Description

2-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile (CAS No. 214360-47-1) is a high-purity boronic ester derivative with the molecular formula C₁₂H₁₄BNO₂. This compound features a benzonitrile moiety tethered to a 5,5-dimethyl-1,3,2-dioxaborinane ring, offering unique reactivity for cross-coupling reactions, particularly in Suzuki-Miyaura couplings. Its rigid cyclic boronate structure enhances stability while maintaining reactivity, making it a valuable intermediate in pharmaceutical synthesis, materials science, and agrochemical research. The product is supplied as a crystalline solid with ≥95% purity (HPLC), rigorously tested for consistency and performance. Ideal for researchers seeking reliable boron-containing building blocks for advanced organic transformations.

Properties

• CAS Number: 214360-47-1
• Complexity: 287
• IUPAC Name: 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile
• InChI: InChI=1S/C12H14BNO2/c1-12(2)8-15-13(16-9-12)11-6-4-3-5-10(11)7-14/h3-6H,8-9H2,1-2H3
• InChI Key: QHAYLPAKZXKQSE-UHFFFAOYSA-N
• Exact Mass: 215.1117589
• Molecular Formula: C12H14BNO2
• Molecular Weight: 215.06
• SMILES: B1(OCC(CO1)(C)C)C2=CC=CC=C2C#N
• Topological: 42.3
• Monoisotopic Mass: 215.1117589
• Synonyms: 214360-47-1, 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, DTXSID80944019, DTXCID101372374, 801-570-0, 2-Cyanophenylboronic acid, neopentyl ester, Benzonitrile, 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-, MFCD04039011, C12H14BNO2, SCHEMBL4491246, QHAYLPAKZXKQSE-UHFFFAOYSA-N, SBB068308, AKOS004116361, CS-W000900, SS-4616, AC-33892, SY101552, DB-010403, H10175, 2-(2-cyanophenyl)-5,5-dimethyl-1,3,2-dioxaborinane, 2-Cyanophenylboronic acid, neopentyl ester, AldrichCPR, 2-(5,5-dimethyl-1,3,2-dioxaboran-2-yl)benzenecarbonitrile

Application

This boronic ester is widely employed as a key intermediate in Suzuki-Miyaura cross-coupling reactions for biaryl formation in drug discovery. It serves as a versatile precursor for functionalized aromatic compounds in materials science, particularly in OLED and liquid crystal development. The sterically hindered dioxaborinane ring improves selectivity in palladium-catalyzed reactions compared to acyclic analogs.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Precautionary Statements

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

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Acute Tox. 4 (100%)
• Skin Irrit. 2 (50%)
• Eye Irrit. 2 (50%)
• Acute Tox. 4 (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.