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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
179.600 g/mol
XLogP3
2.600
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
179.014 Da
Monoisotopic Mass
179.014 Da
Topological Polar Surface Area
26.000 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
153.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
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Recensioni
Recensioni dei clienti
Application Protocols
No assay-specific protocols are provided for this small-molecule building block. Typical laboratory uses include organic synthesis and method development. For cross-coupling or metalation workflows, refer to the Reaction Conditions tab for representative literature conditions, and adjust to your substrate/equipment. For analytical characterization, standard protocols apply (e.g., NMR in CDCl3 or DMSO-d6; LC–MS with MeCN/H2O + 0.1% formic acid).
Biological Roles
Item-specific biological data: Not specified for this item; no biological activity data are provided. For research use only.
General context (literature; not product-specific)
Oxazole is a privileged heteroaromatic motif found in natural products (e.g., oxazole-containing peptides) and medicinal chemistry scaffolds due to its planarity, H-bond acceptor capacity, and ability to modulate electronics/hydrophobicity.
Aryl chlorides serve as synthetic handles rather than biofunctional groups; the chlorine can be replaced to tune potency or ADME properties in lead optimization.
2-Aryloxazoles may act as bioisosteres of amide/ester fragments in ligand design, adjusting conformational bias and lipophilicity.
Practical note
If used in biological screening, ensure analytical confirmation of purity and residual metal/solvent levels. No claims are made for biological efficacy or safety.
Buffer Applications
This compound is a neutral, hydrophobic heteroaromatic building block and is not used as a buffering agent. It lacks acid/base pairs appropriate for maintaining pH in aqueous systems. For work involving this molecule, select an external buffer appropriate to your biological or analytical assay (e.g., phosphate, HEPES) and dissolve the compound using a compatible co-solvent (DMSO, MeCN, or EtOH) if needed.
Green Alternatives
For synthetic steps using 2-(3-chlorophenyl)oxazole, greener choices often focus on solvent and catalyst selection.
Solvent alternatives (general guidance)
Replace DMF/DMAc/NMP with 2-MeTHF, CPME, toluene, MeOH/H2O (with phase-transfer) where feasible.
Use ethanol or isopropanol for some couplings/rearrangements when compatible with catalyst/base.
Comparison (literature-based; example use-cases)
| Use-case | Conventional choice | Greener alternative | Notes |
|---|---|---|---|
| Suzuki coupling | DMF, dioxane | 2-MeTHF, toluene/H2O | Lower toxicity; maintain activity with Pd–XPhos-type ligands |
| Buchwald–Hartwig | Dioxane, toluene | CPME, 2-MeTHF | Good balance of polarity and safety; broad temp window |
| Lithiation at C5 | THF | 2-MeTHF, CPME | Similar coordination; improved safety profile |
| Workup/extraction | DCM | EtOAc, MTBE | Reduced chlorinated solvent use |
Catalysis and bases
Favor highly active Pd catalysts (e.g., Pd-PEPPSI, precatalysts with biaryl phosphines) to lower loadings and temperatures, reducing energy and waste.
Consider nickel catalysis for aryl chloride activation where substrate tolerance permits.
Waste minimization
Implement aqueous workups with salt-efficient separations; use recyclable solvents; capture Pd/Ni for metal recovery.
Note: Validate greener conditions for your substrate/catalyst system; small DoE screens can identify lower-impact options without sacrificing yield.
Pharmaceutical Uses
Item-specific pharmacopeial status: Not specified for this item; no pharmacopoeia monograph is indicated.
General formulation/manufacturing context (non-clinical)
2-(3-Chlorophenyl)oxazole can serve as a synthetic intermediate toward drug substance candidates or as a reference/impurity standard in analytical methods development.
The aryl chloride enables late-stage diversification (C–N/C–O/C–C couplings) in route scouting, while the oxazole ring provides a compact heteroaromatic bioisostere for amide/ester motifs.
For preclinical sample preparation, material is typically dissolved in organic vehicles (DMSO/PEG mixtures) before dilution into assay media; ensure compatibility and solubility profiling.
