4-Ethyl-3,5-dimethoxybenzaldehyde , CAS No.78025-99-7

CAS: 78025-99-7 Cat. No.: E978456 분자식: C₁₁H₁₄O₃ 분자량: 194.230

Storage

Room temperature

Specifications

보관 조건

Room temperature

이름과 식별자

• 정식 스마일: CCC1=C(C=C(C=C1OC)C=O)OC
• IUPAC Name: 4-ethyl-3,5-dimethoxybenzaldehyde
• InChIKey: UJGOCEGHYLGYLV-UHFFFAOYSA-N
• INCHI: 1S/C11H14O3/c1-4-9-10(13-2)5-8(7-12)6-11(9)14-3/h5-7H,4H2,1-3H3
• 분자량: 194.230

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• 분류: Benzene and substituted derivatives
• Subclass: Methoxybenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Dimethoxybenzenes
• Alternative Parents: Phenoxy compounds Benzoyl derivatives Benzaldehydes Anisoles Alkyl aryl ethers Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Dimethoxybenzene - M-dimethoxybenzene - Anisole - Benzaldehyde - Benzoyl - Phenol ether - Phenoxy compound - Aryl-aldehyde - Alkyl aryl ether - Ether - Organooxygen compound - Aldehyde - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• 설명: This compound belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
• 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: 194.230 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 194.094 Da
• Monoisotopic Mass: 194.094 Da
• Topological Polar Surface Area: 35.500 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 167.000
• 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 tested bioassay or imaging protocols are provided for this item. Typical use is as a synthetic intermediate in organic chemistry. For reaction set-up, see the Reaction Conditions and Synthetic Utility sections. If you plan analytical use (e.g., as a reference standard), establish your own calibration and QC protocols (NMR, GC/LC).

Biological Roles

This product is an aromatic aldehyde intended as a synthetic building block. It is not a biological buffer or metabolite and has no established endogenous role.

• General chemistry note (literature): Methoxy-substituted benzaldehydes can appear as synthetic intermediates in fragrance, dye, and probe synthesis. No physiological function is associated with 4-ethyl-3,5-dimethoxybenzaldehyde.

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

Buffer Applications

Not typically applicable. 4-Ethyl-3,5-dimethoxybenzaldehyde is not a buffering agent and does not form a defined conjugate acid/base pair in aqueous media.

Practical note: If aqueous handling is required (e.g., biphasic reactions or oxidations), use co-solvents/surfactants or emulsions; control pH for reaction requirements rather than buffering with this compound.

Green Alternatives

• Solvent substitution (green chemistry focus)

  • Replace chlorinated solvents (DCM/CHCl3) with safer alternatives where feasible: 2-methyltetrahydrofuran (2-MeTHF), cyclopentyl methyl ether (CPME), ethyl acetate, or propylene carbonate depending on reaction class.
  • For carbonyl olefinations and condensations, 2-MeTHF and CPME often reproduce reactivity seen in THF/Et2O while offering better safety and renewability (2-MeTHF from hemicellulose).

• Example comparison (general guidance; not item-specific specs)

  • THF vs 2-MeTHF: Similar solubilizing power; 2-MeTHF is less miscible with water, easing workups; both form peroxides—stabilizer monitoring still needed.
  • DCM vs EtOAc: EtOAc is biodegradable and has a better EHS profile; polarity may be sufficient for many aldehyde transformations, especially reductions/oxidations.
  • DMF/DMSO vs acetonitrile/propylene carbonate: Where possible, acetonitrile or PC can reduce reproductive toxicity concerns; assess catalyst compatibility.

• Process considerations

  • Minimize aldehyde over-oxidation by using oxygen-lean headspace and antioxidants only if compatible; this reduces waste from off-spec acid formation.
  • Favor catalytic protocols (e.g., organocatalytic Knoevenagel, catalytic HWE) over stoichiometric reagents when practicable.

Trade-offs: Green solvents can alter selectivity (e.g., E/Z in HWE), rates, and isolation; always pilot on small scale with the specific substrate.

Pharmaceutical Uses

No pharmacopeial or excipient status is indicated for this item. It is supplied for laboratory research and synthesis only.

General context (non-clinical): Aromatic aldehydes can serve as intermediates en route to APIs, excipients, or analytical derivatization agents. Any such use requires independent qualification and regulatory assessment; this listing does not imply suitability for GMP or clinical use.

