This compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl 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.
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Application Protocols
Not applicable. No tested bioassay/application protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. For synthetic uses, refer to the Reaction Conditions and Synthetic Utility sections for general laboratory guidance.
Biological Roles
Applicability: 4‑Antipyrinecarboxaldehyde is supplied for research use as a synthetic building block. It is not intended for biological exposure or clinical use.
General notes (literature context, not product claims):
Antipyrine (phenazone) is a historic analgesic scaffold; however, 4‑formyl functionalization converts it into a reactive aldehyde used primarily in synthetic and coordination chemistry.
Schiff bases derived from 4‑antipyrinecarboxaldehyde have been explored in bioinorganic model complexes and in analytical probes for certain metal ions; these are research tools rather than biological metabolites.
No established endogenous biological role is associated with this aldehyde; it is not a buffer component or a common biochemical cofactor.
Caution: Avoid extrapolating any pharmacological relevance. Per the Research Use Note, this product is for laboratory research use only.
Buffer Applications
Not typically applicable. 4‑Antipyrinecarboxaldehyde is an organic aldehyde building block and is not used as a buffering agent. If working in partially aqueous systems (e.g., oxime formation), select an appropriate buffer separately (e.g., acetate pH 4–5 for catalysis) and verify compatibility with aldehyde reactivity.
Green Alternatives
Sustainability considerations focus on the processes using 4‑Antipyrinecarboxaldehyde rather than on the reagent itself.
Solvents: Prefer bio-derived ethanol or 2‑MeTHF over DMF/DMSO where feasible. Water/ethanol mixtures can support many imine and oxime formations with reduced toxicity.
Catalysis: Use organocatalysts (e.g., amino acids, citric acid) or heterogeneous solid acids (Amberlyst-15, montmorillonite K‑10) to enable milder, recyclable conditions.
Energy: Conduct condensations at room temperature or under microwave irradiation to reduce time/energy; mechanochemical imine formation (ball milling with a catalytic acid and desiccant) eliminates bulk solvent.
Workup: Replace chlorinated solvents in extraction with EtOAc or MTBE; use aqueous bicarbonate washes judiciously to minimize salt waste.
Illustrative comparison (general):
Traditional: Imine formation in toluene or benzene, Dean–Stark, p‑TsOH.
Greener: Ethanol (99% bio-based) at reflux with catalytic acetic or citric acid; water removal via molecular sieves; or solvent-free mechanochemistry.
Trade-offs:
DMSO/DMF offer excellent solubility but are problematic for waste handling; 2‑MeTHF/EtOAc are greener but may reduce solubility—consider modest heating or co-solvents.
Solid-acid catalysts simplify separation but may alter selectivity; validate with small-scale screens.
Recommendation: Evaluate solvent selection with CHEM21/ACS GCI guides and document EHS impacts in route selection reports.
Pharmaceutical Uses
Not typically applicable to this specific reagent. While the antipyrine scaffold has historical pharmaceutical relevance, 4‑Antipyrinecarboxaldehyde itself is provided as a research chemical/building block and is not an excipient or a compendial substance.
Formulation-related considerations for research:
If preparing analytical derivatization reagents or ligands, standardize solvent content and residual reagents to ensure reproducibility.
Avoid claims of therapeutic utility; any use should remain within laboratory synthesis, analytical chemistry, or materials research contexts.
Physical Properties
Item-specific specifications:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Other specs (mp, bp, density, refractive index, water/peroxide/metals/UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties for guidance only (not item specifications):
Class: Heteroaromatic aldehyde; typically a crystalline solid at ambient temperature.
Solubility tendencies: Many antipyrine derivatives show good solubility in polar aprotic organic solvents (e.g., DMSO, DMF, acetonitrile) and limited solubility in water; aldehyde functionality supports participation in organic condensations (literature).
Reactivity: Aldehyde carbonyl is electrophilic; the pyrazolone ring can engage in tautomerism and hydrogen bonding (literature).
