Ethyl 2-amino-5-methoxybenzoate - ≥97% , CAS No.64018-98-0

CAS: 64018-98-0 Cat. No.: E730013 Fórmula: C₁₀H₁₃NO₃ Peso molecular: 195.22 PubChem CID: 21291483

GRAU & PUREZA ≥97%

Storage

Room temperature

Especificações

Especificações e pureza

≥97%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥97%

Nomes e identificadores

Sorrisos canónicos

CCOC(=O)C1=C(C=CC(=C1)OC)N

IUPAC Name

ethyl 2-amino-5-methoxybenzoate

InChIKey

POJXEDATMPDTHT-UHFFFAOYSA-N

INCHI

1S/C10H13NO3/c1-3-14-10(12)8-6-7(13-2)4-5-9(8)11/h4-6H,3,11H2,1-2H3

SMILES isoméricas

CCOC(=O)C1=C(C=CC(=C1)OC)N

PubChem CID

21291483

Peso molecular

195.22

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives
        • Level5 Methoxybenzoic acids and derivatives
          • Level6 M-methoxybenzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Methoxybenzoic acids and derivatives
• Direct Parent: M-methoxybenzoic acids and derivatives
• Alternative Parents: Benzoic acid esters Aminobenzoic acids and derivatives Methoxyanilines Aminophenyl ethers Phenoxy compounds Methoxybenzenes Benzoyl derivatives Anisoles Alkyl aryl ethers Vinylogous amides Carboxylic acid esters Amino acids and derivatives Primary amines Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: M-methoxybenzoic acid or derivatives - Aminobenzoic acid or derivatives - Benzoate ester - Aminophenyl ether - Methoxyaniline - Anisole - Phenoxy compound - Benzoyl - Phenol ether - Aniline or substituted anilines - Methoxybenzene - Alkyl aryl ether - Vinylogous amide - Carboxylic acid ester - Amino acid or derivatives - Ether - Carboxylic acid derivative - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Amine - Primary amine - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
• 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

Propriedades químicas e físicas

• Peso molecular: 195.210 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 195.09 Da
• Monoisotopic Mass: 195.09 Da
• Topological Polar Surface Area: 61.600 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 196.000
• 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 immunoassay or cell-based application protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block.

• Practical note: For synthetic applications, consult the Reaction Conditions, Synthetic Utility, and Solvent Selection sections for step-by-step guidance on representative transformations.

Biological Roles

This product is provided for research and synthetic use. It is not intended for biological administration.

• General context (literature):

  • Anthranilate derivatives appear in natural product biosynthesis and as motifs in enzyme cofactors and signaling molecules; however, Ethyl 2-amino-5-methoxybenzoate is a synthetic intermediate and not a known endogenous metabolite.
  • The aniline and anisole functionalities can engage in pi–pi and H-bonding interactions in ligand design; thus, the scaffold is sometimes used to explore SAR in discovery chemistry.

• Practical lab relevance:

  • Can serve as a precursor to acids, amides, and heterocycles that are evaluated in biochemical assays after further modification.

No organismal pathway integration, receptor interactions, or metabolic roles are established for this specific compound in the literature cited here. Avoid extrapolating any biological function; consult primary studies if evaluating downstream derivatives.

Buffer Applications

Not typically used as a buffer or pH control reagent. As a neutral aromatic amino ester, it lacks the well-defined pKa separation and high aqueous solubility required for practical buffering systems.

• Practical note: If handling in aqueous media, protonation of the aniline in strong acid can increase apparent solubility, but this is for extraction/purification convenience rather than buffering. For buffer needs, choose dedicated systems (e.g., phosphate, acetate, Tris) aligned with your pH range.

Green Alternatives

Greener choices primarily concern solvent and reagent selection, as the substrate itself is defined by structure.

• Prefer greener solvents when feasible:

  • Replace DCM/chloroform with ethyl acetate, 2-MeTHF, CPME, or toluene where kinetics and selectivity allow.
  • Use ethanol or isopropanol for salt formation and recrystallization instead of methanol when compatible.

