1-(2,2-Diethoxyethoxy)-3-methoxybenzene - ≥98% , CAS No.108639-46-9

CAS: 108639-46-9 Cat. No.: D1248162 Formule: C₁₃H₂₀O₄ Poids moléculaire: 240.29

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Spécifications et pureté

≥98%

Conditions de stockage de stockage

Room temperature

Pureté

≥98%

Noms et identifiants

Sourires canoniques

CCOC(COC1=CC=CC(=C1)OC)OCC

IUPAC Name

1-(2,2-diethoxyethoxy)-3-methoxybenzene

InChIKey

DIQWICPLFJEQKG-UHFFFAOYSA-N

INCHI

1S/C13H20O4/c1-4-15-13(16-5-2)10-17-12-8-6-7-11(9-12)14-3/h6-9,13H,4-5,10H2,1-3H3

Poids moléculaire

240.29

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Phenol ethers
      • Subclass Anisoles

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Phenol ethers
• Subclass: Anisoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Anisoles
• Alternative Parents: Phenoxy compounds Methoxybenzenes Alkyl aryl ethers Acetals Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenoxy compound - Methoxybenzene - Anisole - Alkyl aryl ether - Monocyclic benzene moiety - Ether - Acetal - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
• 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

Propriétés chimiques et physiques

• Poids moléculaire: 240.290 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 240.136 Da
• Monoisotopic Mass: 240.136 Da
• Topological Polar Surface Area: 36.900 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 180.000
• 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 validated bioassay, immunoassay, or imaging protocols are associated with this small-molecule building block in the product data.

For chemical use, see the Reaction Conditions and Synthetic Utility sections for generalized procedures (e.g., acetal hydrolysis, O-demethylation, and downstream aldehyde elaborations). Always optimize conditions for your substrate set and consult primary literature.

Biological Roles

No biological roles are assigned to this catalog item; it is supplied strictly as a synthetic organic building block for research and development.

General context (biochemistry perspective without medical claims):

• The compound comprises ether and acetal functionalities commonly considered metabolically labile in biological systems; acetals can hydrolyze under acidic conditions, potentially yielding aldehydes and alcohols. Such features are sometimes used in pro-moiety design in medicinal chemistry, but this product is not intended for any biological application.
• Lipophilicity: Aryl ethers with aliphatic acetals are typically lipophilic and may partition into membranes; however, no ADME, toxicity, or target interaction data are provided or implied for this item.
• Reactivity concerns: Aldehyde release upon acetal hydrolysis can lead to protein or nucleophile adduction; therefore, direct use in live systems is not advised and is outside the product’s intended scope.

Research use only. Not for diagnostic, therapeutic, or in vivo use.

Buffer Applications

Not typically applicable. 1-(2,2-Diethoxyethoxy)-3-methoxybenzene is a hydrophobic organic building block and is not used as a buffering agent or pH stabilizer.

Practical note:

• If aqueous phases are involved during acetal hydrolysis or workup, choose appropriate buffer systems (e.g., sodium acetate or phosphate) to quench acids after deprotection; however, the compound itself does not function as a buffer.
• Maintain organic/aqueous phase management to prevent unintended acetal cleavage during handling.

Green Alternatives

As a specialty building block, the molecule itself is not readily replaced by a “greener” reagent without altering synthetic strategy. However, greener choices can be made in the processes that use it.

Greener process considerations (general guidance):

• Solvent selection: Prefer biorenewable or lower-toxicity solvents when compatible with the chemistry.
  • Examples: 2-MeTHF or CPME in place of THF/Et2O; anisole or toluene (with proper controls) instead of chlorinated solvents; ethyl acetate for workups.
• Acid-catalyzed acetal hydrolysis: Use solid acids (e.g., Amberlyst-15, sulfonated carbons) to minimize mineral acid waste; run under aqueous ethanol or acetone/water systems that are easier to treat.
• Energy efficiency: Conduct reactions at ambient temperature/pressure where feasible; use microwave or flow to reduce time/energy consumption.
• Waste minimization: Apply catalytic rather than stoichiometric methods for aryl functionalization; employ high atom-economy condensations after aldehyde unmasking.

Illustrative comparison (process-level, not item-specific):

• Traditional: DCM as reaction medium for acetal cleavage; aqueous HCl; multiple neutralization steps.
• Greener alternative: 2-MeTHF/H2O with catalytic solid acid; phase separation simplifies workup; lower chlorinated solvent emissions.

Trade-offs:

• 2-MeTHF and CPME can retain water, affecting acetal stability; ensure adequate drying and monitor for unintended hydrolysis. Solid acids may require longer reaction times but simplify waste handling.