Practical handling implications:
If solid, gentle warming and sonication can aid dissolution in polar organic media.
Minimize exposure to atmospheric moisture and oxygen to limit potential slow oxidation/polymerization of aldehydes.
Important: Do not treat the above as specifications for SKU A354580. For exact numerical values and acceptance criteria, consult the product CoA/SDS.
Quality and Grades
Item-specific grade/purity details:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting quality (general, for researchers planning use of this aldehyde building block):
Typical research grades: “Research grade” or “≥X% purity” indicate suitability for synthetic and analytical work; for sensitive condensations (e.g., imine formation with low nucleophile loading), higher purity and low carbonyl impurities can be critical to minimize side products.
Analytical control: For aldehydes, common release tests include identity (1H/13C NMR, IR carbonyl band), purity by HPLC/GC, residual solvents, and moisture by Karl Fischer. If you require low-UV background for photophysical studies, request UV-Vis trace data.
Stabilizers: None are listed for this SKU. If stabilizers are present in other lots of aldehydes, they can compete in condensations; verify via CoA.
Batch-to-batch: For ligand synthesis where stoichiometry is tight (e.g., Schiff bases, salen-like frameworks from 4‑antipyrinecarboxaldehyde), confirm assay and water content to ensure reproducibility.
Recommendation: Contact Aladdin Scientific for the lot-specific CoA and specification sheet for SKU A354580 to verify assay, impurity profile, and any chromatographic suitability notes relevant to your application.
Reaction and Applications
As a heteroaromatic aldehyde, 4‑Antipyrinecarboxaldehyde is broadly useful in organic and coordination chemistry.
Key application families (literature/general):
Schiff base formation: Condensation with primary amines, hydrazines, hydrazides, or aminothiols to give imines, hydrazones, and thioimines. Antipyrine-derived imines are used as chelating ligands and analytical reagents.
Oxime/semicarbazone formation: Reaction with hydroxylamine, semicarbazide; products serve as carbonyl-protecting derivatives and metal-binding ligands.
Knoevenagel-type condensations: With activated methylene compounds (e.g., malononitrile, cyanoacetates) under base catalysis to form conjugated adducts.
Reductive amination: Two-step imine formation followed by reduction (NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation) to access benzylic amines tethered to the pyrazolone core.
Acetal/hemiacetal chemistry: Under acid catalysis with diols or alcohols for protecting-group strategies or to tune crystallinity.
Metal complexation via Schiff bases: Condensation with diamines/aryl amines yields bidentate/tridentate ligands suitable for Cu, Ni, Co, Zn complex preparation, often used in catalysis or sensing.
Practical tips:
Drive condensations by removing water (3 Å molecular sieves, azeotrope with toluene) and/or using mild acid catalysis (AcOH, p-TsOH).
Maintain inert atmosphere and dry solvents; aldehydes can oxidize to acids over time, reducing yields.
Monitor reactions by TLC/HPLC; aldehyde spot often gives characteristic 2,4-DNP test.
For metal–ligand assemblies, preform the imine ligand, then complex with metal salts in ethanol or methanol with gentle heating; adjust pH to optimize coordination.
Note: Optimize conditions for each nucleophile, as the antipyrine core may influence electron density and sterics compared with simple benzaldehydes.
Reaction Conditions
General literature guidance (optimize per substrate; not product specifications):
Imine (Schiff base) formation:
Solvent: EtOH, MeOH, or MeCN. Optional toluene with Dean–Stark for water removal.
Catalyst: AcOH (0.1–0.5 equiv) or p‑TsOH (1–5 mol%).
Temperature/time: RT to reflux, 1–12 h. Drive equilibrium with molecular sieves (3 Å) or azeotropic removal.
Workup: Quench base traces, concentrate, and crystallize or purify by silica (use minimal protic solvents to limit hydrolysis).
