This compound belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.
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
191.230 g/mol
XLogP3
2.300
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
4
Exact Mass
191.095 Da
Monoisotopic Mass
191.095 Da
Topological Polar Surface Area
52.300 Ų
Heavy Atom Count
14
Formal Charge
0
Complexity
213.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
1
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
1
Covalently-Bonded Unit Count
1
Calcolatori di soluzioni
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Recensioni
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Application Protocols
No application protocols are specified for this item in the Product Data. As a small-molecule building block, it is typically used in synthetic procedures rather than standardized bioassays.
General handling protocol (research use):
Inspect material for homogeneity; if solid, grind gently to free-flowing powder; if oil, ensure complete dissolution before use.
Prepare stock solutions in dry organic solvents (e.g., DCM, THF, MeCN, EtOAc, DMSO) appropriate to the intended reaction.
For aqueous assay introduction, first dissolve in DMSO or ethanol, then dilute into buffer with vigorous mixing to avoid precipitation.
Monitor reactions by TLC/LC–MS; confirm identity/purity by NMR and MS before downstream use.
For any numerical specifications or validated analytical methods, refer to the item-specific CoA/Spec Sheet.
Biological Roles
No specific biological roles are assigned to this catalog item in the Product Data. It is supplied for research use only.
General context (literature; not item-specific claims):
Cinnamate scaffolds are common motifs in natural products and UV-absorbing compounds; the conjugated aryl–alkenyl–ester system imparts characteristic UV absorption.
Aniline substituents modulate electron density and can influence binding interactions in biochemical screening campaigns; thus, anilide/cinnamate derivatives are often explored as fragments or intermediates in discovery chemistry.
The molecule is not a known endogenous metabolite, and no canonical metabolic pathway assignment is implied. In biological matrices, esters can undergo hydrolysis by esterases (general principle), and anilines may undergo phase I (N-oxidation) and phase II (conjugation) metabolism in vivo; these are generalized expectations and not specific to this product.
Practical notes for bioassays:
Solubilize first in DMSO or ethanol to prepare stock solutions; dilute into assay buffers ensuring final cosolvent levels are compatible with the system.
Consider protonation of the aniline to improve aqueous handling if needed; however, protonation will alter lipophilicity and potentially assay outcomes.
All uses must remain within non-clinical, laboratory research settings.
Buffer Applications
This product is not a buffering agent and is not typically used to formulate biological buffers.
Practical handling in buffered systems (general guidance):
If introducing into aqueous buffers for assays, prepare concentrated stocks in a miscible organic cosolvent (e.g., DMSO, ethanol) and add slowly with mixing to avoid precipitation.
Adjust pH carefully if forming the anilinium salt to increase aqueous solubility; avoid conditions that hydrolyze the ester (strong base or strong acid, prolonged exposure).
For buffer recipes and pH control, select established buffer systems (PBS, HEPES, MOPS) appropriate to your application; this product does not substitute for those reagents.
Green Alternatives
While Ethyl 3-(3-aminophenyl)acrylate is a substrate rather than a solvent, greener choices can be made for media and reagents used with it.
Greener solvent options (literature guidance):
Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, 2-MeTHF, CPME, or toluene where feasible.
Favor bio-based alcohols (EtOH, iPrOH) for reductions/hydrogenations.
Use water or aqueous micellar media for some conjugate additions or acylations when compatible (surfactant-enabled catalysis).
Comparison highlights (general):
2-MeTHF vs THF: similar polarity; 2-MeTHF is partially bio-based, has higher boiling point and lower peroxide formation tendency; may improve phase separation.
CPME vs toluene/DCM: broad solvency, low peroxide formation, and easy drying; can support many organometallic and catalytic steps.
EtOAc vs DCM: comparable solvation for esters with significantly reduced toxicity and environmental burden.
Reagent choices:
Prefer catalytic over stoichiometric methods (e.g., organocatalytic Michael additions; catalytic hydrogenation with reusable catalysts).
Use benign bases (K2CO3, DBU) and avoid heavy-metal oxidants when possible.
Waste and safety:
Minimize amine-containing waste by in situ protection/deprotection strategies to enhance selectivity and yield.
Implement solvent recovery and distillation, particularly for EtOAc and 2-MeTHF which recycle efficiently.
