This compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether 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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
219.660 g/mol
XLogP3
3.100
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
219.045 Da
Monoisotopic Mass
219.045 Da
Topological Polar Surface Area
35.300 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
200.000
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
Calculadoras de soluciones
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Application Protocols
Not applicable. No tested bioassay protocols (WB, IHC, IF, FC) or antibody-related applications apply to this small-molecule building block.
For synthetic/analytical use (general):
Prepare stock solutions in DMSO, DMF, or CHCl3 at suitable concentrations (e.g., 10–100 mM) depending on solubility.
Analyze by TLC (UV-active), GC–MS or LC–MS; confirm identity with 1H/13C NMR. Specific method parameters should be developed empirically for your instrumentation.
Refer to the SDS and CoA for any handling and characterization specifics.
Biological Roles
This product is a synthetic, halogenated diphenyl ether bearing an aniline function and does not have an established role in primary metabolism.
General remarks (literature/general):
Aromatic amines can interact with biological macromolecules after metabolic activation (e.g., N-oxidation, N-acetylation), but effects are highly structure- and context-dependent. No specific biochemical role is attributed to 2-(2-chlorophenoxy)aniline.
The compound’s physicochemical profile (aromatic, moderately lipophilic, H-bond donor/acceptor) suggests membrane affinity and potential for protein binding in vitro; this can be relevant when designing biochemical assays (nonspecific binding, solubility limits).
Use context:
Suitable as a chemical building block or reference material in discovery chemistry or mechanistic studies, but not intended for biological administration. All uses are for research/lab applications only.
No organism-specific pathways, receptor interactions, or endogenous functions are established for this substance in the literature; experiments should be designed with appropriate containment and controls.
Buffer Applications
This compound is a neutral/weakly basic, poorly water-soluble aromatic amine and is not typically used to prepare aqueous laboratory buffers.
Practical guidance:
For aqueous work, dissolve first in a water-miscible co-solvent (e.g., DMSO, DMF, ethanol) and then dilute into buffer if needed for assay; watch for precipitation above low millimolar concentrations.
If a protonated form is desired for solubility, prepare anilinium salts by titrating with HCl or other mineral acids in alcoholic solvents; characterize and verify counterion content.
For standard biological or analytical buffers (phosphate, Tris, HEPES), use dedicated buffering agents; this compound serves better as a substrate/ligand than as a buffer component.
Green Alternatives
Solvent choices (literature/general):
Prefer greener solvents for transformations and processing:
Replace DCM/chloroform with ethyl acetate, 2-MeTHF, CPME, or toluene where feasible.
Use water or aqueous ethanol for washings and workups; minimize halogenated waste.
For Pd-catalyzed couplings on the aryl chloride:
Consider bio-derived 2-MeTHF or CPME instead of dioxane/THF; they enable higher temperatures and easier separations.
Comparison (general):
THF vs 2-MeTHF: Similar polarity and reactivity; 2-MeTHF has lower peroxide tendency and better sustainability profile, but may contain more nonpolar impurities and has odor considerations.
DMF/DMAc vs Cyrene/NMP alternatives: Emerging dipolar aprotics (e.g., Cyrene, propylene carbonate) can sometimes substitute; check catalyst/solubility compatibility.
Bases: Replace inorganic bases that generate heavy salt loads (e.g., Cs2CO3) with K3PO4 or organic superbases when compatible to reduce waste cost and toxicity.
Process intensification:
Employ flow chemistry for hazardous steps (diazotization) to reduce inventory of energetic intermediates.
Use catalytic, atom-economical couplings (Suzuki/Buchwald) rather than multi-step halogen–lithium exchange when possible.
Note: The molecule itself is a halogenated aromatic; end-of-life and EHS considerations should prioritize minimal release, closed systems, and proper incineration of waste streams.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or formulation grade is specified for this item; it is provided for research use only.
From Product Data:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Research Use Note: For research use only.
General formulation context (literature/general):
As a small aromatic amine, it could serve as an intermediate in the synthesis of active pharmaceutical ingredient (API) candidates or reference materials in medicinal chemistry workflows.
If used in pre-formulation research, its limited aqueous solubility may necessitate co-solvents, cyclodextrins, or salt formation; such activities remain strictly non-clinical and for lab-scale investigation.
