Ethyl 2,4-dimethoxybenzoate - ≥95% , CAS No.81722-07-8

CAS: 81722-07-8 Cat. No.: E1020527 分子式: C₁₁H₁₄O₄ 分子量: 210.23 PubChem CID: 12908893

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

仕様と純度

≥95%

保管条件

Room temperature

純度

≥95%

名前と識別子

• カノニカル・スマイル: CCOC(=O)C1=C(C=C(C=C1)OC)OC
• IUPAC Name: ethyl 2,4-dimethoxybenzoate
• InChIKey: HITNTFQLHYWLDI-UHFFFAOYSA-N
• INCHI: 1S/C11H14O4/c1-4-15-11(12)9-6-5-8(13-2)7-10(9)14-3/h5-7H,4H2,1-3H3
• 異性体SMILES: CCOC(=O)C1=C(C=C(C=C1)OC)OC
• PubChem CID: 12908893
• 分子量: 210.23

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • 分類 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
• 分類: 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: O-methoxybenzoic acids and derivatives Dimethoxybenzenes Benzoic acid esters Phenoxy compounds Benzoyl derivatives Anisoles Alkyl aryl ethers Carboxylic acid esters Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: O-methoxybenzoic acid or derivatives - P-methoxybenzoic acid or derivatives - Benzoate ester - Dimethoxybenzene - M-dimethoxybenzene - Anisole - Phenoxy compound - Benzoyl - Phenol ether - Methoxybenzene - Alkyl aryl ether - Carboxylic acid ester - Ether - Carboxylic acid derivative - Organic oxygen compound - Organooxygen compound - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound
• 説明: 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

化学的性質と物理的性質

• 分子量: 210.230 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 210.089 Da
• Monoisotopic Mass: 210.089 Da
• Topological Polar Surface Area: 44.800 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

No assay/application protocols are provided in the product data. For general synthetic use, representative workflows include:

• Hydrolysis then amide coupling: Dissolve substrate in MeOH/H2O, saponify with NaOH, isolate the acid, and couple using HATU/DIPEA in DMF with the desired amine.
• O-Demethylation sequence: Cool dry DCM, add BBr3 dropwise to a solution of the ester at low temperature, allow to warm, and quench carefully; isolate the phenolic ester for further derivatization.

These are literature-type procedures intended as starting points; adapt to your substrate and consult primary references.

Biological Roles

This product is intended for research and synthetic chemistry. No specific biological role is assigned in the product data.

General context (not product-specific claims):

• Aromatic benzoate esters with methoxy substituents are common motifs in natural product derivatives and serve as protected forms of methoxy-/phenolic benzoic acids in biosynthetic and medicinal chemistry studies.
• O-Demethylation yields phenolic acids/esters that can interact in hydrogen-bonding networks relevant to supramolecular assemblies and materials used in biochemical assays.
• In enzymology studies, aryl esters can be used as model substrates to probe esterases or lipases, although activity strongly depends on steric/electronic features and solvent composition.

Note: No clinical, diagnostic, or therapeutic uses are implied. Refer to the Research Use Note: For research use only.

Buffer Applications

Not typically applicable. Ethyl 2,4-dimethoxybenzoate is a neutral, poorly water-soluble aromatic ester and is not used as a buffering agent. For aqueous work, consider the corresponding acid (after hydrolysis) if solubility permits, or conventional buffer systems (phosphate, acetate, TRIS, HEPES) appropriate to your pH range.

Green Alternatives

While Ethyl 2,4-dimethoxybenzoate itself is a substrate/building block rather than a solvent, greener choices can be made in transformations and workups involving this compound.

Greener solvent options (literature/general):

• Replace chlorinated solvents (e.g., DCM) with EtOAc or 2-MeTHF where compatible (for extractions, chromatography, and some reactions).
• Use CPME or 2-MeTHF in place of THF for reactions needing ether solvents (better peroxide stability and often improved recyclability), mindful of solubility and rate changes.
• Favor MeOH/EtOH–water mixtures for saponification instead of purely aprotic media.

