Description
3,4-Dihydro-2H-pyran-6-boronic acid pinacol ester (CAS: 1025707-93-0) is a high-purity boronic ester derivative with the molecular formula C11H19BO3. This compound, also known by its IUPAC name 2-(3,4-dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, is a versatile intermediate in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions. Its pinacol ester group enhances stability and solubility, making it ideal for use in anhydrous or moisture-sensitive conditions. Suitable for researchers and industrial applications, this reagent is rigorously tested for quality and consistency, ensuring reliable performance in complex synthetic pathways. Packaged under inert conditions to preserve integrity, it is a critical tool for pharmaceutical, agrochemical, and materials science research.
Properties
- CAS Number: 1025707-93-0
- Complexity: 268
- IUPAC Name: 2-(3,4-dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
- InChI: InChI=1S/C11H19BO3/c1-10(2)11(3,4)15-12(14-10)9-7-5-6-8-13-9/h7H,5-6,8H2,1-4H3
- InChI Key: RNRIMDSCBRDPLC-UHFFFAOYSA-N
- Exact Mass: 210.1427246
- Molecular Formula: C11H19BO3
- Molecular Weight: 210.08
- SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CCCCO2
- Topological: 27.7
- Monoisotopic Mass: 210.1427246
- Synonyms: 3,4-DIHYDRO-2H-PYRAN-6-BORONIC ACID PINACOL ESTER, 864-932-7, 1025707-93-0, 2-(3,4-Dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2H-Pyran, 3,4-dihydro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, MFCD07368233, SCHEMBL319623, 95% (stabilized with 1%BHT), DTXSID70585950, RNRIMDSCBRDPLC-UHFFFAOYSA-N, (3,4-DIHYDRO-2H-PYRAN-6-YL)BORONIC ACID PINACOL ESTER, AKOS015999417, AB31957, FS-4746, DA-16202, SY066203, CS-0097347, EN300-170997, Z1509595073, 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyran
Application
3,4-Dihydro-2H-pyran-6-boronic acid pinacol ester is widely used as a key building block in Suzuki-Miyaura cross-coupling reactions to form carbon-carbon bonds in heterocyclic systems. Its stability and reactivity make it valuable in the synthesis of pharmaceuticals, particularly for modifying pyran-based scaffolds. Researchers also employ it in materials science for constructing boron-containing polymers and advanced organic frameworks.
Safety and Hazards
GHS Hazard Statements
- H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
- H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
- H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
- H332 (100%): 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 (100%)
- Skin Irrit. 2 (100%)
- Eye Irrit. 2A (100%)
- Acute Tox. 4 (100%)
- STOT SE 3 (100%)
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