Ethyl 4-(ethoxymethyl)benzoate - ≥98% , CAS No.133017-02-4

CAS: 133017-02-4 Cat. No.: E972486 분자식: C₁₂H₁₆O₃ 분자량: 208.250

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

사양 및 순도

≥98%

보관 조건

Room temperature

순수함

≥98%

이름과 식별자

• 정식 스마일: CCOCC1=CC=C(C=C1)C(=O)OCC
• IUPAC Name: ethyl 4-(ethoxymethyl)benzoate
• InChIKey: GWYFRLIJNSJBCT-UHFFFAOYSA-N
• INCHI: 1S/C12H16O3/c1-3-14-9-10-5-7-11(8-6-10)12(13)15-4-2/h5-8H,3-4,9H2,1-2H3
• 분자량: 208.250

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• 분류: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoic acid esters
• Alternative Parents: Benzylethers Benzoyl derivatives Carboxylic acid esters Dialkyl ethers Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzoate ester - Benzylether - Benzoyl - Carboxylic acid ester - Ether - Dialkyl ether - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
• 설명: 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

화학 및 물리적 특성

• 분자량: 208.250 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 208.11 Da
• Monoisotopic Mass: 208.11 Da
• Topological Polar Surface Area: 35.500 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 183.000
• 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 protocols are specified for this item. As a small-molecule building block, typical “applications” are synthetic procedures rather than bioassays.

• For practical use, consult the Reaction Conditions, Synthetic Utility, and Solvent Selection sections for representative procedures and conditions.

If you require a step-by-step protocol for a particular transformation (e.g., saponification to the acid, amide coupling, or ether cleavage), contact Technical Support with your target reaction and scale.

Biological Roles

This compound is a synthetic aromatic ester and is not a biochemical metabolite. No endogenous biological role is associated with ethyl 4-(ethoxymethyl)benzoate.

• General context (informational; not product-specific claims):

  • Aromatic esters can serve as hydrophobic scaffolds or pro-moieties in chemical biology probes; hydrolysis yields the corresponding benzoic acids or phenethyl-type alcohols under enzymatic or chemical conditions.
  • The benzylic ether is generally stable under physiological pH but may be subject to oxidative metabolism in vivo (literature precedent for benzylic oxidation of ethers). These are generalized observations and not claims for this item.

• Research relevance:

  • The dual functionality (ester and benzylic ether) can be leveraged for tagging, immobilization, or constructing small-molecule libraries used in biochemical screening workflows.

No medical, therapeutic, or in vivo performance is stated or implied for this product. It is designated for research use only.

Buffer Applications

Not typically applicable. Ethyl 4-(ethoxymethyl)benzoate is a neutral organic building block and does not function as a buffering agent. For experimental design, select appropriate aqueous buffer systems (e.g., phosphate, HEPES, acetate) independently, and consult the Reaction & Applications and Synthetic Utility sections for transformations of this compound.

Green Alternatives

While this product is a solid/liquid building block rather than a solvent, greener choices can be made in its use and transformations.

• Greener solvent choices (literature guidance):

  • Replace chlorinated solvents (DCM/CHCl3) with ethyl acetate, 2-MeTHF, CPME, or dimethyl carbonate when compatible.
  • For base-catalyzed hydrolysis/transesterification, consider aqueous ethanol or propylene carbonate as media; for hydride reductions, 2-MeTHF often substitutes for THF/Et2O.

• Reagent alternatives and process intensification:

  • Amidation: Direct catalytic amidation methods (e.g., boron-based catalysts) can avoid stoichiometric coupling reagents; otherwise, choose water-soluble carbodiimides (EDC·HCl) to minimize halogenated waste.
  • Ester reductions: Hydrogenative reductions using earth-abundant catalysts (Mn, Fe, Co) under H2 can reduce waste versus metal hydrides, if scope allows.
  • Ether cleavage: Consider catalytic hydrogenolysis when using benzylic protecting-group strategies to avoid halogenated Lewis acids; however, benzylic ethyl ethers are less labile than benzyl ethers—assess feasibility.

• Comparative overview (general):

  • DCM vs EtOAc: EtOAc is biodegradable, lower toxicity; may require longer reaction times or higher temperatures.
  • THF vs 2-MeTHF: 2-MeTHF is bio-based, higher boiling, improved phase separation; may alter reaction rates/solubilities.
  • LiAlH4 vs catalytic H2: Hydride is highly effective at low temperature but generates inorganic waste and poses quench hazards; catalytic H2 reduces waste but can require elevated T/P and precious/transition metals.

Adopt in-process controls (IPC), solvent recycling, and minimal protecting-group strategies to improve overall process greenness.