Comparison snapshot (general):

• DCM vs EtOAc: EtOAc is less toxic and biodegradable; suitable for many ester transformations and extractions but has higher polarity and bp.
• THF vs 2-MeTHF/CPME: Green ethers reduce energy and safety burdens; can alter reaction rates/selectivity.
• Hexanes vs Heptane/i-PrOAc: Heptane and isopropyl acetate are greener alternatives for nonpolar elution.

Process considerations:

• Minimize excess strong Lewis acids for demethylation; consider catalytic or milder reagents (e.g., iodide-mediated, MgI2/Me3SiCl systems) when compatible.
• Implement solvent recycling and reduced chromatographic solvent volumes (e.g., crystallization of the hydrolyzed acid when feasible).
• Where possible, use biocatalytic ester interchange or amidation to reduce harsh reagents and energy input.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided for this item. Not specified for this item; refer to CoA/Spec Sheet.

Context (non-clinical, formulation/manufacturing perspective):

• As a synthetic intermediate, this ester can be hydrolyzed to 2,4-dimethoxybenzoic acid and further elaborated to amides/esters frequently encountered in medicinal chemistry libraries.
• The ethyl ester can function as a protecting/transport form of the acid during multi-step synthesis, offering better organic solubility and handling.

Important: This product is for research use only; no therapeutic, diagnostic, or clinical applications are claimed or supported.

Physical Properties

Item-specific numerical specifications (bp, mp, density, UV cutoff, metal/peroxide/water limits, etc.): Not specified for this item; refer to CoA/Spec Sheet.

General/literature-based chemical-physics context for this structure (for planning purposes; not item specifications):

• Polarity and solubility: Aromatic ethyl benzoate esters with methoxy substituents are moderately nonpolar overall but display enhanced solubility in polar organic solvents (e.g., acetone, acetonitrile, ethyl acetate, methanol) due to multiple oxygen atoms. Water solubility is typically very low for aryl esters of this size.
• Volatility: Compared with ethyl benzoate, two aryl methoxy substituents increase molecular weight and polarizability, generally raising boiling point and lowering vapor pressure (reduced odor/volatility relative to ethyl benzoate).
• Spectroscopy: The ester carbonyl typically shows a strong IR band near ~1715–1735 cm⁻¹ (literature). Aryl–OCH3 stretches appear near ~1240–1270 cm⁻¹. 1H NMR commonly shows ethyl quartet/triplet (–OCH2CH3), aryl methoxy singlets (~3.7–3.9 ppm), and aromatic protons (~6.5–7.5 ppm) (literature). 13C NMR typically shows the ester carbonyl ~165–170 ppm and methoxy carbons ~55–57 ppm (literature).
• Chromatography: Increased ring methoxylation often reduces Rf compared with unsubstituted ethyl benzoate on silica; elution with moderately polar eluents (e.g., hexanes/EtOAc) is common (practical observation, literature).

Quality and Grades

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

Guidance on typical grade expectations for this compound class (informational):

• Research-grade aryl esters are commonly supplied at >95% purity for synthetic use. Where HPLC grade is indicated for solvents, that denotes low UV background; for building blocks like this ester, purity is typically established by NMR/GC/LC and may include limits on related aromatic impurities.
• If a stabilizer were present, it would be listed explicitly. No stabilizer is indicated in the product data.
• Verification: For sensitive applications (e.g., kinetic or photophysical studies), consult the CoA for assay methodology, residual solvent content, and impurities profile. Request a Spec Sheet if you require detailed analytical characterization (NMR, LC, GC, HRMS).
• Research Use Note (from product data): For research use only.

Reaction and Applications

Ethyl 2,4-dimethoxybenzoate is a versatile aryl ester and electron-rich anisole derivative. Typical research applications include:

