3,3-Diethoxypropanal - ≥97% , CAS No.6367-37-9

CAS: 6367-37-9 Cat. No.: D991999 Formula: C₇H₁₄O₃ Peso molecolare: 146.180

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Specifiche e purezza

≥97%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥97%

Nomi e identificatori

• Sorrisi canonici: CCOC(CC=O)OCC
• IUPAC Name: 3,3-diethoxypropanal
• InChIKey: WTRPATCGXBMKKJ-UHFFFAOYSA-N
• INCHI: 1S/C7H14O3/c1-3-9-7(5-6-8)10-4-2/h6-7H,3-5H2,1-2H3
• Peso molecolare: 146.180

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Aldehydes
          • Level6 Alpha-hydrogen aldehydes

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Aldehydes
• Direct Parent: Alpha-hydrogen aldehydes
• Alternative Parents: Acetals Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Alpha-hydrogen aldehyde - Acetal - Organic oxide - Hydrocarbon derivative - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl 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

Proprietà chimiche e fisiche

• Peso molecolare: 146.180 g/mol
• XLogP3: 0.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 146.094 Da
• Monoisotopic Mass: 146.094 Da
• Topological Polar Surface Area: 35.500 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 76.900
• 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/biological application protocols are provided for this item. It is supplied as a chemical building block for synthesis. For synthetic operations, see Reaction Conditions and Synthetic Utility sections for general, literature-based procedural guidance.

Biological Roles

This product is intended for research and laboratory use only. No biological or clinical roles are claimed for this item.

General context (literature/general):

• Acetals of small aldehydes are generally synthetic intermediates without intrinsic biological function. The parent dialdehyde (malondialdehyde) is a known lipid peroxidation byproduct in biology; however, 3,3-diethoxypropanal is a protected synthetic variant used in chemical synthesis and is not a native metabolite.

Please avoid inferring biological activity or suitability for in vivo use from its chemical structure. Consult your institutional biosafety office before any non-chemical use.

Buffer Applications

Not typically applicable. 3,3-Diethoxypropanal is an organic building block, not a buffering agent. It does not form defined acid/base pairs suitable for maintaining pH in aqueous systems. For laboratory use, focus on the synthetic and reaction guidance sections.

Green Alternatives

Greenness considerations relate to solvent choice and protecting-group strategy rather than replacing the reagent outright.

• Strategy alternatives (literature/general):

  • Use of water-tolerant protecting groups or temporary tethers can avoid acetal chemistry where acid catalysis would otherwise be required.
  • Direct one-pot cascades that generate and consume malondialdehyde equivalents in situ can minimize isolation and solvent use.

• Solvent greening (literature/general):

  • Prefer 2-MeTHF or CPME over THF/diethyl ether for improved safety (lower peroxide formation) and biorenewable content (2-MeTHF from hemicellulosic sugars).
  • Replace DCM with EtOAc, Me-THF, or toluene where feasible to reduce halogenated solvent waste.

Compact comparison (general):

• THF vs 2-MeTHF: similar polarity; 2-MeTHF often enables easier phase separations and has better EHS profile.
• DCM vs EtOAc: EtOAc is less toxic and biodegradable; note differing Lewis basicity and extraction behavior.

Note: The unique chemoselectivity of 3,3-diethoxypropanal as a monoacetal of malondialdehyde is not always replicated by “greener” substitutes; greening efforts should focus on solvent selection, telescoped processes, and minimization of acid usage and waste.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item. It is offered for research use only and is not formulated for therapeutic, diagnostic, or clinical applications.

General formulation context (literature/general):

• In medicinal chemistry synthesis, aldehyde monoacetals like 3,3-diethoxypropanal can be used as masked dialdehyde building blocks to assemble advanced intermediates prior to formulation development.
• Due to the susceptibility of acetals to acid-catalyzed hydrolysis, such reagents are used at the API/intermediate synthesis stage and are not typical drug product excipients.

Physical Properties

Item-specific numerical specifications (BP, MP, density, refractive index, purity, etc.): Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for compounds of this class (acetalized aldehydes of low molecular mass):

• Physical state: typically colorless to pale liquid with aldehydic odor (literature/general).
• Volatility: low-to-moderate; free aldehyde functionality often lowers boiling point relative to higher acetals, but the diethoxy group increases molecular weight and reduces volatility vs. unsubstituted propanal (literature/general).
• Solubility: expected to be miscible with many organic solvents (ethers, alcohols, esters, chlorinated solvents) and sparingly soluble in water due to the acetal and ethyl groups (literature/general).
• Stability: acetals are generally stable to base and neutral media; the free aldehyde can undergo self-condensation/polymerization if basic or nucleophilic impurities are present. Under aqueous acid, the acetal can hydrolyze to the corresponding carbonyl compound(s) (literature/general).

Note: For quantitative values (boiling point, density, refractive index, water/peroxide/UV specs), consult the lot-specific CoA or specification sheet. Avoid relying on generic literature values for method validation or regulatory work.

