This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic 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.
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Revisões
Avaliações dos Clientes
Application Protocols
No assay/application protocols (e.g., WB, IHC, IF, FC) are applicable or provided for this small-molecule building block. For synthetic use, consider the Reaction Conditions section for representative procedures (ester hydrolysis, amide coupling, aniline derivatization, aryl ether cleavage). For analytical handling:
Prepare analytical standards in acetonitrile, methanol, or DMSO; filter through 0.2 µm PTFE.
Monitor reactions by TLC (silica; visualize with UV and ninhydrin for aniline derivatives) or HPLC-UV.
For purification, use silica gel column chromatography with base-modified eluents (e.g., 0.5–1% triethylamine) to minimize tailing of the aniline.
Biological Roles
This product is offered for research use only and is not assigned a biological role in vivo. As a small aromatic molecule featuring an aniline, an aryl ether, and a benzoate ester, it is primarily a synthetic intermediate.
General considerations (biochemistry-focused, literature context):
Aromatic amines can engage in hydrogen bonding and π–π interactions with protein targets; derivatization of the aniline often modulates basicity and binding in medicinal chemistry campaigns.
Benzoate esters are commonly used as pro-moieties; hydrolysis (enzymatic or chemical) reveals the corresponding acid, which can serve as a pharmacophore in structure–activity studies. Here, the ethyl ester acts as a protecting group in synthetic sequences.
Aryl ethers affect lipophilicity and metabolic stability; dealkylation to the corresponding phenol is a common metabolic pathway for aryl alkyl ethers (literature).
No specific biochemical pathway, receptor, enzyme, or transport mechanism is established for Ethyl 3-amino-4-propoxybenzoate in the provided Product Data. Any use in biological assays should include appropriate controls, purity verification, and confirmation of hydrolytic stability under assay conditions.
Buffer Applications
Not typically applicable. Ethyl 3-amino-4-propoxybenzoate is a hydrophobic aromatic building block, not a buffering agent. It does not form a defined conjugate acid/base pair suitable for maintaining pH in aqueous systems.
If aqueous work is required (e.g., biotesting):
Consider dissolving in DMSO or ethanol to prepare stock solutions, then dilute into buffered media (PBS, HEPES) keeping final cosolvent ≤1–2% v/v to avoid precipitation.
Confirm chemical stability in the chosen buffer (avoid strongly acidic/basic conditions that hydrolyze esters).
Green Alternatives
As a building block, the compound itself is not substituted by a greener reagent; however, greener choices can be made for operations involving it.
Greener solvent choices (literature guidance):
Replace DCM/chloroform with ethyl acetate, 2-MeTHF, cyclopentyl methyl ether (CPME), or toluene where feasible.
For couplings and nucleophilic substitutions, consider 2-MeTHF, CPME, or anisole as alternatives to dioxane/DMF/THF when compatible.
For recrystallization, use EtOAc/ethanol or isopropanol/water systems instead of halogenated solvents.
DCM vs 2-MeTHF: 2-MeTHF reduces halogenated waste and often enables similar solubility; note higher boiling point and possible peroxide formation—deploy inhibitor monitoring and proper storage.
DMF/DMAc vs MeCN/EtOAc: Acetonitrile/EtOAc are less problematic from a regulatory/tox perspective; verify solubility/reactivity.
THF vs CPME: CPME offers broader stability to acids/bases and lower peroxide formation rate; drying may be simpler.
Catalyst/reagent considerations: Choose modern coupling protocols that minimize precious metal loading, utilize ligand-enabled low-Pd systems, or consider copper-catalyzed variants. Employ solid-supported scavengers to reduce metal residues.
Always verify that greener alternatives meet the required selectivity (e.g., preserve ester integrity and aniline functionality).
Pharmaceutical Uses
No pharmacopeial status or excipient role is provided in the Product Data. The product is designated for research use only.
Context for formulation scientists (general):
Role in discovery: Often used as an intermediate in medicinal chemistry to access 3-amino-4-alkoxybenzoic acid derivatives (after ester hydrolysis) or as a masked acid for prodrug exploration.
Developability considerations:
The ethyl ester can be a convenient protecting group during multi-step synthesis; it is typically removed under mild hydrolytic conditions.