Compliance and documentation
For any use in regulated workflows, obtain a detailed CoA, impurity profile, residual metal/solvent data, and stability information. This product is supplied strictly for research use only and not for human or veterinary applications.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (general reference; not item specifications)
Molecular formula: C9H6ClNO (literature)
Molecular weight: ~179.60 g/mol (calculated from literature formula)
Phase/volatility: Aromatic heteroaromatic of modest molecular weight; typically low-volatility liquid or low-melting solid (literature expectation). Confirm actual form on CoA.
Solubility profile: Expected to be sparingly soluble in water; good solubility in common organic solvents (e.g., CH2Cl2, EtOAc, THF, toluene, MeCN) due to aromatic character (literature trend).
Acid–base: Neutral, weakly basic heteroaromatic; oxazole ring has low basicity (pKBH+ large; conjugate-acid pKa often <1) and relatively weak H-bond accepting character at the ring heteroatoms (literature).
LogP: Aromatic chloro substituent typically increases hydrophobicity; an estimated logP in the ~2–3 range would be typical for C9 aryl-oxazoles with one Cl (literature expectation; confirm experimentally if critical).
UV absorption: Aromatic chromophores absorb in the UV (ca. 200–300 nm); exact ε/λmax depends on solvent and substitution (literature).
Note: Boiling point, melting point, density, refractive index, water/peroxide/metal limits, and UV cutoffs are Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting common grades (general guidance)
Research/analytical grade: Suitable for most synthetic and analytical workflows. Typical controls include residual solvent and identity by NMR/GC/LC–MS.
HPLC/UV grade (if offered): Emphasizes low UV background and tightly controlled trace impurities for chromatography; beneficial where photometric detection is used.
Trace-metal specifications: For cross-coupling chemistry, low residual Pd/Cu/Ni and halide content can be important. If you require metal limits, request a CoA with ICP data.
Stabilizers/additives: None specified for this item. If a stabilizer were present, it would be listed on the label/CoA and may influence reactivity or purification.
Verification and documentation
Identity verification by 1H/13C NMR, HRMS, and HPLC/GC purity is recommended upon receipt when material will be used in critical routes.
For regulated workflows, request lot-specific CoA including test methods, acceptance criteria, and results.
Reaction and Applications
Role in synthesis (literature)
Versatile aryl–heteroaryl building block combining an aryl chloride handle with an oxazole. Useful in fragment-based assembly, SAR libraries, heteroaryl–aryl cross-couplings, and materials motifs (electron-deficient heteroaromatic).
Transformations on the aryl chloride (meta-Cl)
Pd-catalyzed C–C couplings: Suzuki–Miyaura (boronic acids/esters), Negishi (organometallic zinc), Stille (stannanes), Kumada (Grignards; more forcing). Modern ligands (e.g., BrettPhos/XPhos/SPhos) enable activation of aryl chlorides.
C–N, C–O, C–S couplings: Buchwald–Hartwig amination, Ullmann-type couplings (Cu). Tailor base/ligand to minimize oxazole coordination to metal.
Borylation: Miyaura borylation to access 3-oxazolylphenyl boronates for diversified coupling.
Transformations on the oxazole ring
Directed metalation: Regioselective deprotonation at C5 with s-BuLi or LDA (often at −78 to −40 °C) enabling electrophile trapping (formylation, halogenation, acylation).
Electrophilic substitution at C4/C5 (under controlled conditions) and N-oxidation to oxazole N-oxides (then further rearrangements).
Ring-opening to β-aminocarbonyls under strong acidic/nucleophilic conditions (used sparingly due to loss of scaffold).
Applications
Late-stage diversification platforms, fluorescent/UV probes (aromatic chromophore), and heteroaryl cores in agrochemical/medchem intermediates. The meta-chloro position facilitates rapid library expansion without ortho/para directing complications.
Practical tips
Use dry, oxygen-free conditions for metal-catalyzed couplings. Pre-ligate Pd sources to mitigate coordination by the oxazole nitrogen. For lithiation, ensure rigorously anhydrous ethers and slow electrophile addition to maintain regioselectivity.
Reaction Conditions
General literature guidance for transformations involving 2-(3-chlorophenyl)oxazole; optimize per substrate and scale.