No therapeutic claims or clinical applications are made or implied.
Physical Properties
From Product Data (item-specific):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (general reference; not item-specific specifications):
Expected physical state: aromatic organics of this size are typically low-melting solids or high-boiling oils (literature/general trend).
Solubility profile (qualitative):
Water: very low solubility expected for chlorinated diphenyl ethers with an aniline function.
Organic: soluble in common organic solvents (e.g., DCM, chloroform, toluene, THF, ethyl acetate, acetone, DMF, DMSO) — literature/general behavior.
Polarity/logP (qualitative): moderately lipophilic due to two aryl rings and a chloro substituent, with some hydrogen-bonding capacity from –NH2 and ether O (literature expectation).
UV characteristics: conjugated aromatic chromophores absorb in the UV (typically 200–300 nm); specific cutoffs/ε not determined here (literature/general).
Note: Definitive values for melting point, boiling point, density, refractive index, pKa, logP, and UV data are Not specified for this item; refer to CoA/Spec Sheet or measure under your laboratory conditions.
Quality and Grades
From Product Data (item-specific):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance (general):
In the absence of a stated grade, users should verify suitability via the Certificate of Analysis (CoA): identity confirmation (NMR/GC–MS/LC–MS), purity assay (GC/HPLC), and residual solvents/metals if application-sensitive.
For sensitive synthetic applications (e.g., cross-coupling, polymerization), pay attention to trace impurities such as phenols (from ether cleavage), aniline homologs, and halogenated byproducts. If UV transparency is important (analytical work), confirm UV cutoffs/absorbance (Not specified for this item; refer to CoA/Spec Sheet).
Stabilizers: None stated. If long-term storage is planned, consider storing under inert gas and/or with desiccant to minimize oxidative discoloration typical of anilines.
Practical tip: If performing moisture- or air-sensitive transformations (e.g., metalation at the aryl chloride), consider pre-drying the solid (if solid) in vacuo at ambient to mild temperature and validate water content by Karl Fischer as needed (water specification: Not specified for this item; refer to CoA/Spec Sheet).
Aryl chloride (on 2-chlorophenyl moiety): electrophilic handle for cross-coupling or SNAr (the ether oxygen mildly activates the ring toward SNAr ortho/para to O, though aryl chlorides typically require strong activation or catalysis).
Ether linkage: generally inert; can direct reactivity and modulate electronics.
Representative applications (literature/general):
Buchwald–Hartwig amination: Replacement of the aryl chloride with amines using Pd catalysts (e.g., XPhos/Pd2(dba)3 or BrettPhos-based systems) to build triarylamines or diaryl ether–arylamines.
Suzuki–Miyaura coupling: Conversion of the aryl chloride to aryl–aryl bonds with boronic acids under Pd catalysis and strong base (e.g., K3PO4, Cs2CO3) at 80–110 C.
N-Acylations/sulfonylations: Rapid formation of amides/sulfonamides under standard Schotten–Baumann or carbodiimide coupling conditions; useful for protecting group strategies or library synthesis.
Diazotization/azo coupling: Formation of diazonium salts from the aniline (NaNO2/HCl, 0–5 C), followed by coupling with activated aromatics for azo dyes/pigments (handle with care).
Directed electrophilic substitution: The –NH2 activates its ring; with o-position occupied by O, para substitution is favored (nitration, halogenation), enabling regioselective elaboration.
Practical tips:
Protect the aniline (e.g., as acetamide, Boc) when performing cross-couplings at the aryl chloride to avoid catalyst poisoning.
Degas solvents and use dry conditions for organometallic steps. Monitor via TLC/LC–MS; the product’s aromatic UV absorbance facilitates detection.
Note: Manufacturer-specific application notes were not provided beyond “For research use only.”
Reaction Conditions
The following are literature/general conditions for common transformations of 2-(2-chlorophenoxy)aniline or closely related substrates. Optimize for your system.
N-Acylation (amide formation):
Solvent: DCM, THF, or acetonitrile.
Reagents: Acid chloride (1.1–1.5 eq) with Et3N (2 eq) or pyridine; or EDCI/HOBt with carboxylic acid (DMF/DCM).