Hydrazone/oxime formation:
Solvent: EtOH/H2O (up to 1:1) or MeOH; MeCN for less soluble partners.
Catalyst: AcOH (cat.).
Temperature/time: RT to 60 °C, 0.5–6 h.
Reductive amination:
Solvent: DCE, MeOH, or MeCN.
Reductant: NaBH3CN (pH 5–6, AcOH buffer) or NaBH(OAc)3 in DCE/MeCN; alternatively H2 (1–5 bar) with Pd/C.
Temperature/time: 0–25 °C for reduction step, 1–6 h.
Knoevenagel condensation:
Solvent: EtOH or toluene.
Base: Piperidine, ammonium acetate, or DBU (5–20 mol%).
Temperature/time: 50–110 °C, 2–8 h; remove water to push conversion.
Monitoring and analytics:
TLC (UV 254 nm) and carbonyl-specific stains (2,4‑DNPH) to track aldehyde consumption.
1H NMR: Disappearance of aldehyde proton (~9–10 ppm) indicates completion (literature ranges; confirm for your system).
Note: Protect moisture/oxygen-sensitive partners; keep under argon as recommended for the aldehyde.
Safety and Handling
Item-specific hazard data from Product Data:
GHS Classification: Not specified for this item; refer to SDS.
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety considerations for heteroaromatic aldehydes (literature/typical):
Hazards: May cause skin/eye irritation and respiratory irritation; harmful if swallowed. Aldehydes can be sensitizers in some cases. Avoid inhalation of dust and contact with skin/eyes.
PPE: Wear lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to avoid exposure to vapors/dust.
First aid overview: If on skin/eyes, rinse with water for at least 15 minutes. If inhaled, move to fresh air. If ingested, rinse mouth; seek medical attention. Always follow site-specific EHS procedures.
Incompatibilities: Strong oxidizers (risk of over-oxidation), strong bases/acids (can catalyze aldol/condensation and decomposition), and nucleophiles that can form adducts with aldehydes (e.g., amines, hydrazines) unless intended.
Special risks: Aldehydes can slowly oxidize to carboxylic acids on air exposure; moisture may promote side reactions. Maintain inert atmosphere per storage guidance.
Storage and shipping (item-specific):
Storage Conditions: Store at 2–8 °C, Argon charged.
Shipped In: Wet ice.
Authoritative data: Always consult the SDS and institutional risk assessments prior to use.
Solvent Selection
Applicability: 4‑Antipyrinecarboxaldehyde is a heteroaromatic aldehyde building block, not a solvent. This section focuses on selecting solvents to dissolve and react this reagent effectively.
General solvent compatibility (literature/guidance):
Polar aprotic (preferred for condensations): DMSO, DMF, acetonitrile—good solubility for antipyrine derivatives; support imine/Schiff-base formation and coupling steps.
Alcohols: Methanol, ethanol can dissolve many antipyrine derivatives and are common media for hydrazone/oxime formation; note that alcohols can participate in acetal formation under acid catalysis.
Nonpolar/medium polarity: Ethyl acetate, toluene, THF may be used for extractions or reflux condensations with water removal (Dean–Stark when using toluene).
Aqueous media: Limited solubility expected; biphasic strategies with phase-transfer catalysts or surfactants may be used when coupling to water-soluble nucleophiles.
Selection tips:
For imine/hydrazone/oxime formation: Use ethanol, methanol, or acetonitrile with catalytic acid; remove water (molecular sieves or azeotrope) to drive equilibrium.
For Knoevenagel-like condensations: Use ethanol or toluene with a weak base (e.g., piperidine) and water removal.
For purification: Crystallization from alcohol/ester mixtures is often effective for aromatic imines; for more polar adducts, use MeOH/Et2O trituration.
Note: Choose the solvent system in concert with base/acid catalysts and with consideration of the heterocycle’s hydrogen-bonding and tautomeric behavior.
