Description

4,4,5,5-Tetramethyl-2-[(1E)-pent-1-en-1-yl]-1,3,2-dioxaborolane (CAS No. 161395-96-6) is a high-purity organoboron compound with the molecular formula C₁₁H₂₁BO₂. This specialized reagent features a dioxaborolane ring substituted with a pentenyl group, making it a valuable intermediate in organic synthesis and cross-coupling reactions. Its well-defined structure and stability under inert conditions ensure reliable performance in Suzuki-Miyaura couplings, hydroborations, and other transition-metal-catalyzed transformations. Ideal for researchers in pharmaceutical, agrochemical, and materials science, this compound is supplied in rigorously controlled conditions to guarantee consistency and reproducibility. Store under inert atmosphere at recommended temperatures to maintain optimal reactivity and shelf life.

Properties

• CAS Number: 161395-96-6
• Complexity: 205
• IUPAC Name: 4,4,5,5-tetramethyl-2-[(E)-pent-1-enyl]-1,3,2-dioxaborolane
• InChI: InChI=1S/C11H21BO2/c1-6-7-8-9-12-13-10(2,3)11(4,5)14-12/h8-9H,6-7H2,1-5H3/b9-8+
• InChI Key: IMIHEZMTQOARIK-CMDGGOBGSA-N
• Exact Mass: 196.1634601
• Molecular Formula: C11H21BO2
• Molecular Weight: 196.10
• SMILES: B1(OC(C(O1)(C)C)(C)C)/C=C/CCC
• Topological: 18.5
• Monoisotopic Mass: 196.1634601
• Synonyms: DTXSID00570091, 4,4,5,5-TETRAMETHYL-2-[(1E)-PENT-1-EN-1-YL]-1,3,2-DIOXABOROLANE, DTXCID90520863, 161395-96-6, (E)-4,4,5,5-tetramethyl-2-(pent-1-en-1-yl)-1,3,2-dioxaborolane, (E)-1-Pentene-1-boronic Acid Pinacol Ester, 4,4,5,5-tetramethyl-2-[(E)-pent-1-enyl]-1,3,2-dioxaborolane, trans-1-Penten-1-ylboronic acid pinacol ester, (E)-1-PENTENYLBORONIC ACID PINACOL ESTER, E-PENTEN-1-YLBORONIC ACID, PINACOL ESTER, 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(1E)-1-penten-1-yl-, MFCD05663882, IMIHEZMTQOARIK-CMDGGOBGSA-N, SCHEMBL1628914, 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(1E)-1-pentenyl-, AKOS015910439, (E)-pent-1-enylboronic acid pinacol ester, CS-0152593, trans-1-Penten-1-ylboronic acid pinacol ester, 97%, trans-1-Penten-1-ylboronic acid pinacol ester, AldrichCPR, (E)-2-(1-Pentenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Application

This compound is widely used as a key intermediate in Suzuki-Miyaura cross-coupling reactions for the synthesis of complex organic molecules. It is particularly valuable in the preparation of styrene derivatives and other unsaturated compounds. Researchers also employ it in hydroboration reactions to create functionalized organoboron reagents. Its stability and selectivity make it suitable for pharmaceutical and materials science applications.

Safety and Hazards

GHS Hazard Statements

• 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

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

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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