4-Methoxy-2-(2-methoxyethoxy)benzoic acid - ≥95% , CAS No.87359-71-5

CAS: 87359-71-5 Cat. No.: M1008014 Formula: C₁₁H₁₄O₅ Peso molecolare: 226.230

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: COCCOC1=C(C=CC(=C1)OC)C(=O)O
• IUPAC Name: 4-methoxy-2-(2-methoxyethoxy)benzoic acid
• InChIKey: FDLGCDVIMKHWSZ-UHFFFAOYSA-N
• INCHI: 1S/C11H14O5/c1-14-5-6-16-10-7-8(15-2)3-4-9(10)11(12)13/h3-4,7H,5-6H2,1-2H3,(H,12,13)
• Peso molecolare: 226.230

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 P-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: P-methoxybenzoic acids and derivatives
• Alternative Parents: 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 - Anisole - Phenoxy compound - Benzoyl - Phenol ether - Methoxybenzene - Alkyl aryl ether - Ether - Dialkyl ether - Carboxylic acid - Carboxylic acid derivative - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Descrizione: 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

Proprietà chimiche e fisiche

• Peso molecolare: 226.230 g/mol
• XLogP3: 1.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 226.084 Da
• Monoisotopic Mass: 226.084 Da
• Topological Polar Surface Area: 65.000 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 218.000
• 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

No vendor-validated bioassay protocols are provided for this small-molecule reagent.

• General guidance

  • For stock preparation in biological assays, dissolve first in DMSO or ethanol to make a concentrated stock (e.g., 10–100 mM), then dilute into the assay buffer/media with vigorous mixing; ensure final cosolvent content is compatible with the system
  • Filter sterilize through 0.22 µm if sterility is required; confirm solubility at working pH and ionic strength

• Analytical use

  • For HPLC/LC–MS method development, prepare calibration solutions in MeOH, MeCN, or DMSO and store aliquots protected from moisture; monitor for adsorption to plastics due to aromaticity and moderate lipophilicity

• Note

  • Any specific application conditions should be established empirically by the researcher.

Biological Roles

This product is provided strictly for research use. No biological activity or clinical use is claimed.

• General biochemical context (literature/analogues)

  • Aromatic carboxylic acids bearing methoxy/alkoxy groups are common motifs in natural products and metabolite derivatives (e.g., anisic/syringic acid families); their physicochemical properties influence membrane partitioning and protein binding
  • The carboxylate/neutral acid equilibrium around mildly acidic pH affects permeability and ion-pairing; ether substituents may enhance solubility in mixed aqueous/organic media

• Experimental utility

  • Can serve as a model compound to study acid–base partitioning, ionization effects on chromatographic retention, and derivatization strategies for LC–MS method development
  • The electron-rich aryl core is useful for evaluating electrophilic substitution selectivity trends in teaching or research labs

• Note

  • Any specific receptor interactions, enzyme inhibition, or biological pathways for this exact compound are not established here and should be evaluated empirically by the researcher if relevant to their study.

Buffer Applications

This compound is not a standard buffering reagent.

• Practical notes (general)

  • The carboxylic acid pKa for analogous anisic acids is typically in the ~4.3–4.7 range (literature), implying potential buffering capacity around pH 3.3–5.7. However, limited aqueous solubility of the neutral acid can constrain utility as a primary buffer component.
  • If a benzoate buffer is desired for method development, sodium or ammonium salts may be prepared in situ for increased solubility; verify compatibility with your analytical detection (UV/MS) and system materials.

• Recommendation

  • For robust buffering, consider dedicated systems (acetate, citrate, MES) rather than this specialized aromatic acid. Use this compound where its chemical structure is specifically required (e.g., as an analyte or derivatization target).

Green Alternatives

Green chemistry considerations center on solvent and coupling-reagent choices rather than the substrate itself.

• Preferable solvents (literature guidance)

  • Replace DCM with EtOAc or 2-MeTHF where feasible (similar polarity, improved environmental profile)
  • Consider MeCN or CPME instead of THF for peroxide risk mitigation and lower VOC impact in some settings
  • Use water/MeOH for salt-form manipulations (carboxylate formation) to enable aqueous processing

• Greener activation and coupling

  • Use EDC·HCl with catalytic DMAP in water-miscible media to avoid urea waste from DCC
  • T3P (propylphosphonic anhydride) offers low-toxicity byproducts and simplified workup for amidations/esterifications
  • Enzymatic esterification in green solvents (2-MeTHF, EtOAc) may be feasible for certain alcohol partners

• Comparison snapshot (general)

  • DCM vs EtOAc: EtOAc is biodegradable, low toxicity; DCM provides faster extractions but higher environmental/health concerns
  • DMF vs MeCN: MeCN has lower boiling point and improved removal; DMF offers broader solvency but is under tighter regulatory control
  • DCC vs EDC/T3P: Avoids insoluble DCU waste and reduces hazard profile

• Energy and waste

  • Favor room-temperature couplings and catalytic methods (DMAP, Sc(OTf)3) to reduce energy use
  • Employ in-process salt switches (acid/base extractions) to minimize chromatographic solvent consumption.

