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
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
118.130 g/mol
XLogP3
-0.500
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
4
Exact Mass
118.063 Da
Monoisotopic Mass
118.063 Da
Topological Polar Surface Area
35.500 Ų
Heavy Atom Count
8
Formal Charge
0
Complexity
58.700
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
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Recensioni
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Application Protocols
No validated bioassay or immunoassay protocols are associated with this chemical reagent. For synthetic procedures, consult standard organic synthesis protocols.
General laboratory protocol guidance (literature/general):
For acetal deprotection: Dissolve in MeOH/H2O, add catalytic p‑TsOH·H2O, stir at rt and monitor by TLC/GC. Quench with NaHCO3, extract with EtOAc, dry, and proceed immediately with trapping of the dialdehyde.
For Wittig olefination: Dry solvent and glassware; generate ylide under inert atmosphere, add aldehyde at 0 °C, allow to warm to rt; standard aqueous workup avoiding strong acid.
Always adapt to your specific substrate set and consult primary literature.
Biological Roles
This product is supplied for research use only. No biological role is assigned for this catalog item.
General context (literature, not product-specific):
Structural theme: 3,3-Dimethoxypropanal is a monoacetal of malondialdehyde (propanedial). Malondialdehyde itself is a lipid peroxidation byproduct and a common target for derivatization in biochemical assays; however, the acetal is a synthetic surrogate used to control reactivity of the dialdehyde framework in chemical synthesis.
Laboratory utility: The compound is a convenient handle to introduce a masked dialdehyde motif into small molecules or materials precursors, facilitating subsequent conjugation (e.g., imine formation) after controlled deprotection.
No claims are made regarding metabolism, signaling, or in vivo function. For any biological testing, users must determine suitability and safety independently and consult the SDS.
Buffer Applications
Not typically applicable. 3,3-Dimethoxypropionaldehyde is an organic building block rather than a buffering agent. It does not serve as a classical acid/base buffer system.
Practical note: If handling in aqueous media (e.g., for acid-catalyzed deprotection), use established buffer systems to control pH (acetate buffer for mildly acidic conditions; phosphate or citrate buffers as needed). Ensure compatibility with aldehyde chemistry and avoid strong acidity if preserving the acetal.
Green Alternatives
Greenness considerations focus on solvent and protecting‑group strategy rather than the reagent itself.
Solvent optimization (literature/general):
Prefer bio‑derived ethers/esters (2‑MeTHF, CPME, EtOAc) over petroleum ethers or chlorinated solvents when compatible with reactivity and workup.
For acidolysis/deprotection, aqueous ethanol or acetone/water mixtures can replace DCM or other halogenated media.
Protecting‑group strategy:
The dimethyl acetal is relatively benign and atom‑efficient, generating MeOH upon hydrolysis. Alternatives (e.g., cyclic acetals from glycerol or ethylene glycol) may improve hydrolytic control and reduce volatility, at the cost of added steps.
Comparison (general guidance):
2‑MeTHF vs THF: similar polarity; 2‑MeTHF offers partial immiscibility with water for easier phase separation and often lower peroxide formation; may change reaction rates/selectivity.
EtOAc vs DCM: EtOAc is biodegradable and lower toxicity; DCM offers higher volatility/rapid concentration but with higher environmental/health burden.
Trade‑offs:
Aldehyde chemistry often benefits from volatile, inert solvents for efficient removal; greener choices may require slightly elevated temperatures or longer times. Validate on small scale before adoption.
Pharmaceutical Uses
No excipient or pharmacopeial status is specified for this item; refer to CoA/Spec Sheet. This product is for research use only and not for human or veterinary use.
General formulation context (literature/general):
Role: Small aldehydes/acetals are occasionally used as synthetic intermediates en route to active ingredients or functional excipients, not as finished formulation components.
Considerations: Residual aldehydes can be reactive toward amines and proteins; stringent residual controls are required in GMP settings. Stability to hydrolysis (acetal) and volatility must be assessed during process development.
No therapeutic or clinical claims are implied.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values (for context only; not product specifications):
Molecular formula: C5H10O3 (literature)
Molecular weight: ~118.13 g/mol (literature)
Physical state: typically a colorless to pale liquid (literature)
Functional polarity: polar, due to aldehyde and acetal oxygens; hydrogen-bond acceptor, weak donor (literature)
Volatility: moderate; aldehydes may exhibit noticeable odor (literature)
Solubility: miscible with many organic solvents (e.g., alcohols, ethers, chlorinated solvents); limited to moderate water solubility expected for small acetals (literature)
Notes for practitioners:
Because aldehydes can hydrate and/or oligomerize, measured properties (density, refractive index, boiling point) can vary with water content and stabilizers. Always consult the item’s CoA/SDS for definitive values, and verify critical parameters (e.g., water content) by Karl Fischer when required for moisture‑sensitive transformations.
