Name: 2-(4-(2-(2-methoxyethoxy)ethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Molecular Formula: C17H27BO5
CAS#: 1366602-62-1
SMILES: CC1(C)OB(OC1(C)C)C2=CC=C(OCCOCCOC)C=C2
MDL#: MFCD27996253
Catalog#: AMTB581-ME12
Molecular weight: 322.2 g/mol
Other names:
- 4-(2-(2-Methoxyethoxy)ethoxy)phenylboronic acid pinacol ester
- Methoxy-PEG3 phenyl boronic ester
- PEG3 aryl boronate linker
Fields of Interest: cross-coupling chemistry, medicinal chemistry, materials science
Background & Applications:
Background
2-(4-(2-(2-methoxyethoxy)ethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS 1366602-62-1) is a boronic ester-functionalized PEG derivative featuring an aryl boronic acid pinacol ester linked to a methoxy-terminated PEG3 chain. The polyethylene glycol segment provides hydrophilicity, flexibility, and enhanced solubility in both aqueous and organic systems, while the boronic ester functionality serves as a stable and efficient partner for Suzuki–Miyaura cross-coupling reactions. Pinacol boronate esters are widely favored over boronic acids due to their improved stability and handling characteristics. This compound represents a versatile intermediate within a comprehensive portfolio of functionalized PEGs designed for modular assembly and carbon–carbon bond formation.
Applications
This PEGylated aryl boronic ester is commonly used in cross-coupling chemistry, medicinal chemistry, and materials science applications where enhanced solubility and controlled PEG incorporation are desired. Typical uses include palladium-catalyzed coupling with aryl or vinyl halides to construct substituted aromatic systems, synthesis of PEG-modified pharmaceutical intermediates, and preparation of functional polymers and advanced materials. The methoxy-capped PEG chain enables monofunctional PEG incorporation, helping to reduce non-specific interactions and improve physicochemical properties. As part of a robust functionalized PEG product line, this compound supports modular design strategies in drug discovery, diagnostics, and specialty chemical synthesis.
Appearance: Yellow to orange solid
Purity: 98%
Storage: Room Temp
Solubility: Dichloromethane, Chloroform, Acetonitrile
Literature:
- JANSSEN PHARMACEUTICA - US2014/364414, 2014, A1
- Journal of Materials Chemistry C, 2015, vol. 3, # 36, p. 9412 – 9424