Description

4,4,5,5-Tetramethyl-2-(oxetan-3-yl)-1,3,2-dioxaborolane (CAS No. 1396215-84-1) is a high-purity boronic ester compound with the molecular formula C₉H₁₇BO₃. This specialized reagent is widely used in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic organic chemistry. The compound features a unique oxetane ring structure, offering enhanced reactivity and stability for advanced pharmaceutical and materials science applications. Our product is rigorously tested to ensure ≥95% purity (HPLC/GC) and is supplied under inert atmosphere to maintain optimal shelf life. Available in convenient packaging options from milligrams to kilograms, this boronic ester is ideal for research-scale experiments and process development.

Key features include:

• High reactivity in palladium-catalyzed coupling reactions
• Exceptional stability under various reaction conditions
• Compatible with a wide range of functional groups
• Stored under nitrogen to prevent degradation
• Comprehensive analytical data included (NMR, MS, HPLC)

Properties

• CAS Number: 1396215-84-1
• Complexity: 195
• IUPAC Name: 4,4,5,5-tetramethyl-2-(oxetan-3-yl)-1,3,2-dioxaborolane
• InChI: InChI=1S/C9H17BO3/c1-8(2)9(3,4)13-10(12-8)7-5-11-6-7/h7H,5-6H2,1-4H3
• InChI Key: LBABXQQSDMILIX-UHFFFAOYSA-N
• Exact Mass: 184.1270746
• Molecular Formula: C9H17BO3
• Molecular Weight: 184.04
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2COC2
• Topological: 27.7
• Monoisotopic Mass: 184.1270746
• Synonyms: 4,4,5,5-Tetramethyl-2-(oxetan-3-yl)-1,3,2-dioxaborolane, 1396215-84-1, 810-856-4, 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(3-oxetanyl)-, MFCD26521383, Oxetane-3-boronic acid pinacol ester, C9H17BO3, SCHEMBL21543500, CS3150, AKOS016339172, CS-W018670, GS-2519, SY096826, DB-194776, OXETAN-3-YLBORONIC ACID PINACOL ESTER, EN300-214041, Z1813103134, 4,4,5,5-Teteamethyl-2-(oxetan-3-yl)-1,3,2-dioxaborolane

Application

This boronic ester is primarily employed as a key building block in pharmaceutical intermediates and material science research. It demonstrates excellent reactivity in Suzuki-Miyaura cross-coupling reactions for biaryl formation. The oxetane moiety provides unique steric and electronic properties that can influence drug bioavailability. Researchers utilize this compound in the synthesis of complex organic molecules, particularly in medicinal chemistry programs targeting CNS-active compounds. Its stability makes it valuable for iterative coupling strategies in polymer chemistry.

Safety and Hazards

GHS Hazard Statements

• H302+H332 (20%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]
• H302 (40%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (80%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (80%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (20%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (80%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

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

Hazard Classes and Categories

• Acute Tox. 4 (40%)
• Skin Irrit. 2 (80%)
• Eye Irrit. 2A (80%)
• Acute Tox. 4 (20%)
• STOT SE 3 (80%)

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