5-Ethoxyfuran-2-carbaldehyde - ≥95% , CAS No.67680-03-9

CAS: 67680-03-9 Cat. No.: E998478 Formule: C₇H₈O₃ Poids moléculaire: 140.140 Numéro CE: 991-653-9

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Room temperature

Pureté

≥95%

Noms et identifiants

• Sourires canoniques: CCOC1=CC=C(O1)C=O
• IUPAC Name: 5-ethoxyfuran-2-carbaldehyde
• InChIKey: NCTBTMFBOIURJB-UHFFFAOYSA-N
• INCHI: 1S/C7H8O3/c1-2-9-7-4-3-6(5-8)10-7/h3-5H,2H2,1H3
• Poids moléculaire: 140.140

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Ethers

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Ethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Alkyl aryl ethers
• Alternative Parents: Aryl-aldehydes Heteroaromatic compounds Furans Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Aryl-aldehyde - Alkyl aryl ether - Heteroaromatic compound - Furan - Oxacycle - Organoheterocyclic compound - Organic oxide - Hydrocarbon derivative - Aldehyde - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl 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

Propriétés chimiques et physiques

• Poids moléculaire: 140.140 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 140.047 Da
• Monoisotopic Mass: 140.047 Da
• Topological Polar Surface Area: 39.400 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 113.000
• 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 biological assay protocols are specified for this item. For synthetic applications, consider the general setups below as starting points (literature guidance; adjust to your context):

• Small-scale Wittig: To a flame-dried flask under N2, dissolve the aldehyde (1.0 equiv) in dry THF (0.05–0.2 M). Cool to 0 °C, add ylide solution (1.2–1.5 equiv), then warm to rt and stir 2–6 h. Quench with sat. NH4Cl, extract, dry, and purify by column.
• Reductive amination: Dissolve aldehyde and amine (1.2–2.0 equiv) in MeOH (0.05–0.2 M). Add AcOH (0.2–0.5 equiv) and NaBH3CN (1.2–1.5 equiv) at 0 °C; stir to rt for 2–4 h. Work up and purify. Monitor for over-reduction.
• Diels–Alder: Combine aldehyde (1.0 equiv) with maleimide (1.5 equiv) in toluene (0.1 M). Stir at 60–80 °C 6–16 h. Monitor by NMR/TLC. Cool, remove solvent, and purify adduct; consider aromatization if desired.

These are illustrative only and not product-specific validations. Always perform appropriate controls and safety assessments.

Biological Roles

This product is supplied strictly for laboratory research; no medical or clinical use is intended or implied.

General context (literature):

• Furan derivatives are encountered as minor components of Maillard reaction mixtures and thermal processing products in foods; substitution patterns (e.g., ethoxy, aldehyde) strongly influence reactivity and biological fate.
• Aldehyde functionality can form reversible Schiff bases with amines (e.g., lysine residues) and react with thiols, underlying common labeling or immobilization strategies in biochemical research. Such reactivity is generic to aldehydes and not a specific biological pathway for this compound.
• No specific endogenous metabolic role is known for 5-ethoxyfuran-2-carbaldehyde. If introduced into biological systems, standard xenobiotic metabolism principles would apply (oxidation to the corresponding acid, reduction to alcohol, or conjugation), but these are general expectations and must be validated experimentally for each system.

For any biological experiments, ensure appropriate containment and toxicity evaluation. Consult the SDS and institutional biosafety guidelines before use.

Buffer Applications

Not typically applicable. 5-Ethoxyfuran-2-carbaldehyde is a neutral organic building block rather than a buffering agent. It does not provide a defined acid/base conjugate pair within physiological pH ranges. For work in aqueous systems, prepare solutions in a compatible organic co-solvent (e.g., DMSO, MeCN, or ethanol) and add to pre-made buffers as needed while monitoring final solvent percentages to maintain solubility and avoid protein denaturation.

