Description

4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (CAS No. 126726-62-3) is a highly versatile boronic ester compound with the molecular formula C₉H₁₇BO₂. This organoboron reagent features a stable dioxaborolane ring system with tetramethyl substitution, enhancing its reactivity and stability for cross-coupling reactions. It is widely used in Suzuki-Miyaura coupling, a pivotal reaction in pharmaceutical and materials science research. The compound is supplied as a clear to pale yellow liquid, stored under inert conditions to ensure purity and longevity. Ideal for advanced synthetic applications, it is a critical building block for constructing complex organic molecules.

Properties

• CAS Number: 126726-62-3
• Complexity: 193
• IUPAC Name: 2-isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• InChI: InChI=1S/C9H17BO2/c1-7(2)10-11-8(3,4)9(5,6)12-10/h1H2,2-6H3
• InChI Key: SVSUYEJKNSMKKW-UHFFFAOYSA-N
• Exact Mass: 168.1321599
• Molecular Formula: C9H17BO2
• Molecular Weight: 168.04
• SMILES: B1(OC(C(O1)(C)C)(C)C)C(=C)C
• Topological: 18.5
• Monoisotopic Mass: 168.1321599
• Synonyms: 126726-62-3, 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane, DTXSID70451202, DTXCID20402022, 627-007-7, Isopropenylboronic acid pinacol ester, 2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(1-methylethenyl)-, 2-Isopropenylboronic acid, pinacol ester, 4,4,5,5-tetramethyl-2-prop-1-en-2-yl-1,3,2-dioxaborolane, MFCD08276843, 4,4,5,5-TETRAMETHYL-2-(1-METHYLETHENYL)-1,3,2-DIOXABOROLANE, SVSUYEJKNSMKKW-UHFFFAOYSA-N, 4,4,5,5-Tetramethyl-2-(1-methylethenyl)-1,3,2-dioxaborolane; 2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 4,4,5,5-Tetramethyl-2-(isopropenyl)-1,3,2-dioxaborolane; 4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane;, 2-Isopropenylboronic acid pinacol ester, SCHEMBL252994, (4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isopropene, 98% (Phenothiazine as stabilizer), BBL102645, STL556448, isopropenyl boronic acid pinacol ester, AKOS005146510, Isopropenylboronic acid pinacol ester, stabilized with 0.5% phenothiazine, CS-W000865, MB06091, AS-11408, DB-062502, I1038, EN300-196435, 2-ISOPROPENYL BORONIC ACID PINACOL ESTER, PROP-1-EN-2-YLBORONIC ACID PINACOL ESTER, 4,4,5,5-TETRAMETHYL-2-(1-METHYLETHENYL)-1, 2-isopropenyl-4,4,5,5-tetramethyl 1,3,2-dioxaborolane, 2-isopropenyl-4,4,5,5-tetramethyl[1,3,2]dioxaborolane, Z1255387555, 2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, 2-isopropenyl-4,4,5,5-tetramethyl-[1.3.2]dioxaborolane, 3-hydroxy-2,3-dimethylbutan-2-yl hydrogen prop-1-en-2-ylboronate, 4,4,5,5-tetra methyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane, 4,4,5,5-TETRAMETHYL-2-(ISOPROPENYL)-1,3,2-DIOXABOROLANE, 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-di oxaborolane, 4.4.5.5-tetramethyl-2-(prop-1-en-2-yl)-1.3.2-dioxaborolane, 2-(1-METHYLETHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE, Isopropenylboronic acid pinacol ester, contains phenothiazine as stabilizer, 95%

Application

This compound is extensively utilized in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions to form carbon-carbon bonds. It serves as a key intermediate in the preparation of pharmaceuticals, agrochemicals, and advanced materials. Researchers value its stability and reactivity in palladium-catalyzed transformations. It is also employed in the synthesis of boron-containing polymers and ligands for catalysis.

Safety and Hazards

GHS Hazard Statements

• H226 (97.9%): Flammable liquid and vapor [Warning Flammable liquids]
• H315 (97.9%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (97.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (93.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501

Hazard Classes and Categories

• Flam. Liq. 3 (97.9%)
• Skin Irrit. 2 (97.9%)
• Eye Irrit. 2 (97.9%)
• STOT SE 3 (93.8%)

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