Description

2,4,4,5,5-Pentamethyl-1,3,2-dioxaborolane (CAS No. 94242-85-0) is a highly versatile and stable boronic ester compound with the molecular formula C₇H₁₅BO₂. This organoboron reagent is widely recognized for its role in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic organic chemistry. The pentamethyl substitution on the dioxaborolane ring enhances its steric and electronic properties, making it an excellent precursor for introducing methyl groups into complex molecular architectures. With a purity of ≥95%, this compound is supplied as a clear, colorless to pale yellow liquid, ensuring consistent performance in demanding applications. Ideal for pharmaceutical, agrochemical, and materials science research, it is packaged under inert gas to maintain stability and shelf life. Store in a cool, dry place away from moisture and oxidizing agents.

Properties

• CAS Number: 94242-85-0
• Complexity: 127
• IUPAC Name: 2,4,4,5,5-pentamethyl-1,3,2-dioxaborolane
• InChI: InChI=1S/C7H15BO2/c1-6(2)7(3,4)10-8(5)9-6/h1-5H3
• InChI Key: FOQJHZPURACERJ-UHFFFAOYSA-N
• Exact Mass: 142.1165099
• Molecular Formula: C7H15BO2
• Molecular Weight: 142.01
• SMILES: B1(OC(C(O1)(C)C)(C)C)C
• Topological: 18.5
• Monoisotopic Mass: 142.1165099
• Synonyms: 2,4,4,5,5-pentamethyl-1,3,2-dioxaborolane, 689-046-6, 94242-85-0, Methylboronic acid pinacol ester, Methyl boronic acid pinacol ester, MFCD09027082, PENTAMETHYL-1,3,2-DIOXABOROLANE, 1,3,2-Dioxaborolane, 2,4,4,5,5-pentamethyl-, SCHEMBL14399, DTXSID00471933, AKOS006343549, CS-W018635, DS-2394, FM38544, MB06754, AC-33927, SY025061, P2602, EN300-316299, 2-methyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Application

2,4,4,5,5-Pentamethyl-1,3,2-dioxaborolane is a key reagent in Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of biaryl compounds for pharmaceuticals and agrochemicals. It serves as a stable methylboron source in palladium-catalyzed transformations, offering superior handling compared to boronic acids. Researchers also utilize it in polymer chemistry to modify materials with boron-containing functional groups. Its moisture-resistant properties make it suitable for air-sensitive applications.

Safety and Hazards

GHS Hazard Statements

• H226 (50%): Flammable liquid and vapor [Warning Flammable liquids]
• H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (50%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Precautionary Statements

• P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P317, P321, P330, P362+P364, P370+P378, P403+P235, and P501

Hazard Classes and Categories

• Flam. Liq. 3 (50%)

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