Aniline functionality may affect photostability and oxidative liability; include appropriate stress tests (light, peroxide, pH) when profiling derivatives.
Regulatory note: Without specific grades (e.g., GMP, USP/Ph. Eur.), this material is not intended for human or veterinary use. For any preclinical formulation work, obtain detailed impurity profiles and metal content limits if relevant; otherwise, use strictly for in vitro/in vivo research according to institutional approvals.
Physical Properties
Item-specific numerical specifications (mp/bp, density, UV cutoff, metals, water/peroxide content) are not provided in the Product Data for this SKU.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula (literature/computed): C12H17NO3
Acid/base character (general): Contains a weakly basic aniline (pKa of the anilinium conjugate typically ~4.5–5.5, literature; free-base pKb ~9–10) and an ester that is neutral under non-hydrolyzing conditions.
Lipophilicity (qualitative, literature expectation): Moderately lipophilic due to aryl ring and propoxy chain; expected good solubility in common organic solvents (e.g., DCM, EtOAc, alcohols) and poor solubility in water.
Hydrogen bonding: One H-bond donor (–NH2) and multiple acceptors (carbonyl O, ester O, ether O, and aniline N as a weak acceptor).
Phase at room temperature (general expectation): Aromatic ethyl benzoate derivatives of this size are often low-melting solids or viscous oils; verify on receipt (refer to CoA/Spec Sheet).
Where precise values (mp, bp, density, refractive index, logP, solubility data) are critical for method development or scale-up, consult the SDS/CoA for this specific lot. Do not treat literature/computed values as item specifications.
Quality and Grades
Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance:
In the absence of a stated grade, material is typically offered for research and development. Purity, residual solvent profile, and analytical controls (NMR, HPLC/GC assay, water by Karl Fischer) should be verified from the CoA.
If offered as ≥95–98% (common for building blocks), expect suitability for most synthetic applications. For structure–activity studies or analytical reference, consider requesting tighter specs (e.g., HPLC ≥98%, residual solvent limits, and verified identity by HRMS and 1H/13C NMR).
Stabilizers/Inhibitors: None are listed in the Product Data. If stabilizers are relevant to your application, confirm absence/presence on the CoA.
UV/fluorescence background: Not specified for this item; if using in analytical detection (HPLC-UV), obtain UV cutoff/trace absorbance data from the CoA.
Documentation to request for regulated workflows: batch CoA, TDS/Spec Sheet, impurity profile (if available), and SDS. If GMP/Ph. Eur./USP suitability is required, note that this product is for research use only unless otherwise stated.
Reaction and Applications
Ethyl 3-amino-4-propoxybenzoate is a versatile aromatic building block combining an aniline, an aryl alkyl ether, and a benzoate ester. Typical research uses include:
Amide/acid derivatives via ester manipulation:
Hydrolysis to the corresponding 3-amino-4-propoxybenzoic acid (acidic or basic conditions, then neutralization) followed by amide coupling (e.g., EDCI/HOBt, HATU) to introduce diverse side chains.
Transesterification to alternative alcohol esters under acidic catalysis (Fischer) or base-catalyzed conditions with the target alcohol.
Aniline functionalization:
Acylation/sulfonylation to afford anilides/sulfonamides (acyl chlorides, anhydrides, or sulfonyl chlorides; base such as pyridine, TEA).
Reductive amination (via aldehyde/ketone with NaBH3CN or NaBH(OAc)3) after converting the aniline to the corresponding imine/imine salt.
Diazotization (NaNO2/HX, 0–5 C) for Sandmeyer-type transformations at C–N, enabling introduction of halides, CN, etc., if desired.
Aryl ether manipulation:
Demethylation-like dealkylation of aryl alkyl ethers to phenols using BBr3, BCl3, or AlCl3 can, under controlled conditions, convert the propoxy to phenolic –OH (aryl–O–Pr cleavage, literature). Conditions must be tuned to avoid ester cleavage.
Cross-coupling strategies:
The aniline can be transformed (e.g., to diazonium or to a halide after diazotization) as a handle for subsequent Suzuki, Heck, or Ullmann-type couplings.
These complementary handles make the compound attractive in medicinal chemistry SAR campaigns and heterocycle construction while retaining or modifying the benzoate moiety as a protected carboxyl group.
