Ethyl 2-amino-5-ethoxybenzoate - ≥95% , CAS No.1178145-53-3

CAS: 1178145-53-3 Cat. No.: E1028563 Formula: C₁₁H₁₅NO₃ Peso molecolare: 209.240

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: CCOC1=CC(=C(C=C1)N)C(=O)OCC
• IUPAC Name: ethyl 2-amino-5-ethoxybenzoate
• InChIKey: ABSSMIOKIYSHBF-UHFFFAOYSA-N
• INCHI: 1S/C11H15NO3/c1-3-14-8-5-6-10(12)9(7-8)11(13)15-4-2/h5-7H,3-4,12H2,1-2H3
• Peso molecolare: 209.240

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoic acid esters
• Alternative Parents: Aminobenzoic acids and derivatives Aminophenyl ethers Phenoxy compounds Benzoyl derivatives Aniline and substituted anilines Alkyl aryl ethers Vinylogous amides Carboxylic acid esters Amino acids and derivatives Primary amines Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Aminobenzoic acid or derivatives - Benzoate ester - Aminophenyl ether - Phenoxy compound - Aniline or substituted anilines - Benzoyl - Phenol ether - Alkyl aryl ether - Vinylogous amide - Amino acid or derivatives - Carboxylic acid ester - Carboxylic acid derivative - Ether - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Primary amine - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Amine - Aromatic homomonocyclic compound
• Descrizione: 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

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 209.240 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 209.105 Da
• Monoisotopic Mass: 209.105 Da
• Topological Polar Surface Area: 61.600 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 208.000
• 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

Application Protocols

Not applicable. No biological assay or imaging protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. For synthetic use, refer to the Reaction Conditions and Synthetic Utility sections for practical guidance.

Biological Roles

This product is a small-molecule aromatic building block without an established endogenous biological role.

• General context (literature):

  • Anthranilate derivatives (o-aminobenzoates) occur in numerous synthetic analogs used in chemical biology, but Ethyl 2-amino-5-ethoxybenzoate itself is not a known metabolite or cofactor.
  • The aniline functionality can engage in hydrogen bonding and may modulate binding in probe development when incorporated into larger scaffolds.

• Research use only:

  • As indicated by the Product Data, this item is for research use only. It is suitable for synthetic workflows that generate candidate tool compounds or materials but is not intended for diagnostic, therapeutic, or other clinical applications.

If biological evaluation is intended for derivatives made from this building block, ensure appropriate in vitro and in vivo safety assessments are conducted under relevant guidelines. No pharmacological or physiological activities are claimed for this item.

Buffer Applications

Not typically applicable. Ethyl 2-amino-5-ethoxybenzoate is a neutral/weakly basic organic building block, not a dedicated buffering agent. It does not constitute a standard laboratory buffer system, and no pH-buffer recipes are associated with this compound.

For aqueous manipulations, consider forming the anilinium salt under acidic conditions to improve water compatibility during extractions or crystallizations, but use conventional buffers (e.g., phosphate, acetate, citrate) for pH control.

Green Alternatives

Greener choices pertain mainly to solvent and reagent selection when using Ethyl 2-amino-5-ethoxybenzoate; the molecule itself is a structural building block.

• Preferred solvents (when feasible):

  • Ethyl acetate and 2-MeTHF as alternatives to dichloromethane and THF, respectively.
  • Acetonitrile or propylene carbonate in place of DMF/DMSO for some condensations, balancing removability and safety.
  • Alcoholic media (EtOH, i-PrOH) for ester interchange or salt formation, when compatible.

• Reagents/catalysts:

  • Switch from stoichiometric coupling reagents to catalytic amidations (e.g., boron-catalyzed, enzyme-assisted) where performance allows.
  • Use carbonate bases (K2CO3, Cs2CO3) in alcohol/green ether solvents for N-alkylations instead of stronger halogenated systems.

• Comparison snapshot (general):

  • DCM vs EtOAc: EtOAc reduces chlorinated solvent use; may require larger volumes or longer reaction times.
  • THF vs 2-MeTHF/CPME: 2-MeTHF and CPME offer better peroxide resistance and higher boiling points, aiding reflux; ensure compatibility with bases and catalysts.
  • DMF vs MeCN: MeCN is more volatile and easier to remove; DMF may be necessary for difficult solubility cases.

