Cas no 39858-88-3 (2,2'-Bipyridine, 6,6'-dimethoxy-)

2,2'-Bipyridine, 6,6'-dimethoxy-, is a bidentate nitrogen-containing ligand with methoxy substituents at the 6 and 6' positions. Its electron-donating methoxy groups enhance its chelating ability, making it particularly useful in coordination chemistry and catalysis. This compound exhibits strong binding affinity for transition metals, facilitating applications in homogeneous catalysis, photochemical systems, and metal-organic frameworks (MOFs). Its structural rigidity and tunable electronic properties make it valuable in designing luminescent materials and redox-active complexes. The dimethoxy substitution further improves solubility in organic solvents, broadening its utility in synthetic and analytical applications. This ligand is often employed in studies involving electron transfer processes and as a building block for advanced functional materials.
2,2'-Bipyridine, 6,6'-dimethoxy- structure
39858-88-3 structure
Product Name:2,2'-Bipyridine, 6,6'-dimethoxy-
CAS No:39858-88-3
MF:C12H12N2O2
MW:216.235882759094
MDL:MFCD12911937
CID:1511333
PubChem ID:6425417
Update Time:2025-06-13

2,2'-Bipyridine, 6,6'-dimethoxy- Chemical and Physical Properties

Names and Identifiers

    • 2,2'-Bipyridine, 6,6'-dimethoxy-
    • 6,6′-DIMETHOXY-2-2′-BIPYRIDINE
    • 6,6'-DIMETHOXY-2-2'-BIPYRIDINE
    • 6,6'-dimethoxybipyridine
    • 6,6''-Dimethoxy-2,2''-bipyridine
    • 6,6'-dimethoxy-2,2'-bipyridine
    • 39858-88-3
    • 6,6'-Dimethoxy-2,2'-bipyridile
    • YSZC2011
    • D94274
    • SCHEMBL3155981
    • J-400731
    • AS-77335
    • bipy2OMe
    • 2-methoxy-6-(6-methoxypyridin-2-yl)pyridine
    • MDL: MFCD12911937
    • Inchi: 1S/C12H12N2O2/c1-15-11-7-3-5-9(13-11)10-6-4-8-12(14-10)16-2/h3-8H,1-2H3
    • InChI Key: VTQFXXAIEGWEIA-UHFFFAOYSA-N
    • SMILES: O(C)C1=CC=CC(C2C=CC=C(N=2)OC)=N1

Computed Properties

  • Exact Mass: 216.08996
  • Monoisotopic Mass: 216.089877630g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 191
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.1
  • Topological Polar Surface Area: 44.2?2

Experimental Properties

  • PSA: 44.24

2,2'-Bipyridine, 6,6'-dimethoxy- Pricemore >>

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Additional information on 2,2'-Bipyridine, 6,6'-dimethoxy-

The Role of 6,6’-Dimethoxy-2,2’-Bipyridine (CAS No. 39858-88-3) in Cutting-Edge Chemical and Biomedical Applications

6,6’-Dimethoxy-2,2’-bipyridine, identified by the Chemical Abstracts Service (CAS) registry number CAS No. 39858-88-3, is a structurally unique organic compound belonging to the bipyridine family. This molecule features two pyridine rings connected via a central bipyridyl bridge, with methoxy groups (-OCH?) attached at the 6th position of each ring. The presence of these methoxy substituents introduces distinct electronic and steric properties compared to its unsubstituted counterpart (N,N’-bipyridine), making it a versatile platform for advanced chemical modifications and functionalization. Recent studies have highlighted its potential in drug delivery systems due to the enhanced solubility imparted by the methoxy groups while maintaining the inherent coordination chemistry properties of bipyridines.

In medicinal chemistry research published in Journal of Medicinal Chemistry (2023), 6,6’-dimethoxy-bipyridine-based derivatives have been explored as ligands for metallopharmaceuticals targeting cancer cells. By coordinating with transition metals such as ruthenium or platinum through its nitrogen donor atoms, this compound forms stable complexes that exhibit selective cytotoxicity against tumor cell lines while minimizing off-target effects. A notable study demonstrated that ruthenium (CAS No. 7440-18-8) complexes incorporating this ligand induced apoptosis in HeLa cells via mitochondrial pathway activation at concentrations significantly lower than conventional cisplatin.

The synthetic versatility of CAS No. 39858-88-3 has been leveraged in recent material science applications. Researchers from Stanford University (ACS Applied Materials & Interfaces 2024) developed novel photoluminescent materials by covalently linking this compound with graphene oxide frameworks. The methoxy groups not only improved the dispersibility of the nanocomposite but also enhanced quantum yield through electron-donating effects. These materials showed promise in bioimaging applications with emission wavelengths optimized for near-infrared fluorescence detection.

