This compound belongs to the class of organic compounds known as phenyl-1,3-oxazoles. These are aromatic heterocyclic compounds containing a 1,3-oxazole substituted at one or more positions by a phenyl group.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
No tested biological or analytical application protocols are provided in the Product Data for this item.
General laboratory use suggestions (non-validated; for guidance only):
Preparation of stock solutions: Dissolve an accurately weighed amount in dry DMSO, acetonitrile, or dichloromethane to prepare standards or reaction stock solutions. Filter through 0.2 µm PTFE if particulate is present.
Reaction setup: Dry glassware, inert atmosphere (N2/Ar) for moisture-sensitive steps; choose solvent per Solvent Selection and Reaction Conditions tabs.
For any validated protocols specific to this lot (e.g., assay conditions, reference spectra), refer to the CoA/Spec Sheet.
Biological Roles
Item-specific biological roles: Not applicable; this product is supplied for research use only and is not assigned any biological function.
General context (literature; not product-specific):
Oxazole rings are common heteroaromatic motifs found in natural products and bioactive small molecules. They act primarily as rigid, planar, hydrogen-bond-accepting scaffolds that modulate binding orientation and electronic distribution in ligands.
The p-ethylphenyl substituent increases hydrophobic character, potentially enhancing membrane permeability when incorporated into larger molecules.
In medicinal chemistry, aryl–oxazole fragments are used as bioisosteres of amide/ester groups to tune metabolic stability and conformational bias; they can participate in π–π stacking and polar interactions via ring heteroatoms.
Experimental use considerations:
When used as a fragment or intermediate, downstream biological activity arises from the final compounds, not from this building block itself.
Any biological testing should adhere to appropriate regulations for research chemicals; no clinical or diagnostic use is implied.
Buffer Applications
This compound is a neutral, hydrophobic heteroaromatic building block and is not used as a buffering agent. It does not define a useful acid/base pair in aqueous media nor provide ionic strength control.
Practical note: If dissolution in aqueous systems is required for an assay, consider co-solvent systems (e.g., DMSO or acetonitrile stocks diluted into buffered media) while verifying solubility limits and avoiding precipitation.
Green Alternatives
Green chemistry considerations apply primarily to the solvents and reagents used with 4-(4-ethylphenyl)oxazole rather than the compound itself.
Greener solvent choices (literature guidance):
Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, 2‑MeTHF, or cyclopentyl methyl ether (CPME) where feasible.
Use bio-derived solvents (2‑MeTHF) or greener polar aprotics (propylene carbonate, dimethyl carbonate) when compatible with your reaction.
Illustrative comparison (general; not item-specific):
2‑MeTHF: Bio-based, higher boiling; good for organometallics; hydrophobic; can form peroxides on storage (manage with inhibitors/testing).
EtOAc: Readily biodegradable; moderate polarity; broad utility; limited for very nonpolar systems at high concentration.
CPME: Hydrophobic, stable to bases/acids in many cases; low peroxide formation relative to ethers; higher bp enables higher‑temp reactions.
Process considerations:
Catalyst loading: Optimize Pd/Cu catalyst loadings and recycle ligands where possible.
Energy: Favor room-temperature couplings or flow chemistry to reduce energy input.
Workup/waste: Minimize halogenated waste; adopt aqueous biphasic or solventless conditions when compatible with oxazole stability.
Note: No specific green certification is assigned to this item; these are general alternatives to consider during method development.
Pharmaceutical Uses
Item-specific pharmacopeial status or excipient role: Not specified for this item; refer to CoA/Spec Sheet.
General context (literature; not product-specific):
4-(4-Ethylphenyl)oxazole is primarily a synthetic intermediate or fragment in drug discovery, used to construct larger candidate molecules where oxazole functions as an amide bioisostere and conformationally constrained heteroaryl.
Typical roles in R&D: scaffold incorporation via cross-coupling (after appropriate functionalization), heteroaryl core for SAR exploration, and as a chromophore element in assay probes.
Formulation note:
As a hydrophobic, neutral small molecule, it is not used as an excipient. Any formulation considerations would pertain to final bioactive compounds derived from it rather than to this building block itself.