Pharmaceutical Uses

No direct pharmaceutical or excipient use is claimed for this item. It is provided for research and synthetic applications only.

General formulation context (non-clinical, non-therapeutic):

• Potential role as an intermediate: The acetal acts as a protected aldehyde, allowing staged introduction of an aldehyde handle in discovery workflows. Such intermediates may appear in route scouting or library synthesis.
• Excipient status: Not a recognized buffer, filler, or solvent excipient in pharmacopeias; no monograph status indicated.
• Impurity control considerations during process development: If incorporated into upstream steps, monitor for hydrolysis products (aldehydes/ethanol) and residual starting materials by GC/HPLC and NMR; validate purge factors in later steps to comply with ICH guidelines in a manufacturing setting (general guidance only).

Physical Properties

Item-specific numeric specifications are not provided in the product data.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point, melting point, density, refractive index, UV cutoff, water/peroxide content: Not specified for this item; refer to CoA/Spec Sheet.

General expectations (literature/general chemistry knowledge; not item specifications):

• Physical state: acetal-functional aryl ethers of comparable size are typically colorless, low-to-moderate viscosity liquids at ambient temperature.
• Polarity/solubility: expected to be hydrophobic to moderately lipophilic; miscible with many organic solvents (e.g., dichloromethane, toluene, ethers) and poorly soluble in water due to the predominance of ether/acetal moieties.
• Volatility: likely lower volatility than simple anisole because of the higher molecular weight and acetal side chain; handle in a fume hood to minimize inhalation.
• Stability: acetals are generally stable to base and neutral conditions, but undergo hydrolysis in the presence of aqueous acids (especially mineral acids or strong organic acids) and prolonged moisture exposure, yielding the corresponding aldehyde functionality on the side chain.

Note: For exact assay values, residual solvents, and detailed physico-chemical parameters specific to this lot, consult the Certificate of Analysis (CoA) or Specification Sheet.

Quality and Grades

• 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 interpreting grades (general information for professional users):

• AR/Reagent grade: Suitable for most synthetic applications. Trace impurities may be present at levels acceptable for routine lab use.
• High-purity or 95–99%: Typical for building blocks; residual solvents and closely related species may be controlled. For sensitive catalysis or materials work, verify trace metals/halides if relevant.
• HPLC grade (for solvents) or LC/MS grade: Not applicable here as this is a substrate/building block, but low-UV-absorbance and particulate control are features of such grades.

What to verify for this item:

• Identity confirmation: 1H/13C NMR showing acetal methine (≈4.8–5.5 ppm region, literature), ethoxy CH3 triplets (≈1.1–1.3 ppm), O–CH2 signals (≈3.3–4.2 ppm), and anisole aromatic/OMe resonances. HRMS consistent with the molecular formula (see CoA).
• Purity: Review NMR integration, GC or HPLC area percent, and water content (Karl Fischer) if hydrolysis sensitivity is a concern.
• Stability: Confirm absence of hydrolysis by checking for formation of aldehydic signals (≈9–10 ppm) after storage; request fresh CoA if critical.

Reaction and Applications

Use as a masked-aldehyde anisole derivative and versatile aryl ether building block.

Typical application families (general/literature guidance):

• Acetal unmasking to aldehyde: The 2,2-diethoxy terminus is an acetal that can be hydrolyzed under aqueous acid to unveil an aldehyde-bearing side chain (–O–CH2–CHO). This enables late-stage introduction of an aldehyde handle for condensations (e.g., oxime formation, reductive amination after further conversion, Wittig/HWE on the newly formed aldehyde).
• Electrophilic aromatic substitution (EAS): The anisole (–OMe) substituent is activating and ortho/para-directing; however, the ring substitution pattern (1,3-disubstituted) constrains positions available. Directed metalation strategies (e.g., with sBuLi/TMEDA) on anisole derivatives can allow further functionalization when combined with appropriate protecting strategies.
• O-Demethylation to phenol: Conversion of the 3-methoxy group to phenol (e.g., BBr3, BCl3, or AlCl3/thiols) provides a phenolic handle for subsequent etherification/esterification or cross-coupling after aryl activation.
• Cross-coupling after aryl activation: Although the substrate lacks a halide, electrophilic activation (e.g., via diazotization from an aniline precursor or directed C–H functionalization using modern catalysis) can introduce coupling handles.
• Acetal transformations: Exchange to other acetals/ketals or selective reduction (e.g., acetal to ether under specific hydride conditions) can tailor the side chain. Following hydrolysis to the aldehyde, downstream elaborations (e.g., formation of Strecker-type adducts, aldolizations with enolates) become accessible.

