This compound belongs to the class of organic compounds known as aminophenyl ethers. These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring.
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
180.200 g/mol
XLogP3
0.000
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
4
Exact Mass
180.09 Da
Monoisotopic Mass
180.09 Da
Topological Polar Surface Area
78.300 Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
173.000
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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Application Protocols
No tested biological application protocols (e.g., WB, IHC, IF, FC) are provided for this product. As a research chemical/building block, typical “protocols” relate to dissolution and handling:
Preparation of stock solutions (general):
Dissolve in anhydrous DMSO (e.g., 10–50 mM). Sonication or mild warming may help. Filter (0.22 μm PTFE) if needed for sterile applications.
For aqueous work, pre-dissolve in DMSO or MeOH before dilution into buffer to prevent precipitation; final organic ≤1–2% v/v is often acceptable in enzyme/cell-free assays.
Synthetic use examples (literature-type setups):
Aniline acylation: dissolve substrate in DCM, cool to 0 °C, add base (DIPEA), then dropwise add acyl chloride; stir to completion by TLC/LC–MS.
Urea formation: activate with CDI in THF, then add amine partner; quench and purify by silica chromatography.
These are general, non-validated examples. For any specific application, develop and validate conditions empirically. Always consult the SDS for safe handling.
Biological Roles
Item-specific biological roles: Not specified for this item; refer to primary literature if investigating target interactions.
General biochemical considerations (literature-based; not product-specific):
Functional group profile: The molecule presents two H-bond donors (amide NH2 and aniline NH2) and two acceptors (amide C=O and ether O), enabling diverse noncovalent interactions with proteins and nucleic acids.
Ionization: The aniline nitrogen is a weak base (conjugate acid pKa typically ~4.6–5.2). At physiological pH, the molecule is largely unprotonated, although microenvironmental effects in binding sites can stabilize the anilinium form.
ADME-relevant features: Modest molecular weight (~180 g/mol) and moderate polarity suggest potential for cell permeability in its neutral form; however, anilines can undergo metabolic oxidation (N-oxidation, ring hydroxylation) and conjugation (glucuronidation/sulfation of phenoxy-linked phenols if dealkylated in vivo).
Use in research: Such scaffolds are often employed in probe or fragment discovery efforts as amine-containing aryl ethers with tunable polarity and a built-in amide for solubility and H-bonding. The ortho relationship between aniline and phenoxy can influence intramolecular H-bonding and conformation, affecting binding geometries.
No clinical or therapeutic claims are made. For any bioassay use, confirm purity and counter-screen for aniline-associated assay interference (e.g., redox- or aggregation-related artifacts) as standard best practice.
Buffer Applications
This product is not a buffering agent and is not typically used to formulate biochemical buffers. It does not constitute a conjugate acid/base pair with an appropriate pKa near physiological ranges for buffering capacity.
Practical guidance:
For aqueous handling, dissolve first in a miscible organic co-solvent (e.g., DMSO or MeOH) before dilution into buffer, or prepare as an anilinium salt with a volatile acid to increase water solubility.
Select standard buffers (e.g., phosphate, HEPES, Tris) for pH control in assays involving this compound.
If a specific aqueous protocol is required, validate solubility and stability empirically at the target pH and ionic strength.
Green Alternatives
While the compound itself is a building block (not a solvent), greener choices can be made in its use, especially for aniline derivatizations and amide/urea formations.
Prefer ethyl acetate, 2-MeTHF, CPME, or MeOH/EtOH over DMF/DMAc/NMP where feasible.
For reactions requiring polarity, MeCN is a reasonable compromise compared with DMF; water/MeOH co-solvent systems can sometimes replace DMSO.
Coupling/activation strategies:
Use carbonyldiimidazole (CDI) or green peptide coupling reagents (e.g., DMTMM) instead of HATU/HBTU when compatible, to reduce hazardous waste.
Enzymatic acylations or aqueous micellar catalysis (e.g., TPGS-750-M) can enable milder, water-rich processes.
Workup and purification:
Minimize chlorinated solvents; when needed (e.g., DCM), consider substitution with EtOAc or toluene and employ closed-loop solvent recovery.
Apply crystallization or trituration in preference to extensive flash chromatography; if chromatography is needed, use heptane/EtOAc rather than hexane/DCM when possible.
Energy and safety:
Favor room-temperature or flow processes; avoid diazotizations unless necessary, and if performed, use in-flow to improve safety and reduce waste.
Comparison highlights (general):
DMF vs 2-MeTHF: similar solvating ability for many couplings; 2-MeTHF is biorenewable, lower toxicity, easier to remove, but less polar.
