3-(Ethoxymethyl)-4-methoxybenzoic acid - ≥97% , CAS No.723265-09-6

CAS: 723265-09-6 Cat. No.: E1043160 PubChem CID: 7131191

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Specifications & Purity

≥97%

Storage

Room temperature

Purity

≥97%

Names and Identifiers

Canonical Smiles

CCOCC1=C(C=CC(=C1)C(=O)O)OC

IUPAC Name

3-(ethoxymethyl)-4-methoxybenzoic acid

InChIKey

YAODNZKZSDFQHS-UHFFFAOYSA-N

INCHI

1S/C11H14O4/c1-3-15-7-9-6-8(11(12)13)4-5-10(9)14-2/h4-6H,3,7H2,1-2H3,(H,12,13)

Isomeric SMILES

CCOCC1=C(C=CC(=C1)C(=O)O)OC

PubChem CID

7131191

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Methoxybenzoic acids and derivatives
• Direct Parent: P-methoxybenzoic acids and derivatives
• Alternative Parents: Benzylethers Benzoic acids Phenoxy compounds Methoxybenzenes Benzoyl derivatives Anisoles Alkyl aryl ethers Dialkyl ethers Carboxylic acids Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: P-methoxybenzoic acid or derivatives - Benzoic acid - Benzylether - Anisole - Phenoxy compound - Benzoyl - Phenol ether - Methoxybenzene - Alkyl aryl ether - Ether - Dialkyl ether - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organooxygen compound - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 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

Chemical and Physical Properties

• Molecular Weight: 210.230 g/mol
• XLogP3: 1.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 210.089 Da
• Monoisotopic Mass: 210.089 Da
• Topological Polar Surface Area: 55.800 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 205.000
• 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. This product is not an antibody, enzyme, or kit with standardized bioassay protocols. For chemical applications, see the Reaction Conditions and Synthetic Utility sections for general laboratory guidance.

Biological Roles

Applicability note: This is a synthetic aromatic carboxylic acid building block without known intrinsic biological role.

General information (literature perspective)

• Structural class: Substituted benzoic acids are common motifs in natural products and xenobiotics, but 3-(ethoxymethyl)-4-methoxybenzoic acid itself is a man-made derivative used in chemical synthesis.
• Functional moieties:
  • Carboxylic acid groups can engage in ionic interactions and hydrogen bonding; in biological contexts they are often masked as esters to improve permeability (prodrug strategy in medicinal chemistry research). No claims are made for this specific compound.
  • Methoxy and benzylic ether substituents modulate electron density and lipophilicity, which can influence binding properties of derived analogues in screening libraries.

Research use limitation

• As stated in Product Data: For research use only. Not for human or veterinary use, diagnostics, or clinical applications.

Buffer Applications

Not typically applicable. 3-(Ethoxymethyl)-4-methoxybenzoic acid is not used as a buffering agent in biochemical assays. If aqueous handling is needed, it can be solubilized by forming the corresponding carboxylate salt with base; however, for buffering purposes consider dedicated buffers (e.g., phosphate, Tris, HEPES). Refer instead to the Synthetic Utility and Reaction sections for relevant uses.

Green Alternatives

Context: This product is a solid building block; “green alternatives” primarily concern solvent/reagent choices in its use rather than a substitute for the molecule itself.

Greener choices in common transformations (literature/practice)

• Amide couplings
  • Prefer carbodiimide-free strategies (e.g., T3P in EtOAc/2-MeTHF) or catalytic coupling with recyclable reagents where feasible.
  • Use greener solvents: 2-MeTHF or EtOAc over DMF/NMP when compatible.
• Esterification
  • Employ catalytic acids (e.g., methanesulfonic acid) in bio-based alcohols (EtOH) and remove water by azeotropy (Dean–Stark with 2-MeTHF) in place of toluene/benzene.
• Demethylation of aryl methoxy
  • Consider AlCl3/thiols or oxidative demethylations (e.g., ceric ammonium nitrate under aqueous acetonitrile) when compatible to avoid BBr3; note trade-offs in selectivity and waste.
• Benzylic ether cleavage
  • Aqueous Brønsted acids (H2SO4, HCl) in EtOH/H2O at controlled temperature can be milder/greener than halogenated Lewis acids; confirm substrate stability.

Illustrative comparison (general)

• Solvent: 2-MeTHF vs THF — similar polarity; 2-MeTHF has lower peroxide tendency and is biomass-derived; often superior for extractions.
• Solvent: EtOAc vs DCM — EtOAc offers lower toxicity and is readily biodegradable; check solubility/loading.

Trade-offs

• Greener media may reduce solubility or reaction rate; small-scale scouting and DoE can identify viable conditions while minimizing hazardous solvent usage.