Green Alternatives

Greener practice with 5-ethoxyfuran-2-carbaldehyde focuses on solvent selection, oxidant/reductant choice, and energy minimization.

• Solvent choices (comparison, literature):
  • Ethers: prefer 2-MeTHF or CPME over THF for reduced peroxide formation rate, higher boiling points, and bio-based sourcing (2-MeTHF). These maintain solubility for aldehyde chemistry and organometallics.
  • Chlorinated solvents: replace DCM with EtOAc, MeTHF, or toluene where reaction performance allows; DCM may still be needed for certain Lewis-acid-promoted steps.
  • Polar aprotics: consider propylene carbonate or sulfolane as safer alternatives to DMF/DMAc when compatible.
• Redox reagents:
  • Favor TEMPO/bleach or oxygen-catalyzed oxidations over chromium(VI) reagents for converting aldehyde to acid.
  • For reductions, use hydrogenation (H2/Pd) or transfer hydrogenation (isopropanol/Ru, organocatalysts) in lieu of hydrides where selectivity permits.
• Energy and intensification:
  • Employ microwave or flow to shorten reaction times and improve heat/mass transfer for condensations or Diels–Alder reactions.
• Waste minimization:
  • Implement solvent recycling and in-process controls to prevent overreaction/polymerization.

Trade-offs: greener solvents may alter rates/selectivity (e.g., Diels–Alder endo/exo balance, Wittig E/Z). Screen a small solvent matrix to verify outcomes before scale-up.

Pharmaceutical Uses

No pharmacopeial or excipient status is specified for this item; refer to CoA/Spec Sheet. Content below is general and for research discussion only.

• Role in discovery chemistry (literature): heteroaromatic aldehydes like 5-ethoxyfuran-2-carbaldehyde are commonly used as intermediates in medicinal chemistry to build focused libraries via reductive amination, Wittig/HWE, and condensations, enabling rapid SAR exploration around a furan core.
• Derivatization handles: the aldehyde enables incorporation into scaffolds that may later be oxidized to acids (for prodrugs or salt formation) or transformed into alcohols/ethers; the 5-ethoxy substituent modulates lipophilicity and electronics of the scaffold.
• Analytical standards: such compounds can serve as reference materials for method development (e.g., LC–MS stability-indicating methods) for furan-containing series.

No therapeutic claims are made or implied. For any work approaching regulated development, verify impurity profiles, residual solvents, and trace metals according to relevant guidelines (ICH Q3A/B, Q3D) using the specific lot CoA.

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: ~140.14 g/mol (literature/computed from C7H8O3; see Structure & Identity)
• Boiling point: Not specified for this item; literature for closely related furan-2-carbaldehydes suggests moderate bp in the 180–210 °C range under ambient pressure; verify for this specific derivative.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (qualitative, literature expectations):
  • Miscible with many organic solvents (e.g., dichloromethane, ethyl acetate, THF, alcohols); limited solubility in water expected for aryl/heteroaryl aldehydes with one ethoxy group.
• Partitioning: A neutral, moderately polar organic compound; cLogP likely in the low-to-moderate range for substituted furans (literature expectation; confirm experimentally for quantitative work).
• Spectral features (general):
  • IR: strong C=O stretch of aldehyde typically ~1670–1730 cm⁻¹ (literature, solvent-dependent); furan ring C–O–C and C=C bands in the 1000–1600 cm⁻¹ region.
  • 1H NMR: aldehyde proton near 9.3–9.8 ppm (literature typical); furan ring protons 6.1–7.4 ppm; ethoxy CH2 around 3.9–4.3 ppm; CH3 ~1.2–1.4 ppm.