Temperature/time: 0–25 C, 0.5–4 h. Typical isolated yields: 80–95% (literature for anilines).
N-Sulfonylation (sulfonamide):
Solvent: DCM or acetonitrile; base: Et3N or NaHCO3.
Reagents: Sulfonyl chloride (1.1 eq).
Temperature/time: 0–25 C, 1–3 h. Yields: 80–95% (literature for anilines).
Buchwald–Hartwig amination at aryl–Cl (distal ring):
Catalyst: Pd2(dba)3 (1–2 mol%) with XPhos/BrettPhos (2–4 mol%) or preformed Pd-precatalyst.
Base: NaOtBu or Cs2CO3 (2–3 eq).
Solvent: Toluene, dioxane, or CPME.
Temperature/time: 90–110 C, 6–16 h. Yields: 60–90% depending on partner and ligand (literature for aryl chlorides adjacent to ether).
Suzuki–Miyaura coupling at aryl–Cl:
Catalyst: Pd(PPh3)4 (2–5 mol%) or Pd-PEPPSI; ligand tuning often required.
Base: K3PO4 or Cs2CO3 (2–3 eq).
Solvent: Dioxane/H2O (10:1) or toluene/EtOH/H2O.
Temperature/time: 80–105 C, 6–18 h. Yields: 55–85% (literature for comparable substrates).
Diazotization/azo coupling (from –NH2):
Conditions: NaNO2 (1.1 eq) in HCl (2–3 M), 0–5 C; couple with activated aromatics at 0–10 C.
Caution: Diazotization generates energetic intermediates—use small scale or flow.
These are general guidance values from literature; verify with small-scale screening for your specific reagents and equipment.
Safety and Handling
From Product Data (item-specific):
GHS Classification: Not specified for this item; refer to SDS.
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety guidance for aromatic amines and chlorinated diphenyl ethers (literature/general):
Hazards: Aromatic amines can be harmful by inhalation, ingestion, or skin absorption; may cause skin/eye irritation and can affect blood (methemoglobinemia) after significant exposure. Handle as a potential toxicant.
PPE: Wear lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of vapors/dust.
Handling: Avoid dust generation; prevent contact with skin/eyes. Do not breathe dust or vapor. Keep away from heat/ignition sources.
Incompatibilities: Strong oxidizers (risk of exotherm/oxidation), strong acids (possible salt formation with aniline; exotherm on neutralization), acylating/sulfonylating agents (react readily with –NH2). Avoid prolonged exposure to light/air if purity is critical.
First aid (overview; refer to SDS for details): Move to fresh air if inhaled; flush eyes/skin with water for ≥15 min upon contact; remove contaminated clothing; seek medical attention if symptoms persist.
Spills: Absorb with inert material (vermiculite, sand), collect for disposal. Prevent entry into drains.
Waste: Dispose according to local regulations for halogenated organic/amine-containing waste.
Always consult the SDS for authoritative hazard classification and response measures.
Solvent Selection
This compound is a moderately lipophilic, bifunctional aromatic amine/diphenyl ether.
Polarity and miscibility (literature/general):
Expected to be sparingly soluble in water, but readily soluble in medium- to high-polarity organic solvents (DCM, chloroform, ethyl acetate, acetone, acetonitrile, THF) and in polar aprotics (DMF, DMSO, NMP). Good solubility in aromatic solvents (toluene, xylene).
For analytical solutions: DMSO or acetonitrile for LC; THF or DCM for GC (check thermal stability).
Choosing solvents by task:
N-acylation/sulfonylation: DCM, THF, or acetonitrile with base (e.g., Et3N) provide good rates and solubility.
Pd-catalyzed coupling at the aryl chloride: Toluene, dioxane, or CPME with strong bases (e.g., Cs2CO3, tBuONa) are commonly used; DMF/DMAc for higher polarity.
Metal–halogen exchange on the 2-chlorophenyl ring: Ethers (THF, 2-MeTHF) at low temperature.
Salt formation (for purification): Alcohols/ethers can assist precipitation of anilinium salts formed with HCl/H2SO4.
Small comparison (literature/general):
THF vs 2-MeTHF: 2-MeTHF offers improved sustainability and water tolerance; both dissolve this substrate well.