Pharmaceutical Uses

For research use only. No therapeutic or clinical claims are made for this product.

• Formulation/excipient context (general)

  • Aromatic carboxylic acids of this type are not typical excipients. Their primary value in pharmaceutical R&D is as synthetic intermediates for structure–activity relationship exploration or as reference materials in analytical method development.

• Process chemistry relevance (literature)

  • The benzoic acid function enables convergent coupling to amines/alcohols to generate amide/ester analogs during lead optimization
  • The ether-rich substituents modulate lipophilicity and solubility, allowing fine-tuning of physicochemical properties when incorporated into target molecules

• Regulatory status

  • No compendial monograph is implied. Any GMP or pharmacopeial suitability would require separate qualification and vendor documentation (not provided here).

Physical Properties

Item-specific specifications are not provided in the Product Data; consult the CoA/Specification Sheet for certified values.

• Item-specific (Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature calculation: ~226.23 g/mol for C11H14O5.)

• Literature/expected properties for closely related anisic acids and aryl carboxylic acids with ether substituents (informational, not product specifications)

  • Physical state: typically crystalline solid or low-melting solid for analogous compounds
  • Acid dissociation: pKa (carboxyl) commonly ~4.3–4.7 for para-methoxybenzoic acids; additional ortho-alkoxy may slightly raise pKa due to electron donation
  • Solubility profile: low in neutral water as the free acid; readily soluble in polar organics (MeOH, EtOH, acetone, acetonitrile, DMSO, DMF, DCM, EtOAc); highly soluble in basic aqueous media as the carboxylate salt
  • Partitioning: multiple ether groups generally increase polarity versus unsubstituted anisates; expect moderate lipophilicity with good organic solvent compatibility
  • UV characteristics: aromatic acids with anisole substituents typically show strong absorbance in the 200–280 nm region (literature). Exact UV cutoff/ε: Not specified for this item; refer to CoA/Spec Sheet.
  • Boiling/melting point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

• Practical handling note (general)

  • Free acids often exhibit broadened, concentration-dependent solubility; dissolution is rapid in a small volume of DMSO or base, then dilute with the working solvent.

Quality and Grades

• Item-specific (Product Data)

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Research Use Note: For research use only

• Guidance on grades (general information for context)

  • Research-grade small molecules are typically assayed by HPLC/GC/1H NMR for identity and purity. If labeled as “analytical” or “HPLC grade,” that would imply control of UV-absorbing impurities suitable for chromatographic applications; such designations are not specified for this item.
  • If a stabilizer or hydrate/solvate form were present, that would be declared on the specification. None is stated in the Product Data.

• What to check on receipt (practical tips)

  • Review CoA for purity assay, identity (1H/13C NMR, MS), water content (if reported), and residual solvents. Where exact limits are critical, request current batch CoA.
  • For reactions sensitive to protic impurities (e.g., coupling via mixed anhydrides), pre-dry under vacuum and verify by KF titration if needed (limits: Not specified for this item; refer to CoA/Spec Sheet).

Reaction and Applications

As a functionalized benzoic acid with two ether substituents, this molecule is a versatile building block for derivatization of the acid and for transformations that leverage an electron-rich anisole ring.

• Transformations of the carboxylic acid (literature)

  • Amide coupling: EDC·HCl/HOBt, HATU/DIPEA, or T3P to access benzamides bearing ortho/para alkoxy donors; useful in library synthesis
  • Esterification: Fischer (ROH/H+), Steglich (DCC/DMAP) for mild conditions; selective formation of alkyl aryl esters
  • Acid chloride: SOCl2 or (COCl)2 (cat. DMF) to give the corresponding benzoyl chloride; enables acylation of alcohols/amines
  • Curtius rearrangement: activation to acyl azide (e.g., DPPA) to access isocyanates, ureas, or carbamates
  • Decarboxylative couplings: photoredox/Ni- or Cu-catalyzed decarboxylative arylations/alkylations from activated carboxylates (e.g., NHPI esters)

• Ring-based chemistry (literature)

  • Electrophilic aromatic substitution: the two alkoxy groups (o, p-directing) increase ring electron density; however, substitution sites are limited by existing ortho/para occupancy
  • Directed metalation can be challenging due to strong electron donation and potential coordination by the ortho-ether; protection or halogenation-first strategies are typical

• Application contexts (general)

  • Synthesis of anisate-derived ligands, monomers, and advanced intermediates where solubility-tuning ether arms are desired
  • Preparation of PEG-like ester/amide conjugates leveraging the 2-(2-methoxyethoxy) handle for polarity modulation

• Practical tips

  • For acid chloride formation, remove residual SOCl2/oxalyl chloride thoroughly to prevent downstream side reactions
  • In couplings, include catalytic DMAP for hindered alcohols; monitor for O→N acyl transfer if using HOBt/HOAt systems.

