This compound belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl 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
No manufacturer application protocols or validated assay procedures are provided for this item.
Item-specific
Manufacturer Applications: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature-based examples; not item-specific validation)
Preparing a Schiff base: Dissolve the aldehyde and a primary amine (1.0–1.1 eq) in ethanol, add a few drops of acetic acid, and stir at RT–reflux until TLC indicates completion; add 3Å sieves to improve conversion. Filter, wash with cold ethanol, and dry under vacuum.
Knoevenagel dye: Combine aldehyde (1 eq), malononitrile (1.1 eq), and catalytic piperidine in ethanol; heat to 50–70 C for 1–2 h; cool to induce crystallization; collect solid and wash with cold ethanol.
Storage during multistep work: Protect intermediates from light/air; store solutions cold and under inert gas to minimize oxidation.
For application-specific SOPs and safety measures, consult peer-reviewed literature and your institutional protocols.
Biological Roles
This product is intended for research use only; no biological role is assigned for this catalog item.
Aromatic salicylaldehydes with dimethylamino donors are frequently used as precursors to fluorescent probes that leverage intramolecular charge transfer (ICT) and excited-state intramolecular proton transfer (ESIPT). Resulting imines/hydrazones can respond to pH, metal coordination, or nucleophiles, enabling sensing in biochemical assays.
The parent aldehyde may be used to derivatize biomolecules (e.g., primary amines on peptides or proteins) to form reversible imines under controlled conditions for analytical labeling; however, stability in aqueous media is limited without further modification (e.g., reduction to secondary amines).
Phenolic and anilino functionalities can engage in π–π and H-bonding interactions relevant for studying supramolecular recognition with biomacromolecules in vitro.
Cautions
Avoid inferring pharmacological or clinical properties; this compound is not approved for therapeutic use.
For biological experiments, ensure removal of unreacted aldehyde due to potential cytotoxicity/irritancy; validate with appropriate controls.
For any in vitro or ex vivo applications, refer to your institutional biosafety and chemical safety protocols.
Buffer Applications
This compound is not a buffering reagent and is not typically employed to prepare biological buffers or electrophoresis running solutions.
Practical note
If used in aqueous assay media (e.g., as part of a fluorescent probe), dissolve first in a suitable co-solvent (DMSO or ethanol) and add to the buffered system at low percentage. Select buffers that do not react with aldehydes (avoid primary amine buffers like Tris when imine formation must be avoided).
For dedicated buffer components, see appropriate buffering agents (e.g., phosphate, HEPES, MOPS).
Green Alternatives
As a solid building block, the main greenness opportunities are in solvent/catalyst selection and process design rather than substituting the substrate.
Greener solvent choices (literature/general)
Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, 2-MeTHF, or cyclopentyl methyl ether (CPME) for extractions and reactions where feasible.
Favor bio-derived alcohols (ethanol, isopropanol) over methanol or acetonitrile when reactivity allows, especially for imine and Knoevenagel condensations.
Use water or water/alcohol mixtures with organocatalysts (e.g., L-proline, ammonium acetate) for condensations to minimize VOC use.
Energy and waste minimization
Employ azeotropic water removal (Dean–Stark) only when necessary; molecular sieves can reduce energy input for imine formation.
Consider solvent recycling and in-line drying (activated alumina columns) to reduce waste.
Comparison snapshot (general)
Toluene vs 2-MeTHF: 2-MeTHF offers similar solvency and higher renewable content; immiscibility with water simplifies workups; however, peroxide management and cost must be considered.
Acetonitrile vs ethanol: ethanol is less toxic and renewable but may alter reaction rates/selectivity; evaluate with small-scale DoE.
Catalysis and reagents
Swap stoichiometric bases (e.g., piperidine) with recyclable solid bases (KF/alumina, basic resins) when compatible.
Explore mechanochemistry (ball milling) for condensations to eliminate solvents (reported for aromatic aldehyde–barbiturate/malononitrile systems, literature).
Pharmaceutical Uses
No pharmacopeial or excipient status is provided for this item.
Item-specific
Pharmaceutical/Excipient grade: Not specified for this item; refer to CoA/Spec Sheet.
General context (non-clinical)
Aromatic aldehydes like this may serve as synthetic intermediates to research-stage APIs, dyes for diagnostics, or affinity/labeling reagents in drug discovery workflows. Any such uses remain confined to laboratory synthesis and characterization.
The phenolic and dimethylamino substituents facilitate tuning of electronic properties in lead-like scaffolds; however, aldehyde functionalities are typically masked or transformed during medicinal chemistry optimization due to reactivity.
No therapeutic, diagnostic, or clinical claims are made for this product. For GMP or regulated uses, request documentation and assess suitability separately.
Physical Properties
Item-specific values in Product Data are not supplied for this listing.
Item-specific (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.
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/general (provide context; not product specifications)
Typical physical state: aromatic aldehyde solids of this class are often yellow to orange crystalline solids due to push–pull chromophore character.
Solubility (qualitative): commonly soluble in polar organic solvents (e.g., ethanol, methanol, acetonitrile, acetone, DMF, DMSO); limited aqueous solubility expected due to aromatic core despite one phenolic OH.
Acid–base character: phenolic OH is weakly acidic (pKa of salicylaldehyde phenols typically ~9–10, literature), dimethylamino is a weak base (anilinium conjugate acids typically pKaH ~5–6, literature). Intramolecular H-bonding between OH and CHO is common in salicylaldehydes.
