Description

Potassium 2-methoxyethoxymethyltrifluoroborate (CAS No. 910251-13-7) is a highly specialized organoboron reagent with the molecular formula C₄H₉BF₃KO₂. This air-stable, crystalline compound is a valuable building block in synthetic organic chemistry, particularly in Suzuki-Miyaura cross-coupling reactions where it serves as a robust trifluoroborate nucleophile. The 2-methoxyethoxymethyl (MEM) protecting group enhances solubility in organic solvents while maintaining excellent stability under various reaction conditions. With a purity typically ≥95% (NMR), this reagent is rigorously characterized by ¹H, ¹¹B, ¹³C NMR, and mass spectrometry to ensure batch-to-batch consistency. Ideal for pharmaceutical intermediates and advanced material synthesis, it offers superior handling characteristics compared to traditional boronic acids.

Properties

• CAS Number: 910251-13-7
• Complexity: 89.9
• IUPAC Name: potassium;trifluoro(2-methoxyethoxymethyl)boranuide
• InChI: InChI=1S/C4H9BF3O2.K/c1-9-2-3-10-4-5(6,7)8;/h2-4H2,1H3;/q-1;+1
• InChI Key: ANDVAALQZRZFEH-UHFFFAOYSA-N
• Exact Mass: 196.0284757
• Molecular Formula: C4H9BF3KO2
• Molecular Weight: 196.02
• SMILES: [B-](COCCOC)(F)(F)F.[K+]
• Topological: 18.5
• Monoisotopic Mass: 196.0284757
• Synonyms: Potassium 2-methoxyethoxymethyltrifluoroborate, 910251-13-7, potassium trifluoro((2-methoxyethoxy)methyl)borate, POTASSIUM TRIFLUORO[(2-METHOXYETHOXY)METHYL]BORANUIDE, potassium;trifluoro(2-methoxyethoxymethyl)boranuide, MFCD13195184, KLB25113, ZB0256, AKOS013014776, Potassium 2-methoxyethoxymethyltrifluoroborat, CS-0209266, A50059, EN300-6489303, potassiumtrifluoro((2-methoxyethoxy)methyl)borate, Potassium trifluoro(2-methoxyethoxymethyl)boranuide

Application

This potassium trifluoroborate salt is primarily employed as a stable alternative to boronic acids in palladium-catalyzed cross-coupling reactions for biaryl formation. The MEM-protected trifluoroborate moiety demonstrates enhanced stability toward protodeboronation while maintaining high reactivity in Suzuki-Miyaura couplings. It finds particular utility in synthesizing complex molecules where traditional boronic acids might decompose under basic conditions. Researchers value this compound for its compatibility with both aqueous and organic reaction media, enabling versatile synthetic strategies in medicinal chemistry and materials science applications.

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