tetramethyl-10-(2,5,8,11,14-pentaoxapentadecyl) -5H-4l4,5l4-dipyrrolo [1,2-c:2′,1′-f][1,3,2]diazaborinine (98.7%)

tetramethyl-10-(2,5,8,11,14-pentaoxapentadecyl)-5H-4l4,5l4-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine

Molecular Formula: C23H35BF2N2O5

CAS#: 2490666-27-6

SMILES: COCCOCCOCCOCCOCC1=C(C(C)=CC2C)N2B(F)(F)[NH]3C1=C(C)C=C3C

MDL#: None

Catalog#: AMTB1294-BD19

Molecular weight: 468.34 g/mol

Other names:

• 5,5-Difluoro-1,3,7,9-tetramethyl-10-(2,5,8,11,14-pentaoxapentadecyl)-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine
• PEG-functionalized tetramethyl BODIPY
• Oligoethylene glycol-substituted BODIPY
• PEGylated BODIPY fluorophore
• Hydrophilic BODIPY dye
• Oligoethylene glycol BODIPY probe
• PEG-modified fluorescent BODIPY building block

Appearance: Red Liquid

Purity: 98.7%

Storage: Protected from light, tightly sealed, kept dry

Solubility: Chloroform

Fields of Interest:

• probe development
• chemical biology
• imaging & sensing
• materials science

Background:

5,5-Difluoro-1,3,7,9-tetramethyl-10-(2,5,8,11,14-pentaoxapentadecyl)-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine (CAS 2490666-27-6) is a PEG-functionalized BODIPY fluorophore that combines a boron-dipyrromethene (BODIPY) fluorescent core with a flexible, methoxy-terminated oligoethylene glycol chain. The BODIPY scaffold is valued for its strong fluorescence, chemical stability, and favorable photophysical characteristics, while the PEG-like side chain increases polarity and provides greater compatibility with polar environments than an unmodified hydrophobic fluorophore. This combination makes the compound a useful fluorescent building block for applications requiring both optical functionality and a flexible, hydrophilic molecular substituent.

Applications:

CAS 2490666-27-6 is of interest in fluorescent probe development, chemical biology, imaging, sensing, and materials science. Its BODIPY core provides a fluorescent reporter suitable for incorporation into molecular probes and functional materials, while the oligoethylene glycol substituent can improve dispersibility and reduce hydrophobic interactions associated with the dye scaffold. Potential applications include development of fluorescent labels, molecular sensors, imaging agents, functional polymers, and BODIPY-containing supramolecular or materials systems. Unlike azido-, amino-, or carboxyl-functional PEG linkers, the PEG-like chain in this molecule is primarily a solubility- and property-modifying substituent rather than a terminal reactive handle.

Literature:

Although peer-reviewed literature explicitly identifying CAS 2490666-27-6 cannot be found, the compound belongs to a well-established class of oligoethylene glycol-functionalized BODIPY fluorophores. Singh et al. demonstrated that incorporation of oligoethylene glycol side chains into BODIPY derivatives can significantly influence solubility, molecular packing, film formation, and electronic properties, while Kamkaew et al. showed that oligoethylene glycol substitution can increase the hydrophilicity of BODIPY-type dyes and facilitate their use as intracellular fluorescent probes. More recently, PEGylated BODIPY derivatives have been investigated for advanced imaging and photodynamic therapy, further demonstrating the value of PEG/OEG substitution for tuning BODIPY solubility, biological compatibility, and functional performance.

• Singh, S.; Venugopalan, V.; Krishnamoorthy, K. “Organic soluble and uniform film forming oligoethylene glycol substituted BODIPY small molecules with improved hole mobility.” Physical Chemistry Chemical Physics 2014, 16, 13376–13382. DOI: 10.1039/C4CP01098A.
  • This is particularly relevant because the authors directly synthesized BODIPY molecules bearing oligoethylene glycol side chains and investigated how those chains affected molecular packing, film formation, and electronic properties.
• Kamkaew, A.; Thavornpradit, S.; Puangsamlee, T.; Xin, D.; Wanichacheva, N.; Burgess, K. “Oligoethylene glycol-substituted aza-BODIPY dyes as red emitting ER-probes.” Organic & Biomolecular Chemistry 2015, 13, 8271–8276. DOI: 10.1039/C5OB01104C.
  • This paper demonstrates how attaching oligoethylene glycol fragments to BODIPY-type fluorophores increases hydrophilicity and enables their use as intracellular fluorescent probes. The compounds localized in the endoplasmic reticulum of several cell types.
• Wen, H.; Wu, Q.; Xiang, X.; Sun, T.; Xie, Z.; Chen, X. “PEGylated BODIPY Photosensitizer for Type I Dominant Photodynamic Therapy and Afterglow Imaging.” ACS Applied Materials & Interfaces 2024, 16, 61739–61750. DOI: 10.1021/acsami.4c14754.
  • This more recent work demonstrates how PEGylation of a BODIPY scaffold improves water compatibility and enables nanoparticle formation, with applications in fluorescence/afterglow imaging and photodynamic therapy.