Description

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-5-(trifluoromethyl)aniline (CAS No. 1196972-92-5) is a high-purity boronate ester compound with the molecular formula C₁₃H₁₇BF₃NO₂. This specialized reagent features a dioxaborolane-protected boronic acid moiety and a trifluoromethyl-substituted aniline group, making it a valuable intermediate in cross-coupling reactions such as Suzuki-Miyaura couplings. The tetramethyl dioxaborolane ring enhances stability while maintaining reactivity under appropriate conditions. With a molecular weight of 287.09 g/mol, this compound is supplied as a crystalline solid with ≥95% purity (HPLC). Ideal for pharmaceutical research and material science applications, it is packaged under inert gas to ensure maximum shelf life. Synonyms include MB20254 and MFCD16996232.

Properties

• CAS Number: 1196972-92-5
• Complexity: 357
• IUPAC Name: 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)aniline
• InChI: InChI=1S/C13H17BF3NO2/c1-11(2)12(3,4)20-14(19-11)9-6-5-8(7-10(9)18)13(15,16)17/h5-7H,18H2,1-4H3
• InChI Key: SKIXIDYMMJBOTF-UHFFFAOYSA-N
• Exact Mass: 287.1304434
• Molecular Formula: C13H17BF3NO2
• Molecular Weight: 287.09
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C=C(C=C2)C(F)(F)F)N
• Topological: 44.5
• Monoisotopic Mass: 287.1304434
• Synonyms: 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-5-(TRIFLUOROMETHYL)ANILINE, 1196972-92-5, SCHEMBL24596359, SKIXIDYMMJBOTF-UHFFFAOYSA-N, MFCD16996232, MB20254, BS-44384, DB-191583, CS-0368684, F71923, EN300-6249807, 5-(Trifluoromethyl)aniline-2-boronic Acid pinacol ester, 2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)aniline, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)benzenamine, 5-(trifluoromethyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine

Application

This compound serves as a key boronic ester building block in medicinal chemistry for the synthesis of trifluoromethyl-containing bioactive molecules. It is particularly useful in Suzuki-Miyaura cross-coupling reactions to create biaryl structures common in drug discovery. The trifluoromethyl group enhances metabolic stability and lipophilicity of resulting compounds. Researchers also utilize it in PET tracer development due to the favorable properties of fluorine-18 labeled derivatives.

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