All numerical specifications not provided in Product Data are not specified for this item; consult the CoA/Spec Sheet for authoritative values before process design.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Interpreting common grades (general guidance):
  • Analytical/Reagent Grade: Typically supports routine synthesis and analysis; impurity thresholds suitable for most bench chemistry.
  • High-purity/Synthesis Grade: Lower trace metals/water; suitable for moisture-sensitive and organometallic transformations.
  • HPLC/GC Grade (for solvents): Controlled UV absorbance and low non-volatile residue; relevant only if used as solvent or standard.
• Stabilizers: Not specified for this item; aldehydes are sometimes supplied without stabilizers. If a stabilizer is listed on the CoA, consider its impact on downstream reactions (e.g., traces of acid/base promoting side reactions).
• Verification:
  • For route-critical steps (e.g., stereospecific Wittig/HWE or low-level impurity specs), review the CoA for water content, peroxide level (if applicable), residual solvents, and assay method.
  • Use a small verification test (e.g., 1H NMR or GC) upon receipt to confirm identity and assess aldehyde integrity (check for hydrate or acetal formation).

Reaction and Applications

5-Ethoxyfuran-2-carbaldehyde is a versatile building block that merges an electron-rich furan with a reactive aldehyde handle.

Key application families (literature):

• Carbon–carbon construction via the aldehyde:
  • Wittig/Horner–Wadsworth–Emmons (HWE) to access 2-substituted alkenyl furans; control E/Z via ylide/phosphonate choice and temperature.
  • Knoevenagel/Doebner condensations with active methylenes (malononitrile, Meldrum’s acid, barbiturates) under base or amine catalysis.
  • Henry (nitroaldol) and cyanohydrin formation under basic or Lewis acid catalysis.
• Carbon–heteroatom reactions:
  • Reductive amination to secondary/tertiary amines (NaBH3CN, BH3·THF, or H2/Pd), often in MeOH or THF.
  • Oxime/hydrazone formation as protecting/analytical derivatives.
• Functional group interconversions:
  • Oxidation to the corresponding carboxylic acid (e.g., NaClO2, TEMPO/bleach) or ester; reduction to benzyl-type alcohol (NaBH4/DIBAL) or to methylene (Wolff–Kishner/Clemmensen equivalents, if compatible).
• Pericyclic chemistry of the furan:
  • Diels–Alder as a diene with maleimides, acrylates, and anhydrides; the 5-ethoxy substituent enhances diene reactivity and can direct regiochemistry.
• Diverse heterocycle elaboration: electrophilic substitution on the furan ring (e.g., Vilsmeier–Haack at C-5/C-3 in related systems), halogenation (NBS/NCS) followed by cross-coupling.

Practical tips:

• Keep reactions oxygen- and moisture-controlled to avoid aldehyde autoxidation; add antioxidants only if compatible.
• Monitor by TLC/GC; aldehydes can overreact (e.g., double addition). Use slight excess of nucleophile or control temperature to tune chemoselectivity.

Reaction Conditions

General, literature-based guidance for reactions involving 5-ethoxyfuran-2-carbaldehyde (optimize for your system):

• Wittig olefination: Use stabilized ylide in dry THF or toluene (0–25 °C), 1–4 h to overnight. E/Z ratio depends on ylide type and temperature. Work under inert atmosphere.
• Horner–Wadsworth–Emmons (HWE): Phosphonate (1.2–1.5 equiv), NaH or K2CO3 in THF/DMF, 0–25 °C, 2–12 h; often favors E-alkenes with stabilized phosphonates.
• Knoevenagel condensation: Active methylene (1.1–1.5 equiv), catalytic piperidine or ammonium acetate in toluene/EtOH/MeCN, 25–110 °C, 2–16 h; azeotropic water removal improves conversion.
• Reductive amination: Amine (1.2–2.0 equiv), NaBH3CN or H2/Pd; solvent MeOH/EtOH/THF; pH control with AcOH (for NaBH3CN), 0–25 °C, 1–6 h.
• Aldehyde reduction: NaBH4 (1.2–2.0 equiv) in MeOH/EtOH at 0–25 °C, 0.5–2 h to give the alcohol; DIBAL in toluene at −78 to 0 °C for chemoselectivity.
• Oxidation to acid: Pinnick (NaClO2, NaH2PO4, 2-methyl-2-butene) in tBuOH/H2O, 0–25 °C, 1–3 h; or TEMPO/bleach in biphasic systems.
• Diels–Alder (furan as diene): With maleimides/anhydrides in toluene or DCM, 0–80 °C, 2–24 h; monitor for retro-DA. Endo selectivity often favored at lower temperature; aromatization requires subsequent steps.

