Description
9-Phenanthracenylboronic Acid (CAS No. 68572-87-2) is a high-purity boronic acid derivative with the molecular formula C14H11BO2. This compound is a valuable building block in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds with exceptional efficiency. Its phenanthrene backbone provides unique steric and electronic properties, making it ideal for constructing complex polycyclic aromatic systems. Suitable for research and industrial applications, this product is rigorously tested for quality, ensuring consistent performance in catalytic transformations, material science, and pharmaceutical development. Available in various quantities with detailed analytical data (NMR, HPLC) upon request.
Properties
- CAS Number: 68572-87-2
- Complexity: 269
- IUPAC Name: 9-phenanthrylboronic acid
- 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
- InChI Key: JCDAUYWOHOLVMH-UHFFFAOYSA-N
- Exact Mass: 222.0852098
- Molecular Formula: C14H11BO2
- Molecular Weight: 222.05
- SMILES: B(C1=CC2=CC=CC=C2C3=CC=CC=C13)(O)O
- Topological: 40.5
- Monoisotopic Mass: 222.0852098
- Synonyms: 9-Phenanthracenylboronic acid, 627-783-7, 9-Phenanthreneboronic Acid, 68572-87-2, Phenanthren-9-ylboronic Acid, Phenanthrene-9-boronic acid, 9-Phenanthreneboronicacid, 9-phenanthrene boronic acid, PHENANTHRACENE-9-BORONIC ACID, 9-phenanthrenylboronic acid, MFCD00143524, CHEMBL140467, 9-Phenanthreneboronic Acid (contains varying amounts of Anhydride), Boronic acid, 9-phenanthrenyl-, 9-BAPA, SCHEMBL368234, (phenanthren-9-yl)boronic acid, DTXSID80472347, BCP22764, BBL101771, BDBM50067909, SBB071325, STL555568, AKOS008901242, AB03875, BCP9000204, CS-W002428, FP16124, AS-15952, SY014923, P1093, EN300-7383692
Application
9-Phenanthracenylboronic acid is widely used in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions to synthesize biaryl and polyaromatic compounds. It serves as a key intermediate in the development of organic electronic materials, such as OLEDs and semiconductors, due to its extended conjugation. Researchers also employ it in medicinal chemistry for the design of bioactive molecules targeting enzyme inhibition or receptor modulation.
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 (100%): 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%)
- STOT SE 3 (100%)
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