Description

2-Ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 82954-89-0) is a high-purity organoboron compound with the molecular formula C₈H₁₇BO₂. This specialized boronic ester is widely utilized in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions, due to its stability and reactivity. The compound features a dioxaborolane ring with ethyl and tetramethyl substitutions, offering excellent solubility in common organic solvents such as THF, DCM, and DMF. Ideal for researchers in pharmaceuticals, materials science, and catalysis, it is supplied in rigorously controlled conditions to ensure optimal performance. Available in various packaging options, this reagent is a critical tool for advanced synthetic applications.

Properties

• CAS Number: 82954-89-0
• Complexity: 138
• IUPAC Name: 2-ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• InChI: InChI=1S/C8H17BO2/c1-6-9-10-7(2,3)8(4,5)11-9/h6H2,1-5H3
• InChI Key: NPUBDPDASOEIOA-UHFFFAOYSA-N
• Exact Mass: 156.1321599
• Molecular Formula: C8H17BO2
• Molecular Weight: 156.03
• SMILES: B1(OC(C(O1)(C)C)(C)C)CC
• Topological: 18.5
• Monoisotopic Mass: 156.1321599
• Synonyms: 82954-89-0, 2-ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, DTXSID50449122, DTXCID20399943, 808-111-3, Ethylboronic Acid Pinacol Ester, 1,3,2-Dioxaborolane, 2-ethyl-4,4,5,5-tetramethyl-, 2-Ethylboronic acid, pinacol ester, MFCD19441153, SCHEMBL1106850, SCHEMBL28838409, AKOS016005653, CS-W000975, AS-32775, DA-02544, SY055285, E1116, EN300-244103, 2-ethyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, (4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)ethane

Application

2-Ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is primarily employed as a boronating agent in Suzuki-Miyaura cross-coupling reactions, enabling the formation of carbon-carbon bonds in complex organic molecules. Its stability under ambient conditions makes it suitable for use in pharmaceutical intermediates and agrochemical synthesis. Researchers also leverage its reactivity in polymer chemistry and materials science for functionalizing organic frameworks.

Safety and Hazards

GHS Hazard Statements

• H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Precautionary Statements

• P210, P233, P240, P241, P242, P243, P264, P264+P265, P280, P302+P352, P303+P361+P353, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P235, and P501

Hazard Classes and Categories

• Flam. Liq. 3 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)

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