Notes:

• Furan rings can be sensitive to strong acids/bases and high temperatures; control conditions to avoid ring opening or polymerization.
• Exclude oxygen/moisture for organometallics. All conditions are general literature guidance and should be validated for scale and substrate pairing.

Safety and Handling

• GHS/Classification: Not specified for this item; refer to the SDS for authoritative hazard classification, pictograms, and H/P statements for 5-ethoxyfuran-2-carbaldehyde.
• General hazards (literature-based, similar aldehydes):
  • Aldehydes can be irritating to skin, eyes, and respiratory tract; avoid inhalation of vapors and contact with skin/eyes.
  • Furan derivatives can be flammable; handle away from ignition sources in a fume hood.
• PPE: Safety glasses or goggles, lab coat, appropriate chemically resistant gloves (e.g., nitrile), and use within a functioning chemical fume hood.
• Handling:
  • Minimize exposure to air and moisture to limit oxidation/polymerization of the aldehyde; keep containers tightly closed.
  • Use dry, oxygen-free techniques if high reactivity is required (e.g., for organometallic additions).
• Incompatibilities (general): Strong oxidizers (risk of rapid oxidation), strong bases/acids (may catalyze aldol-type self-condensation or acetalization), and strong nucleophiles (can react with the aldehyde).
• First aid (summary; defer to SDS):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical advice.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Waste: Collect aldehyde-containing organic waste in properly labeled containers; dispose via licensed hazardous waste contractor consistent with local regulations.

Always consult the product SDS for final guidance on hazards, spill response, and transport classifications.

Solvent Selection

As a moderately polar, non-ionizable heteroaromatic aldehyde, 5-ethoxyfuran-2-carbaldehyde dissolves in many organic solvents. Select solvent based on the reaction class and sensitivity of the aldehyde.

• Polarity/Miscibility (general):
  • Good solubility expected in ethers (THF, MTBE, CPME), chlorinated solvents (DCM, chloroform), esters (EtOAc), and polar aprotics (MeCN, DMF, DMSO).
  • Limited water solubility typical for ethoxy-substituted furans; use co-solvents if aqueous media are required.
• Selection tips:
  • Nucleophilic additions/Grignard/organolithiums: rigorously dry ethers (e.g., THF, 2-MeTHF, CPME). Avoid protic solvents.
  • Condensations (Knoevenagel/aldol variants): toluene, MeCN, or EtOH depending on base/catalyst; azeotropic removal of water (Dean–Stark) may benefit equilibrium.
  • Reductions (NaBH4, DIBAL, catalytic hydrogenation): alcohols (MeOH/EtOH/iPrOH) or ethers/chlorinated solvents for chemoselectivity control.
  • Diels–Alder with the furan ring: nonpolar to moderately polar solvents (toluene, DCM); temperature control is key for endo/exo selectivity and reversibility.
• Comparative considerations:
  • DCM vs EtOAc: DCM often enhances rate in electrophile–nucleophile couplings; EtOAc is greener but may participate in transacylation under strong base.
  • THF vs 2-MeTHF/CPME: greener ethers can match solubility with improved safety/handling; check organometallic initiation behavior.

Confirm final solvent choice experimentally; no item-specific solvent constraints are specified in Product Data.