Reaction Conditions
Typical literature conditions for transforming functionalities present in Ethyl 3-amino-4-propoxybenzoate (guidance only; optimize per substrate):
Ester hydrolysis to acid:
Basic: NaOH or K2CO3 (1–2 equiv) in EtOH/H2O or MeOH/H2O, rt–60 C, 1–6 h; then acidify to pH ~2 to precipitate the acid. Avoid prolonged strong base if the aryl ether is sensitive.
Acidic: Aqueous HCl or H2SO4 (1–3 M) in dioxane/THF, reflux 2–12 h. Acidic conditions avoid anilide formation.
Amide coupling (from acid): HATU or EDCI/HOBt in DMF, DCM, or MeCN; DIPEA or NMM base; 0 C to rt, 1–16 h; typical yields 60–90% (literature ranges).
Aniline acylation/sulfonylation: Acyl chloride/sulfonyl chloride (1.1–1.5 equiv), pyridine or TEA, DCM or toluene, 0 C to rt, 1–3 h.
Reductive amination at aniline: Pre-form imine with aldehyde (AcOH or TiCl4 trace to activate if needed), then reduce with NaBH3CN or NaBH(OAc)3 in MeOH/THF, 0 C to rt.
Aryl ether dealkylation to phenol: BBr3 (1–3 equiv) in DCM at −78 to 0 C, then warm to rt, 2–16 h; quench carefully with MeOH or water. Monitor to prevent ester cleavage; protection of the acid (when present) may help if hydrolyzed first.
Diazotization/Sandmeyer: tBuONO or NaNO2/HX at 0–5 C to form diazonium, then CuX (X = Cl, Br, CN) or H3PO2 for deamination; inert atmosphere recommended.
Always conduct small-scale trials; moisture control and exclusion of oxygen can improve outcomes for aniline-based transformations.
Safety and Handling
GHS classification, hazard statements, and pictograms are not provided in the Product Data for this item. Always consult the product SDS for authoritative safety information.
General hazards (class-based): Aromatic amines and benzoate esters can cause skin/eye irritation and may be harmful if swallowed or inhaled. Avoid aerosol formation. Anilines can undergo oxidation to colored species; handle under well-ventilated conditions.
PPE: Laboratory coat, safety glasses or chemical splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to minimize inhalation exposure.
Handling notes:
Avoid strong acids/bases that may promote ester hydrolysis or aniline protonation; avoid strong oxidizers that may oxidize the aniline or aryl ether.
Prevent prolonged exposure to air and light to minimize oxidative discoloration of the aniline moiety.
If preparing salts (e.g., anilinium), be aware of possible hygroscopicity.
First aid (overview; defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical attention if irritation persists.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Fire safety: Organic compound; treat as combustible. Use CO2, dry chemical, or foam. Thermal decomposition may release CO/CO2 and nitrogen oxides.
Spill response: Absorb with inert material (vermiculite, sand), collect in suitable container for disposal. Prevent entry into drains.
Signal word, H-statements, and pictograms: Not specified for this item; refer to SDS.
Solvent Selection
This compound is a neutral aromatic ester with an aniline and an aryl ether, giving it moderate lipophilicity and limited hydrogen-bond basicity.
Solubility guidance (general/literature):
Good: dichloromethane (DCM), chloroform, ethyl acetate, acetone, acetonitrile, THF, 2-MeTHF, toluene, methanol/ethanol (protonation of aniline can increase solubility in alcohols under acidic conditions).
Poor: water and highly nonpolar alkanes unless warmed.
Polarity class: Moderately polar, aprotic organic solute; compatible with a range of polar aprotic solvents for synthesis and purification.
Chromatography: Normal-phase silica gel elution typically requires moderately polar eluents (e.g., hexanes/EtOAc 2:1 to 1:2). Aniline functionality can tail on silica; adding a small percentage of triethylamine to mobile phase or using neutralized silica can improve band shape.
Crystallization/recrystallization: EtOAc/hexanes, toluene/hexanes, or MeOH/water mixtures are common starting points. Adjust based on actual physical form.
When to choose alternatives:
For base-sensitive operations (avoid ester saponification), prefer neutral solvents (DCM, toluene, EtOAc) over alcoholic or strongly basic media.