Adopt solvent selection guides (e.g., GSK/ACS) to align with sustainability without compromising reaction performance.
Pharmaceutical Uses
No pharmacopeial grade or excipient designation is provided in the Product Data for this item.
General context (non-clinical; literature):
Ethyl 3-(3-aminophenyl)acrylate may serve as a synthetic intermediate in medicinal chemistry programs to access cinnamamide/cinnamate derivatives, enabling SAR exploration around an aniline-substituted cinnamate core.
The conjugated ester allows late-stage diversification (e.g., amidation after hydrolysis), while the aniline can be derivatized (acylation, sulfonylation) to tune physicochemical properties during lead optimization.
Formulation considerations for research materials:
For in vitro use, prepare DMSO or ethanol stock solutions; filter if necessary through 0.22 µm PTFE to remove particulates.
No official pharmacopeial monograph or excipient status is implied. This product is not intended for human or veterinary use.
Refer to the CoA/Spec Sheet for purity and impurity profiles if using the material to prepare reference standards or screening samples.
Physical Properties
Item-specific physicochemical constants have not been provided for this catalog entry.
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/general expectations for this structural class (for context; not item specifications):
Phase: many aryl cinnamate esters with an aniline substituent are oils or low-melting solids, depending on substitution pattern.
UV/Vis: conjugated cinnamate chromophores typically show π→π* absorption in the near-UV (roughly 260–330 nm), intensity modulated by ring substituents.
Solubility profile: expected to be sparingly soluble in water in neutral form; freely soluble in common organic solvents (EtOAc, DCM, THF, toluene, MeOH). Protonation of the aniline with acids can increase aqueous solubility as the corresponding ammonium salt.
Acid–base: aniline nitrogen is weakly basic (typical aniline pKaH ~4.5–5.5, literature); the acrylate is not acidic but is an activated Michael acceptor.
For authoritative values (bp, mp, density, refractive index, purity, UV cutoff, water or metal content), please consult the item’s CoA/Spec Sheet. Aladdin will not infer specifications beyond the provided Product Data.
Quality and Grades
From Product Data (item-specific):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades for this compound class (general information):
Research/technical grade: suitable for synthesis and method development where ultra-low impurities are not critical.
High-purity/synthetic grade: preferred for sensitive transformations (e.g., asymmetric catalysis, photochemistry) where trace acids, peroxides, or metals could interfere. For Michael additions and cross-coupling sequences involving pre-functionalization, lower residual water and amines can be advantageous.
HPLC grade solvents vs reagents: While this product is a reagent, purification and analysis in HPLC may require low UV-absorbing solvents; reagent’s own UV chromophore (cinnamate) will strongly absorb in the UV, so mobile phase baselines should be adjusted accordingly.
What to check on the CoA for this item:
Identity confirmation (NMR, HRMS, or GC/LC purity).
Purity assay and residual solvent profile.
If applicable, E/Z ratio of the acrylate double bond.
Water content (Karl Fischer) and assay of free amine functionality.
Interpret all numeric specifications from the CoA/Spec Sheet; values are not provided in the Product Data.
Reaction and Applications
As an aniline-bearing cinnamate ester, Ethyl 3-(3-aminophenyl)acrylate is a versatile building block that combines an electrophilic Michael acceptor with a nucleophilic/aromatic aniline handle.
Transformations at the acrylate motif:
Conjugate (Michael) additions of soft nucleophiles (thiols, malonates, 1,3-dicarbonyls, amines) to the β-carbon; organocatalytic enamine or phase-transfer approaches are common (literature).
Hydrogenation: selective reduction of C=C (to saturated ethyl 3-(3-aminophenyl)propanoate) via Pd/C or Rh catalysts; full hydrogenolysis to alcohols after ester reduction under stronger conditions.
Hydrolysis/transesterification: base- or acid-catalyzed conversion to the corresponding acid or different esters.
Transformations at the aniline:
Acylation/sulfonylation to modulate electronics and directivity for downstream reactions.
Diazotization (if desired) to access diverse functionalizations via Sandmeyer-type processes after prior conversion to an anilinium salt.
Electrophilic aromatic substitution (nitration, halogenation), typically ortho/para-directing relative to –NH2; note the meta relationship to the side chain affects regiochemical outcomes (literature).