Pharmaceutical Uses

• Item-specific note: Research Use Only (per Product Data). No pharmacopeial status or excipient listing is provided for this item.

• General, non-clinical context:

  • As a functionalized benzoate, this material may serve as a synthetic intermediate in the preparation of more complex research compounds, including potential API intermediates or screening library members. The para benzylic ether enables late-stage diversification while the ester allows standard acid/amide interconversions.
  • It is not typically employed directly as a pharmaceutical excipient or formulation component. No claims are made regarding safety or efficacy in humans or animals.

Any use in GMP or regulated environments would require independent qualification, specification setting (assay, impurities, residual solvents, metals), and compliance with applicable pharmacopeial monographs if/when relevant to derivatives. Such details are not specified for this item; refer to CoA/Spec Sheet and perform internal validation.

Physical Properties

• Item-specific (from Product Data):

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Storage conditions: Room temperature (per Product Data)

• Literature/general expectations for this structure (informational; not item specifications):

  • Physical state: Typically a neutral organic liquid or low-melting solid; many para-alkoxymethyl benzoate esters are colorless to pale liquids at ambient temperature due to reduced crystallinity.
  • Volatility: Expected to be low to moderate; boiling point generally higher than ethyl benzoate due to increased molecular mass and polarity from the benzylic ether.
  • Solubility: Sparingly soluble in water; miscible with common organic solvents (e.g., dichloromethane, ethyl acetate, toluene, THF, acetone, acetonitrile, alcohols).
  • Polarity: Moderately lipophilic aromatic core with two oxygen-bearing functions yielding modest polarity; expected cLogP in the low-to-mid 3 range (qualitative).
  • Acid/base: Neutral; no ionizable centers in the typical aqueous pH range. Ester hydrolyzes only under acidic or basic conditions.
  • Spectroscopic features: Aromatic 1H signals ~7.2–8.2 ppm (para pattern); benzylic –CH2–O– around 4.4–4.7 ppm; ethyl ester –O–CH2– at ~4.1–4.4 ppm; carbonyl 13C ~165–167 ppm (literature ranges).

Note: Exact numeric values (bp, mp, density, refractive index, UV cutoff, water/peroxide/metal content) are not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Item-specific information:

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
  • UV-Vis/LC specifications, water/metal limits: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting common grades (general guidance):

  • Research or Reagent grade: Suitable for most synthetic and analytical tasks. Trace impurities may vary batch-to-batch.
  • High-purity or ≥98% organic building block: Often supports catalysis-sensitive operations (e.g., Pd-catalyzed steps) with reduced side reactions from protic or peroxidic impurities.
  • HPLC grade (if applicable): Refers primarily to solvent background; for solutes, low UV-absorbing impurities and tight assay are typical.

• Practical quality considerations for this structure:

  • Water sensitivity: While the compound is not acutely hydrolytic, moisture can slowly promote ester hydrolysis under basic or acidic conditions; dry storage limits degradation during long-term use.
  • Benzylic ether integrity: Acidic traces can promote cleavage; low-acid content and neutral packaging are beneficial if downstream chemistry requires intact –CH2OEt.
  • Chromatographic behavior: Aromatic ester exhibits strong UV absorbance (254 nm), facilitating HPLC/GC-MS quality checks. Two oxygenated substituents typically give good normal-phase retention and clear reversed-phase elution.

Refer to the batch CoA for exact assay, impurity profile, and any stabilizer presence for SKU E972486.

Reaction and Applications

Ethyl 4-(ethoxymethyl)benzoate is a versatile, bifunctional building block combining an electron-withdrawing benzoate ester with a benzylic ether handle.

• Transformations of the ester:

  • Hydrolysis to 4-(ethoxymethyl)benzoic acid under basic (NaOH, K2CO3, aq. MeOH/THF) or acidic conditions, enabling subsequent amide coupling (EDCI/HOBt, HATU, CDI) or acid chloride formation (SOCl2, oxalyl chloride).
  • Transesterification to alternate alkyl esters using acid/base catalysis in corresponding alcohols.
  • Reduction to primary alcohols: LiAlH4 or DIBAL-H to 4-(ethoxymethyl)benzyl alcohol; catalytic hydrogenation (e.g., Ru/C, Mn- or Co-based catalysts) under hydrogen can effect ester hydrogenolysis (literature).