• Catalysis and reagents:

  • For amide couplings from the corresponding acid, favor catalytic coupling approaches (e.g., CDI or catalytic HOAt-alternatives) or green coupling systems (DEPBT alternatives), and minimize use of stoichiometric carbodiimides; consider aqueous micellar catalysis when solubility allows.
  • N-acylations can be run with acid anhydrides and catalytic DMAP in EtOAc or 2-MeTHF, limiting halogenated waste.

• Workup/waste minimization:

  • Exploit the basicity of the aniline for phase-switching purifications (acid/base extraction) to reduce silica usage.
  • Crystallization from green solvents (EtOAc/EtOH, toluene/EtOH) can replace chromatographic purifications.

• Small comparison (general guidance):

  • DCM vs EtOAc: EtOAc is biodegradable and has lower toxicity; bp is higher, so plan energy use for solvent removal.
  • THF vs 2-MeTHF/CPME: Bio-based 2-MeTHF offers improved safety (lower peroxide tendency than THF) and better phase separation; CPME provides broad compatibility and lower formation of peroxides than ethers like THF.

Always confirm that greener substitutions maintain required selectivity and yield; pilot on small scale before scale-up.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item. It is offered for research use only.

• General formulation context (literature):

  • Aromatic amino benzoate esters (e.g., anthranilate/para-aminobenzoate derivatives) are widely used as intermediates in medicinal chemistry campaigns. This specific isomer can be transformed into acids, amides, ureas, sulfonamides, and heterocycles for structure–activity exploration.
  • If used in pre-formulation screening of derivatives, solubility can be modulated by salt formation at the aniline nitrogen; however, such activities remain within research settings and not finished dosage forms.

• Compliance note: No compendial monograph or GMP grade information is supplied. For any application beyond early discovery, obtain batch-specific documentation (CoA, residual solvents, elemental impurities) and assess against ICH guidelines.

No therapeutic or clinical claims are made or implied for this product.

Physical Properties

Item-specific values are not provided in the Product Data. Do not treat the following as specifications.

• Item-specific specifications:

  • 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/general expectations (for reference only):

  • Empirical formula (literature): C10H13NO3
  • Formula weight (literature): ~195.22 g/mol
  • Physical state: Many aryl amino benzoate esters are crystalline solids at ambient temperature; specific MP/appearance for this isomer is not confirmed here.
  • Melting point, boiling point, density, refractive index: Not specified for this item; consult primary literature or CoA.
  • Solubility (qualitative, literature): Expected to be sparingly soluble in water; soluble in common organic solvents (EtOAc, DCM, THF, MeOH, EtOH, toluene, acetonitrile). The aniline may exhibit limited basicity (protonation in strong acid aqueous media increases apparent solubility).
  • Acid–base behavior (literature): Aniline pKaH typically ~4.5–5.5; ester is not ionizable under neutral conditions. Overall, neutral at physiological pH.
  • Partitioning (literature): Aromatic amino esters often show moderate lipophilicity (cLogP ca. 1.5–2.5); exact value for this isomer not confirmed here.

Always verify critical physical constants on the Certificate of Analysis/SDS before process design.

Quality and Grades

• 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 common grades for small-molecule building blocks (general information):

  • Research grade: Suitable for routine synthesis and screening; typical organic impurities controlled by NMR/GC/HPLC. Residual solvents often conform to ICH Class 2/3 limits when requested.
  • ≥98% or ≥99% purity (assay by HPLC/GC/NMR): Preferred for SAR studies and sensitive catalysis. Trace amines/phenols, water, and residual acids/bases can influence metal-catalyzed couplings and acylations; pre-dry and, if needed, recrystallize prior to use.
  • Low-UV or LC/MS grade is more relevant to solvents; for solids used as standards, certified reference materials (CRM) may be available from other sources when quantitative analysis is critical.