Quality and Grades

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

Guidance on grades for this reagent class (literature/general):

• Synthetic/intermediate grade: typically appropriate for most organic syntheses. Verify aldehyde content and check for hydrolysis or polymerization by 1H NMR before use in sensitive transformations.
• High-purity or GC/HPLC grade: desirable when using in analytical syntheses or when trace acidic/alkaline impurities would perturb acid/base-sensitive steps (e.g., acetal stability during storage).
• Low-peroxide specifications: More critical for ethers; not typically specified for acetals unless the product contains significant ether solvent as stabilizer. For this item, stabilizers are Not specified for this item; refer to CoA/Spec Sheet.

Batch-to-batch quality control suggestions (general):

• Verify identity by 1H/13C NMR (diagnostic aldehyde proton ~9–10 ppm; ethoxy signals; acetal carbon around 100–110 ppm) and IR (strong C=O ~1720–1740 cm−1; C–O stretches) (literature/general).
• Assess water content if moisture-sensitive steps are planned (Karl Fischer). Specific water limits: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

3,3-Diethoxypropanal is a versatile masked-dialdehyde synthon. The free aldehyde reacts while the diethoxy acetal protects the second carbonyl, enabling sequential or chemoselective transformations (literature/general).

Representative applications (literature/general):

• Controlled access to malondialdehyde chemistry: Acidic hydrolysis of the acetal unmasks the second carbonyl, generating malondialdehyde in situ under controlled conditions.
• Aldol condensations: The aldehyde can undergo base-catalyzed aldol or Knoevenagel-type condensations with active methylene partners while the acetal remains intact under mild base. Subsequent deprotection reveals a 1,3-dicarbonyl-like motif.
• Heterocycle synthesis: Valuable in pyridine and dihydropyridine constructions (e.g., Hantzsch-type condensations) where stepwise unveiling of carbonyls is advantageous.
• Wittig/olefination: Selective olefination at the free aldehyde affords alkenyl acetals; acid workup then provides α,β-unsaturated carbonyl frameworks.
• Reductive elaborations: Chemoselective reduction of the aldehyde (e.g., NaBH4, mild hydride) provides the corresponding primary alcohol while preserving the acetal; downstream oxidation or acetal cleavage diversifies scaffolds.

Practical tips:

• Maintain neutral to mildly basic conditions to keep the acetal intact; add acid only when intentional deprotection is desired.
• For acid-catalyzed hydrolysis, use dilute mineral acid (e.g., HCl, H2SO4) at 0–25 °C and monitor by TLC/NMR to avoid over-degradation (literature/general).
• Validate structure and purity before multi-step use; aldehydes can polymerize or oxidize on storage—run a quick 1H NMR check.

Reaction Conditions

General literature guidance for this reagent class (verify and optimize for your system):

• Acid-catalyzed acetal hydrolysis (to unmask malondialdehyde):

  • Solvent: aqueous THF, dioxane, or acetone; or alcohol–water mixtures (MeOH/H2O, EtOH/H2O).
  • Catalyst: HCl, H2SO4, p-TsOH (0.5–10 mol%).
  • Temperature: 0–25 °C for controlled, stepwise deprotection; higher temperatures accelerate but risk side reactions.
  • Monitoring: TLC (vanillin/anisaldehyde stains) or 1H NMR to observe disappearance of acetal methylene signals and growth of second aldehyde proton.

• Aldol/Knoevenagel at the free aldehyde:

  • Base: secondary amines (pyrrolidine) + acetic acid (catalytic) for Knoevenagel; or Na2CO3/DBU for milder aldol variants.
  • Solvent: toluene, THF, MeCN, or EtOH depending on partner; 0–60 °C.

• Wittig/HWE olefination:

  • Base: NaHMDS or KHMDS for stabilized ylides at −78 to 0 °C; milder conditions for preformed ylides.
  • Solvent: THF/2-MeTHF or toluene; inert atmosphere.

• Reductive amination:

  • Reagents: amine + NaBH3CN or NaBH(OAc)3; AcOH or TFA (substoichiometric) as activator while keeping conditions sufficiently mild to avoid acetal cleavage.
  • Solvent: MeOH, DCE, or THF; 0–25 °C.

Note: Expected yields and exact conditions are substrate-dependent; run small-scale screens. Avoid strong mineral acid in workup unless deprotection is intended.

Safety and Handling

Authoritative safety information is in the Safety Data Sheet (SDS). The following are general considerations for aldehyde–acetal reagents.

• GHS classification and pictograms: Not specified for this item; refer to SDS.
• Common hazards (literature/general):
  • Aldehydes are often skin/eye irritants and can be harmful if inhaled; acetals are usually less reactive but may form flammable mixtures with air.
  • Combustible/flammable liquid risk typical of low-mass organics; keep away from ignition sources.
  • Acid-catalyzed hydrolysis may release more reactive carbonyl species with stronger irritancy.
• Incompatibilities (general):
  • Strong acids (hydrolysis of acetal) and strong bases (can promote aldol-type reactions of the free aldehyde).
  • Strong oxidizers (risk of exotherm/oxidation of aldehyde moiety).
• PPE (typical lab practice): lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood to control vapors.
• First aid (general guidance; defer to SDS):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical advice for persistent irritation.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Spill/leak response: absorb with inert material (vermiculite, silica), ventilate area, and dispose of in accordance with local regulations.
• Waste: collect as halogen-free organic waste unless process introduced halogens; confirm with institutional EHS.