DCM vs EtOAc: EtOAc is less toxic and biodegradable; DCM offers higher volatility and sometimes superior chromatographic performance but with higher environmental impact.
Pharmaceutical Uses
Item-specific pharmacopeial/excipient status: Not specified for this item; refer to CoA/Spec Sheet. No therapeutic claims are made.
General formulation/manufacturing context (literature-based; not product-specific):
Role in discovery: 3-(2-Aminophenoxy)propanamide is best viewed as a medicinal chemistry building block for structure–activity relationship (SAR) exploration rather than as an excipient. The aniline enables straightforward derivatization (e.g., amide/urea/sulfonamide series), and the propanamide side chain moderates lipophilicity.
Salt screening: Formation of an anilinium salt with volatile acids (HCl, TFA) can transiently improve crystallinity and aqueous processability for screening or analytical standards. Reconvert to the free base as needed.
Analytical control: For release testing of research materials, typical methods include HPLC with UV detection (210–254 nm suitable for aromatic amides), orthogonal LC–MS, and NMR for structural confirmation.
Stability considerations: Anilines can slowly oxidize on prolonged air/light exposure; storing under inert atmosphere and limiting light can be beneficial for long-term stability in discovery workflows.
If GMP or clinical-grade material is required, separate sourcing and qualification would be necessary; this listing is for research use only (per Product Data).
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature-based expectations (general guidance, not product specifications):
Molecular weight: ~180.20 g/mol (computed from formula C9H12N2O2)
Physical state: Likely a solid at ambient temperature for a small aromatic amide; exact appearance Not specified for this item; refer to CoA/Spec Sheet.
Solubility (qualitative):
Polar aprotic organics (DMSO, DMF, NMP): high solubility expected due to multiple H-bond donors/acceptors.
Alcohols (MeOH, EtOH): moderate to good solubility expected.
Water: moderate solubility possible (amide and aniline), but may be limited by the hydrophobic aryl; salt formation on the aniline N (e.g., dilute HCl) can enhance aqueous solubility.
Nonpolar solvents (hexanes, toluene): low to moderate solubility expected.
Acid–base behavior (literature): aniline pKaH typically ~4.6–5.2 (conjugate acid), implying the free base is weakly basic; the amide is essentially neutral (non-basic) and weakly acidic (pKa of amide NH typically >15 in water).
Partitioning (qualitative): overall moderate polarity; cLogP likely in the 0.5–1.5 range for similar aryl ether amides (literature comparison; not measured for this item).
Thermal properties (literature expectations for small aromatic amides): melting points commonly in the 80–160 °C range; boiling point not typically defined due to decomposition; precise values Not specified for this item.
Always consult the actual CoA/SDS for definitive properties before process design.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Context for interpretation (general guidance):
Research grade: Typically suitable for synthetic chemistry, screening, and assay development. Purity is usually provided on the CoA by HPLC/GC/elemental analysis; low levels of residual solvents, water, and inorganic salts are disclosed when relevant.
Stabilizers/inhibitors: None specified for this listing. If present in other products (e.g., radical inhibitors), they are declared because they can influence reactivity/purification. For this item, no stabilizer is indicated in Product Data.
Documentation: Lot-specific CoA commonly reports identity (NMR/HRMS/IR), purity (e.g., HPLC area%), and sometimes residual solvents (GC) and water (KF). For chromatography-driven applications, an HPLC chromatogram and UV trace (if applicable) may be provided.
Fit-for-purpose notes: As a multifunctional building block (aniline + amide), trace amine-containing impurities or hydrolysis products could impact downstream coupling yields. Reviewing CoA impurity profile is recommended when using in SAR or bioconjugation workflows.
If you require a defined grade (e.g., ≥98% purity, LCMS-verified), please contact us for the current specification sheet or a tighter QC lot.
Reaction and Applications
As a bifunctional aryl ether bearing an aniline and a terminal primary amide, 3-(2-aminophenoxy)propanamide is a versatile building block for medicinal and materials chemistry.
Transformations on the aniline (Ar–NH2):
Acylation/sulfonylation to form anilides/sulfonamides (e.g., using acyl/sulfonyl chlorides, anhydrides, CDI). Useful for SAR libraries and polarity tuning.
Urea/carbamate formation with isocyanates or chloroformates. CDI/DPPA-based urea couplings are common.
Reductive amination after prior formylation/aldehyde introduction on the ring (via directed ortho-metalation of appropriately protected aniline, literature-dependent).
Diazotization (NaNO2/HCl, 0–5 °C) to access diazonium chemistry for azo coupling or Sandmeyer-type substitutions (requires careful control; safety considerations apply).