Quality and Grades
Item-specific grade/purity, stabilizers, and analytical limits: Not specified for this item; refer to CoA/Spec Sheet.
Professional considerations:
Aldehyde content vs. acetal integrity: For stepwise syntheses, users often require a well-defined ratio of free aldehyde to protected site. Review CoA for assay method (e.g., 1H NMR qNMR, GC) and limits on related species (hemiacetal, hydrolysis products).
Water and acid traces: Even ppm levels of mineral acid can catalyze acetal cleavage. If unstabilized, confirm neutrality (pH of aqueous wash or absence of acidic signals) and water content (Karl Fischer). If stabilized (e.g., with base/neutralizer), understand downstream impact (removal prior to acid-catalyzed steps).
Chromatography compatibility: If an HPLC or GC assay grade is offered, that implies low nonvolatile residue and low UV background appropriate for analytical methods; otherwise, standard synthetic grade is typically adequate.
Batch-to-batch consistency: Check CoA for identity (1H/13C NMR), purity (GC/HPLC), and residual solvents. For sensitive catalysis, request metals screening where relevant.
Documentation: Always defer to the item’s CoA/SDS for definitive specifications and handling notes.
Reaction and Applications
3,3-Dimethoxypropionaldehyde is a stepwise malondialdehyde equivalent: a C3 synthon with one reactive aldehyde and one masked as a dimethyl acetal.
Key applications (literature/general):
Chemoselective transformations at the free aldehyde:
Wittig/Horner–Wadsworth–Emmons olefinations to give α,β‑unsaturated acetals; subsequent acidolysis reveals α,β‑unsaturated dialdehydes.
Aldol/Knoevenagel condensations with active methylenes (malonates, cyanoacetates), enabling downstream deprotection to 1,3‑dialdehyde motifs.
Acetal deprotection (unmasking malondialdehyde):
Mild Brønsted acid (e.g., 0.1–1.0 equiv p‑TsOH·H2O, catalytic HCl) in MeOH/H2O or acetone/H2O at rt–50 °C typically affords propanedial (malondialdehyde), often captured in situ as imines/hydrazones to prevent polymerization.
Heterocycle construction:
Stepwise condensations with diamines/hydrazines to access nitrogen heterocycles (e.g., pyrazines, pyridazines) using the latent second aldehyde unveiled later.
Materials/ligand precursors:
Assembly of conjugated dialdehydes for Schiff‑base ligands, macrocycles, and small‑molecule materials following olefination then deprotection.
Practical notes:
Maintain neutral to basic conditions to preserve the acetal during C–C bond formation.
When acid is required catalytically, maintain low water activity or short contact times to avoid premature unmasking.
Reaction Conditions
General literature guidance (not item-specific; optimize per substrate/lab):
Wittig/HWE olefination at the aldehyde:
Solvent: THF, toluene, or CH2Cl2 (anhydrous).
Base: For HWE, NaH or DBU; 0 to rt, 1–4 h typical.
Note: Maintain neutral to basic conditions; avoid acid to protect the acetal.
Nucleophilic addition (Grignard/organolithium):
Solvent: Et2O or THF, −78 to 0 °C; quench with buffered NH4Cl to minimize acid exposure.
Expected outcomes: High chemoselectivity for the free aldehyde; acetal intact.
Aldol/Knoevenagel condensations:
Solvent: MeCN, toluene, or EtOH; base: piperidine, ammonium acetate, or weak inorganic base; rt–80 °C, 2–12 h.
Acetal deprotection to malondialdehyde:
Conditions: 1–10 mol% p‑TsOH·H2O or dilute HCl in MeOH/H2O (9:1 to 1:1), rt–50 °C, 0.5–4 h.
Workup: Neutralize carefully; capture dialdehyde as imine/hydrazone or proceed in situ to next step to avoid polymerization.
Employ molecular sieves for moisture control when acetal integrity is critical.
These ranges are typical literature conditions; verify and adapt based on scale and sensitivity.
Safety and Handling
GHS information (item-specific): Signal word, H-statements, classification, and pictograms: Not specified for this item; refer to SDS.
General safety guidance for aldehydic acetals (literature/industry practice):
Likely hazards: Irritation to eyes/skin/respiratory tract; aldehydes may be sensitizers in some contexts. Treat as flammable organic liquid unless SDS indicates otherwise.
PPE: Use chemical-resistant gloves (e.g., nitrile), lab coat, splash goggles. Handle in a fume hood to avoid inhalation of vapors.
Handling: Minimize exposure to moisture and strong acids—acid can hydrolyze the acetal to malondialdehyde (more reactive/irritant). Avoid bases that could trigger aldol/self‑condensation of the aldehyde under strong/basic conditions.
