Description

3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester (CAS No. 287944-16-5) is a high-purity boronic ester derivative widely used in organic synthesis and pharmaceutical research. This compound, with the molecular formula C₁₁H₁₉BO₃, is a versatile building block for Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds in complex molecular architectures. Its IUPAC name is 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and it features a stable pinacol boronate group, ensuring excellent handling and storage stability. The dihydropyran moiety offers unique reactivity for functionalization, making it valuable in medicinal chemistry and material science applications. Supplied as a crystalline solid or solution, it is rigorously tested for purity (typically ≥95% by HPLC or NMR) to meet the stringent demands of research and industrial processes.

Properties

• CAS Number: 287944-16-5
• Complexity: 268
• IUPAC Name: 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• InChI: InChI=1S/C11H19BO3/c1-10(2)11(3,4)15-12(14-10)9-5-7-13-8-6-9/h5H,6-8H2,1-4H3
• InChI Key: DOSGEBYQRMBTGS-UHFFFAOYSA-N
• Exact Mass: 210.1427246
• Molecular Formula: C11H19BO3
• Molecular Weight: 210.08
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CCOCC2
• Topological: 27.7
• Monoisotopic Mass: 210.1427246
• Synonyms: 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester, 683-692-2, 287944-16-5, 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 3,6-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyran, 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRAN, MFCD11052631, 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran, 2H-PYRAN, 3,6-DIHYDRO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-, SCHEMBL67926, 3,6-Dihydro-2H-pyran-4-boronic acid, pinacol ester, CHEMBL3942505, DTXSID50459069, DOSGEBYQRMBTGS-UHFFFAOYSA-N, BDBM204460, (3,6-DIHYDRO-2H-PYRAN-4-YL)BORONIC ACID PINACOL ESTER, BCP07783, CS-B0643, BBL103359, SBB094288, STL557169, AKOS015842137, CL-0787, PB10870, AC-31780, SY011822, T3217, EN300-111490, 3,6-dihydro-2H-pyran-4-boronic acid pinacolester, US9242996, 135, 3,6 dihydro-2H-pyran-4-boronic acid pinacol ester, 3,6-dihydro-2 h-pyran-4-boronic acid pinacol ester, Z1436075878, 3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester, 97%, 5H-pyran-4-yl-(4,4,5,5 tetramethyl)-1,3,2 dioxaborolane, 2-(2H-5,6-dihydropyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-(3,6-dihydro-2 h-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane, 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2- dioxaborolane, 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydropyran, 4-(4,4,5,5-tetramethyl-[1, 3, 2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran

Application

3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester is a key intermediate in Suzuki-Miyaura cross-coupling reactions, facilitating the synthesis of biaryl and heteroaryl compounds. It is employed in the preparation of pharmaceuticals, agrochemicals, and functional materials due to its robust reactivity under mild conditions. Researchers also utilize it to introduce dihydropyran motifs into target molecules for drug discovery and polymer chemistry.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (11.4%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (11.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (11.4%): 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 (100%)
• Skin Irrit. 2 (11.4%)
• Eye Irrit. 2A (11.4%)
• STOT SE 3 (11.4%)

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