• Workup/waste:

  • Favor aqueous base/acid washes and minimal halogenated waste. Employ phase-transfer catalysis to reduce solvent volumes.

Adopt green metrics (E-factor, PMI) and LCA-informed choices, validating reaction efficiency and product quality under the greener conditions.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided in the Product Data. This compound is sold for research use only.

• Formulation context (general):
  • As a synthetic intermediate, it may be incorporated into discovery-scale routes to candidate molecules but is not intended as an API or excipient.
  • If handled in a GMP-like setting for route scouting, obtain full impurity profiles, residual solvent data, and stability information from a CoA/Spec Sheet and perform your own qualification per internal SOPs.

No clinical or therapeutic claims are made for this product.

Physical Properties

Item-specific specifications are not provided in the Product Data for this SKU; therefore no numeric specifications are stated here.

• Item-specific (from Product Data):

  • Appearance: 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 context (for professional reference only; not product specifications):

  • Estimated molecular formula from structure: C11H15NO3
  • Calculated molecular weight: ~209.25 g/mol
  • Polarity: Moderately polar aromatic ester with H-bond donor (–NH2) and acceptors (carbonyl O, ether O)
  • Expected solubility profile: High solubility in common organic solvents (EtOAc, dichloromethane, acetonitrile, THF, alcohols); low solubility in water due to hydrophobic aryl/alkoxy/ethyl ester scaffold. Protonation of the aniline in strong acid may increase aqueous solubility.
  • Partitioning: Anticipated logP in the 2–3 range for analogous amino-alkoxy benzoate esters (literature analogs); exact value not determined for this compound.
  • Acid/base behavior: Aniline pKaH typically ~4.5–5.5 (literature, conjugate acid). The ester is not basic and is weakly hydrogen-bond accepting.

Always consult the product’s CoA/Spec Sheet for definitive numerical specifications if required for method validation or regulatory documentation.

Quality and Grades

• Item-specific (from Product Data):

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance on interpreting grades (general):

  • Research grade: Suitable for most synthetic and discovery workflows; impurity limits are typically fit-for-purpose but may not include exhaustive trace analyses.
  • Purified/isolated building blocks are often specified by NMR/LC-MS/HPLC area %; where UV cutoffs, water, or residual-solvent limits are critical, consult the CoA.

• Chromatography considerations (general):

  • For use as an analytical standard or in trace-sensitive applications, request HPLC purity and residual solvent/metals data. If UV transparency is relevant (e.g., LC detection near 210–254 nm), review UV absorbance of the aromatic chromophore and baseline behavior in your mobile phase.

• Stabilizers/antioxidants:

  • None stated for this item. If a stabilizer is present in a particular lot, it will be disclosed on the CoA/Spec Sheet. The structure (aromatic amino ester) does not typically require added stabilizers under normal storage.

Contact Aladdin Scientific for current lot CoA, analytical methods used (e.g., HPLC, 1H/13C NMR), and any additional qualification data needed for your workflow.

Reaction and Applications

With an aniline (–NH2), an aryl ether (–OEt), and an ethyl benzoate, Ethyl 2-amino-5-ethoxybenzoate serves as a versatile intermediate for medicinal and materials chemistry.

• Transformations leveraging the aniline:

  • N-acylation/sulfonylation to prepare amides/sulfonamides; typical reagents: acyl/sulfonyl chlorides or anhydrides with tertiary base (DIPEA, pyridine). Protecting groups (Boc, Cbz) can modulate ring activation.
  • Diazotization of the aniline (NaNO2/HX, 0–5 °C) to access aryl diazonium salts for Sandmeyer-type substitutions (–CN, –Cl/Br/I, –OH) at C2.
  • Reductive amination at the nitrogen is less relevant; the aniline is already primary.

• Transformations at the ester:

  • Hydrolysis (acidic or basic) to the 2-amino-5-ethoxybenzoic acid for subsequent amide coupling (EDC/HOBt, HATU, or CDI) to afford benzamides.
  • Transesterification to other alkyl esters (acid- or base-catalyzed) when tuning lipophilicity or volatility.
  • Reduction to the corresponding benzyl alcohol (e.g., DIBAL-H at low temperature) enabling further derivatization.