For cross-couplings on the aniline (e.g., Buchwald–Hartwig), polar aprotic solvents (dioxane, toluene, xylene, CPME, or 2-MeTHF) are often effective.
Where precise solubility or partition data are required, determine experimentally for your lot.
Storage and Reconstitution
Storage conditions (item-specific): Room temperature (as provided). Store tightly closed in a dry, well-ventilated place. Protect from excessive heat and prolonged light exposure to minimize aniline oxidation.
Shipped in (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Physical form (item-specific): Not specified; verify upon receipt (oil vs solid). If solid, minimize headspace humidity; if oil, consider storing under inert gas.
Long-term stability (general): Aromatic anilines/esters are generally stable at ambient conditions when dry. Avoid strong acids/bases that can hydrolyze the ester or protonate the aniline.
Reconstitution/stock solutions:
Dissolve in DCM, EtOAc, THF, MeOH/EtOH, acetonitrile, or DMSO to prepare stocks. Filter if needed.
For biological assays, prepare concentrated stocks in DMSO or ethanol; store aliquots at −20 C to reduce freeze–thaw cycles. Confirm stability over time by HPLC.
For any storage beyond routine timelines or for stability-indicating analytics, consult the CoA/SDS and perform small-scale stability checks under your intended conditions.
Structure and Identity
Compound type: Aromatic benzoate ester bearing an aniline (–NH2) and an aryl alkyl ether (–O–Pr) substituent.
Product name (item-specific): Ethyl 3-amino-4-propoxybenzoate (SKU: E947831)
CAS (item-specific): 342044-71-7
PubChem CID (item-specific): 1712632
InChIKey (item-specific): 325760 (as provided). For definitive identifier, refer to CoA/Spec Sheet.
SMILES (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula (literature/computed from name): C12H17NO3
A benzene ring substituted with three groups: (1) an ethyl benzoate ester (–C(=O)OEt) at the carboxyl carbon; (2) a meta-amino group at the 3-position relative to the carboxyl; (3) a para-propoxy group (–O–CH2–CH2–CH3) at the 4-position.
Functional groups: aromatic ring, aryl ether, primary aniline, and an aromatic ester.
No stereocenters; expected as a single constitutional isomer without stereoisomerism.
2D structure (verbal): Starting from the benzoate carbonyl carbon as position 1, positions 2–6 proceed clockwise; position 3 carries –NH2, position 4 carries –O–CH2–CH2–CH3, and the benzoate carbonyl is esterified as –C(=O)–O–CH2–CH3.
Synthetic Utility
Key reactivity stems from three orthogonal handles on the aromatic core:
Ester (–CO2Et):
Hydrolysis to the carboxylic acid (acidic or basic conditions), then amide/ester formation (HATU/EDCI/DCC; DMAP catalysis for esterification). The ethyl ester also supports Curtius/Schmidt pathways after conversion to acyl azides or hydrazides (via the acid).
Nucleophilic substitution at the carbonyl is generally not favored; use activated derivatives (acyl chloride via SOCl2/oxalyl chloride) formed from the acid.
Aniline (–NH2):
Electrophilic acylation/sulfonylation to fine-tune electronics and solubility.
Formation of ureas, thioureas, and carbamates (e.g., using CDI, isocyanates, or chloroformates).
Diazotization to access diverse substituents at the amino position (Sandmeyer chemistry) or to install leaving groups for cross-couplings.
Aryl ether (–OPr):
Can be cleaved to the phenol with Lewis acids (BBr3, BCl3) enabling subsequent O-functionalization (etherifications, carbonate formation). Bulky alkyl ethers may require stronger/longer conditions than anisoles.
Strategic value in retrosynthesis:
The ester masks the acid during electrophilic aromatic substitutions on the ring.
Orthogonal protection/activation allows late-stage diversification: modify the aniline independently from the acid/phenol handles.
Compatible with common palladium-catalyzed couplings after suitable activation (e.g., convert aniline to diazonium/halide or derivatize to enable C–N couplings).
Target Specificity
Not applicable to this product type. Ethyl 3-amino-4-propoxybenzoate is a small-molecule building block and does not possess antigen/epitope specificity, clone/isotype information, or species reactivity attributes. Refer instead to the Synthetic Utility and Reaction & Applications sections for relevant use-cases.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