Compliance: For research use only; no clinical, diagnostic, or therapeutic use.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (general guidance; not item specifications):
Molecular formula (computed): C11H11NO
Molecular weight (computed): ~173.21 g/mol
Phase/appearance: Aromatic oxazoles of this size are often low-melting solids or high-boiling liquids; actual state depends on purity and crystallinity.
Solubility: Expected to be sparingly soluble in water and freely soluble in common organic solvents (e.g., DCM, THF, EtOAc, toluene, acetonitrile). Oxazole heteroatoms can engage in H-bond acceptance with polar aprotic solvents.
Polarity/logP: A p-ethylphenyl increases hydrophobicity; logP is expected to be moderate (literature estimates for analogous 4-aryl-oxazoles ~2–3).
UV–Vis: Oxazole–phenyl conjugation typically yields UV absorption in the near-UV (approx. 230–290 nm) with longer-wavelength tails depending on substitution (literature trends for aryl-oxazoles). No UV cutoff is assigned for this item.
pKa: Oxazole N is weakly basic; ring C2–H (if present) of oxazoles is slightly acidic in highly basic conditions; for a 4-aryl-oxazole typical pKa’s are not used operationally (literature: very weakly basic/neutral overall).
Handling implications from properties (general):
Low volatility relative to small ethers; aromatic odor possible.
Drying prior to air/moisture-sensitive reactions advisable, though oxazoles are generally air-stable.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general):
Research-grade small molecules may be supplied at an assay purity sufficient for synthesis or screening (e.g., >95% by HPLC/GC). Absent a declared grade, users should verify suitability for their application by reviewing the CoA, particularly assay, residual solvents, and related impurities.
Stabilizers: None indicated for this item. Many aryl-oxazoles are stable without stabilizers; if present in a particular lot, the CoA will list any additives.
Chromatographic performance: If using in photophysical studies or analytical calibrations, confirm low-level UV-absorbing impurities by HPLC/UV or LC–MS; aromatic heterocycles can have tailing impurities from synthesis.
Recommended quality checks (user considerations):
Identity: 1H/13C NMR consistent with oxazole and p-ethylphenyl resonances; HRMS consistent with [M+H]+ ~174.1.
Purity: HPLC or GC purity and residual solvent profile.
Water content: Karl Fischer as appropriate for moisture-sensitive transformations (if relevant); Not specified for this item.
Documentation: For definitive specifications (assay, impurity limits, metal content, residual solvents), consult the CoA/Spec Sheet for this SKU.
Reaction and Applications
Use domain: 4-(4-Ethylphenyl)oxazole is a heteroaromatic building block used in small-molecule discovery, materials motifs, and as a scaffold for further functionalization.
Representative application areas (literature-based):
Late-stage diversification on the phenyl ring: Electrophilic aromatic substitution (EAS) is feasible but typically requires activating conditions; practical routes involve prior halogenation (e.g., para-ethylphenyl to bromo/iodo derivatives) followed by cross-couplings (Suzuki–Miyaura, Buchwald–Hartwig if amination, Sonogashira, Negishi).
Oxazole ring transformations: Oxazoles participate in ring-opening or rearrangement under strong acidic or nucleophilic conditions; C2 of oxazole can be metalated with strong bases (e.g., s‑BuLi/TMEDA, LDA) enabling electrophile trapping (formylation, alkylation, acylation) in analogous substrates. Substitution at C4 by an aryl group modulates acidity and directs reactivity.
Photophysics/materials: Aryl–oxazole units are used as conjugated chromophores in OLED/OFET materials and fluorescent probes; the ethyl group tunes lipophilicity and electronic properties.
Oxidative and annulation chemistry: Oxazole scaffolds can serve as masked functional groups in cycloaddition or annulation sequences (e.g., 1,3-dipolar cycloadditions with activated partners in certain systems).
Practical tips:
Maintain anhydrous conditions for organometallic steps; pre-dry the compound over P2O5 or under high vacuum if necessary.
The oxazole ring is sensitive to strong mineral acids; avoid prolonged exposure to concentrated H2SO4/HCl at elevated temperature.