Application domains: fragrance intermediate synthesis, fine-chemical scaffolds, and materials monomer precursors where controlled late-stage aldehyde unveiling on an aryl ether is advantageous.

Reaction Conditions

The following are general literature-guided conditions for transformations relevant to acetal-bearing aryl ethers; they are not item-specific specifications.

• Acetal hydrolysis (unmasking to aldehyde):
  • Typical: 0.5–2 M aqueous HCl or p-TsOH (5–10 mol%) in acetone/H2O or THF/H2O (3:1 to 1:1), 20–50 °C, 0.5–6 h. Monitor by TLC/GC. Quench with NaHCO3, extract, and dry rapidly to minimize overreaction of the aldehyde.
  • Solid-acid option: Amberlyst-15 in EtOH/H2O at 25–40 °C; longer times (4–16 h) but easier workup.
• O-Demethylation (anisole to phenol):
  • BBr3 in dry DCM (1–3 equiv), −78 to 0 °C, 1–3 h; quench with MeOH then aqueous workup. Maintain strictly anhydrous conditions to avoid acetal cleavage; use stoichiometry/temperature control to preserve the acetal.
  • Alternatives: BCl3 or AlCl3/thiol systems under non-aqueous conditions.
• Aldehyde elaboration (post-hydrolysis):
  • Reductive amination: Aldehyde + amine in MeOH or EtOH with NaBH3CN (pH 6–7, AcOH buffer) or with catalytic hydrogenation (Pd/C, H2) of imines; 0–25 °C, 1–6 h.
  • Wittig/HWE: Ph3P=CHR (or phosphonate/strong base) in THF or toluene, 0–25 °C; yields and E/Z selectivity depend on reagent and conditions.
• Workup/storage cautions: Remove acids thoroughly after hydrolysis; dry organic layers over neutral desiccants (Na2SO4). Store aldehyde products under inert gas at low temperature to limit polymerization/oxidation.

Expected outcomes: Clean acetal deprotection and high chemoselectivity are achievable with careful pH and water control; side reactions increase under strong acid/heat.

Safety and Handling

Safety information specific to this catalog item is not provided in the Product Data. Always consult the SDS for authoritative guidance.

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

General handling guidance for aryl ethers bearing acetals (general chemistry knowledge):

• Hazards: Organic liquids can be combustible/flammable; vapors may be irritating. Acetals may hydrolyze in strong acids to release aldehydes/alcohols, which can be irritants/sensitizers. While dialkyl acetals are not classic peroxide formers, the ether functionalities merit routine caution and periodic peroxide testing for long-stored material is prudent if opened frequently.
• PPE: Wear safety glasses or splash goggles, lab coat, and suitable chemically resistant gloves (e.g., nitrile). Use in a fume hood to control vapors and prevent inhalation exposure.
• Incompatibilities: Avoid strong acids (risk of acetal hydrolysis), strong oxidizers, and prolonged moisture exposure. Avoid strong electrophiles (which may react at the anisole ring under activating conditions).
• First aid (overview): If inhaled, move to fresh air. On skin contact, wash with soap and water. If in eyes, rinse cautiously with water for several minutes and seek medical advice. If ingested, rinse mouth—do not induce vomiting; seek medical attention. Follow SDS instructions.
• Spill/fire: Absorb small spills with inert material; for fires use CO2, dry chemical, or foam. Ground/bond during transfer if handling bulk quantities.

Research use only. Not for human or animal use.

Solvent Selection

This product is a synthetic building block rather than a chromatography or reaction solvent. Selection here refers to solvents in which to dissolve or react the compound.

General solvent compatibility (general chemistry knowledge):

• Likely good solubility in moderately polar aprotic solvents (e.g., dichloromethane, THF, acetonitrile, DMF) and in nonpolar aromatics (toluene). Poor water solubility expected.
• For acetal integrity: Prefer neutral or basic anhydrous media. Avoid aqueous acids which promote hydrolysis.

Use-case guidance:

• Nucleophilic substitutions or metal-catalyzed transformations on the aryl ring (after appropriate activation) commonly use DCM, THF, 1,4-dioxane, toluene, or MeCN, depending on catalyst/ligand system.
• Deprotection (acetal hydrolysis) is intentionally run in mixed aqueous organic solvents (e.g., acetone/water or THF/water) with catalytic mineral acid—select solvent ratios to tune rate and phase behavior.