Solvent Selection

This product is an organic building block rather than a solvent. Selection below refers to solvents suitable for handling and reactions involving 3,3-diethoxypropanal (general guidance).

• Polarity needs: The reagent bears one aldehyde and an acetal moiety; it dissolves well in moderately polar aprotic and many protic organic solvents (literature/general). Common media:
  • Aprotic: dichloromethane (DCM), toluene, THF, MeTHF, EtOAc, acetonitrile.
  • Protic: methanol, ethanol (can participate in acetal exchange under acid).
• When to choose which:
  • Acid-catalyzed acetal hydrolysis or exchange: use aqueous alcohol (MeOH, EtOH) or wet acetone/THF with catalytic mineral acid.
  • Aldol/condensation steps: choose dry aprotic solvents (DCM, toluene, THF) and control base strength to avoid premature acetal cleavage.
  • Reductive transformations (e.g., selective reduction of aldehyde): EtOAc or DCM often provide good chemoselectivity; avoid strong acids (literature/general).
• Moisture considerations: To preserve the acetal, use dry solvents and avoid strong acids unless deprotection is intended.

Quick comparison (literature/general):

• DCM: excellent for acid-catalyzed reactions at low temperature; immiscible with water for biphasic workups.
• THF/2-MeTHF: good for base-mediated condensations; ethers support organometallics but avoid strong acids (acetal cleavage risk).
• MeOH/EtOH: enable transacetalization; monitor to prevent over-exchange.

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.
• Reconstitution: Not applicable; supplied as a neat chemical (no reconstitution required). If solidification occurs on cold storage, allow to warm gently to ambient and ensure homogeneity by brief swirling.

Good handling practices (literature/general):

• Store tightly closed under inert gas (e.g., nitrogen) to minimize oxidation/polymerization of the aldehyde function.
• Protect from moisture and strong acids to prevent acetal hydrolysis during storage.
• If long-term storage is planned, consider refrigeration (e.g., 2–8 °C) in amber glass to reduce volatility and degradation; allow to equilibrate to room temperature before opening to avoid moisture condensation.
• Check integrity before use by 1H NMR (aldehyde proton signal and ethoxy resonances).

Structure and Identity

Short description: 3,3-Diethoxypropanal is an aldehyde bearing a geminal diethoxy (acetal) substituent at the terminal C-3 carbon, functioning as a masked dialdehyde/malonaldehyde equivalent in synthesis.

• Preferred name: 3,3-Diethoxypropanal
• Synonym notes (literature): Often described as the monoacetal of malondialdehyde (propanedial), i.e., an acetal-protected dialdehyde with one free aldehyde function (literature/general).
• CAS: 6367-37-9 (from Product Data)
• 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 features (general description from name):

• Functional groups: one free aldehyde (–CHO) at C-1; a geminal diethoxy acetal [–C(H)(–OEt)2] at C-3 (literature/general).
• Backbone: a three-carbon propanal chain (CHO–CH2–C(–)(–)), with the terminal carbon bearing two ethoxy substituents and a hydrogen (tertiary acetal center) (literature/general).
• Stereochemistry: acetal center is tetrahedral but not stereogenic when bearing a hydrogen and two identical ethoxy substituents (literature/general).
• 2D description in words: An aldehyde carbonyl at one end (C-1), followed by a methylene (C-2), then a tertiary carbon (C-3) substituted by two –O–CH2–CH3 groups and one hydrogen (literature/general).

Synthetic Utility

Functional group profile (literature/general):

• Free aldehyde: engages in nucleophilic additions (e.g., Grignard/organolithium under carefully controlled conditions), aldol/Knoevenagel condensations, Wittig/HWE olefinations, reductive aminations.
• Gem-dialkoxy (acetal) group: robust to base and many nucleophiles; cleaves under aqueous acid to reveal a second carbonyl, enabling stepwise dialdehyde chemistry.

Retrosynthetic value:

• Serves as a mono-protected malondialdehyde equivalent, allowing selective operations at one carbonyl prior to unveiling the second. This underpins convergent routes to 1,3-dicarbonyl frameworks, α,β-unsaturated aldehydes/ketones, and heteroaromatics.

Named/typical transformations (literature/general):

• Hantzsch-type condensations (controlled access to dihydropyridines/pyridines via staged carbonyl availability).
• Wittig/Horner–Wadsworth–Emmons to introduce defined alkene geometry, followed by acidic deprotection to elaborate conjugated systems.
• Reductive amination at the aldehyde (NaBH3CN/NaBH(OAc)3) yielding protected amino alcohols/aldehydes that can be further manipulated after acetal cleavage.

Selectivity notes:

• Maintain pH neutrality during base-mediated steps to preserve the acetal. If organometallic additions are attempted, use low temperature and avoid prolonged exposure to strong acids in workup.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent, not a biologic or affinity reagent. No antigen/epitope or species reactivity applies.