Cross-coupling strategies:
Although not pre-halogenated, the ring can be halogenated (e.g., bromination) and then subjected to Suzuki–Miyaura, Buchwald–Hartwig (after protection), or Heck couplings to elaborate the aryl moiety.
Applications (general):
Useful intermediate for UV-absorbing materials, fragment libraries in medicinal chemistry, and synthesis of cinnamamide/cinnamate analogs.
Maintain inert atmosphere and control temperature to suppress polymerization/isomerization of the activated alkene during base-catalyzed steps.
Reaction Conditions
No item-specific, validated reaction conditions are provided in the Product Data. Below are general literature-style guidelines for common transformations of an aniline-substituted cinnamate ester; adapt and verify experimentally.
Conjugate (Michael) addition:
Typical solvents: MeCN, THF, toluene, EtOH, or DMF.
Bases/catalysts: tertiary amines (Et3N, DABCO), DBU, or chiral organocatalysts for enantioselective variants.
Temperature: 0–25 °C for sensitive nucleophiles; 25–60 °C for less reactive partners.
Atmosphere: inert (N2/Ar) to limit oxidation/polymerization.
Hydrogenation of C=C:
Catalyst: Pd/C (5–10 wt%).
Solvent: EtOH, iPrOH, or EtOAc.
Conditions: 1–5 bar H2, 20–40 °C, 2–12 h (literature ranges). Protect –NH2 if over-reduction/acylation is a concern.
Ester reduction (to alcohol/aldehyde):
DIBAL-H in toluene or CH2Cl2 at −78 to 0 °C for partial reduction to aldehyde; LiAlH4 in THF for full reduction to primary alcohol.
Hydrolysis/transesterification:
Base hydrolysis: K2CO3 or NaOH in MeOH/H2O, 0–25 °C; acid hydrolysis requires stronger conditions.
Transesterification: catalytic acid (p-TsOH) or base (NaOMe) in corresponding alcohol; remove alcohol or water to drive equilibrium.
Aniline derivatization:
Acylation: acyl chloride/anhydride with base (pyridine, Et3N) in DCM or THF at 0–25 °C.
These are schematic ranges from literature; optimize per substrate and scale, and confirm by analytical monitoring (TLC, LC/MS, NMR).
Safety and Handling
From Product Data (item-specific):
GHS classification: Not specified for this item; refer to SDS.
Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
Storage conditions: Room temperature.
General safety considerations for aryl acrylate anilines (literature/good practice; not a substitute for SDS):
Hazards: Acrylate double bonds can act as electrophiles (sensitization potential is known for some acrylates). Anilines may cause irritation and are harmful if swallowed or inhaled in many cases. Avoid skin contact and inhalation of vapors/aerosols.
PPE: Use chemical-resistant gloves (e.g., nitrile), lab coat, and eye protection. Handle in a fume hood to control vapors and avoid exposure.
Incompatibilities: Strong oxidizers; strong acids/bases (can hydrolyze the ester under harsh conditions); radical initiators (risk of unintended polymerization for activated alkenes). Avoid prolonged exposure to light/heat that may promote isomerization or polymerization.
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; do not induce vomiting; seek medical attention.
Spill/cleanup: Absorb with inert material, collect for disposal. Prevent entry into drains. Dispose of in accordance with local regulations.
Always consult the product-specific Safety Data Sheet (SDS) before use.
Solvent Selection
This product is an organic reagent, not a solvent. Selection below refers to media for its handling and reactions.
The molecule is moderately polar (ester + aniline) yet largely hydrophobic; it is typically soluble in common organic solvents: DCM, chloroform, EtOAc, THF, toluene, MeOH, and acetonitrile (literature). Water solubility is expected to be low in the neutral form but can increase upon protonation of the aniline (use dilute HCl to form a water-soluble ammonium salt when desired for extractions).
Choosing a solvent by task:
Nucleophilic additions/Michael reactions: polar aprotic media (DMF, DMSO, MeCN, THF) often enhance rates; alcohols can also be used with base for transesterification.
Reductions (C=C or ester): protic solvents (EtOH, iPrOH) for catalytic hydrogenation; ethereal solvents for hydride reductions (DIBAL-H, LiAlH4).
Electrophilic aromatic substitutions on the aniline ring: nonpolar to moderately polar solvents (toluene, DCM, AcOH) depending on electrophile.