Comparison notes (general):

• DCM vs toluene: DCM offers faster acetal hydrolysis when acid is present (better water miscibility), while toluene helps preserve acetal under neutral conditions and facilitates azeotropic drying (Dean–Stark with a co-solvent).
• THF vs MeCN: THF offers better solubility for many organometallics; MeCN is advantageous for polar catalytic systems and higher boiling point under reflux.

Always verify solvent dryness (molecular sieves) to minimize unintended acetal cleavage.

Storage and Reconstitution

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

Practical storage guidance (general for acetals/aryl ethers):

• Keep container tightly closed in a dry, well-ventilated place. Protect from moisture and strong acids to prevent acetal hydrolysis.
• Use amber glass or store away from strong light to minimize potential photodegradation of sensitive functionalities.
• After opening, consider storing under inert gas (N2/Ar) with a desiccant in the cabinet to limit humidity ingress. Wipe bottle lip and recap promptly.
• If using septum-access techniques, ensure headspace is dry and use oven-dried syringes/needles.

Reconstitution/handling:

• If material is viscous or contains precipitated solids (seasonal), warm gently to ambient temperature and swirl to homogenize; do not heat above mild warmth without assessing thermal stability.
• For solution preparation, use anhydrous solvents (e.g., dry DCM, THF, toluene) to preserve the acetal. If aqueous/acidic media are required (e.g., for deliberate deprotection), prepare immediately before use and avoid prolonged standing.

Research use only. Refer to the product’s SDS for detailed handling and storage precautions.

Structure and Identity

A protected-aldehyde aryl ether building block featuring an anisole core bearing a pendant 2,2-diethoxyethoxy chain.

• SKU: D1248162
• Product name: 1-(2,2-Diethoxyethoxy)-3-methoxybenzene
• CAS: 108639-46-9
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• 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.

Structural description (general chemistry knowledge):

• Aromatic ring substituted at the 1- and 3-positions (meta relationship):
  • A 3-methoxy group (anisole motif; aryl–O–CH3, an electron-donating ether substituent).
  • A 1-(2,2-diethoxyethoxy) group: an aliphatic ether tether (–O–CH2–) terminating in an acetal center [–CH(OC2H5)2]. This functions as a masked aldehyde (acetal), stable to base but cleavable under acid/water.
• Functional groups: aryl ether (Ph–O–), aliphatic ether (–O–CH2–), and an acetal carbon bearing two ethoxy groups (–CH(OR)2).
• Stereochemistry: no defined stereocenters expected in the named structure (the acetal carbon is prochiral but not configurationally stable under typical conditions). 2D depiction in words: a benzene ring with OMe at C3 and, at C1, an –O–CH2–CH(OC2H5)2 substituent extending as an acetal-terminated side chain.

Synthetic Utility

Key functional motifs and their reactivity (general chemistry knowledge):

• Anisole core (aryl–OMe): Strongly activating/ortho,para-directing for EAS; serves as a handle for directed metalation, oxidative functionalization, or demethylation to phenol.
• Pendant acetal (–CH(OR)2): A classic protected form of an aldehyde. Stable to base and many nucleophiles in aprotic media; readily unmasked under aqueous acid to give an aldehyde side chain suitable for condensations, reductions, and couplings.
• Aliphatic ether linkage (–O–CH2–): Provides conformational flexibility and can be cleaved under strong Lewis acids or reductive conditions in selected protocols.

Strategic uses:

• Late-stage aldehyde unveiling enables convergent couplings (e.g., Wittig/HWE to extend carbon skeletons from the aryl ether side chain) while preserving sensitive ring substituents.
• Orthogonal protection: The aryl methoxy group can be demethylated (BBr3) without disturbing the acetal under carefully controlled, anhydrous conditions, unlocking phenol derivatization (e.g., carbonate/ether/aryl triflate formation for cross-coupling).
• Scaffold diversification: After aldehyde formation, reductive amination, oxime/oxime ether formation, or formation of cyanohydrins provide rapid library expansion around the anisole framework.

Analytical facilitation:

• The acetal typically gives diagnostic NMR signals (acetal methine, ethoxy CH3) allowing quick purity/identity checks.
• Stability screening: Small-scale tests across pH 1–7 elucidate process windows that preserve the acetal during upstream steps and deprotect cleanly downstream.

Target Specificity

Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, nucleic acid, or biologic with definable binding targets. No antigen/epitope or species reactivity information applies.

Foire aux questions

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 108639-46-9, the molecular formula is C13H20O4, and the molecular weight is 240.29 g/mol. InChIKey DIQWICPLFJEQKG-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.