• What matters for this molecule:

  • Water content can affect coupling and acylation steps (aniline acylations, Ugi, isocyanate formation). If critical, verify by KF (item-specific value: Not specified for this item; refer to CoA/Spec Sheet.).
  • Metals/halides are typically low for isolated organics; if using in Pd-catalyzed couplings, consider running a blank to ensure no catalyst poisons are present.
  • UV impurities: The anisole/aniline chromophores absorb in near-UV; for photochemical work, verify background absorbance.

Use the CoA for definitive assay, impurity profile, and recommended analytical methods.

Reaction and Applications

As a bifunctional aromatic building block, Ethyl 2-amino-5-methoxybenzoate is valuable for assembling heterocycles, amide libraries, and substituted anisoles/anthranilates.

• Transformations at the aniline nitrogen:

  • Acylation/sulfonylation to give anilides and sulfonamides (rapid, often at 0–25 C in DCM, THF, or EtOAc with base). Carbamoylation with chloroformates to access urethanes.
  • Reductive amination on N-protected derivatives; N-alkylation under Mitsunobu or alkyl halides (beware over-alkylation to tertiary amines).
  • Diazotization (NaNO2/HX, 0–5 C) to form diazonium intermediates for Sandmeyer-type substitutions on the ring; ortho arrangement with ester can enable intramolecular cyclizations in tailored contexts.

• Transformations on the aromatic ring:

  • Electrophilic substitution directed by –NH2/–OMe (both ortho/para directors); the –CO2Et group is meta-directing/deactivating, shaping regiochemistry. Nitration and halogenation typically occur at positions activated by –OMe and –NH2, controlling conditions to prevent polysubstitution.
  • Transition-metal-catalyzed C–N and C–O couplings from prefunctionalized aryl halide derivatives of this scaffold.

• Ester group chemistry:

  • Hydrolysis (saponification) to the corresponding acid; amidation via acid chloride/coupling reagents (EDC/HOBt, HATU) yields amide libraries retaining the 2-amino-5-methoxy aryl core.
  • Reduction (LiAlH4, DIBAL-H) to benzyl-type alcohols may proceed, though chemoselectivity must be planned to avoid reducing the aryl ether.

• Applications (general):

  • Intermediate for 2-aminobenzoate-based heterocycles (e.g., benzoxazoles/benzimidazoles after appropriate functional group interconversions).
  • Aryl anisole cores used in agrochemical and materials leads; the anthranilate motif is common in fragrance chemistry, though this specific substitution is a research intermediate.

Ensure orthogonal protection strategies if selective N- vs O-functionalization is required.

Reaction Conditions

General literature guidance for typical transformations of this scaffold (not item-specific specifications):

• N-acylation/sulfonylation of the aniline:

  • Conditions: Acyl chloride/sulfonyl chloride (1.05–1.2 eq), base (2–3 eq DIPEA, pyridine, or Na2CO3), solvent DCM/THF/EtOAc, 0–25 C, 0.5–2 h. Often quantitative to high yields.

• Ester hydrolysis (to 2-amino-5-methoxybenzoic acid):

  • Basic: NaOH or KOH (1–2 eq) in MeOH/H2O or THF/H2O, 20–60 C, 1–6 h. Acidify to precipitate product. Protect aniline if competitive reactions are problematic.
  • Acidic: Aqueous HCl or H2SO4 (refluxed EtOH/H2O), longer times; may lead to N-protonation aiding solubility.

• Demethylation of anisole (to phenol):

  • BBr3 (1–3 eq) in DCM, −78 to 0 C then to rt, 2–16 h; or AlCl3/thiol methods. Boc-protect the aniline beforehand to avoid side reactions.

• Diazotization/Sandmeyer at the aniline position:

  • NaNO2 (1.1 eq) in 2–4 M HCl, 0–5 C to form diazonium salt, then CuX (X = Cl, Br, CN) for substitution; typical 40–80% yields depending on substitution pattern.

• Coupling chemistry from the acid (after hydrolysis):

  • HATU/DIPEA in DMF or DCM, 0–25 C, 1–4 h for amide formation; or T3P (50% in EtOAc) with amine, 0–60 C, operationally simple and greener.