Reaction Conditions

General literature guidance for reactions commonly applied to substituted benzoic acids like this compound. These are not product-specific specifications.

• Amide coupling

  • EDC·HCl (1.1–1.5 equiv), HOBt or Oxyma (0.1–1.0 equiv), amine (1.0–1.5 equiv), base (DIPEA 2–3 equiv); solvent: DMF, DCM, or MeCN; 20–25 °C; 2–16 h; typical isolated yields 70–95% depending on sterics
  • HATU (1.1–1.3 equiv) with DIPEA in DMF/NMP for hindered amines at 0–25 °C

• Esterification

  • Fischer: ROH (5–20 equiv) with catalytic H2SO4 or p-TsOH; reflux (MeOH: 50–65 °C; EtOH: 78 °C); 2–24 h
  • Steglich: DCC (1.1–1.3 equiv), DMAP (0.1 equiv) in DCM/DMF at 0–25 °C; 2–18 h

• Acid chloride formation

  • SOCl2 (3–5 equiv) or (COCl)2 (2–3 equiv), catalytic DMF, solvent DCM or toluene; 0–25 °C to reflux; 1–4 h; remove excess reagent under reduced pressure; use immediately

• Curtius rearrangement

  • DPPA (1.1–1.3 equiv), base (triethylamine), toluene or PhMe/DMF; 60–110 °C; trap isocyanate with alcohols/amines

• Decarboxylative coupling (redox-active esters)

  • Prepare NHPI ester (DCC/DMAP or EDC/DMAP), then Ni/photoredox cross-couplings under blue LEDs in MeCN/DMF with tertiary amines; ambient to 40 °C; 6–24 h

• Workup tips

  • Use pH-switching (acid/base extractions) to separate unreacted acid vs neutral/ionic products; monitor by TLC/HPLC. Ensure removal of DCU (if DCC used) by filtration prior to aqueous workup.

Safety and Handling

Always read the SDS before use. The following guidance is general for aromatic carboxylic acids with ether substituents.

• Item-specific (Product Data)

  • GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
  • Storage conditions: Room temperature (per Product Data)
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• General hazards (literature/analogues)

  • May cause skin/eye irritation; dust may irritate the respiratory tract
  • Low volatility; ingestion or high-dose exposure can cause GI irritation
  • Not known as a strong oxidizer/reducer; incompatible with strong bases/acids (reaction/neutralization), strong oxidants, and acylation/chlorination reagents unless in a controlled synthetic context

• PPE and engineering controls

  • Wear lab coat, safety glasses or goggles, and suitable gloves (e.g., nitrile)
  • Handle powders in a fume hood to minimize dust inhalation; avoid aerosol formation

• First aid (general)

  • Eye/skin contact: rinse with water for at least 15 min; remove contaminated clothing; seek medical attention if irritation persists
  • Inhalation: move to fresh air; seek medical advice if symptoms occur
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention

• Stability and reactivity (general)

  • Stable under ambient lab conditions when kept dry and protected from strong reagents; no known tendency for peroxide formation
  • Carboxylic acids can slowly esterify in alcohols under acidic conditions; avoid strong dehydrating acids unless intended.

Solvent Selection

This compound is an aromatic carboxylic acid bearing two ether substituents; it shows amphiphilic behavior: a polar acid headgroup and moderately lipophilic, ether-rich aryl moiety.