Physical Properties

• Item-specific specifications (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.
  • Water/peroxide/metal limits, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed (general reference values; not item specifications)

  • Molecular formula: C11H14O3 (computed from structure)
  • Molecular weight: ~194.23 g/mol (calculated)
  • Acid/base: aromatic aldehyde (no titratable basic center); phenyl methoxy groups are weakly donating; no relevant pKa for the neutral species under aqueous conditions.
  • Polarity: moderately lipophilic due to aryl/alkyl core; polar functionality from –CHO and two –OMe groups.
  • Expected solubility: good in common organic solvents (EtOAc, DCM, THF, MeOH, acetonitrile, toluene); low in water (qualitative, literature expectation for aryl aldehydes).
  • Partitioning behavior: logP likely in the moderate range for aryl aldehydes with two methoxy groups; exact value not established here.
  • Melting/boiling point, density, refractive index: Not found in standard references for this exact derivative; consult CoA/SDS or measure as needed.

Notes for users: If you require precise physical constants for process design or analytical calibration, please request the lot-specific CoA or perform in-house characterization (DSC for mp, Karl Fischer for water, densitometry or pycnometry if liquid, refractometry if applicable).

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet for assay method, purity basis (GC, HPLC, NMR), and impurity profile.

• Guidance for users selecting grade (general information)

  • For synthetic applications (e.g., Wittig/HWE/Knoevenagel), a GC/HPLC purity ≥95% is typically sufficient; trace acid may catalyze side reactions—consider verifying acidity or neutralizing prior to base-sensitive steps.
  • For analytical reference use, consider NMR/LCMS verification and water content (Karl Fischer). Aldehydes can hydrate or partially oxidize; CoA should indicate peroxide/acid number if relevant. If not, perform a quick pre-use check (e.g., 1H NMR for –CHO ~9.8–10.2 ppm).
  • Low-UV grade is generally unnecessary unless using as a mobile-phase additive; for detector-linearity studies in HPLC/UV, ensure baseline cleanliness of the solvent, not the analyte.

• Stabilizers/antioxidants: None specified for this item; if an antioxidant or acid scavenger is used, it will be declared on the CoA/label. Absence of declaration should not be assumed; verify if critical to your work.

Reaction and Applications

4-Ethyl-3,5-dimethoxybenzaldehyde is a versatile building block for constructing substituted anisole/ethylated aromatics, heterocycles, and side-chain elaborations. Its 3,5-dimethoxy pattern is strongly activating and directs electrophilic aromatic substitution meta to the methoxy groups (i.e., at C2 and C6 are deactivated; C4 is already ethylated), while the aldehyde enables numerous carbon–carbon bond formations.

• Typical transformations (literature/general chemistry)

  • Carbonyl olefinations: Wittig, Horner–Wadsworth–Emmons (HWE), and Julia–Kocienski to install styrenes or extended conjugation; electron-rich ring can enhance E-selectivity in HWE under basic, polar aprotic conditions.
  • Knoevenagel condensations: With active methylenes (malonates, cyanoacetates) under basic or ammonium acetate catalysis to give arylidene products used as dye intermediates or ligands.
  • Reductive conversions: NaBH4, DIBAL, or catalytic hydrogenation to the corresponding benzyl alcohol; subsequent ether manipulations (demethylation with BBr3/BCl3) allow access to phenolic analogs.
  • Oxidation: Jones/PDC/PCC or catalytic aerobic oxidation to the carboxylic acid; Baeyer–Villiger is not applicable to aldehydes (forms formates from ketones), but Pinnick oxidation is suitable for aldehydes to acids under mild, aqueous conditions.
  • Acetal/hemiacetal chemistry: Protection as acetals (e.g., with ethylene glycol/acid) to mask –CHO during electrophilic aromatic substitutions on the ring.
  • Electrophilic aromatic substitution: Although methoxy groups activate ortho/para, the 1,3,5-trisubstitution pattern limits available positions; formyl can be used as a directing/protecting handle.

• Practical notes

  • Dry, oxygen-limited handling preserves aldehyde integrity (minimizes over-oxidation to acids).
  • Monitor reactions by 1H NMR (–CHO ~9.8–10.2 ppm) or HPLC/LC-MS; methoxy singlets (~3.7–3.9 ppm) are convenient integrators.
  • For base-mediated reactions, pre-neutralize trace acid and use molecular sieves to suppress aldol side pathways with enolizable partners.