• Reduction of ester to alcohol:

  • DIBAL-H (1.5–2.0 eq) in toluene or DCM, −78 to 0 C, quench carefully; LiAlH4 in THF at 0–25 C reduces to benzyl alcohol, but can affect other functions—plan protections.

Optimize equivalents and temperature based on scale and specific reactivity; monitor by TLC/HPLC and confirm identity by NMR/MS.

Safety and Handling

• Product-specific hazard entries (from Product Data):

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

• General safety profile (literature/analog-based guidance; not a specification):

  • Aromatic amines may cause skin/eye irritation and can be harmful if swallowed or inhaled. Esters and aromatic solvents can be irritant; avoid aerosol formation.
  • Not known as a strong oxidizer/reducer. Combustible organic solid; keep away from ignition sources.
  • Incompatibilities: Strong oxidizing agents; strong acids/bases (can hydrolyze the ester under forcing conditions). Nitrosating agents (e.g., nitrites in strong acid) may convert anilines to N-nitroso species—avoid such conditions unless intended.
  • Peroxide formation: Not a peroxide-forming solvent (risk is low compared with ethers).

• Recommended PPE and handling (standard lab practice):

  • Wear lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dust or vapors during heating or reactions.
  • First aid (overview; defer to SDS): If on skin/eyes, rinse with water for ≥15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth—do not induce vomiting; seek medical attention.
  • Spill/cleanup: Avoid dust; collect with inert absorbent for disposal per institutional and local regulations.

Always consult the product SDS for authoritative hazard classification and response measures.

Solvent Selection

This substrate is an aniline-containing aromatic ester with moderate polarity and good solubility in common organic solvents.

• Polarity/miscibility (literature, qualitative):

  • Soluble: DCM/CH2Cl2, chloroform, ethyl acetate, acetone, THF, MeOH/EtOH, acetonitrile, toluene (warm).
  • Poorly soluble: Water at neutral pH; solubility increases in acidic aqueous media (anilinium salt formation) and may decrease upon basification.

• Selection by task:

  • N-acylation/carbamoylation: DCM or THF with a base (DIPEA, pyridine). For greener profiles, use EtOAc or 2-MeTHF.
  • Electrophilic aromatic substitutions (e.g., nitration under mild conditions is disfavored by –CO2Et; for formylation or sulfonylation): Use acetic acid, nitromethane, or dichloroethane depending on reagent compatibility.
  • Metal-catalyzed couplings at the aniline (Buchwald–Hartwig to form anilides/diarylamines): Toluene, dioxane, CPME, or tAmylOH; ensure substrate solubility at reaction temperature.
  • Ester hydrolysis/amidation: MeOH/THF/H2O or dioxane/H2O for basic hydrolysis; DCM or MeCN for acid chloride formation followed by aminolysis.

• Comparison notes (general):

  • DCM vs EtOAc: DCM offers faster dissolution and lower bp for easy removal; EtOAc is greener and often sufficient for workups and extractions.
  • THF vs 2-MeTHF: Similar solvation; 2-MeTHF provides improved sustainability and phase-split advantages in aqueous workups.
  • Alcohols (MeOH/EtOH): Useful for salt formation of the aniline under HCl gas or HCl in alcohol for purification as anilinium salts.

Dry solvents can improve outcomes in acylations and metal-catalyzed reactions; degas when using air-sensitive catalysts.

Storage and Reconstitution

• Item-specific storage (from Product Data):

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

• General storage guidance (small-molecule aromatic esters/anilines; not a specification):

  • Store tightly capped in a dry place, protected from prolonged light. If long-term storage is planned, keep under inert atmosphere or include a desiccant to limit hydrolysis/oxidation.
  • Avoid exposure to strong acids/bases and moisture to prevent ester hydrolysis. For highly moisture-sensitive operations, consider transferring to a glovebox vial.