Pharmaceutical Uses

Applicability note: No pharmacopeial grade or excipient designation is provided for this item; it is intended for research use only.

General formulation/manufacturing context (literature/general)

• Role as an intermediate: Substituted benzoic acids are frequently used as intermediates toward active pharmaceutical ingredient (API) candidates and analog libraries via amide coupling or esterification. This compound’s orthogonal handles (acid, aryl methoxy, benzylic ether) permit stepwise diversification.
• Salt formation: For purification or crystallinity control in discovery chemistry, transient formation of carboxylate salts (e.g., sodium, triethylammonium) can aid isolation or enable aqueous processing; these are process aids rather than final drug substances.
• No medical or therapeutic claims are made for this compound.

Physical Properties

Item-specific (from Product Data)

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Storage conditions: Room temperature (as provided)

Hazard/Molecular data fields in Product Data

• 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 (general reference values; not item-specific specifications)

• Approximate molecular formula and weight: C11H14O4; MW ~210.23 g/mol (computed from structure)
• Acid/base: Contains a benzoic acid moiety (weak acid; pKa of unsubstituted benzoic acids typically ~4.0–4.5, literature). Electron-donating methoxy/benzylic ether may slightly modulate acidity.
• Solubility (qualitative, literature expectations):
  • Likely sparingly soluble in water at neutral pH; increased solubility in basic aqueous media (formation of carboxylate salt).
  • Expected good solubility in polar organic solvents (MeOH, EtOH, acetone, acetonitrile) and moderate in less polar solvents (EtOAc, DCM); limited in alkanes.
• Partitioning: Aryl ether + carboxylic acid suggests moderate lipophilicity in neutral form; ionizes in base.
• Phase/thermal: Solid is expected at ambient conditions for analogous substituted benzoic acids; exact MP/BP: Not specified for this item; refer to CoA/Spec Sheet.
• Other common parameters (density, refractive index, UV cutoff, water content): Not specified for this item; refer to CoA/Spec Sheet.

Quality & Grades

Item-specific (from Product Data)

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

Guidance on quality considerations (general; for planning purposes)

• Identity confirmation: Verify by NMR (1H: diagnostic signals for benzylic –CH2–O–, ethoxy –CH3 triplet, –OCH3 singlet, aromatic pattern 1,3,4-trisubstituted), IR (broad O–H and C=O ~1680–1720 cm−1), and HRMS.
• Purity assessment: HPLC/UPLC with UV detection (aromatic chromophore). If HPLC-grade specifications (e.g., low UV baseline) are required for analytical uses, confirm via CoA—do not assume.
• Stabilizers/inhibitors: None specified for this item. If necessary, add-ons (e.g., desiccants) should be evaluated for compatibility with carboxylic acids.
• Trace limits (metals, water, peroxides, UV cutoffs): Not specified for this item; refer to CoA/Spec Sheet.
• Lot-to-lot consistency: For synthetic building blocks, review CoA for assay, residual solvents, and related-substance profile judged against project tolerances.
• Regulatory status: Not pharmacopeial grade unless explicitly stated. For GMP or regulated workflows, qualify via your quality system and vendor documentation.

Reaction & Applications

Scope and role (general; expand-from-manufacturer intent)

• Versatile aromatic building block combining a benzoic acid handle with a para-methoxy group and a meta-benzylic ether (ethoxymethyl, EOM). Useful in medicinal chemistry and materials synthesis where orthogonal reactivity is advantageous.

Representative applications (literature/general)

• Amide formation: Convert the carboxylic acid to amides with amines using EDC·HCl/HOBt, HATU, or CDI. The para-methoxy is typically inert; the benzylic ether survives mild coupling conditions.
• Esterification: Fisher esterification in the corresponding alcohol; or DCC/DMAP-mediated Steglich esterification under milder conditions.
• Cross-coupling after activation: Transform to acid chloride (SOCl2, oxalyl chloride) followed by acylation or coupling (e.g., to form aryl amides/ketones via acylation of organometallics—use caution due to acid sensitivity of ether).
• Demethylation of aryl –OMe: BBr3 or BCl3 (DCM, −78 to 0 °C) to access the 4-hydroxy analogue, enabling subsequent etherification, sulfonylation, or metalation.
• Benzylic ether transformations: The –CH2–OEt can be hydrolyzed/cleaved under acidic or Lewis-acid conditions to reveal benzyl alcohol (–CH2OH), which can be oxidized (e.g., to aldehyde via Dess–Martin or MnO2) or converted to halides (PBr3) as a handle for C–C bond formation.
• Directed metalation/sequestration: The methoxy substituent is ortho-directing; however, the acid function deactivates and complicates strong-base metalations—protect as an ester if ortho-functionalization is pursued.
• Library synthesis: Provides divergent routes to amides/esters combined with benzylic functional group interconversion (FGI), supporting SAR exploration.

