Description

Methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (CAS No. 653589-95-8) is a high-purity boronic ester derivative widely utilized in organic synthesis and pharmaceutical research. This compound, with the molecular formula C₁₄H₁₉BO₄, features a benzoate ester group coupled with a 4,4,5,5-tetramethyl-1,3,2-dioxaborolane moiety, making it a versatile intermediate for Suzuki-Miyaura cross-coupling reactions. Its stable boronate ester structure ensures excellent handling and storage properties under inert conditions. Ideal for researchers seeking reliable borylation reagents, this product is rigorously tested for quality, ensuring consistent performance in complex synthetic pathways. Available in various quantities, it is packaged under nitrogen to maintain stability and purity.

Properties

• CAS Number: 653589-95-8
• Complexity: 337
• IUPAC Name: methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• InChI: InChI=1S/C14H19BO4/c1-13(2)14(3,4)19-15(18-13)11-9-7-6-8-10(11)12(16)17-5/h6-9H,1-5H3
• InChI Key: GWSGJWIUSIAFOP-UHFFFAOYSA-N
• Exact Mass: 262.1376392
• Molecular Formula: C14H19BO4
• Molecular Weight: 262.11
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2C(=O)OC
• Topological: 44.8
• Monoisotopic Mass: 262.1376392
• Synonyms: 653589-95-8, Methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, DTXSID30375011, DTXCID10326041, 675-007-0, 2-Methoxycarbonylphenylboronic acid pinacol ester, 2-methoxycarbonylphenylboronic acid, pinacol ester, MFCD05663866, 2-(methoxycarbonyl)benzeneboronic acid pinacol ester, 2-(methoxycarbonyl)benzeneboronic acid, pinacol ester, SCHEMBL9986523, methyl 2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, GWSGJWIUSIAFOP-UHFFFAOYSA-N, (2-(METHOXYCARBONYL)PHENYL)BORONIC ACID PINACOL ESTER, methyl2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, AKOS015852330, AB21978, AS-3257, CS-W000957, SY003284, M3233, EN300-363379, 2-Methoxycarbonylphenylboronic acid, pinacol ester, AldrichCPR

Application

Methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate is a key reagent in palladium-catalyzed cross-coupling reactions, enabling the synthesis of biaryl compounds for pharmaceutical and material science applications. Its boronate ester group facilitates efficient transmetalation in Suzuki-Miyaura couplings, making it valuable for constructing complex organic frameworks. Researchers also employ it in the development of boron-containing polymers and advanced functional materials. The compound’s stability and reactivity make it suitable for high-throughput screening and combinatorial chemistry.

Safety and Hazards

GHS Hazard Statements

• H302+H312+H332 (96.6%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Precautionary Statements

• P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Acute Tox. 4 (100%)
• Acute Tox. 4 (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.