• Manipulation of the para benzylic ether (–CH2–OEt):

  • Ether cleavage to the benzylic alcohol (–CH2OH) using BBr3, BCl3, or HI under controlled conditions; alternatively, oxidative demasking strategies (DDQ, CAN) may access aldehydes/ketones from benzylic ethers depending on conditions (literature precedent for benzylic oxidations).
  • Conversion to leaving groups: After revealing –CH2OH, Appel (PPh3/CX4) or mesylation/tosylation enables further SN2 elaboration (e.g., –CH2–X).
  • Oxidation of –CH2OH (post-cleavage) to aldehyde/acid (Swern, Dess–Martin, TEMPO/bleach), furnishing para-formyl/para-carboxyl derivatives.

• Aromatic chemistry:

  • The ester moderates electrophilic substitution; metalation on the ring is disfavored, but cross-coupling can be enabled after installing a halide or boronate via directed lithiation strategies on properly protected derivatives (literature, advanced applications).

• Use cases:

  • Late-stage diversification of benzoate scaffolds.
  • Orthogonal two-handle platform for medicinal chemistry SAR libraries and polymer/monomer precursors.

Employ inert atmosphere where strong Lewis acids/hydrides are used; temperature control is critical to prevent competing ether/ester cleavage.

Reaction Conditions

General, literature-style guidance for this structural class (informational; not item specifications):

• Base hydrolysis (ester → acid):

  • Conditions: 1–2 M NaOH or KOH in MeOH/H2O or THF/H2O, 0–50 °C, 1–12 h. Workup: acidify to pH ~2, extract with EtOAc.
  • Notes: The benzylic ether generally survives basic hydrolysis; avoid prolonged reflux if ether integrity is critical.

• Acidic hydrolysis/transesterification:

  • Conditions: catalytic H2SO4 or p-TsOH (1–10 mol%) in ROH (MeOH/EtOH), 25–70 °C, 2–24 h; remove alcohol to drive equilibrium.
  • Caution: Strong acids or extended heating can promote benzylic ether cleavage.

• Reduction (ester → alcohol):

  • LiAlH4 (1.5–2.5 equiv) in dry THF or 2-MeTHF, 0 °C to rt, 1–4 h; quench carefully (ice/aqueous Na2SO4).
  • DIBAL-H (2–3 equiv) in toluene/THF, −78 to 0 °C to stop at aldehyde (if feasible) or proceed to alcohol.

• Ether cleavage (–CH2–OEt → –CH2OH):

  • BBr3 (1–3 equiv) in DCM, −78 to 0 °C, 1–3 h; or HI (57%) reflux, monitoring by TLC/LCMS. Optimize to minimize ester cleavage.

• Oxidation sequences (after –CH2OH reveal):

  • Dess–Martin or Swern oxidation to aldehyde at 0 to rt; TEMPO/NaOCl for selective alcohol → acid.

• Workup/purification:

  • Silica gel chromatography with hexanes/EtOAc or toluene/EtOAc gradients typically provides good separation. Monitor at 254 nm.

Yields and exact times vary with scale, reagent quality, and substitution; always run small-scale scouts and consult primary literature for chosen transformations.

Safety and Handling

• Item-specific hazard data: Not specified for this item; refer to SDS for authoritative classification, GHS codes, pictograms, and first-aid measures.
• General guidance for benzoate esters with benzylic ethers (informational; not item specifications):
  • Expected hazards: May cause skin/eye irritation and respiratory irritation if mist/vapor is formed; harmful if swallowed. Avoid prolonged exposure.
  • PPE: Use lab coat, safety glasses or chemical splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood to minimize inhalation.
  • Incompatibilities: Strong acids/bases can induce ester hydrolysis and/or ether cleavage; strong oxidizers may oxidize the benzylic position; strong reducing agents (e.g., LiAlH4) reduce the ester.
  • Stability: Typically stable under ambient conditions away from strong reagents and moisture. No specific peroxide-forming tendency expected (non-ether solvent), but avoid unnecessary air/heat exposure.
  • Spill/first aid (overview): Absorb small spills with inert material; ventilate area. For skin/eye contact, rinse with water for ≥15 minutes and seek medical advice. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention.

Always consult the product’s SDS for definitive hazard, handling, disposal, and transport information. Waste should be collected as halogen-free organic waste unless process residues dictate otherwise per institutional policy.

Solvent Selection

This product is a functionalized aromatic building block, not a solvent. Solvent choice should be dictated by the intended transformation.

• General solvent compatibility (literature guidance):

  • Good solubility in moderately polar organic solvents: dichloromethane, chloroform, ethyl acetate, THF, acetone, acetonitrile; also soluble in toluene and alcohols.
  • Limited solubility in water.