Storage and Reconstitution

• Storage conditions (as provided): Room temperature.
• General best practices for aldehydes:
  • Store in a tightly sealed amber vial under inert gas (N2/Ar) to minimize oxidation and polymerization.
  • Keep dry; consider a desiccant in secondary containment. Avoid prolonged exposure to air, heat, and light.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution/Use:
  • Typically supplied neat; no reconstitution required. For solution use, prepare fresh solutions in dry, oxygen-free solvent (e.g., THF, DCM, MeCN, EtOAc) immediately before experiments.
  • If long-term stock solutions are needed, store at low temperature in sealed, inerted containers and verify stability by NMR/GC before critical use.
• Stability notes (general):
  • Aldehydes may form hydrates/acetals in the presence of water/alcohols and acids; avoid acidic impurities unless acetalization is intended.
  • Periodically check for peroxide formation only if ether solvents are present in stored solutions; the aldehyde itself is not an ether solvent but may be dissolved in one.
• Research Use Note: For research use only.

For definitive shelf-life and any lot-specific stabilizers, consult the CoA/Spec Sheet and the SDS.

Structure and Identity

5-Ethoxyfuran-2-carbaldehyde (SKU: E998478) is a heteroaromatic aldehyde: a furan ring bearing an aldehyde at the 2-position and an ethoxy substituent at the 5-position. The furan oxygen is position 1; the aldehyde is alpha to the ring oxygen.

• CAS: 67680-03-9
• Preferred name: 5-Ethoxyfuran-2-carbaldehyde
• Category Path: 全部 / 可售 / 生命科学
• InChIKey (as provided): 235097
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: C7H8O3 (literature/computed from name)
• Molecular weight: ~140.14 g/mol (literature/computed)

Structural features (descriptive):

• Functional groups: aromatic heterocycle (furan), aldehyde (–CHO), alkoxy substituent (–OCH2CH3).
• Electronics: the ethoxy group donates electron density into the ring (−I/ +M context), typically increasing the diene character of furan and activating the 5-position; the aldehyde is strongly electron-withdrawing, enabling condensations and nucleophilic additions at C-2.
• 2D description: a five-membered planar ring with one oxygen atom; at the ring carbon next to oxygen (C-2) is a formyl group (–CHO). At the carbon opposite the aldehyde (C-5) is an ethoxy substituent attached via oxygen (–O–CH2–CH3). No stereocenters are present.

Notes:

• Identifiers not explicitly listed in the product data (e.g., SMILES) are not specified for this item and should be confirmed on the CoA/Spec Sheet before regulatory or analytical use.

Synthetic Utility

Functional group set: an electron-rich furan ring with a 5-ethoxy substituent and a 2-aldehyde. This constellation supports diverse, chemoselective transformations.

• Electrophile at C-2 (aldehyde):
  • Nucleophilic additions (RMgX, R2CuLi, cyanide, nitroalkanes) provide rich access to secondary alcohols, cyanohydrins, and Henry adducts.
  • Carbonyl olefinations (Wittig/HWE) give substituted vinyl furans with tunable geometry.
  • Interconversions: oxidation (acid), reduction (alcohol/methylene), and protection (acetals, oximes, hydrazones).
• Furan core:
  • Diels–Alder diene with maleimides/anhydrides/acrylates; subsequent aromatization or rearrangement expands access to benzofused or substituted cyclohexanone frameworks.
  • Electrophilic substitution/halogenation at activated positions followed by Suzuki/Negishi/Sonogashira couplings after halide installation.
• Ethoxy substituent:
  • Acts as a directing and electron-donating group; can be transformed under harsh conditions (e.g., demethylation analogies do not directly apply; ethoxy cleavage typically requires stronger acids or reductive conditions).

Retrosynthetic perspectives:

• Target molecules bearing a furan-2-ylmethyl unit can be accessed by reduction of the aldehyde then functionalization of the benzylic alcohol.
• Acid derivatives arise via Pinnick oxidation of the aldehyde, followed by esterification/amidation.

This makes 5-ethoxyfuran-2-carbaldehyde a practical node for library synthesis and heterocycle diversification.

Target Specificity

Not applicable. This product is a small-molecule heteroaromatic aldehyde, not a biological macromolecule or antibody. No antigen/epitope specificity, species reactivity, clone, or isotype information applies.