Description

4,4,5,5-Tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborolane (CAS No. 126689-00-7) is a highly specialized organoboron compound with the molecular formula C₁₀H₁₉BO₂. This dioxaborolane derivative features a reactive boronate ester group, making it a valuable intermediate in synthetic organic chemistry, particularly in Suzuki-Miyaura cross-coupling reactions and other transition-metal-catalyzed processes. Its stable tetramethyl-substituted dioxaborolane ring enhances solubility in organic solvents while maintaining reactivity. The compound is supplied as a clear, colorless to pale yellow liquid with high purity (>95%) and is packaged under inert gas to ensure stability. Ideal for researchers in pharmaceuticals, materials science, and catalysis, this reagent is stored at 2-8°C to prolong shelf life. Always handle under nitrogen/argon and use in a fume hood.

Properties

• CAS Number: 126689-00-7
• Complexity: 211
• IUPAC Name: 4,4,5,5-tetramethyl-2-(2-methylprop-1-enyl)-1,3,2-dioxaborolane
• InChI: InChI=1S/C10H19BO2/c1-8(2)7-11-12-9(3,4)10(5,6)13-11/h7H,1-6H3
• InChI Key: LWXHOCHDERDUID-UHFFFAOYSA-N
• Exact Mass: 182.1478100
• Molecular Formula: C10H19BO2
• Molecular Weight: 182.07
• SMILES: B1(OC(C(O1)(C)C)(C)C)C=C(C)C
• Topological: 18.5
• Monoisotopic Mass: 182.1478100
• Synonyms: 126689-00-7, 4,4,5,5-Tetramethyl-2-(2-methylprop-1-en-1-yl)-1,3,2-dioxaborolane, DTXSID50569071, DTXCID40519843, 801-924-4, 2,2-DIMETHYLETHENYLBORONIC ACID PINACOL ESTER, 1,3,2-DIOXABOROLANE, 4,4,5,5-TETRAMETHYL-2-(2-METHYL-1-PROPEN-1-YL)-, 2-Methyl-1-propenylboronic acid pinacol ester, MFCD09842762, 4,4,5,5-Tetramethyl-2-(2-methyl-1-propenyl)-1,3,2-dioxaborolane, 4,4,5,5-TETRAMETHYL-2-(2-METHYLPROP-1-ENYL)-1,3,2-DIOXABOROLANE, 2-Methylprop-1-enylboronic acid pinacol ester, LWXHOCHDERDUID-UHFFFAOYSA-N, 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(2-methyl-1-propenyl)-, SCHEMBL115787, (2-METHYLPROP-1-EN-1-YL)BORONIC ACID PINACOL ESTER, 4,4,5,5-tetramethyl-2-(2-methyl-propenyl)-[1,3,2]dioxaborolane, AKOS016000184, AB53739, CS-W003667, AS-18690, SY026551, DB-355069, T3469, 2-methyl-1-propenyl boronic acid pinacol ester, EN300-260121, (2-Methyl-1-propenyl)boronic Acid Pinacol Ester, 2-Methyl-1-propenylboronic acid pinacol ester, 97%, Z1255403604

Application

This boronate ester is widely used as a key reagent in Suzuki-Miyaura cross-coupling reactions for constructing biaryl and heteroaryl scaffolds in drug discovery. It also serves as a protected boronic acid equivalent in multistep syntheses, enabling C-C bond formation under mild conditions. Applications extend to polymer chemistry, where it acts as a monomer or chain-transfer agent. Its stability and reactivity make it suitable for high-throughput screening in medicinal chemistry.

Safety and Hazards

GHS Hazard Statements

• H227 (66.7%): Combustible liquid [Warning Flammable liquids]
• H302 (66.7%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P210, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403, P403+P233, P405, and P501

Hazard Classes and Categories

• Flam. Liq. 4 (66.7%)
• Acute Tox. 4 (66.7%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.