• Selection tips by transformation:

  • Ester hydrolysis/transesterification: alcohol solvents (MeOH, EtOH) with acid/base catalysis; or biphasic aqueous base (NaOH/KOH) with THF/MeTHF as co-solvent.
  • Amidation (via acid after saponification): DMF, DCM, or acetonitrile with coupling agents (EDCI/HOBt, HATU) after generating 4-(ethoxymethyl)benzoic acid.
  • Reductions (ester → alcohol): Et2O/THF for hydride reagents (LiAlH4, DIBAL-H); greener alternatives include 2-MeTHF or CPME when compatible.
  • Benzylic ether cleavage: DCM or toluene commonly used with BBr3, BCl3, or HI conditions; protic solvents avoided to limit side reactions.

• Comparison note:

  • DCM vs EtOAc: DCM offers higher solvating power for aromatic esters and many Lewis acids; EtOAc is a greener alternative when feasible but may participate in transesterification under strong conditions.

Ensure solvent dryness and oxygen control as needed for moisture- or air-sensitive steps; verify workup compatibility with the ester and benzylic ether functions.

Storage and Reconstitution

• Item-specific storage: Room temperature (per Product Data). Store in a tightly closed container.
• General best practices:
  • Protect from moisture and strong acids/bases to preserve both the ester and the benzylic ether.
  • Store under inert gas (nitrogen/argon) if opening frequently or for long-term storage to minimize oxidative or hydrolytic degradation.
  • Keep away from strong oxidizers and reducing agents.
• Reconstitution: Not applicable—supplied as a neat organic compound. If preparing stock solutions, use dry, compatible organic solvents (e.g., DCM, EtOAc, THF, MeCN) and store solutions in amber vials at 2–8 °C or as appropriate for the solvent stability.
• Shelf life: Not specified for this item; refer to CoA/Spec Sheet. Periodically verify integrity by NMR/LCMS if stored for extended periods or prior to critical applications.

Structure and Identity

Ethyl 4-(ethoxymethyl)benzoate is an aromatic benzoate ester bearing a para benzylic ethoxy substituent. The molecule features a benzene ring substituted with an ethyl ester (–CO2Et) and a para –CH2–O–Et group, providing orthogonal handles for selective transformations.

• Item-specific (from Product Data):

  • CAS: 133017-02-4
  • InChIKey: 113733 (as provided)
  • SMILES: 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 (informational; not item specifications):

  • Typical molecular formula: C12H16O3 (computed by composition of substituents)
  • Typical molecular weight: ~208.26 g/mol (computed)
  • Example SMILES (literature): CCOC(=O)c1ccc(CCOCC)cc1
  • Functional groups: aromatic ring, ethyl benzoate ester, benzylic ether (ethoxymethyl)
  • Structural notes: The para relationship between the electron-withdrawing ester and the benzylic ether modulates ring reactivity; the benzylic position is susceptible to electrophilic cleavage/oxidation while the ester can be hydrolyzed or transformed independently.

• 2D structural description: A benzene core bearing an ethyl ester at C-1 (–C(=O)–O–CH2–CH3) and, para to it (C-4), a –CH2–O–CH2–CH3 substituent. No stereogenic centers are present; the compound is achiral.

Synthetic Utility

• Functional group handles:

  • Benzoate ester (–CO2Et): amenable to hydrolysis (acid/base), transesterification, reduction to primary alcohol, or conversion to amide via saponification/coupling. Can be activated to acid chloride or mixed anhydride for acylations.
  • Benzylic ether (–CH2–OEt): can be cleaved to –CH2OH (Lewis acids, HI) or elaborated after conversion to alcohol to halides/sulfonates for SN2 chemistry.

• Orthogonality advantages:

  • The ester and benzylic ether respond to different reagent classes, enabling stepwise manipulation. For example, base-catalyzed ester hydrolysis can proceed while retaining the ether; conversely, Lewis-acidic ether cleavage can be achieved under conditions that preserve the ester.

• Retrosynthetic value:

  • Serves as a para-functionalized benzene platform. After deprotecting the benzylic ether to –CH2OH and oxidizing to –CHO, the system can enter benzylation, Wittig, or reductive amination pathways (post-amide formation at the carboxyl site), enabling rapid library expansion around a para-disubstituted core.

• Representative downstream transformations (literature):

  • Saponification → amide coupling (HATU/DIPEA, DMF) to yield 4-(ethoxymethyl)benzamides.
  • LiAlH4 reduction (THF, 0–25 °C) → 4-(ethoxymethyl)benzyl alcohol; subsequent ether cleavage affords p-xylylene-type motifs.
  • Electrophilic aromatic substitution is deactivated by the ester; directed metalation strategies require specialized conditions if arene functionalization is desired.

Target Specificity

Not applicable. This product is a small-molecule organic reagent and does not possess antigen/epitope specificity, clone information, or species reactivity. No biochemical target specificity is defined for SKU E972486.