2-(4,5-Dihydro-1H-imidazol-2-yl)phenol: Properties & Lab Use
2-(4,5-Dihydro-1H-imidazol-2-yl)phenol: Properties & Lab Use
2-(4,5-Dihydro-1H-imidazol-2-yl)phenol is a heterocyclic organic compound featuring a 4,5-dihydroimidazole (imidazoline) ring directly bonded to a phenol moiety, making it a versatile building block and reference standard in medicinal chemistry and synthetic research.
- Product Name
- 2-(4,5-Dihydro-1H-imidazol-2-yl)phenol
- SKU
- D468788
- Core Structural Features
- 4,5-dihydroimidazoline ring fused to a 2-hydroxyphenyl (phenol) group
- Compound Class
- Imidazoline derivative / phenol heterocycle
- Reference Cross-listing
- Sigma-Aldrich No. 654698
- Supplier
- Aladdin Scientific
Chemical Structure and Key Properties
2-(4,5-Dihydro-1H-imidazol-2-yl)phenol consists of a phenol ring bearing an ortho-substituted 4,5-dihydroimidazole (imidazoline) group at the 2-position. The imidazoline ring is a five-membered nitrogen-containing heterocycle in a partially saturated state, distinguishing it from the fully aromatic imidazole. The presence of both a phenolic hydroxyl group and a basic imidazoline nitrogen endows this compound with bifunctional character, enabling hydrogen-bond donation and acceptance, as well as potential coordination chemistry with metal centres.
The intramolecular proximity of the phenolic –OH and the imidazoline C=N group at the ortho position may facilitate intramolecular hydrogen bonding or tautomeric interactions, influencing the compound's pKa profile, solubility, and reactivity. These structural features are commonly exploited in ligand design and pharmaceutical intermediate synthesis.
Synthesis and Preparation Context
Imidazoline-phenol hybrids of this type are commonly accessed through condensation reactions between 2-aminophenol derivatives and appropriate nitrile or imidate electrophiles, followed by ring closure to give the 4,5-dihydroimidazole scaffold. Alternatively, reaction of 2-cyanophenol with ethylenediamine under controlled conditions is a well-established route to 2-arylimidazoline compounds bearing ortho-hydroxyl substitution.
The product is supplied by Aladdin Scientific (SKU D468788) and cross-listed as Sigma-Aldrich No. 654698, indicating its availability as a catalogue research reagent for use without further custom synthesis. Researchers should consult the current certificate of analysis (CoA) for purity grade, melting point, and spectral confirmation data.
Laboratory Applications
Compounds in the 2-arylimidazoline class have broad utility across several research domains. As bifunctional ligands, 2-(imidazolinyl)phenols can coordinate to transition metals through both the phenolate oxygen and the imidazoline nitrogen, making them candidates for catalyst design and coordination chemistry studies. This bidentate N,O-donor motif is well recognised in the metallosupramolecular and catalysis literature.
In medicinal chemistry contexts, imidazoline-containing scaffolds have been investigated in relation to adrenergic receptor pharmacology and related biological targets; however, researchers should conduct their own literature surveys to confirm the specific biological relevance of this particular ortho-hydroxyl substituted analogue. The compound may also serve as a synthetic intermediate for constructing more complex heterocyclic architectures, or as a reference standard for analytical method development.
Handling, Storage, and Safety Considerations
As with all research-grade organic reagents, 2-(4,5-Dihydro-1H-imidazol-2-yl)phenol should be handled in a well-ventilated laboratory environment with appropriate personal protective equipment (PPE), including nitrile gloves, safety glasses, and a laboratory coat. Avoid inhalation of dust or aerosols.
Storage conditions (temperature, light sensitivity, moisture requirements) should be confirmed from the product's Safety Data Sheet (SDS) and current CoA provided by Aladdin Scientific at the time of purchase. General guidance for imidazoline-phenol compounds suggests storage in a cool, dry environment away from strong oxidising agents and strong acids or bases. Dispose of waste material in accordance with local institutional and regulatory requirements.
Frequently asked questions
What is the catalogue number for 2-(4,5-Dihydro-1H-imidazol-2-yl)phenol at Aladdin Scientific?
The Aladdin Scientific SKU for 2-(4,5-Dihydro-1H-imidazol-2-yl)phenol is D468788. It is also cross-listed as Sigma-Aldrich No. 654698.
What makes 2-(4,5-Dihydro-1H-imidazol-2-yl)phenol useful as a ligand in coordination chemistry?
The compound possesses both a phenolate oxygen donor and an imidazoline nitrogen donor in an ortho arrangement, enabling bidentate N,O-coordination to metal centres. This bifunctional donor ability makes it attractive for the design of metal complexes and catalysts.
How should I store 2-(4,5-Dihydro-1H-imidazol-2-yl)phenol in the laboratory?
Always follow the specific storage instructions on the Aladdin Scientific SDS and CoA supplied with your order. Generally, imidazoline-phenol compounds should be stored in a cool, dry, well-sealed container away from strong oxidants, strong acids, and direct light.
Is 2-(4,5-Dihydro-1H-imidazol-2-yl)phenol the same as an imidazole-phenol compound?
No. The 4,5-dihydro prefix indicates that the imidazoline ring is partially saturated (containing one C=N double bond), whereas imidazole is fully aromatic with two endocyclic double bonds. This difference in saturation significantly affects the compound's basicity, reactivity, and application profile.
References
- Aladdin Scientific product page: 2-(4,5-Dihydro-1H-imidazol-2-yl)phenol, SKU D468788.
- Sigma-Aldrich catalogue entry No. 654698: 2-(4,5-Dihydro-1H-imidazol-2-yl)phenol.
- General reference on imidazoline chemistry and N,O-donor ligands in coordination chemistry — textbook-level knowledge; specific citation to be confirmed by editor.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
危险品化学品经营许可证（带存储）