Suzuki–Miyaura coupling (Ar–Cl → Ar–C(sp2))
Catalyst: Pd2(dba)3 (1–2 mol% Pd) with XPhos/SPhos (3–5 mol%) or commercial precatalysts (e.g., XPhos Pd G3, 1–2 mol%).
Base: K3PO4, Cs2CO3, or Na2CO3 (2–3 equiv).
Solvent: 2-MeTHF/H2O, toluene/H2O, or dioxane/H2O.
Temperature: 70–100 °C; 2–12 h. Typical isolated yields: 70–95% for suitably matched partners (literature ranges).
Buchwald–Hartwig amination (Ar–Cl → Ar–NR2)
Catalyst/ligand: Pd-precatalyst with BrettPhos or RuPhos (1–3 mol% Pd; 2–6 mol% ligand).
Base: NaOtBu, KOtBu, or Cs2CO3 (2–3 equiv).
Solvent: Toluene, CPME, or dioxane.
Temperature: 80–110 °C; 4–16 h.
Borylation (Ar–Cl → Ar–Bpin)
Catalyst: Pd(dppf)Cl2 (1–3 mol%) or NiCl2(dppp) with B2pin2 (1.2–1.5 equiv).
Base: KOAc or Cs2CO3.
Solvent: DMSO, dioxane, or 2-MeTHF; 60–90 °C.
Directed metalation at oxazole C5
Base: s-BuLi or LDA (1.1–1.5 equiv) in dry THF/2-MeTHF at −78 to −40 °C under N2/Ar.
The oxazole nitrogen may coordinate to Pd/Ni; pre-ligated catalysts or excess ligand improves turnover.
Exclude moisture/air for base- and metal-catalyzed operations. Conduct small-scale screens (ligand/base/solvent) to finalize conditions.
Safety and Handling
Item-specific hazard/GHS
Signal word / H-statements / GHS classification / pictograms: Not specified for this item; refer to SDS.
General safety guidance (literature-based; not a substitute for SDS)
Likely hazards: Aromatic heterocycles and aryl chlorides commonly cause skin/eye irritation and may be harmful if inhaled or ingested. Avoid dust/vapor formation and prolonged exposure.
PPE: Use lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Employ fume hood to control vapors/aerosols.
Incompatibilities: Strong oxidizers (risk of oxidation); strong acids/bases may promote ring-opening or electrophilic reactions under forcing conditions. Avoid extended contact with reducing agents/metals in the presence of strong bases (potential for metalation).
Handling: Minimize exposure to light/air if long-term purity of heteroaromatics is critical; keep container tightly closed. Use inert gas blanket for sensitive synthetic operations.
First-aid overview: If on skin/eyes, rinse with water for several minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth. Seek medical attention as needed. Consult SDS for detailed procedures.
Fire safety: Combustible organic compound; use CO2, dry chemical, or foam. Thermal decomposition may release COx, NOx, and HCl-containing fumes.
Always consult the Aladdin SDS for authoritative hazard, exposure limits, and spill/fire response information.
Solvent Selection
This compound is a neutral, moderately hydrophobic aryl–oxazole bearing a meta-chloro substituent.
Polarity/miscibility (literature trends)
Poorly soluble in water; readily soluble in common organics (DCM, EtOAc, THF, MeCN, toluene, DMF, DMSO).
Dielectric environment: Reactions on the aryl chloride often benefit from polar aprotic solvents (DMF, DMAc, NMP, MeCN) or mixed systems; lithiation of the oxazole C5 typically uses ethers (THF, 2-MeTHF, CPME) at low temperature.
Selection by task
Purification: Normal-phase silica with hexanes/EtOAc or toluene/EtOAc gradients; reverse-phase MeCN/H2O (with formic acid or ammonium buffer) if needed for LC purification.
Cross-couplings on the aryl chloride: Toluene, dioxane, CPME, or Me-THF are robust; DMF/DMAc for challenging couplings with bulky ligands.
Metalation/functionalization of the oxazole ring: Anhydrous ethers (THF, TBME, CPME) under inert atmosphere are preferred.
