Description

Phenylboronic acid pinacol ester (CAS No. 24388-23-6) is a highly versatile and stable boronic ester derivative, widely utilized in organic synthesis and pharmaceutical research. With the molecular formula C₁₂H₁₇BO₂, this compound is a crystalline solid that offers excellent solubility in common organic solvents, making it ideal for cross-coupling reactions such as Suzuki-Miyaura couplings. Its pinacol ester structure enhances stability and handling compared to free boronic acids, reducing decomposition risks during storage and reactions. This reagent is a critical intermediate in the synthesis of bioactive molecules, agrochemicals, and advanced materials. Available in high purity (≥97%), it ensures reliable performance in sensitive applications.

Properties

• CAS Number: 24388-23-6
• Complexity: 216
• IUPAC Name: 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane
• InChI: InChI=1S/C12H17BO2/c1-11(2)12(3,4)15-13(14-11)10-8-6-5-7-9-10/h5-9H,1-4H3
• InChI Key: KKLCYBZPQDOFQK-UHFFFAOYSA-N
• Exact Mass: 204.1321599
• Molecular Formula: C12H17BO2
• Molecular Weight: 204.08
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2
• Topological: 18.5
• Monoisotopic Mass: 204.1321599
• Synonyms: Phenylboronic acid pinacol ester, 629-233-1, 24388-23-6, 4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane, (4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene, phenylboronic acid, pinacol ester, benzeneboronic acid, pinacol ester, 2-Phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, MFCD00966985, 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-phenyl-, Pinacolborane Impurity 4, phenylboronic pinacol ester, (PINACOLBORYL)BENZENE, PINACOL PHENYLBORONATE, SCHEMBL90476, SCHEMBL241124, SCHEMBL2177117, SCHEMBL12475452, SCHEMBL21382720, OSM-S-460, phenyl boronic acid pinacol ester, DTXSID50341152, BCP03949, MFCD31699955, AKOS015951124, AB07838, AS-2256, BCP9000025, CS-W015437, Phenylboronic acid pinacol ester, 97%, SY029010, SY246300, tetramethyl-2-phenyl-1,3,2-dioxaborolane, DB-003816, P1855, 4,4,5,5-tetramethyl-1,3,2-dioxaborolylbenzene, EN300-1425744, (4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)benzene, 4,4,5,5-tetramethyl-2-phenyl-[1,3,2]dioxaborolane, 4,4,5,5-tetramethyl-2-phenyl-1,3,2,-dioxaborolane, 4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane #, Z1336745080, (4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzene

Phenylboronic acid pinacol ester is extensively used in Suzuki-Miyaura cross-coupling reactions to form biaryl compounds, a cornerstone in drug discovery and material science. It serves as a key building block for pharmaceuticals, enabling the introduction of phenyl groups into complex molecules. Researchers also employ it in polymer chemistry and as a precursor for sensors and catalysts. Its stability under ambient conditions makes it preferable over boronic acids in prolonged synthetic workflows.

Safety and Hazards

GHS Hazard Statements

• H302 (97.7%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (97.7%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (97.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (97.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (97.7%)
• Skin Irrit. 2 (97.7%)
• Eye Irrit. 2 (97.7%)
• STOT SE 3 (97.7%)

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