• Access to 2,4-dimethoxybenzoic acid by hydrolysis/saponification (acidic or basic conditions), followed by downstream amidation, ester variation, or acyl activation (e.g., acid chlorides, mixed anhydrides) (literature).
• Late-stage O-demethylation to unveil catechol-type or phenolic benzoate frameworks (BBr3, BCl3, AlCl3/thiols, or HI as literature methods). The presence of an ester requires condition control to minimize transesterification or cleavage.
• Electrophilic aromatic substitution (EAS) on the methoxy-activated ring (e.g., halogenation, nitration under mild conditions), enabling subsequent cross-couplings after introduction of a leaving group (literature). Methoxy groups are ortho/para-directing; the 2,4-pattern biases further substitution predictably.
• Transesterification to tailor the alcohol component (e.g., to methyl, benzyl, or bulky alkyl esters) using acid or base catalysis, or enzymatic approaches (lipases) for milder selectivity (literature).
• Photophysical and materials contexts: Electron-rich benzoates are sometimes used as model substrates in photocatalysis (e.g., oxidative demethylation, C–O activation under photoredox), though condition optimization is substrate- and catalyst-dependent (literature).

Practical tips:

• For basic hydrolysis, use alcoholic aqueous base (NaOH or KOH) with reflux as needed; then acidify to precipitate the acid. For acid hydrolysis, conc. mineral acids under reflux in alcohol/water mixtures can be used.
• For demethylation, employ dry, oxygen-free conditions and low temperatures initially (e.g., −78 to 0 °C) to moderate exotherms with BBr3; quench cautiously with MeOH/H2O (literature).

Reaction Conditions

General literature guidance for this class of substrates (not item specifications):

• Basic hydrolysis (saponification):
  • Typical: 1–2 M NaOH or KOH in MeOH/H2O or EtOH/H2O (3:1 to 1:1 v/v), 25–65 °C, 1–6 h depending on scale and solubility. Monitor by TLC/LC. Acidify to pH ~1–2 to precipitate 2,4-dimethoxybenzoic acid; isolate by filtration.
• Acidic hydrolysis:
  • Aqueous HCl or H2SO4 (2–6 M) in alcohol/water, reflux, hours; may risk partial demethylation under harsher conditions.
• O-Demethylation (to phenols):
  • BBr3 (1–3 eq/OMe) in dry CH2Cl2, −78 to 0 °C addition, then 0–25 °C, 1–16 h. Quench with MeOH/H2O. Alternative: BCl3 or TMSI under analogous conditions. Ester group is generally tolerated but monitor for transesterification.
• Electrophilic halogenation (for later cross-coupling):
  • NBS/NIS in AcOH/MeCN or DMF, 0–25 °C to control regioselectivity; conditions tailored to avoid over-bromination.
• Amide coupling (after hydrolysis):
  • HATU/DIPEA in DMF or EDCI/HOBt in DCM/DMF, 0–25 °C, 1–12 h; typical isolated yields: good to excellent when substrates are clean (literature).

Always optimize on small scale; verify compatibility of the ester with chosen reagents and adjust stoichiometry/temperature accordingly.

Safety and Handling

GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS.

General hazards and precautions for aromatic esters (informational; consult SDS for definitive guidance):

• Likely to cause eye/skin irritation upon contact and irritation upon inhalation of vapors or mists. Avoid aerosols and prolonged exposure.
• Use in a chemical fume hood. Wear appropriate PPE: lab coat, safety glasses or splash goggles, and chemically resistant gloves (e.g., nitrile). Avoid open flames and hot surfaces when heating solvents during workups or purifications.
• Incompatibilities: Strong bases/acids (can hydrolyze the ester), strong oxidizers (may react with aryl ether functions), and strong Lewis acids (can promote demethylation/transesterification under forcing conditions). Store away from alkali metals.
• Spill/first aid (overview): For small spills, absorb with inert material and dispose per institutional protocols. In case of skin contact wash with soap/water; for eye exposure rinse with water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air. If ingested, do not induce vomiting; seek medical attention.
• Waste: Dispose of organic waste per local regulations; avoid release to the environment.
• Always defer to the product’s SDS for authoritative, product-specific safety information.

Solvent Selection

This compound is an aromatic ethyl ester bearing two methoxy groups—overall moderately nonpolar with limited aqueous solubility but good solubility in common organic media.

