Description

2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 190788-60-4) is a high-purity boronic ester compound with the molecular formula C₁₃H₁₉BO₃. 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 and handling compared to free boronic acids, making it ideal for air- and moisture-sensitive applications. With exceptional batch-to-batch consistency (typically >95% purity by HPLC), this product is supplied as a white to off-white crystalline solid that exhibits excellent solubility in common organic solvents like THF, DMF, and dichloromethane. Proper storage at 2-8°C under inert atmosphere ensures long-term stability for demanding research applications in pharmaceutical development, materials science, and asymmetric synthesis.

Properties

• CAS Number: 190788-60-4
• Complexity: 262
• IUPAC Name: 2-(2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• InChI: InChI=1S/C13H19BO3/c1-12(2)13(3,4)17-14(16-12)10-8-6-7-9-11(10)15-5/h6-9H,1-5H3
• InChI Key: ASDFSWMHZSWXPO-UHFFFAOYSA-N
• Exact Mass: 234.1427246
• Molecular Formula: C13H19BO3
• Molecular Weight: 234.10
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2OC
• Topological: 27.7
• Monoisotopic Mass: 234.1427246
• Synonyms: 190788-60-4, 2-(2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, DTXSID10464770, DTXCID50415589, 675-099-2, 2-Methoxyphenylboronic acid pinacol ester, 2-METHOXYPHENYLBORONIC ACID, PINACOL ESTER, 1,3,2-DIOXABOROLANE, 2-(2-METHOXYPHENYL)-4,4,5,5-TETRAMETHYL-, MFCD05863916, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anisole, 2-(2-METHOXYPHENYL)4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE, 2-Methoxybenzeneboronic acid, pinacol ester, SCHEMBL2774133, SCHEMBL16429138, ASDFSWMHZSWXPO-UHFFFAOYSA-N, AKOS015960110, AB22719, AS-2576, CS-W012915, NCGC00662568-01, 2-Methoxybenzeneboronic acid pinacol ester, 2-Methoxybenzeneboronic acid,pinacol ester, SY045457, DB-044744, T3708, EN300-201482, H10869, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)anisole, 2-Methoxyphenylboronic acid, pinacol ester, AldrichCPR, Z1336745076, 2-(2-methoxy-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-(2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxa borolane

This boronic ester serves as a key building block in palladium-catalyzed cross-coupling reactions for constructing biaryl systems prevalent in drug discovery. It demonstrates particular utility in synthesizing ortho-substituted biphenyl scaffolds for kinase inhibitors and GPCR modulators. The methoxy substituent enables subsequent functionalization via demethylation or directed metalation strategies. Researchers value its enhanced stability over boronic acids in automated synthesis platforms.

Safety and Hazards

GHS Hazard Statements

• H302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (33.3%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (66.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (33.3%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (66.7%): 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 (33.3%)
• Acute Tox. 4 (33.3%)
• Skin Irrit. 2 (66.7%)
• Eye Irrit. 2A (66.7%)
• Acute Tox. 4 (33.3%)
• STOT SE 3 (66.7%)

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