Description

4,4,5,5-Tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane (CAS No. 269410-26-6) is a high-purity boronate ester compound with the molecular formula C₁₈H₂₁BO₃. This organoboron reagent is widely utilized in Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of biaryl and heteroaryl structures critical to pharmaceutical and materials science research. The compound features a stable dioxaborolane ring with tetramethyl substitution, enhancing its shelf stability and reactivity under mild conditions. Its 4-phenoxyphenyl moiety offers versatile functionalization potential for advanced organic synthesis. Supplied as a crystalline solid, it is rigorously tested for purity (typically >95% by HPLC) and is ideal for catalytic applications, ligand design, and polymer chemistry. Store under inert conditions to maintain optimal performance.

Properties

• CAS Number: 269410-26-6
• Complexity: 353
• IUPAC Name: 4,4,5,5-tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane
• InChI: InChI=1S/C18H21BO3/c1-17(2)18(3,4)22-19(21-17)14-10-12-16(13-11-14)20-15-8-6-5-7-9-15/h5-13H,1-4H3
• InChI Key: SFCRPRMZQXUXOG-UHFFFAOYSA-N
• Exact Mass: 296.1583747
• Molecular Formula: C18H21BO3
• Molecular Weight: 296.2
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)OC3=CC=CC=C3
• Topological: 27.7
• Monoisotopic Mass: 296.1583747
• Synonyms: 269410-26-6, 4,4,5,5-tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane, DTXSID50590406, DTXCID50541170, 807-311-8, Phenoxyphenyl-4-boronic acid pinacol ester, 4-Phenoxyphenylboronic acid pinacol ester, (4-PHENOXY)PHENYLBORONIC ACID PINACOL ESTER, 4-PHENOXYPHENYLBORONIC ACID, PINACOL ESTER, MFCD06795691, 1,3,2-DIOXABOROLANE, 4,4,5,5-TETRAMETHYL-2-(4-PHENOXYPHENYL)-, SCHEMBL5899727, SCHEMBL14785793, SFCRPRMZQXUXOG-UHFFFAOYSA-N, BCP22829, AKOS015919530, AB29271, AS-2976, CS-W000906, SY033545, T3831, EN300-316755, Z1336745187

Application

4,4,5,5-Tetramethyl-2-(4-phenoxyphenyl)-1,3,2-dioxaborolane is a key intermediate in palladium-catalyzed cross-coupling reactions, facilitating the construction of complex aromatic systems for drug discovery. It is employed in the synthesis of OLED materials and liquid crystals due to its electron-rich aromatic backbone. Researchers also use it to modify polymers and ligands for catalytic systems, leveraging its air-stable boronate ester functionality.

Safety and Hazards

GHS Hazard Statements

• H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (50%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (50%): 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 (50%)
• Acute Tox. 4 (50%)
• Skin Irrit. 2 (50%)
• Eye Irrit. 2A (50%)
• Acute Tox. 4 (50%)
• STOT SE 3 (50%)

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