Incompatibilities: Strong acids (acetal hydrolysis), strong oxidizers (over‑oxidation), strong bases (condensation). Avoid prolonged contact with air/heat that can promote oxidation/polymerization of the aldehyde.
First aid (overview; defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eyes: Rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical advice.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire: Use CO2, dry chemical, or alcohol-resistant foam. Combustion may produce CO/CO2 and irritating aldehydic fumes.
Spill: Contain, absorb with inert material, ventilate area; dispose in accordance with local regulations.
Solvent Selection
This compound functions as a polar, aprotic organic reagent. Solvent choice should balance aldehyde reactivity control and acetal stability.
Water: limited to moderate solubility expected; avoid acidic aqueous media to prevent hydrolysis.
Selection guidance by task:
Nucleophilic additions/organometallics to the aldehyde: Use dry ethereal solvents (THF, Et2O) or toluene; exclude protic solvents and strong acids to preserve the acetal.
Acid-catalyzed deprotection to malondialdehyde: Employ protic solvents (MeOH/H2O, EtOH/H2O) or aqueous acetone with catalytic mineral or sulfonic acid.
Aldol/Knoevenagel condensations at the free aldehyde: Polar aprotic (MeCN, THF) or alcohol solvents with buffered base (e.g., ammonium acetate) to avoid overreaction.
Practical tips:
Drying: Use 3 Å molecular sieves or distill solvents to minimize adventitious water.
Compare to alternatives: If high water compatibility is needed, consider conducting hydrolysis/deprotection in biphasic systems (DCM/H2O, MTBE/H2O) to moderate reaction rate and simplify workup.
Storage and Reconstitution
Item-specific storage (Product Data): Store at room temperature.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General handling and stability (literature/industry practice):
Keep tightly closed under inert gas (nitrogen or argon) to limit oxidation and moisture uptake. Store away from acids to prevent acetal hydrolysis.
If long-term storage is planned, cool dark storage (e.g., 2–8 °C) can further enhance stability; allow to equilibrate to room temperature before opening to avoid condensation.
Do not freeze aqueous solutions; prepare fresh solutions for reactions. No reconstitution is generally required—use as supplied.
After opening, record open date and consider verifying purity by GC/NMR before critical uses.
Research Use Only: For laboratory use; not for human or veterinary use.
Structure and Identity
A masked dialdehyde building block featuring a terminal aldehyde and a geminal dimethoxy (acetal) at the distal carbon of a three‑carbon chain.
Item-specific identifiers (Product Data):
CAS: 19060-10-7
CID: 29398
InChIKey: 192527 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers (general reference, not item-specific):
Common name: 3,3-Dimethoxypropanal (malondialdehyde dimethyl acetal, monoacetal)
Example SMILES (literature): O=CHCC(OC)(OC)
Structural features (description):
Carbon skeleton: a three‑carbon chain bearing an aldehyde at C1 and a gem‑dimethoxy (acetal) substituent at C3.
Functional groups: one free aldehyde (–CHO); one acetal carbon [–CH(OMe)2]. No stereocenters in the free aldehyde; the acetal carbon is tetrahedral but not stereogenic in the absence of chiral substitution.
Motif/Use: Serves as a protected form of malondialdehyde (propanedial), enabling stepwise chemoselective transformations at the unmasked aldehyde followed by acidolysis to unveil the second aldehyde.
Synthetic Utility
Functional logic:
Chemoselectivity: The free aldehyde (C1) is accessible for transformations while the C3 aldehyde is protected as a dimethyl acetal. This enables stepwise assembly of dialdehyde-containing frameworks.
Carbonyl olefinations: Wittig or HWE reactions on the free aldehyde afford α,β‑unsaturated acetals. Subsequent acidic deprotection unveils α,β‑unsaturated dialdehydes, useful for Schiff‑base ligands and conjugated materials.
Nucleophilic additions: Organomagnesium/organolithium reagents add to the free aldehyde; the acetal generally survives under anhydrous, non‑acidic conditions. Workups should avoid strong acid to retain protection.
Condensations: Aldol with enolates or Knoevenagel with active methylene partners provides extended carbon frameworks bearing a latent aldehyde for later unveiling.
Oxidation/reduction orthogonality: The acetal is typically stable to many neutral oxidants (e.g., PCC, Swern conditions) or selective reductions (e.g., NaBH4 reduction of the aldehyde to alcohol, if desired before deprotection), enabling orthogonal manipulation.
Deprotection: Mild Brønsted or Lewis acids in aqueous or alcoholic media hydrolyze the acetal to regenerate malondialdehyde in situ; trapping as imines/hydrazones can enhance isolation.
Workflow tip: Plan sequences to exploit acetal stability (base/neutral) and avoid prolonged acidic exposures until the final unmasking step.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological targeting agent (e.g., antibody, enzyme inhibitor). No antigen, epitope, clone, or species reactivity information applies.
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