Transformations on the amide (–CONH2):
N-derivatization is limited (already primary amide); can be dehydrated to nitrile (SOCl2, POCl3) or hydrolyzed to the corresponding acid (basic or acidic conditions) for subsequent coupling to other amines/alcohols.
Activation to imidazolide or mixed anhydride after converting to the acid enables linker strategies.
Ether/side-chain chemistry:
O-dealkylation is generally harsh; instead, the phenoxy–propyl linker can be leveraged as a spacer in conjugates.
Application contexts:
Library synthesis: orthogonal functional handles allow late-stage diversification (aniline functionalization while leaving amide intact, or vice versa).
Probe/linker design: the propanamide offers H-bonding and polarity; the aniline enables conjugation to tags or reporters.
Note: The above are literature/practice-based strategies; select conditions based on specific substrate compatibility.
Reaction Conditions
General literature guidance for common transformations on this scaffold (not item-specific specifications):
Aniline acylation/sulfonylation:
Solvent: DCM, MeCN, THF, or 2-MeTHF
Base: NEt3 or DIPEA (1.5–2.5 equiv)
Temperature: 0 °C to rt; 1–4 h typical
Workup: aqueous quench with NaHCO3 or dilute acid depending on reagent; extract with EtOAc.
Urea formation (CDI-mediated):
Activate CDI (1.1–1.5 equiv) in THF/MeCN at rt, add second amine; 25–50 °C, 2–16 h; monitor by LC–MS.
Diazotization/azo coupling (for derivatization):
Generate diazonium salt at 0–5 °C with NaNO2 in 2–4 M HCl (aqueous/EtOH); immediately consume with coupling partner (e.g., phenol) under basic conditions. Safety note: handle small scale; avoid isolating dry diazonium salts.
Amide hydrolysis to acid:
Basic: 2–4 M NaOH, 80–100 °C, 2–12 h; then acidify to pH ~2 to precipitate acid.
Acidic: 6 M HCl, reflux 4–16 h; neutralize and isolate.
Dehydration to nitrile:
Reagents: SOCl2 (3–5 equiv) or POCl3 with catalytic DMF; solvent: DCM or toluene; 0 °C to reflux; monitor for overreaction.
Stock solutions for assays:
DMSO stocks at 10–50 mM; store aliquots to avoid freeze–thaw; dilute into buffer to ≤1–2% DMSO.
Yields and exact times vary with substituents and scale; use TLC/LC–MS for real-time monitoring and adjust stoichiometry accordingly.
Safety and Handling
GHS/CLP classification and pictograms: Not specified for this item; refer to SDS.
Signal word and H-statements: Not specified for this item; refer to SDS.
General safety guidance for aromatic amide/aniline-containing compounds (literature-based; not product-specific):
Potential hazards: May cause skin/eye irritation and respiratory irritation; aniline derivatives can be harmful if inhaled/ingested and may cause methemoglobinemia in severe exposures—exercise caution and avoid inhalation/ingestion.
PPE: Lab coat, nitrile gloves, safety goggles; handle powders in a fume hood to avoid dust exposure.
Handling: Avoid dust generation; prevent contact with oxidizers and strong acids/bases that could lead to decomposition or salt formation (with acids). Use clean, dry tools to minimize contamination.
Incompatibilities (general): Strong oxidizing agents; nitrosating conditions (for anilines) can form diazonium species—avoid unintended nitrosation.
First aid (summary; consult SDS for details):
Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation persists.
Inhalation: Move to fresh air; monitor for symptoms; seek medical attention if unwell.
Ingestion: Rinse mouth; do not induce vomiting; obtain medical attention.
Spill/leak: Avoid dust; collect mechanically; dispose per local regulations.
Fire safety: Use CO2, dry chemical, or foam; combustion may produce CO/CO2 and nitrogen oxides.
Always defer to the product-specific SDS for authoritative hazard classification, exposure controls, and emergency procedures.
Solvent Selection
This compound is a moderately polar, multifunctional small molecule (primary amide + aniline + aryl ether). Solvent choice should balance solubility, stability, and downstream processing.
Likely good solvents (literature-based):
DMSO, DMF, NMP: excellent solubility for stock solutions and coupling reactions; high boiling points aid homogeneous reactions but complicate removal.
Alcohols (MeOH, EtOH, i-PrOH): moderate to good solubility; convenient for crystallization/anti-solvent workups.
Acetonitrile and ethyl acetate: moderate solubility; useful in LC-MS analysis and extractions, respectively.
Water: limited neutral solubility; aqueous solubility can be increased by forming the anilinium salt (e.g., dilute HCl) or using co-solvents.
For biological assays, prepare concentrated DMSO stocks (e.g., 10–50 mM) and dilute into buffer with ≤1–2% final DMSO to minimize precipitation.