Comparison to alternatives:
Versus non-protic esters lacking an aniline: this substrate may exhibit stronger solvation needs due to H-bonding of –NH2; dry, deoxygenated solvents are advisable to minimize side reactions (e.g., polymerization or oxidation).
Always dry solvents appropriately for moisture-sensitive steps and match solvent to base/catalyst compatibility.
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 storage guidance for aryl acrylate anilines (good practice):
Keep tightly closed in a dry, inert atmosphere (desiccator or with desiccant) to minimize moisture ingress and ester hydrolysis.
Protect from prolonged light and heat to reduce risk of E/Z isomerization or unintended polymerization of the activated alkene.
If extended storage is anticipated, aliquot to minimize repeated headspace exposure; consider storing under nitrogen/argon.
Reconstitution/solution preparation:
Dissolve in suitable anhydrous solvent (DCM, THF, MeCN, EtOAc, MeOH, or DMSO) with gentle warming if needed.
Prepare concentrated stocks (e.g., 0.1–1.0 M) for synthetic use; filter if necessary through PTFE (0.22 µm) to remove particulates.
For aqueous applications, form the anilinium salt by adding a stoichiometric acid (e.g., HCl in ethanol) if higher water solubility is required; avoid strong acidic/basic conditions that could hydrolyze the ester unless intended.
Always defer to the product’s CoA/SDS for definitive storage and handling instructions. Research use only.
Structure and Identity
Ethyl 3-(3-aminophenyl)acrylate is an aniline-substituted cinnamate ester featuring a conjugated aryl–alkene–ester motif.
From Product Data (item-specific):
CAS: 125872-97-1
PubChem CID: 5355747
InChIKey: 358048 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/Computed identifiers and description (for context; not item specification):
Typical molecular formula reported: C11H13NO2 (literature)
Representative SMILES (literature): CCOC(=O)C=CC1=CC(=CC=C1)N (placement of substituents corresponds to meta-amino on the ring)
Structural features (general chemistry):
Functional groups: primary aniline (–NH2) meta to a trans-β-aryl acrylate; ethyl ester; conjugated C=C–C(=O)OEt system.
Conjugation: extended π-system across the phenyl–alkenyl–carbonyl framework, supporting UV absorption and electrophilic alkene character.
2D description: an ethyl ester of acrylic acid attached to a phenyl ring at the β-carbon; the phenyl bears an –NH2 at the 3-position relative to the alkenyl linkage (meta). Stereochemistry of the C=C is typically E in related cinnamate esters (literature), but not specified for this item.
Category path: 全部 / 可售 / 生命科学
Research use note: For research use only.
Synthetic Utility
This bifunctional building block integrates an electrophilic α,β-unsaturated ester and a nucleophilic aniline, enabling orthogonal diversification.
Retrosynthetic value:
Hydrolysis to the corresponding acid followed by amide coupling yields 3-(3-aminophenyl)cinnamamide analogs.
Protection of –NH2 (Boc, Cbz) allows selective manipulation of the acrylate (e.g., conjugate additions, reductions) without competing N-acylation.
Key reactivity handles:
Michael acceptor reactivity at the β-carbon; soft nucleophile additions and organocatalytic enantioselective variants are accessible (literature).
Ester transformations: transesterification, reduction to alcohols/aldehydes (DIBAL-H), or conversion to acid chlorides after hydrolysis.
Aniline derivatization: acylation/sulfonylation to modulate directing effects; diazotization for diversification (Sandmeyer-type substitutions) after prior formation of anilinium diazonium salts.
Named/representative reactions (general):
Conjugate addition under base or Lewis acid catalysis; Morita–Baylis–Hillman adduct formation with aldehydes (using the acrylate as acceptor) in the presence of tertiary amine catalysts.
Catalytic hydrogenation of the C=C (Pd/C, H2) to yield saturated esters; chemoselectivity can be guided by N-protection.
Practical notes:
Control E/Z geometry if relevant to downstream steps; confirm by NMR.
Avoid strong base/heat in protic media to minimize ester hydrolysis unless intended.
In multistep sequences, sequence protection and conjugate additions to prevent undesired N-acylation or polymerization.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological targeting agent (e.g., antibody, probe). No antigen/epitope, species reactivity, clone, or isotype information applies.
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