Practical tips

• Maintain anhydrous conditions for coupling and Lewis-acid steps. For steps impacting the benzylic ether, perform small-scale trials to confirm stability/selectivity.

Reaction Conditions

General literature guidance (illustrative; not item-specific specifications)

• Amide coupling
  • Solvent: DMF, DCM, or MeCN.
  • Reagents: EDC·HCl (1.2–1.5 eq) + HOBt/HOAt (0.1–0.2 eq) or HATU (1.1–1.2 eq) with DIPEA (2–3 eq).
  • Temperature/time: 0–25 °C, 2–16 h. Monitor by TLC/HPLC. Typical yields for analogous substrates: 60–95% depending on amine.
• Esterification (Fischer)
  • Solvent/reagent: Neat alcohol (MeOH/EtOH) with catalytic H2SO4 or TsOH; azeotropic water removal if needed (2-MeTHF Dean–Stark for higher alcohols).
  • Temperature/time: Reflux, 2–24 h. Work up by neutralization and extraction.
• Acid chloride formation
  • Reagent: SOCl2 (3–5 eq) with a catalytic DMF drop; solvent-free or DCM.
  • Temperature/time: 0–25 °C then gentle reflux 1–3 h. Distill off excess SOCl2; quench carefully.
• Demethylation of aryl –OMe
  • Reagent: BBr3 (1–3 eq per –OMe) in anhydrous DCM.
  • Temperature/time: −78 to 0 °C addition, then 0–25 °C for 1–6 h. Quench with MeOH/water at low temperature. The benzylic ether may also be affected under harsh conditions—scout conditions.
• Benzylic ether cleavage (to –CH2OH)
  • Conditions: Aqueous mineral acid (e.g., 1–3 M HCl) in EtOH/H2O, 50–80 °C, or Lewis acids (e.g., BCl3) at low temperature. Selectivity must be verified against the aryl –OMe group.
• Oxidation of –CH2OH (after cleavage)
  • Reagents: MnO2 (DCM), Dess–Martin (DCM), or Swern (DMSO/oxalyl chloride) to aldehyde; NaClO2 (pH 6) or Pinnick to acid if needed.

Notes

• Use anhydrous conditions for couplings and Lewis acid steps. Employ bases (DIPEA, TEA) judiciously to avoid ether cleavage.
• Always confirm compatibility of the benzylic ether with the chosen conditions on small scale.

Safety & Handling

Item-specific (from Product Data)

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
• Storage: Room temperature (per Product Data)

General safety guidance (literature/standard laboratory practice; defer to SDS)

• Likely hazards: Aromatic carboxylic acids with ether substituents are typically of low acute toxicity but can cause eye/skin irritation. Dust may cause respiratory irritation.
• PPE: Wear lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Use in a fume hood to avoid dust/inhalation.
• Handling: Avoid generating dust and contact with strong oxidizers. For weighing, use antistatic measures and closed containers.
• Incompatibilities: Strong oxidizing agents (risk of exotherm/oxidation), strong bases (forms carboxylate salts; may promote ether cleavage under forcing conditions), strong acids (can catalyze cleavage of benzylic ether and demethylation with halide Lewis acids such as BBr3—reaction risk, not a storage condition).
• First aid overview: If on skin/eyes—rinse with water for 15 minutes. If inhaled—move to fresh air. If ingested—rinse mouth; do not induce vomiting; seek medical attention. Always consult the SDS for definitive instructions.
• Fire safety: Organic solids may burn; use CO2, dry chemical, or foam. Combustion may release CO/CO2 and phenolic/benzylic fragments.
• Waste: Dispose of in accordance with institutional and local regulations for organic laboratory waste.

Solvent Selection

Applicability note: This product is a solid aromatic carboxylic acid building block, not a solvent. Solvent choice pertains to its dissolution and use in reactions/purifications.

General solvent guidance (literature/practice)

• Polarity needs: The acid function and aryl ethers favor polar aprotic or polar protic solvents for dissolution.
• Common solvents for dissolution and reactions:
  • Polar protic: MeOH, EtOH, i-PrOH (good solubility; enable esterification/transesterification under acid catalysis).
  • Polar aprotic: DMF, DMSO, NMP, MeCN (excellent for amide coupling; ensure anhydrous grades where needed).
  • Moderately polar: THF, 2-MeTHF, EtOAc, DCM (useful for extractions and some reactions; may require mild warming to fully dissolve).
  • Aqueous basic media: Solubility increases markedly as the carboxylate salt (pH > pKa).
• Selection tips:
  • For amide couplings (EDC/HATU): DMF, DCM, or MeCN are typical. Add base (DIPEA) as required.
  • For esterification: Use the corresponding alcohol solvent (e.g., MeOH) with acid catalysis (H2SO4 or HCl gas) and water removal.
  • For demethylation (aryl –OMe to –OH): DCM or toluene under Lewis acid conditions (e.g., BBr3) is common; strictly anhydrous.
• Workup/purification: Acid-base extraction exploits the carboxyl function (alkaline wash to remove unreacted acid). Silica gel chromatography with gradients of hexanes/EtOAc or DCM/MeOH is typical.