• Aromatic ring chemistry:

  • Electrophilic substitution is strongly activated by –NH2 and –OEt; regioselectivity must be managed (often via protecting the amine) to avoid polysubstitution.
  • Cross-coupling typically targets aryl halides; thus halogenation (via diazonium or directed halogenation) can set the stage for Suzuki, Buchwald–Hartwig, or Ullmann couplings.

• Representative uses:

  • Scaffold in library synthesis of substituted anthranilate derivatives, benzoxazole precursors (via cyclodehydration after acylation), and fragments for SAR campaigns.

These are literature-style applications; optimize conditions for your substrate set.

Reaction Conditions

General, literature-style guidance for typical transformations; optimize for your substrate and scale.

• N-Acylation/N-Sulfonylation of the aniline:

  • Solvent: DCM, THF, or MeCN. Base: DIPEA, TEA, or pyridine (1.5–2.0 equiv).
  • Temperature: 0 °C to rt; 1–4 h typical. Monitor by TLC/HPLC. Avoid strong base that could drive ester hydrolysis.

• Diazotization/Sandmeyer at C2:

  • Conditions: NaNO2 (1.1–1.5 equiv) in 2–4 M HCl or HBF4 at 0–5 °C to form diazonium; quench into CuX, KI, KCN, or water for substitution.
  • Notes: Protect the phenolic site is unnecessary (no phenol here), but control amine protonation. Safety: handle diazonium intermediates at low temperature, in dilute solution.

• Ester hydrolysis to acid:

  • Basic: K2CO3/KOH in MeOH/H2O (rt–reflux, 1–6 h). Acidic: HCl or H2SO4 in aqueous dioxane/THF (reflux).
  • Workup: Acidify (basic route) to precipitate acid; extract with EtOAc.

• Reduction of ester:

  • DIBAL-H (1.2–2.0 equiv) in toluene/THF at −78 to −20 °C to aldehyde/alcohol; or LiAlH4 to primary alcohol (strictly anhydrous, ether solvents).

• Electrophilic aromatic substitution (nitration, sulfonation):

  • Strong activation from –NH2/–OEt may cause polysubstitution; consider N-acyl protection (e.g., acetanilide) to moderate reactivity.

Yields vary with substituents and conditions; consult reaction-specific literature for analogous o-amino, m-alkoxy benzoate substrates.

Safety and Handling

• Item-specific hazard data (from Product Data):

  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • GHS Classification: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.

• General laboratory safety guidance for aromatic amino esters (literature/good practice; defer to SDS):

  • Likely hazards: May cause skin/eye irritation and respiratory irritation. Aromatic amines can be sensitizers in some cases. Avoid inhalation of dusts/aerosols and contact with skin/eyes.
  • PPE: Lab coat, safety glasses or chemical goggles, and suitable gloves (e.g., nitrile). Use in a fume hood to control vapors/particulates.
  • Handling: Avoid strong acids/bases that can promote hydrolysis or salt formation unless intended. Prevent prolonged exposure to elevated temperatures that could induce ester cleavage.
  • Incompatibilities: Strong oxidizers; strong bases/acids (can hydrolyze the ester). Nitrosating agents may react with anilines.
  • First aid (overview):
    • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice as needed.
    • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
    • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
  • Fire safety: Combustible organic solid/liquid; use CO2, dry chemical, or foam. Combustion may produce CO, CO2, NOx.

Always consult the product’s SDS for authoritative hazard classification and response instructions.

Solvent Selection

Ethyl 2-amino-5-ethoxybenzoate is a moderately polar aromatic building block that dissolves readily in many organic media.

• Solubility/miscibility (literature expectations):

  • Good: ethyl acetate, dichloromethane, chloroform, acetonitrile, THF, toluene, DMF, DMSO, methanol/ethanol (heating may improve rate).
  • Poor: water at neutral pH; solubility may increase in acidic aqueous media due to anilinium salt formation.

• Selection tips by application:

  • N-acylation/sulfonylation of the aniline: Use non-protic polar solvents (DCM, THF, MeCN) with a non-nucleophilic base (DIPEA, TEA) to control selectivity and minimize ester transesterification.
  • Electrophilic aromatic substitution on the ring: Choose solvents that balance reactivity and solubility (AcOH, nitrobenzene, DCM) and consider protection of the amine if over-activation is a risk.
  • Hydrolysis or alcoholysis of the ester: Aqueous-organic biphasic systems (THF/H2O, MeOH/H2O) with acid or base catalysts as needed.