• Polarity/miscibility (general):
  • Readily soluble in ethyl acetate, dichloromethane, chloroform, THF, acetone, toluene, and alcohols (methanol/ethanol) (literature/general).
  • Poorly soluble in water (typical for aryl esters of this size).
• Dielectric/polarity considerations: For reactions involving ionic species (e.g., saponification), mixed protic solvent systems (MeOH/H2O or EtOH/H2O) often enhance rates. For neutral transformations or chromatographic handling, EtOAc/hexanes or toluene are common choices.
• Selection guidance:
  • Hydrolysis/saponification: MeOH/H2O or EtOH/H2O with NaOH or KOH.
  • Demethylation of aryl OMe: Non-protic halogenated solvents (e.g., CH2Cl2) under Lewis-acid conditions are typical, while ensuring ester compatibility or using protecting strategies.
  • Coupling after hydrolysis to acid: DMF, DCM, or MeCN are frequently used for amide couplings once the carboxylic acid is generated.

Comparison notes:

• Versus ethyl benzoate: Increased polarity and H-bond acceptor count often improve solubility in polar organics, aiding handling and chromatography.
• Versus higher alkyl benzoates: Ethyl ester remains relatively less hydrophobic, often giving better rates in base-catalyzed hydrolysis.

Storage and Reconstitution

• Storage Conditions (product data): Room temperature.
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution: Not applicable—this is a neat organic compound (no reconstitution buffer required). If supplied as a solid or viscous oil, dissolve in a suitable dry organic solvent (e.g., DCM, EtOAc, MeOH, or acetone) as needed for use.
• Stability considerations (general): Store tightly closed in a dry place away from strong acids/bases and oxidizers. Protect from prolonged exposure to light and moisture to prevent hydrolysis over extended periods. For long-term storage, an inert atmosphere (argon or nitrogen) and anhydrous conditions are prudent but not mandatory for routine use.
• Freeze–thaw: Not applicable.
• Labeling note: Always refer to the product label and SDS for handling and storage specifics. For analytical acceptance criteria and retest dates, consult the CoA/Spec Sheet.

Structure and Identity

Ethyl 2,4-dimethoxybenzoate is an electron-rich aromatic ester derived from 2,4-dimethoxybenzoic acid, bearing an ethyl ester at the benzoate carboxyl.

• Product name: Ethyl 2,4-dimethoxybenzoate (SKU: E1020527)
• CAS: 81722-07-8 (product data)
• InChIKey: 122613 (as provided in product data)
• SMILES: CCOC(=O)c1ccc(OC)cc1OC (literature)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (descriptive):

• Aromatic ring (benzene) para- and ortho-substituted with two methoxy groups (–OCH3) at the 2- and 4-positions relative to the benzoate carbonyl.
• Benzoate functional group present as an ethyl ester (–CO2Et), conferring typical aryl ester reactivity (hydrolyzable to the corresponding acid under acidic/basic conditions).
• No stereocenters (achiral molecule); planar aromatic core with three oxygen-containing substituents (two aryl ethers and one ester).

Synthetic Utility

Functional groups and reactivity:

• Ethyl aryl ester (–CO2Et): susceptible to hydrolysis (acidic or basic), transesterification, and activation to acid derivatives after saponification.
• Aryl methoxy groups (2,4-OMe): strong electron-donating/activating, ortho/para-directing for EAS; convertible to phenols via demethylation, enabling further diversification (e.g., etherification, esterification, Mitsunobu coupling on phenols after deprotection).

Representative transformations (literature/general):

• Saponification → 2,4-dimethoxybenzoic acid → amide coupling (EDC/HOBt, HATU, CDI, or acid chloride route).
• Selective demethylation (e.g., BBr3, BCl3, TMSI) to mono- or di-phenolic benzoates, then O-alkylation/acylation to tune electronics.
• Electrophilic ring functionalization (bromination/iodination) guided by 2,4-OMe activation, enabling Pd-catalyzed cross-couplings (Suzuki, Sonogashira) after introduction of halides.
• Transesterification to install sterically demanding or cleavable esters (e.g., tBu via isobutylene/H2SO4 to tert-butyl ester after prior acid formation, or benzyl esters for hydrogenolytic cleavage).

Strategic value:

• The 2,4-dimethoxy pattern modulates electron density, often enhancing rates in EAS and affecting regioselectivity in downstream metalations or couplings.
• The ethyl ester serves as a benign, hydrolyzable handle—stable to many neutral conditions yet readily unmasked when needed.

Target Specificity

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