DCM vs EtOAc: DCM increases solubility and rate in acylations; EtOAc is greener but may require longer times.
Note: Specific solubility numbers and UV cutoffs are Not specified for this item; refer to CoA/Spec Sheet or determine experimentally.
Storage and Reconstitution
From Product Data (item-specific):
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature/practice for aromatic amines):
Store in a tightly closed container under dry, ambient conditions, protected from light to minimize oxidative discoloration common to anilines.
If long-term storage is planned, consider inert gas overlay (N2/Ar) and inclusion of a desiccant. Avoid prolonged exposure to air and moisture.
Do not store near strong oxidizers or acids.
Reconstitution/preparation of solutions:
For stock solutions, dissolve in dry organic solvents (e.g., DMSO, DMF, THF, CH2Cl2, toluene) to the desired concentration. Filter if particulates are present.
For aqueous assays, dissolve first in a miscible co-solvent (DMSO/DMF/EtOH), then dilute into buffer with vigorous mixing; monitor for precipitation.
Stability of solutions is substrate- and solvent-dependent; prepare fresh as needed or store aliquots at 2–8 C or −20 C (light-protected) if solution stability is verified empirically.
All information above is non-binding guidance. For definitive item-specific instructions, consult the CoA/Spec Sheet and SDS.
Structure and Identity
Short description: 2-(2-Chlorophenoxy)aniline is a bifunctional diphenyl ether bearing an aniline (–NH2) on one ring and a chloro substituent on the other ring, positioned ortho to the ether linkage.
From Product Data:
SKU: C1068805
Product Name: 2-(2-Chlorophenoxy)aniline
CAS: 56966-47-3
CID: 12569012
InChIKey: 188142 (as provided; note: this appears non-standard/shortened)
Storage Conditions: Room temperature
Research Use Note: For research use only
Literature/computed (general reference values; not item-specific specifications):
Molecular formula (calculated from structure): C12H10ClNO
Structural features: Two aromatic rings connected by an ether (Ar–O–Ar); one ring bears an aniline –NH2 at the 2-position relative to the ether, and the other ring bears Cl at the 2-position relative to the ether. No stereocenters; planar aromatic system with an intramolecular H-bond donor (NH2) and an ether acceptor.
2D description in words: A 2-aminophenyl ring linked through oxygen to a 2-chlorophenyl ring (o,o′-substituted diphenyl ether).
Synthetic Utility
Functional group leverage:
–NH2 (aniline):
Protect as acyl (Ac), sulfonyl (Ts, Ms), Boc, or Cbz to modulate electronics during metal-catalyzed couplings.
Transform to amides, ureas, sulfonamides, isocyanates (via phosgene equivalents), and azo compounds (via diazotization/coupling).
Aryl–Cl (on the 2-chlorophenyl ether):
Cross-coupling handle (Suzuki, Buchwald–Hartwig, Negishi, Kumada) to diversify the distal ring.
Under forcing conditions, can undergo lithium–halogen exchange enabling further electrophile trapping (–CHO, –CO2Et, etc.).
Strategic roles (literature/general):
Scaffold for o,o′-disubstituted diphenyl ethers, allowing orthogonal functionalization on each ring: the aniline ring is activated (para-selective), while the chloro-bearing ring is primed for Pd-catalyzed diversification.
Intramolecular H-bonding between NH2 and ether O can influence conformation and reactivity; consider when predicting EAS/C–H activation outcomes.
Retrosynthetic value:
Can converge from 2-fluoro- or 2-chloroanisole analogs via nucleophilic substitution with 2-aminophenol derivatives, or via Ullmann/Golberg C–O coupling followed by selective halogenation.
Purification notes:
Products and intermediates often purify well by silica chromatography using hexanes/EtOAc or toluene/EtOAc gradients; the aniline can streak—form transient salts (e.g., with 1% TEA) or protect to improve band shape.
Target Specificity
Not applicable. This product is a small organic molecule, not a biological macromolecule or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.
Preguntas frecuentes
How should this product be stored?
Store at room temperature.
What is the purity of this product?
This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 56966-47-3, the molecular formula is C12H10ClNO, and the molecular weight is 219.67 g/mol. InChIKey KSDCPEXSRBLIRA-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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