Description

2-Isopropoxy-4,4,6-trimethyl-1,3,2-dioxaborinane (CAS: 61676-61-7) is a highly specialized organoboron compound with the molecular formula C₉H₁₉BO₃. This cyclic boronic ester features a dioxaborinane core substituted with isopropoxy and three methyl groups, offering unique reactivity and stability for advanced synthetic applications. The compound is supplied as a high-purity liquid (typically >95% by GC) with careful handling recommended due to its moisture sensitivity. Researchers value this chemical for its role as a versatile intermediate in cross-coupling reactions, particularly in Suzuki-Miyaura couplings where its sterically hindered structure can influence selectivity. The product is packaged under inert gas in amber glass bottles with secure closures to ensure maximum shelf life and is ideal for pharmaceutical research, materials science, and catalytic system development.

Properties

• CAS Number: 61676-61-7
• Complexity: 170
• IUPAC Name: 2-isopropoxy-4,4,6-trimethyl-1,3,2-dioxaborinane
• InChI: InChI=1S/C9H19BO3/c1-7(2)11-10-12-8(3)6-9(4,5)13-10/h7-8H,6H2,1-5H3
• InChI Key: AHCZPHINTQYKPU-UHFFFAOYSA-N
• Exact Mass: 186.1427246
• Molecular Formula: C9H19BO3
• Molecular Weight: 186.06
• SMILES: B1(OC(CC(O1)(C)C)C)OC(C)C
• Topological: 27.7
• Monoisotopic Mass: 186.1427246
• Synonyms: 2-ISOPROPOXY-4,4,6-TRIMETHYL-1,3,2-DIOXABORINANE, 636-406-5, 61676-61-7, 1,3,2-Dioxaborinane, 4,4,6-trimethyl-2-(1-methylethoxy)-, 2-isopropoxy-4,4,6-trimethyl-[1,3,2]dioxaborinane, MFCD15143641, 4,4,6-trimethyl-2-propan-2-yloxy-1,3,2-dioxaborinane, SCHEMBL1157781, DTXSID30500285, AHCZPHINTQYKPU-UHFFFAOYSA-N, AKOS025295544, BS-44194, SY053016, DB-314107, CS-0359275, I0833, D91204, 2-Isopropoxy-4,4,6-trimethyl-1,3,2-dioxaborinane, 99%, 4,4,6-Trimethyl-2-[(propan-2-yl)oxy]-1,3,2-dioxaborinane

Application

This boronic ester serves as a key intermediate in palladium-catalyzed cross-coupling reactions for constructing complex organic molecules. Its sterically demanding structure makes it particularly useful for synthesizing hindered biaryl compounds in medicinal chemistry applications. The compound has shown utility in polymer chemistry as a modifying agent for resins and as a precursor for boron-containing materials. Researchers also employ it in the development of new catalytic systems for asymmetric synthesis.

Safety and Hazards

GHS Hazard Statements

• H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
• H318 (97.5%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Precautionary Statements

• P210, P233, P240, P241, P242, P243, P264+P265, P280, P303+P361+P353, P305+P354+P338, P317, P370+P378, P403+P235, and P501

Hazard Classes and Categories

• Flam. Liq. 3 (100%)
• Eye Dam. 1 (97.5%)

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