• Reconstitution/handling:

  • The compound dissolves in common organic solvents (e.g., DCM, EtOAc, MeOH, THF, acetone). Prepare stock solutions freshly; if solutions are stored, keep in amber vials at 2–8 C to minimize degradation.
  • Solid handling: If clumping occurs due to moisture uptake, gently dry under high vacuum at ambient temperature before use (verify no loss of integrity by NMR/HRMS).

Always refer to the lot-specific CoA/SDS for definitive storage and stability instructions.

Structure and Identity

Ethyl 2-amino-5-methoxybenzoate is an anthranilate-derived aromatic ester bearing an aniline (o-amino) and a meta-methoxy substituent relative to the ester carbonyl. The scaffold provides orthogonal reactivity at the aniline nitrogen, the aryl positions, and the ethyl ester.

• Item-specific identifiers (from Product Data):

  • SKU: E730013
  • CAS: 64018-98-0
  • InChIKey: 282813 (as provided; truncated/partial — full InChIKey not specified for this item; refer to CoA/Spec Sheet.)
  • Storage Conditions: Room temperature
  • Category: Chemical and Biochemical Reagents (research use only)

• Literature/computed identity (for reference; not item-specific specifications):

  • Preferred name: Ethyl 2-amino-5-methoxybenzoate
  • Synonyms (literature): Ethyl 2-aminovanillate isomer; Ethyl 5-methoxy-2-aminobenzoate
  • Molecular formula (literature): C10H13NO3
  • Molecular weight (literature): ~195.22 g/mol
  • Representative SMILES (literature): CCOC(=O)c1cc(OC)cc(N)c1
  • 2D structural description: A benzene ring bearing three substituents: at C1 an ethyl ester (–CO2Et), at C2 an amino group (–NH2) ortho to the ester, and at C5 a methoxy group (–OCH3) meta to the ester and para to the amino. No stereocenters; planar aromatic core.

• Functional groups and features:

  • Aromatic ester (benzoate ethyl ester)
  • Aromatic amine (aniline-type, ortho to the ester)
  • Anisole-type methoxy ether on the ring
  • Multiple directing groups for electrophilic aromatic substitution (–NH2 strongly activating/ortho,para-directing; –OMe activating/ortho,para-directing; –CO2Et deactivating/meta-directing).

Synthetic Utility

Key reactive elements enable a broad suite of downstream transformations:

• Aniline (–NH2):

  • Readily acylated or sulfonylated to give robust protecting/derivatizing groups (Ac, Boc via carbamate, Ts/Ns for chemoselective manipulations). N–N bond formation (e.g., azides via diazotization/azidation) or N-arylation (Buchwald–Hartwig) expands diversity.
  • Can be converted to diazonium salts enabling Sandmeyer substitutions to introduce halides, cyano, or trifluoromethyl groups (after proper positioning/activation).

• Methoxy (–OMe):

  • Serves as a latent phenol after demethylation (BBr3, AlCl3/thiols), granting access to salicylate-type motifs for etherification or esterification cascades.
  • Directs electrophilic substitutions; facilitates regioselective functionalization ortho/para to –OMe.

• Ethyl ester (–CO2Et):

  • Easily hydrolyzed to the acid; converted to amides using standard coupling reagents (HATU, EDCI, T3P). Can participate in intramolecular cyclizations with adjacent aniline/phenol after suitable activation to form benzoxazoles/benzimidazoles.

• Orthogonality and protecting-group strategy:

  • Sequence N-protection (e.g., Boc) before demethylation to avoid complications; carry ester through metal-catalyzed steps as a stable handle, then unmask at the end.

• Retrosynthetic value:

  • A convergent entry to 2-amino-5-methoxybenzoic acid derivatives; serves as a masked acid allowing late-stage diversification (amidation, Suzuki on aryl halide derivatives, etc.).

Target Specificity

Not applicable. This product is a small-molecule chemical reagent, not a biological targeting reagent (e.g., antibody, enzyme, or ligand with defined biological specificity). No antigen/epitope, species reactivity, clone, or isotype information applies.