For cross-coupling on the aryl ring, confirm halide installation regioselectivity and minimize protodehalogenation by tuning base/ligand and temperature.
Reaction Conditions
General (literature-based; adapt to your substrate set):
C2 Metalation of oxazoles (analogous systems):
Base: s‑BuLi or LDA, often with TMEDA.
Solvent: Anhydrous THF or MTBE.
Temperature: −78 to −40 °C for deprotonation; then add electrophile at low temperature and allow to warm as needed.
Notes: Aryl substitution at C4 can reduce acidity; adjust base strength/time accordingly.
Electrophilic aromatic substitution on the phenyl ring:
Conditions: Friedel–Crafts acylations (Acyl chloride/AlCl3) in DCM or nitrobenzene at 0–25 °C; monitor for oxazole tolerance to Lewis/Brønsted acids.
Caution: Excessively harsh acid conditions can compromise the oxazole ring.
Cross-coupling after aryl halogenation:
Suzuki–Miyaura: Pd(0/II) catalysts (e.g., Pd(PPh3)4 or Pd-PEPPSI), K2CO3 or Cs2CO3 base, dioxane/H2O or toluene/EtOH/H2O, 50–100 °C.
Buchwald–Hartwig amination: Pd2(dba)3/XPhos or BrettPhos, NaOtBu or Cs2CO3, toluene/dioxane, 80–110 °C.
Sonogashira: Pd/Cu co-catalysis or copper-free systems, amine base, THF/Et3N or DMAc, 25–80 °C.
Oxazole ring transformations:
Nucleophilic ring opening typically requires strong nucleophiles and heat; conditions must be tuned to avoid overreaction.
Workup/analytics:
Quench organolithiums at low temperature with electrophile or MeOH, then standard aqueous workup.
Monitor by LC–MS/UPLC; aryl‑oxazoles usually give strong UV at 230–280 nm.
Note: No item-specific reaction data are provided; optimize for your system.
Safety and Handling
Item-specific hazard statements/GHS: Not specified for this item; refer to the SDS for authoritative information.
General safety guidance for aryl-oxazoles (literature-based; not product-specific):
Expected hazards: May cause irritation to eyes/skin/respiratory tract upon contact or inhalation of vapors or dust.
PPE: Use chemical-resistant gloves (e.g., nitrile), safety goggles, lab coat. Handle in a fume hood to avoid inhalation of vapors or dust.
Incompatibilities: Strong oxidizers; strong acids (prolonged exposure can degrade the oxazole ring); very strong bases can deprotonate ring C2 in oxazoles leading to ring reactivity.
Fire safety: Aromatic heteroarenes are typically combustible. Keep away from ignition sources. Use CO2, dry chemical, or foam for extinguishing.
Spill/cleanup: Absorb small liquid spills with inert material (vermiculite/sand) and place in suitable waste. For solids, avoid dust formation; sweep gently and contain. Ventilate area.
First aid (general):
Inhalation: Move to fresh air; seek medical advice if symptoms persist.
Skin contact: Wash with soap and water; remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Always consult the product-specific SDS before use. For research use only.
Solvent Selection
Relevance: This product is a neutral, hydrophobic heteroaromatic. Solvent choice primarily concerns dissolution for reactions, characterization, and handling.
General solubility/miscibility expectations (literature-based):
Good solvents: Dichloromethane, chloroform, ethyl acetate, THF, acetonitrile, toluene, DMF/DMSO.
Poor solvents: Water and very polar protic media are typically unsuitable for concentrated solutions.
Polarity profile:
Heteroatom-bearing aromatic (oxazole) attached to an alkylated phenyl increases hydrophobicity. Polar aprotic solvents often balance solubility with reaction compatibility.
Selection tips by application:
Spectroscopy: Use dry acetonitrile, DMSO‑d6, or CDCl3 depending on solubility and intended UV/fluorescence window.
Metal-catalyzed functionalization on the phenyl ring (after halogenation): Toluene, dioxane, or DMAc are common media.
Strong-base operations (e.g., directed lithiation on oxazole C2 in analogous systems): Use anhydrous THF or MTBE at low temperature with rigorous exclusion of moisture.