Reaction Conditions

General literature guidance for aromatic aldehydes of this class (optimize for your system):

• Wittig/HWE olefination

  • Solvent: THF, toluene, or acetonitrile (anhydrous)
  • Base: NaH, KHMDS (for stabilized ylides/HWE reagents); triethylamine for pre-formed ylides
  • Temperature: 0 °C to reflux depending on reagent; often 0–25 °C for HWE
  • Atmosphere: nitrogen/argon, dry glassware
  • Workup: aqueous quench, extract, silica gel purification; monitor E/Z by NMR/UPLC

• Knoevenagel condensation

  • Solvent: toluene, ethanol, acetonitrile, or 2-MeTHF
  • Catalyst: piperidine, ammonium acetate, or amine-functionalized resins
  • Temperature: ambient to reflux; Dean–Stark in nonpolar solvents to remove water
  • Tip: Molecular sieves (3Å) improve conversion by water scavenging

• Reduction to benzyl alcohol

  • Reagent: NaBH4 or catalytic hydrogenation (Pd/C, H2 1–3 bar)
  • Solvent: THF/MeOH or EtOAc/MeOH; avoid strong acid to limit acetal formation
  • Temperature: 0–25 °C; short reaction times typically sufficient

• Oxidation to acid (Pinnick)

  • Solvent: aqueous tert-butanol/MeCN
  • Oxidant: NaClO2 with NaH2PO4 buffer; 2-methyl-2-butene as ClO2 scavenger
  • Temperature: 0–25 °C; monitor by HPLC

• Protection as acetal

  • Reagents: ethylene glycol, catalytic p-TsOH or camphorsulfonic acid
  • Solvent: toluene; remove water azeotropically

Yields and exact parameters vary with substrate and substituents; run small-scale trials and monitor by NMR/LC–MS. Always dry solvents and exclude air/moisture for base-sensitive or oxidation-prone steps.

Safety and Handling

• Item-specific hazard statements/classification: Not specified for this item; refer to the SDS for authoritative GHS classification, signal word, pictograms, and H/P statements.

• General safety considerations for aromatic aldehydes (literature guidance; not product-specific classification)

  • Hazards: Many aromatic aldehydes can cause eye/skin irritation and may be harmful if swallowed or inhaled. Aldehydes can be sensitizers for some individuals.
  • PPE: Use lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Avoid skin contact and inhalation of vapors/dust.
  • Engineering controls: Handle in a fume hood. Provide local exhaust if weighing fine solids or handling heated liquids.
  • Incompatibilities: Strong oxidizers (risk of over-oxidation to carboxylic acids), strong bases (can cause aldol/self-condensation in presence of enolizable partners), strong reducing agents (may reduce –CHO to –CH2OH). Avoid prolonged exposure to air and light which can promote slow oxidation.
  • Peroxide formation: Not applicable to the substance itself (not an ether solvent); however, store away from peroxide-forming solvents.
  • First aid (general): If on skin/eyes, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Always follow site SOPs and consult the SDS.

• Fire safety: Organic compound; treat as combustible. Use CO2, dry chemical, or foam. Avoid water jets on burning liquids.

Defer to the product SDS for definitive hazard, exposure limits, spill response, and disposal guidance.

Solvent Selection

This compound is an electron-rich aromatic aldehyde with moderate lipophilicity and polar functionality (–CHO, –OMe×2).

• Polarity and miscibility (literature-based expectations)

  • Readily soluble in: dichloromethane, chloroform, ethyl acetate, acetone, THF, acetonitrile, methanol, toluene.
  • Poorly soluble in: water; aliphatic hydrocarbons may require warming or co-solvent.

• Practical selection tips

  • Carbonyl reactions (Wittig/HWE/Knoevenagel): THF, toluene, or acetonitrile commonly offer good solubility and manageable dielectric properties. For strong bases (NaH, KOtBu), use dry, aprotic solvents (THF, DMF) under inert atmosphere.
  • Nucleophilic additions (cyanohydrin, bisulfite adduct, Grignard to related substrates): Use anhydrous ethereal solvents (THF, Et2O) or toluene; ensure aldehyde is dry to minimize side reactions.
  • Oxidation/reduction: For reduction to alcohols, MeOH/EtOH with NaBH4 may cause acetalization; aprotic solvents (THF/EtOAc) can minimize side pathways. For oxidations (e.g., to acid), use acetonitrile or acetone with catalytic systems as appropriate.