• Comparison (general guidance):

  • DCM vs. EtOAc: DCM offers higher solubility and inertness for acylations; EtOAc is a greener alternative with broader compatibility but may require longer times.
  • DMF/DMSO vs. MeCN/THF: DMF/DMSO enhance solubility for challenging transformations; MeCN/THF are easier to remove and often adequate.

Always verify solubility and stability experimentally under your exact conditions.

Storage and Reconstitution

• Item-specific (from Product Data):

  • Storage Conditions: Room temperature.
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance (small organic building blocks):

  • Keep container tightly closed in a dry, well-ventilated area. Protect from strong acids/bases that can promote ester hydrolysis. Avoid prolonged exposure to elevated temperatures.
  • If long-term storage is planned, consider desiccation and protection from light to minimize potential discoloration or slow degradation.

• Reconstitution/solution preparation:

  • Dissolve in a suitable organic solvent (e.g., DCM, EtOAc, MeCN, THF, MeOH, DMSO) to prepare stock solutions. For aqueous systems, formation of anilinium salts under acidic conditions may aid solubility.
  • Filter solutions (0.2 µm PTFE) if particulates are present. Label solutions with solvent, concentration, and date; many solutions remain stable for weeks at 2–8 °C, but verify by LC/HPLC.

• Freeze–thaw:

  • Not generally applicable to the neat solid/liquid. If storing solutions, avoid repeated freeze–thaw cycles; prepare single-use aliquots where practical.

Always refer to the product’s CoA and SDS for lot-specific stability and handling details.

Structure and Identity

Ethyl 2-amino-5-ethoxybenzoate is an aniline-bearing substituted benzoate ester featuring both an electron-donating amino group and an ethoxy ether on the aromatic ring.

• Item-specific identifiers (from Product Data):
  • CAS: 1178145-53-3
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists "1279", which is not a valid InChIKey.)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Computed/literature identity details (for reference; not item specifications):
  • Expected molecular formula (by composition from the name): C11H15NO3 (literature inference)
  • Approximate molecular weight: ~209.25 g/mol (literature/computed from formula)
• Structural features (descriptive, literature-based):
  • Core: Benzoate ester (ethyl ester of benzoic acid)
  • Substituents: o-amino (2-position) and m-ethoxy (5-position) relative to the carboxylate carbonyl
  • Functional groups: aromatic amine (aniline), aryl ether (ethoxy), aryl ester (ethyl benzoate)
  • 2D structure (verbal): A benzene ring bearing a carbomethoxy-ethyl group (–C(=O)OEt) at C1, an –NH2 at C2 (ortho to the ester), and an –OEt at C5 (meta to the ester). No stereocenters present.

Notes:

• Values not provided in Product Data are given as literature/computed context only and should not be construed as product specifications.

Synthetic Utility

Ethyl 2-amino-5-ethoxybenzoate combines three orthogonal handles that enable diverse downstream chemistry:

• Aniline (–NH2):

  • Convert to amides, ureas, sulfonamides; install protecting groups (Boc, Cbz, Fmoc) to control reactivity and regioselectivity in ring substitutions.
  • Diazotize to aryl diazonium for Sandmeyer substitutions, enabling access to halo, cyano, hydroxy, or trifluoromethyl variants at C2.

• Ethyl ester (–CO2Et):

  • Hydrolyze to the acid for peptide-like couplings (EDC/HATU/DIC). Cyclodehydration with adjacent amide/oxime partners can yield benzoxazoles/benzoxazinones.
  • Reduce to benzyl alcohols/benzylamines (via subsequent steps) for further diversification.

• Aryl ethoxy (–OEt):

  • Typically inert under many conditions; serves as an activating ortho/para director for electrophilic aromatic substitution. Can be cleaved under strong Lewis/Brønsted acidic conditions or via demethylation-type strategies adapted to ethoxy, though more forcing than anisoles.

• Retrosynthetic value:

  • The scaffold can be accessed from 2-nitro-5-ethoxybenzoates via reduction or from 2-amino-5-hydroxybenzoates by O-alkylation, offering points of diversity for SAR libraries.

Overall, it is a practical entry to 2-substituted anthranilate derivatives and heteroaromatic frameworks after strategic functional group interconversions.

Target Specificity

Not applicable. This product is a small organic building block, not an antibody, enzyme, or biological targeting reagent. No target, epitope, or species reactivity data are associated with this item.