General storage guidance (small aromatic heterocycles):
Container: Store in a tightly sealed amber glass bottle to limit light exposure and solvent loss (if liquid). For solids, keep desiccated to avoid moisture uptake.
Atmosphere: Typically air-stable; for maximum shelf life, store under dry air or nitrogen, especially if frequent opening is expected.
Stability: Oxazoles are generally stable at ambient conditions; avoid prolonged exposure to strong acids/bases.
Reconstitution/solution preparation:
Solvents: DMSO, acetonitrile, THF, dichloromethane, toluene depending on use.
Stock solutions: Prepare at known concentration (e.g., 10–100 mM) and store at 2–8 °C or room temperature depending on solvent stability; protect from moisture. For long-term storage, consider aliquoting and freezing for high-boiling polar aprotics (e.g., DMSO) if appropriate.
Specifications not provided for this item (consult CoA/Spec Sheet):
Appearance, exact purity/grade, water content, residual solvents, metal limits, and analytical acceptance criteria.
Research Use Note: For research use only.
Structure and Identity
Brief: 4-(4-Ethylphenyl)oxazole is a biaryl–heteroaryl system comprising an oxazole ring para-linked to an ethyl-substituted phenyl ring.
From Product Data (item-specific):
SKU: E1249805
Product Name: 4-(4-Ethylphenyl)oxazole
CAS: 54289-72-4
CID: 57297368
InChIKey: 69914 (as provided)
Storage: Room temperature; shipped under normal conditions
Literature/computed identifiers and features (for reference; not item specifications):
Typical molecular formula: C11H11NO (computed from structure)
Representative SMILES: CCc1ccc(cc1)c2ocnc2 (one of several equivalent aromatic SMILES)
Core structural motifs: an aromatic 1,3-oxazole (five‑membered ring with O at position 1 and N at position 3) para-bonded via C4 to a p-ethylphenyl ring.
2D structural description:
The oxazole ring (O–C–N–C–C, aromatic) bears the aryl substituent at the C4 position.
The phenyl ring is para-substituted: one para position connects to the oxazole, the opposite para position bears an ethyl group (–CH2CH3). The remaining ring positions are hydrogen.
Notes:
Where exact identifiers for this item are required (e.g., definitive SMILES/InChIKey used for this lot), consult the CoA/Spec Sheet.
Synthetic Utility
Key functional elements:
Oxazole ring: aromatic 1,3-oxazole with two heteroatoms (O and N) providing H-bond acceptor capacity and directing effects.
p-Ethylphenyl group: hydrophobic aryl substituent that modulates electronics and sterics.
Utility in synthesis (literature-based):
Directed metalation: Oxazoles can undergo C2 metalation with strong bases (e.g., s‑BuLi/TMEDA) enabling electrophile trapping (formylation, acylation, alkylation). Aryl substitution at C4 influences acidity and regiochemistry.
Cross-couplings on the phenyl ring: After halogenation or via C–H activation strategies, the phenyl unit can be elaborated through Suzuki–Miyaura, Sonogashira, Heck, and Buchwald–Hartwig couplings to diversify substitution patterns.
Electrophilic substitution: Nitration, sulfonation, or Friedel–Crafts acylation on the phenyl ring are feasible under controlled conditions; oxazole stability toward strong acids must be considered.
Oxazole transformations: Under specific conditions, oxazoles can be converted to other motifs (e.g., ring-opening to amide/acid derivatives), offering masked functionality strategies in synthesis.
Retrosynthetic value:
Serves as a convergent junction: preassembled oxazole core with a common aryl substituent, allowing rapid diversification at the aryl para-ethyl side chain or elsewhere post-functionalization.
Practical tips:
Protect the oxazole core from prolonged exposure to strong protic acids or nucleophiles at elevated temperature.
Use anhydrous conditions for organometallic steps; quench carefully to avoid decomposition.
Target Specificity
Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or targeted biological reagent. No target specificity data are provided in the Product Data.
Perguntas frequentes
How should this product be stored?
Store at room temperature.
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 54289-72-4, the molecular formula is C11H11NO, and the molecular weight is 173.21 g/mol. InChIKey DQBWKFGHEULUPN-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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