Quick comparison (general)
THF vs 2-MeTHF: Similar coordinating ability; 2-MeTHF offers improved safety/greenness and broader temperature window.
Toluene vs dioxane: Toluene is less polar but greener; dioxane is more polar/boiling but has regulatory concerns.
Note: For spectroscopic work, CDCl3 or DMSO-d6 typically give well-resolved NMR spectra for aryl-oxazoles.
Storage and Reconstitution
Item-specific storage
Storage Conditions: Room temperature (per Product Data). Keep tightly closed in a dry, well-ventilated place.
General handling and stability (literature guidance)
Protect from prolonged exposure to light and moisture to preserve assay purity. If opening repeatedly, consider storing under inert gas, especially if material will be used for air/moisture-sensitive reactions (e.g., lithiation).
No reconstitution is required for neat solid/liquid. If preparing stock solutions, use dry, oxygen-free solvents (e.g., anhydrous THF, toluene, or MeCN) for synthetic work; for analytical or bioassay stocks, DMSO or MeCN are common.
Stock solutions
Prepare in clean, dry glassware; record concentration and solvent. For DMSO stocks, store in amber vials at 2–8 °C or −20 °C for longer term and avoid repeated freeze–thaw cycles by aliquoting.
Shipping
Shipped-in conditions: Not specified for this item; refer to CoA/Spec Sheet.
Always consult the product label/CoA/SDS for lot-specific storage guidance and stability data.
Structure and Identity
Brief description: 2-(3-Chlorophenyl)oxazole is a chlorinated aryl–heteroaryl scaffold combining a meta-chlorophenyl ring with an oxazole ring via a C–C bond at oxazole C2.
Item-specific identifiers (from Product Data)
CAS: 62882-06-8
PubChem CID: 12371742
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/structural information (for reference; not item-specific specifications)
Common name: 2-(3-chlorophenyl)oxazole; m-chlorophenyl-2-oxazole
One 1,3-azole ring (oxazole: five-membered ring containing adjacent O and N at positions 1 and 3)
A 3-chlorophenyl ring bonded at oxazole C2 (aryl–aryl biaryl-type linkage)
No stereocenters; fully aromatic system
2D description (words): A meta-chloro substituent on a benzene ring; the benzene carbon para to the chlorine is bonded to C2 of an oxazole ring. The oxazole ring has O at position 1, N at position 3, and carbons at 2, 4, 5.
Note: Exact identifiers (SMILES/InChI) and any registry synonyms should be verified on the product CoA/SDS for this specific lot.
Synthetic Utility
Orthogonal reactivity
Aryl chloride handle (meta to linkage): Amenable to Pd/Ni-catalyzed couplings (Suzuki, Buchwald–Hartwig, borylation), nucleophilic aromatic substitution under activating conditions, and radical halogen-abstraction strategies.
Oxazole core: Directs metalation (C5 > C4) enabling electrophile incorporation (formyl, acyl, halogen). Oxidation to N-oxide provides further diversification via rearrangements.
Retrosynthetic value
Disconnection at the biaryl bond suggests access by (i) cyclodehydration of α-acylamino ketones followed by arylation, or (ii) cross-coupling of 2-halooxazoles with 3-chlorophenyl boronates/stannanes. Alternatively, Chan–Lam coupling of oxazolyl boron species with aryl halides.
Protecting-group compatibility
The oxazole tolerates a range of bases and oxidants; avoid strong acids over prolonged times to prevent ring opening. Coordinate-binding to metals can inhibit catalysis—use ligand selection or additive strategies (e.g., excess phosphine, pre-activation of Pd) to mitigate.
Downstream diversification examples (literature)
Convert Ar–Cl to Ar–Bpin, then iterate Suzuki couplings for rapid SAR.
Buchwald–Hartwig amination to introduce anilines/carbamates.
Metalate C5, then quench with DMF (Vilsmeier-like) to give 5-formyl derivatives as versatile pivots (e.g., Wittig/Knöevenagel).
Target Specificity
Not applicable. This product is a small-molecule heteroaromatic building block and is not an antibody, enzyme, or biological probe with defined macromolecular targets. No antigen/epitope or species reactivity data apply.
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