• Polarity/miscibility (literature-informed)

  • Expected to dissolve well in polar organics (DMSO, DMF, MeOH, EtOH, acetone, acetonitrile, EtOAc, DCM)
  • Poorly soluble in neutral water as a free acid; forms water-soluble carboxylate salts in basic aqueous media (e.g., pH > 7.5 with NaOH/TEA)

• Choosing solvents by task

  • Stock solutions: DMSO (50–200 mg/mL common), DMF, or MeOH for subsequent dilution
  • Acid chloride formation: anhydrous toluene, DCM, or neat SOCl2/oxalyl chloride with catalytic DMF
  • Amide couplings (EDC/HOBt, HATU): DMF, NMP, DCM, or MeCN with a tertiary amine base
  • Esterifications: MeOH/EtOH with catalytic acid; Dean–Stark in toluene for higher-boiling alcohols
  • Aqueous workups: adjust pH to switch between organic and aqueous phases via acid/base extraction

• Quick comparison (general)

  • DMSO vs DMF: DMSO gives rapid dissolution and is greener but higher boiling; DMF offers lower viscosity and easier removal but greater regulatory scrutiny
  • EtOAc vs DCM: EtOAc is a greener, biodegradable alternative; DCM provides superior solvency for rapid phase separations

• Drying advice

  • If anhydrous conditions are required (e.g., acid chloride formation), pre-dry solid under vacuum at ambient temperature; dry solvents over molecular sieves.

Storage and Reconstitution

• Item-specific (Product Data)

  • Storage conditions: Room temperature

• General storage guidance

  • Keep tightly closed in a dry, well-ventilated place; protect from moisture and strong acids/bases or oxidants
  • If long-term storage is planned, consider desiccation and protection from light to minimize potential slow degradation or discoloration common to some anisole derivatives

• Reconstitution and stock solutions

  • Prepare concentrated stocks in DMSO, DMF, MeOH, or EtOH; typical laboratory stocks: 10–200 mg/mL depending on solvent and intended use
  • For aqueous applications, dissolve in a minimal amount of organic solvent or convert to a soluble salt by neutralizing with equimolar base (e.g., NaOH, TEA), then dilute with water or buffer
  • Filter if particulate persists; warming to 30–40 °C and sonication can aid dissolution (avoid prolonged heating of neat solids)

• Stability after reconstitution (general)

  • Organic solvent stocks are commonly stable for weeks at 2–8 °C in sealed vials; for longer durations, store aliquots at −20 °C to minimize freeze–thaw cycles. Exact stability for this item: Not specified; refer to CoA/Spec Sheet.

• Shipping

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

Structure and Identity

Research-use aromatic carboxylic acid bearing two ether substituents on the ring.

• Item-specific (Product Data)

  • SKU: M1008014
  • Product name: 4-Methoxy-2-(2-methoxyethoxy)benzoic acid
  • CAS: 87359-71-5
  • CID: 13450766
  • InChIKey: 79861 (as provided; full standard InChIKey not specified for this item)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature (structure description)

  • Core scaffold: substituted benzoic acid (benzenecarboxylic acid)
  • Substitution pattern: carboxyl at C1; a 2-(2-methoxyethoxy) group at the ortho (C2) position; a methoxy group at the para (C4) position
  • Functional groups: carboxylic acid (–CO2H); anisole-type methoxy (–OCH3); ortho ether chain (–O–CH2–CH2–O–CH3)
  • Stereochemistry: achiral; no stereocenters
  • 2D description: a benzene ring with –CO2H at C1, –O–CH2–CH2–O–CH3 at C2, and –OCH3 at C4 (para to –CO2H)

• Computed/literature (formula & mass; for reference only)

  • Empirical formula (computed from name): C11H14O5 (literature/structure-derived)
  • Relative molecular mass: ~226.23 g/mol (literature, calculated from C11H14O5)

• General notes

  • The two electron-donating alkoxy substituents render the ring electron-rich and strongly ortho/para-directing in electrophilic aromatic substitution (literature).

Synthetic Utility

Key reactivity arises from the carboxylic acid handle and the electron-rich anisole ring bearing an ortho 2-(2-methoxyethoxy) substituent.

• Functional group interconversions (literature)

  • Acid → amide/ester: EDC/HOBt, HATU, DCC/DMAP, or acid chloride pathways
  • Acid → acyl azide → isocyanate (Curtius) → ureas/carbamates
  • Acid → mixed anhydrides for selective acyl transfer
  • Acid → NHPI redox-active ester for decarboxylative couplings (Ni/photoredox)

• Arene chemistry

  • The dual alkoxy substitution enhances electron density; further electrophilic substitution is limited by site availability but can allow halogenation or nitration at remaining activated positions under controlled conditions
  • O-Dealkylation of methoxy groups (e.g., BBr3) could reveal phenols for subsequent diversification, though the ortho-ether may be sensitive; conditions must be screened

• Retrosynthetic value

  • Serves as a masked “anisole + short PEG” synthon; downstream amide/ester derivatives can introduce polarity without sacrificing aromatic character

• Protecting group compatibility

  • Carboxyl can be masked as methyl/benzyl esters; aryl ethers are generally stable to many bases/nucleophiles but can cleave under strong Lewis acids (BBr3, AlCl3) or hot HI.

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 target specificity). No target, epitope, clone, or isotype information applies.