For synthetic transformations on the aniline, polar aprotic media (DMF, DMAc, DCM with base, or MeCN) are common. For greener choices, consider 2-MeTHF or EtOAc when reaction compatibility allows.
During purification, normal-phase silica with EtOAc/hexanes or DCM/MeOH gradients often works; basic modifiers (0.1–1% NEt3) can prevent streaking of anilines.
Dielectric constant reference (solvents, literature): DMSO ~47, DMF ~37, MeCN ~36, EtOAc ~6, 2-MeTHF ~7; use to tune polarity in method development.
Storage and Reconstitution
Item-specific storage (from Product Data): Store at room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature/practice-based; not product-specific):
Protect from prolonged exposure to air and light to minimize potential aniline oxidation. For long-term storage, consider an amber, tightly sealed container; optional inert gas backfill (N2/Ar) is beneficial.
Avoid moisture ingress; while the compound is not highly hygroscopic, maintaining dryness aids reproducible weighing and purity over time.
Reconstitution:
Prepare concentrated stock solutions in anhydrous DMSO (e.g., 10–50 mM) or DMF. Record exact concentration by weight-in/volume or by UV if a calibrated method is available.
For aqueous use, consider forming a transient anilinium salt with a volatile acid (e.g., HCl in dioxane) or use co-solvents to enhance solubility.
Freeze–thaw: If storing solutions, aliquot to avoid repeated freeze–thaw. DMSO stocks are typically stable at −20 °C for months when protected from moisture and light.
Shelf life: Not specified for this item; monitor by HPLC/LC–MS periodically if used in sensitive applications.
Research Use Note (from Product Data): For research use only.
Structure and Identity
Brief description: 3-(2-Aminophenoxy)propanamide is an anilide-containing aryl ether bearing a terminal primary amide. It combines a 2-aminophenyl ring (aniline) with a propanamide chain via a phenoxy (aryl–O–alkyl) linkage.
Item-specific identifiers (from Product Data):
CAS: 1094235-02-5
SKU: A942956
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product data lists "28072", which is not a standard InChIKey format.)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature structural information (not item-specific):
Molecular formula (computed from IUPAC name): C9H12N2O2
Ring system: single benzene ring with ortho substitution (2-amino vs. O–alkyl)
H-bonding: 2 donors (amide NH2, aniline NH2), 2 acceptors (amide C=O, ether O); aniline N is a weak base
No stereocenters; achiral
2D description (verbal): A benzene ring bearing adjacent substituents: an –NH2 at the ortho position and –O–(CH2)2–CONH2 as the second substituent. The alkyl side chain length is three atoms from the amide carbonyl carbon to the aryl oxygen (C(=O)–CH2–CH2–O–Ar).
Category path (from Product Data): 全部 / 可售 / 生命科学
Intended use (from Product Data): For research use only.
Synthetic Utility
Key reactivity handles:
Aniline (Ar–NH2): readily acylated, sulfonylated, or transformed into ureas/carbamates. Can be diazotized for subsequent substitutions or azo coupling (exercise appropriate safety controls).
Primary amide (–CONH2): can be hydrolyzed to the corresponding acid for further coupling, dehydrated to a nitrile, or engaged in condensation reactions (e.g., to imidates under strongly acidic alcoholysis conditions).
Aryl ether (Ar–O–(CH2)2–CONH2): generally robust under many conditions, providing a conformationally defined, polar spacer for conjugation.
Retrosynthetic/value propositions:
Serves as a convergent junction between an aniline-bearing aryl fragment and a polarity-imparting propanamide tail—useful for tuning solubility and H-bonding profile in lead optimization.
Orthogonal chemistry: aniline functionalization can proceed under conditions that leave the primary amide intact; alternatively, amide-to-acid hydrolysis enables coupling on the side chain while preserving the aryl aniline.
Representative transformations (literature):
Formation of anilides: acyl chlorides or activated esters in presence of base (e.g., NEt3, DIPEA) in DCM/MeCN.
Urea synthesis: reaction with isocyanates or via CDI-mediated coupling to another amine.
Amide hydrolysis: aq. NaOH or HCl (reflux) to access 3-(2-aminophenoxy)propanoic acid, then EDCI/HOBt or DMTMM couplings.
Dehydration to nitrile: POCl3 or SOCl2 (careful temperature control) to yield the corresponding 3-(2-aminophenoxy)propanenitrile.
These are general synthetic options; optimize based on substrate sensitivity and desired selectivity.
Target Specificity
Not applicable to this product. This is a small-molecule building block, not a biological targeting reagent (e.g., antibody, ligand-validated probe). No target, epitope, species reactivity, clone, or isotype information is provided in the Product Data.
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