Description

2-(3,4-Dihydro-2H-pyran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 1046811-99-7) is a high-purity boronic ester compound with the molecular formula C₁₁H₁₉BO₃. This organoboron reagent features a 3,4-dihydro-2H-pyran-5-yl group tethered to a pinacol boronate moiety, making it a versatile intermediate for Suzuki-Miyaura cross-coupling reactions and other transition-metal-catalyzed transformations. Its stability under anhydrous conditions and compatibility with diverse reaction environments make it ideal for pharmaceutical, agrochemical, and materials science research. Supplied as a clear to pale-yellow liquid or low-melting solid, it is packaged under inert gas to ensure longevity and reactivity. Store in a cool, dry place away from moisture and oxidizing agents.

Properties

• CAS Number: 1046811-99-7
• Complexity: 268
• IUPAC Name: 2-(3,4-dihydro-2H-pyran-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• InChI: InChI=1S/C11H19BO3/c1-10(2)11(3,4)15-12(14-10)9-6-5-7-13-8-9/h8H,5-7H2,1-4H3
• InChI Key: UQPQMEFVQNERGS-UHFFFAOYSA-N
• Exact Mass: 210.1427246
• Molecular Formula: C11H19BO3
• Molecular Weight: 210.08
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=COCCC2
• Topological: 27.7
• Monoisotopic Mass: 210.1427246
• Synonyms: 2-(3,4-DIHYDRO-2H-PYRAN-5-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE, 800-737-5, 1046811-99-7, 3,4-DIHYDRO-2H-PYRAN-5-YLBORONIC ACID, PINACOL ESTER, MFCD13195758, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyran, 3,4-Dihydro-2H-pyran-5-ylboronic acid pinacol ester, 2-(5,6-dihydro-4H-pyran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 3,4-Dihydro-2H-pyran-5-boronic acid pinacol ester, SCHEMBL1304193, DTXSID90682253, UQPQMEFVQNERGS-UHFFFAOYSA-N, AKOS015855721, MB13512, AS-55555, SY254685, DB-346045, CS-0055079, C90128, 3,4-Dihydro-2H-pyran-5-ylboronic acid,pinacol ester, (3,4-DIHYDRO-2H-PYRAN-5-YL)BORONIC ACID PINACOL ESTER

Application

This compound is widely used as a boronating agent in Suzuki-Miyaura couplings to introduce the 3,4-dihydro-2H-pyran-5-yl group into aromatic systems. It is also employed in the synthesis of heterocyclic compounds for drug discovery and as a building block for functionalized polymers. Researchers leverage its stability and reactivity in palladium-catalyzed C-C bond formations for advanced material design.

Safety and Hazards

GHS Hazard Statements

• H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (50%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (100%): 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, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (50%)
• Acute Tox. 4 (50%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• Acute Tox. 4 (50%)
• STOT SE 3 (100%)

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