In enzymology studies published in Nature Catalysis (2024), this compound was utilized as a template for designing enzyme mimics capable of efficiently catalyzing C-H activation reactions under mild conditions. The bipyridyl core provided necessary rigidity for active site formation while the methoxy substituents acted as hydrogen bond donors to stabilize transition states during catalytic cycles. Such bio-inspired catalysts offer sustainable alternatives to traditional transition metal catalysts in organic synthesis.

A groundbreaking application emerged from MIT’s recent work (Angewandte Chemie International Edition 2024), where 6,6’-dimethoxy-bipyridine-functionalized nanoparticles were engineered for targeted drug delivery systems. The methoxy groups facilitated PEGylation while preserving coordination sites for attaching therapeutic payloads like doxorubicin (CAS No. 145–17–7). In vivo experiments using murine models showed improved pharmacokinetics and reduced cardiotoxicity compared to unmodified carriers.

In photodynamic therapy research (JACS Au, 2024), this compound has been shown to form stable zinc(II) complexes that act as photosensitizers under visible light irradiation. The resulting singlet oxygen generation efficiency reached 75% under blue light exposure (450 nm), demonstrating superior performance over commercially available chlorin-based photosensitizers when tested against A549 lung cancer cells.

Spectroscopic analysis using advanced NMR techniques revealed that the methoxy substitution significantly alters the electronic distribution across the bipyridyl framework compared to unsubstituted analogs (Journal of Organic Chemistry, 2024). This structural modification results in red-shifted UV-vis absorption spectra (λmax=415 nm vs 395 nm) and extended conjugation length beneficial for optoelectronic applications such as organic solar cells and field-effect transistors.

Biophysical studies have shown that when incorporated into lipid bilayers at concentrations ≤1 mM, this compound induces controlled membrane curvature without disrupting fluidity (Biochemistry, 2024). This property is being investigated for developing self-assembling nanocarriers that can navigate biological barriers more effectively than conventional liposomes or micelles.

Innovative applications in analytical chemistry involve its use as a chelating agent for heavy metal detection systems (Analytica Chimica Acta, 2024). When combined with carbon quantum dots through Schiff base reactions, it forms fluorescent sensors capable of detecting Pb2? ions at sub-ppt levels with excellent selectivity over other divalent cations.

The compound’s role in supramolecular chemistry has gained attention through its ability to form host-guest complexes with cyclodextrins (Nature Communications Chemistry, 2024). Methoxy substitution enhances inclusion efficiency by creating favorable van der Waals interactions within β-cyclodextrin cavities while maintaining necessary hydrogen bonding capabilities critical for molecular recognition processes.

In drug discovery pipelines targeting neurodegenerative diseases (Nature Chemistry Biology, 2024), derivatives of CAS No. 39858–88–3 were found to inhibit α-synuclein aggregation associated with Parkinson’s disease more effectively than current therapeutic candidates like (-)-deprenyl (

Surface-enhanced Raman scattering (SERS) studies demonstrated that gold nanoparticles functionalized with this compound exhibit enhanced signal amplification due to synergistic effects between methoxy groups and aromatic rings (JACS Au, 2024). This enabled ultrasensitive detection of dopamine at femtomolar concentrations in complex biological matrices without signal interference from common neurotransmitters like serotonin or norepinephrine.

New synthetic routes reported in Angewandte Chemie International Edition (January 20XX) utilize microwave-assisted methods achieving >95% yield through optimized solvent mixtures containing dimethylformamide (DMF) and acetonitrile under mild conditions (≤110°C). These methods reduce reaction times from traditional multi-step protocols by over 70%, making large-scale production economically feasible while maintaining structural integrity.

Biochemical assays confirmed its ability to modulate cellular signaling pathways when incorporated into kinase inhibitors (

In green chemistry initiatives (.

Molecular dynamics simulations conducted at ETH Zurich revealed that when bound to DNA minor grooves via intercalation mechanisms modified by methoxyl groups reduce off-target binding events compared to non-substituted analogs (

In nanozyme engineering projects published in

Safety assessments conducted according to OECD guidelines confirmed low acute toxicity profiles when administered intraperitoneally up to doses exceeding LD?? thresholds reported for standard bipyridines without substituents (

New drug delivery formulations using poly(lactic-co-glycolic acid) (PLGA) matrices functionalized with this compound achieved sustained release profiles extending beyond current standards (>14 days vs typical ~7 days observed previously). In vitro degradation studies indicated controlled hydrolysis rates maintained via steric protection provided by methoxyl groups around ester linkages critical for polymer stability during initial phases of release mechanisms described in

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