• Comparison considerations

  • Versus less substituted benzaldehydes, the two methoxy groups improve solubility in moderately polar organics and can stabilize electron-demanding transition states; choose solvents that balance reactivity and solubility without promoting unwanted acetalization (limit prolonged exposure to alcohols under acid).

Storage and Reconstitution

• Item-specific storage: Room temperature (as provided in Product Data). Shipments: Not specified for this item; refer to CoA/Spec Sheet.

• General guidance for aldehydes (literature-based; not item specifications)

  • Store tightly sealed under air- and moisture-minimized conditions. A desiccator or inert-gas backfill can help limit slow oxidation to the corresponding benzoic acid.
  • Protect from prolonged light and heat. Avoid storing with strong oxidizers or bases.
  • If long-term storage is planned, consider aliquoting to minimize headspace exposure during repeated openings.

• Solution preparation

  • Prepare stock solutions in dry, oxygen-free solvents (e.g., anhydrous THF, acetonitrile, toluene, or DCM). For analytical stocks, use amber vials and add molecular sieves if compatible.
  • Aqueous solutions are not recommended except transiently during workups; aldehydes can hydrate or form acetals/hemiacetals in alcoholic media under acidic conditions.

For any lot-specific stability, water content, or inhibitor information, consult the CoA/SDS.

Structure and Identity

Brief overview: 4-Ethyl-3,5-dimethoxybenzaldehyde is an electron-rich, meta,meta-dimethoxy–substituted benzaldehyde bearing a para-ethyl group. It is a useful aromatic aldehyde building block.

• Item-specific (from Product Data)

  • Product Name: 4-Ethyl-3,5-dimethoxybenzaldehyde
  • CAS: 78025-99-7
  • SKU: E978456
  • InChIKey: 361326 (as provided)
  • Storage Conditions: Room temperature
  • Research Use: For research use only

• Literature/computed identifiers and features (not item specifications)

  • Molecular formula (computed from name): C11H14O3
  • Molecular weight (calculated): ~194.23 g/mol
  • Structural features: benzaldehyde core (–CHO) at position 1; methoxy substituents at 3 and 5; ethyl at 4. The 3,5-dimethoxy pattern creates a 1,3,5-trisubstituted aromatic system with two strong electron-donating groups and one weakly donating alkyl.
  • Functional groups: aromatic aldehyde, two aryl ethers (–OCH3), alkyl substituent.
  • 2D description: a benzene ring bearing, clockwise from the formyl carbon (C1), at C3 and C5 –OCH3 groups, at C4 an –CH2CH3 group, and at C1 an –CHO.
  • SMILES (literature, representative): COc1cc(CC)c(OC)cc1C=O

• Stereochemistry: none (achiral).

Synthetic Utility

Key reactivity arises from the aldehyde and the electron-rich aryl ring bearing two methoxy groups.

• Functional group leverage

  • Aldehyde (–CHO): Enables C–C bond construction through Wittig/HWE/Julia olefinations, Knoevenagel condensations, nucleophilic additions (cyanohydrin formation), and reductive aminations (via imine formation with amines followed by reduction).
  • Aryl ethers (–OMe): Serve as protected phenols; demethylation (BBr3, BCl3, AlCl3/thiols) gives 3,5-dihydroxy-4-ethylbenzaldehyde for further derivatization (esterification, etherification, metalation–coupling after protection).
  • Ethyl substituent: Provides steric/electronic tuning and a handle for benzylic functionalization after side-chain oxidation (e.g., benzylic bromination then substitution), although ring activation/disubstitution pattern may influence selectivity.

• Retrosynthetic value

  • The aldehyde enables late-stage diversification without altering ring substitution. Its presence also allows temporary protection as acetals during harsh electrophilic steps.
  • Electron-rich ring can undergo directed ortho-metalation adjacent to methoxy groups under strong base, subject to substitution pattern constraints, allowing access to further elaborated scaffolds.

• Cross-coupling strategies

  • While the substrate lacks a halide, formyl-directed C–H activation or pre-functionalization (bromination/iodination) can introduce handles for Suzuki, Buchwald–Hartwig, or Kumada couplings on the anisole framework.

Overall, this aldehyde is a convenient entry point to 3,5-dimethoxy-4-alkyl anisole derivatives, styrenes, chalcones, and heteroaromatic adducts used across materials and probe synthesis.

Target Specificity

Not applicable. This product is a small-molecule reagent and is not an antibody, enzyme inhibitor with defined biomolecular targets, or a biological probe validated for specific targets. No target specificity data are provided in the Product Data.