OLED emitters and hole-transport materials due to its electron-rich carbazole moiety. Researchers also employ it in medicinal chemistry to create carbazole-based bioactive molecules targeting neurodegenerative diseases.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.