Storage and Reconstitution
Item-specific storage and shipping:
Storage Conditions: Store at 2–8 °C, Argon charged.
Shipped In: Wet ice.
General handling recommendations for aldehydes (literature/practice):
Keep container tightly closed under inert gas (argon) to minimize oxidation to the corresponding acid and prevent moisture uptake.
After opening, promptly reseal, purge headspace with argon, and return to 2–8 °C storage.
If solid and clumpy upon cooling, allow to warm to room temperature under inert gas before opening to avoid condensation of moisture.
Prepare stock solutions fresh in dry solvent (e.g., anhydrous MeCN, EtOH, or DMSO) just prior to use. If longer-term solution storage is unavoidable, keep under inert gas at 2–8 °C and verify integrity by NMR/LC before use.
Avoid repeated freeze–thaw of solutions; aliquot under inert atmosphere if multiple uses are planned.
Stability notes:
Aldehydes can slowly oxidize or polymerize on prolonged exposure to air/light; store in amber glass if possible and limit light exposure.
Refer to the product’s CoA/SDS for definitive stability and storage guidance specific to SKU A354580.
Structure and Identity
Brief description: 4‑Antipyrinecarboxaldehyde is an aldehyde-functionalized antipyrine (pyrazolone) derivative used as a heteroaromatic building block for Schiff-base ligands and related condensations.
Item-specific (from Product Data):
SKU: A354580
Product Name: 4-Antipyrinecarboxaldehyde
CAS: 950-81-2
PubChem CID: 70371
InChIKey: 295925 (as provided; appears truncated in the source data)
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.
Literature/structural description (general):
Core scaffold: Antipyrine (1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one) framework bearing an aldehyde (–CHO) substituent.
Functional groups: Aromatic ring, pyrazolone (lactam-like) ring containing two ring nitrogens, and an aldehyde carbonyl.
Likely substitution pattern: “4-” denotes substitution at the 4-position of the antipyrine/pyrazolone ring (literature), yielding an electrophilic formyl handle for imine (Schiff base) formation.
2D description in words: A five-membered pyrazolone ring N-fused system carrying two N-methyl/aryl substituents typical of antipyrine, with a pendant aldehyde either on the heterocycle or the attached phenyl ring depending on naming convention; the aldehyde carbonyl is conjugated to an aromatic system (literature).
Notes:
For authoritative identifiers (SMILES/InChI/InChIKey, exact formula and mass), consult the item’s CoA/SDS/spec sheet associated with this SKU.
Synthetic Utility
Functional group leverage:
Aldehyde handle: High electrophilicity enables condensations with amines (imines), hydrazines (hydrazones/azines), hydroxylamine (oximes), and active methylenes (Knoevenagel-type). Protect as acetal if needed for downstream steps.
Pyrazolone core: Provides conjugation and potential H‑bonding sites; imparts rigidity and donor atoms to ligands, tuning metal-binding geometry and electronics.
Hydrazone probes: Condensation with 2,4‑dinitrophenylhydrazine analogs or acylhydrazides for analytical derivatization.
Reductive amination: Formation of secondary/tertiary benzylic amines on the antipyrine framework with NaBH(OAc)3 or catalytic H2/Pd.
Knoevenagel adducts: Reaction with malononitrile/cyanoacetates to generate push–pull chromophores.
Retrosynthetic value:
Serves as a convergent node linking nitrogen-rich heterocycles to diverse nucleophiles, enabling rapid library synthesis for ligand screening or materials discovery.
Practical notes:
Maintain low water activity (molecular sieves) and inert gas blanket (argon, as per storage) to maximize aldehyde integrity.
For sequential condensations, form the most labile imine last; purify intermediates by crystallization where possible to avoid hydrolysis during chromatography.
Target Specificity
Not applicable. This product is a small-molecule aldehyde building block, not a biological macromolecule or antibody. No antigen/epitope/isotype or species reactivity data apply.
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