Description

4,4,5,5-Tetramethyl-2-(3-methylbut-2-en-1-yl)-1,3,2-dioxaborolane (CAS No. 141550-13-2) is a high-purity boronic ester compound with the molecular formula C₁₁H₂₁BO₂. This organoboron reagent is widely utilized in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic organic chemistry. The pinacol ester moiety enhances stability while maintaining reactivity, making it an ideal intermediate for pharmaceutical, agrochemical, and materials science applications. Supplied as a clear to pale yellow liquid, this compound is rigorously tested to ensure >95% purity (GC) and is packaged under inert gas to prevent degradation. Store in a cool, dry place away from moisture and oxidizing agents.

Properties

• CAS Number: 141550-13-2
• Complexity: 224
• IUPAC Name: 4,4,5,5-tetramethyl-2-(3-methylbut-2-enyl)-1,3,2-dioxaborolane
• InChI: InChI=1S/C11H21BO2/c1-9(2)7-8-12-13-10(3,4)11(5,6)14-12/h7H,8H2,1-6H3
• InChI Key: QXDMQRNIDKVRCN-UHFFFAOYSA-N
• Exact Mass: 196.1634601
• Molecular Formula: C11H21BO2
• Molecular Weight: 196.10
• SMILES: B1(OC(C(O1)(C)C)(C)C)CC=C(C)C
• Topological: 18.5
• Monoisotopic Mass: 196.1634601
• Synonyms: 141550-13-2, 4,4,5,5-Tetramethyl-2-(3-methylbut-2-en-1-yl)-1,3,2-dioxaborolane, DTXSID40572251, DTXCID60523023, 3-Methylbut-2-enylboronic acid, pinacol ester, 3-Methyl-2-butenylboronic acid pinacol ester, 4,4,5,5-tetramethyl-2-(3-methylbut-2-enyl)-1,3,2-dioxaborolane, 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(3-methyl-2-buten-1-yl)-, MFCD10567001, 3-Methylbut-2-enylboronic acid pinacol ester, 3,3-Dimethylallylboronic acid pinacol ester, 2-(3-methyl-but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 3,3-Dimethylallylboronic acid pinacol ester, 2-(3-Methyl-but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-d, QXDMQRNIDKVRCN-UHFFFAOYSA-N, 3-Methylbut-2-enylboronic acid,pinacol ester, SCHEMBL14247074, 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(3-methyl-2-butenyl)-, AKOS016006354, AS-55169, SY013340, DS-016571, CS-0129552, Y10589, 3-Methyl-2-butenylboronic acid pinacol ester, 96%

Application

This boronic ester is a versatile building block in palladium-catalyzed cross-coupling reactions, enabling efficient carbon-carbon bond formation. Researchers employ it in the synthesis of complex organic molecules, particularly in drug discovery for creating biaryl scaffolds. Its stability makes it valuable for multi-step synthetic routes where air- or moisture-sensitive intermediates are problematic.

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