Storage & Reconstitution

Item-specific (from Product Data)

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

General guidance (literature/practice)

• Physical form: Likely supplied as a solid. Keep container tightly closed, protected from moisture and direct light.
• Stability: Aromatic carboxylic acids and aryl ethers are generally stable under ambient dry conditions. Avoid prolonged exposure to strong acids/bases that may induce ether cleavage.
• Hygroscopicity: Not expected to be strongly hygroscopic, but store with desiccant if opening frequently.
• Reconstitution/dissolution: For stock solutions, dissolve in dry organic solvents (DMF, DMSO, MeOH, EtOH, DCM, or EtOAc) as appropriate. Filter if particulates are observed. Record solvent, concentration, and date.
• Solution storage: If solutions are prepared, store in amber vials at 2–8 °C for short term, or at −20 °C for longer term. Bring to ambient temperature before opening to minimize moisture ingress.
• For research use only (per Product Data).

Structure & Identity

Brief description: 3-(Ethoxymethyl)-4-methoxybenzoic acid is a para-methoxy, meta-ethoxymethyl substituted benzoic acid bearing both ether and carboxylic acid functionalities on an aromatic ring.

Item-specific (from Product Data)

• Product name: 3-(Ethoxymethyl)-4-methoxybenzoic acid (SKU: E1043160)
• CAS: 723265-09-6
• PubChem CID: 7131191
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed identification (for reference; not item-specific specs)

• Molecular formula (derived from structure): C11H14O4 (literature/computed)
• Molecular weight: ~210.23 g/mol (literature/computed)
• Core scaffold: substituted benzoic acid (benzene ring bearing –CO2H)
• Functional groups: carboxylic acid (–CO2H), aryl methoxy (–OCH3 at 4-position), benzylic ether (–CH2–O–CH2CH3 at 3-position)
• Regiochemistry: 1,3,4-trisubstituted ring (carboxyl at C1; ethoxymethyl at C3 meta to –CO2H; methoxy at C4 para to –CO2H)

2D structure description (verbal)

• A benzene ring with: position-1 carboxylic acid; position-4 methoxy directly bound to the ring oxygen; position-3 benzylic methylene (–CH2–) linking to an ethoxy group (–O–CH2CH3). No stereocenters; molecule is achiral.

Synthetic Utility

Key reactive features (literature/general)

• Carboxylic acid (–CO2H): amenable to activation (acid chlorides, anhydrides), coupling (EDC/HATU/CDI), esterification, Curtius/Schmidt-like rearrangements after activation.
• Aryl methoxy (–OMe): an electron-donating, ortho/para-directing group; can be demethylated (BBr3/BCl3) to a phenol for further derivatization (etherification, acylation, sulfonylation).
• Benzylic ether (–CH2–O–Et): a masked benzyl alcohol. Cleavage or transetherification yields –CH2OH, enabling oxidation (MnO2/Swern/Dess–Martin) or conversion to halides (PBr3) for benzylic substitution or cross-coupling after further transformation.

Strategic applications

• Divergent synthesis: From a single scaffold, access amides/esters (acid handle), phenolic derivatives (demethylation), and benzylic functionalizations (FGI of –CH2–OEt). This supports SAR matrices in medicinal chemistry.
• Protecting group logic: If the phenol (after demethylation) must be preserved during amide couplings, keep the benzylic ether intact; alternatively, reveal –CH2OH first and protect as carbonate/ether for orthogonality.
• Retrosynthetic value: The scaffold can arise from alkylation of a 3-(hydroxymethyl)-4-methoxybenzoate with bromoethane under Williamson conditions, or by electrophilic substitution on anisic acid derivatives followed by functional group interconversions.

Select cautions

• Strong acids/Lewis acids may cleave the benzylic ether; plan sequence accordingly.
• During acid chloride formation (SOCl2/oxalyl chloride), control temperature and add catalytic DMF judiciously; verify stability of the benzylic ether under these conditions.

Target Specificity

Not applicable. This product is a small-molecule chemical, not a biological affinity reagent. No antigen/epitope/clone/isotype information applies.