Spectroscopic notes (general): strong aldehyde C=O stretch near ~1670–1700 cm⁻¹ (IR), phenolic O–H stretch (broad, H-bonded), and donor–acceptor π→π*/ICT absorption in UV–Vis; 1H NMR typically shows aldehyde singlet near 10 ppm and phenolic OH often >10 ppm (intramolecularly H-bonded).
For definitive numeric properties (mp, bp, density, refractive index, UV cutoff, residuals), consult the specific CoA/SDS for this batch.
Quality and Grades
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/antioxidants: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grades (general guidance)
Research grade: Suitable for most synthetic and analytical research; impurity profiles vary by lot. Verify by NMR/LC–MS if sensitive to trace acids/bases.
High-purity/analytical grades (if offered): Lower residual solvents/water; beneficial for photophysical measurements or precision kinetics.
HPLC/UV grades: Controlled UV background; useful if using this chromophore as a reference standard. For this product, UV specifications are not provided; check CoA if needed.
Implications for this scaffold
Trace water can impact imine formation rates/yields; rigorous drying of solvents and use of molecular sieves is recommended for Schiff base chemistry regardless of listed purity.
Peroxide content is generally a concern for ethers rather than for this solid; however, aldehydes benefit from minimized oxygen exposure to limit formation of corresponding acids.
If photophysical measurements are planned (e.g., fluorescence quantum yields), select lots with documented high purity and low fluorescent impurities; request detailed CoA.
For batch-specific assay, residual solvents, water content (KF), and metal limits, consult the product’s CoA/Spec Sheet.
Reaction and Applications
Use this donor–acceptor salicylaldehyde as a versatile building block across organic, materials, and coordination chemistry.
Typical reaction families (literature/general)
Imine/Schiff base formation with primary amines and diamines to give salicylaldimines; subsequent metal complexation (e.g., with Cu, Ni, Zn) affords salen-type or related ligands.
Knoevenagel condensation with active methylenes (malononitrile, cyanoacetates) to yield push–pull styryl dyes with strong ICT and often ESIPT-assisted fluorescence.
Oxime/hydrazone formation for analytical derivatization and probe design.
O-alkylation/acylation at phenolic OH for protecting group strategies or tuning photophysics.
Electrophilic formyl chemistry: acetalization (protection), reductive transformations (e.g., to benzylic alcohols), or Wittig/Julia–Kocienski olefinations from the aldehyde.
Application domains
Fluorescent probe precursors: the 2-hydroxy-5-dimethylamino motif supports ESIPT and ICT, enabling environment-sensitive fluorophores for sensing pH, metal ions (via imines), and polarity (literature applications).
Polymer/materials: incorporation into donor–acceptor polymers and small-molecule OLED/dye systems.
Coordination chemistry: imine derivatives act as chelating ligands, enabling catalysis or magnetic materials studies.
Practical considerations
Maintain anhydrous conditions for equilibrium-limited condensations; use molecular sieves or Dean–Stark.
Control light/oxygen during dye synthesis to prevent photooxidation of intermediates.
If strong bases are employed, monitor for side reactions and potential phenolate-induced pathways.
Note: Specific performance data for this catalog item are not provided; the above reflects literature precedents for this scaffold.
Reaction Conditions
General, literature-based guidance for common transformations of salicylaldehyde-type substrates; optimize for your system.
Imine (Schiff base) formation
Typical conditions: equimolar aldehyde and amine in ethanol or methanol, catalytic acid (e.g., acetic acid) to accelerate; room temperature to reflux, 1–12 h. Water removal via 3Å molecular sieves or Dean–Stark in toluene enhances yields. Many systems crystallize on cooling.
Knoevenagel condensation
Conditions: aldehyde with malononitrile or ethyl cyanoacetate, catalytic piperidine, ammonium acetate, or L-proline; solvents include ethanol, acetonitrile, or solvent-free/mechanochemical setups. Temperatures range RT–80 C; reaction times 0.5–6 h. Push–pull styryls often precipitate from reaction media, simplifying isolation.
Oxime/hydrazone formation
Conditions: hydroxylamine hydrochloride or hydrazines in ethanol/water with base (NaOAc) or mild acid catalysis; RT–reflux, 1–4 h. Protect from air to avoid oxidative background.
O-alkylation of phenol
Conditions: alkyl halide (e.g., MeI, benzyl bromide) with K2CO3/Na2CO3 in acetone or acetonitrile, RT–reflux, 2–24 h; phase-transfer catalysts (TBAB) can enable milder temperatures in biphasic systems.
Reductive amination (two-step via imine)
Conditions: form imine with amine, then reduce with sodium cyanoborohydride or hydrogenation (Pd/C); maintain pH 5–6 for selectivity.
Note: No batch-specific performance or yields are specified for this item. Reaction scales, catalysts, and solvents should be validated with small trials and appropriate analytics (TLC, HPLC, NMR).
Safety and Handling
Always handle according to your institutional EHS guidance and the product SDS.
Item-specific (from Product Data)
GHS classification / pictograms / H-statements / signal word: Not specified for this item; refer to SDS.
Storage conditions: Room temperature (per Product Data).
General safety profile (literature-based guidance for aromatic aldehydes/phenols)
Hazards: Aromatic aldehydes can be skin/eye irritants and may cause respiratory irritation; phenolic OH may increase local tissue irritation. Tertiary anilines can be harmful if swallowed or absorbed in large amounts. Avoid inhalation of dust.
Incompatibilities: Strong oxidizers (risk of over-oxidation), strong bases (can trigger self-condensation/Knoevenagel with active methylenes), strong acids (possible decomposition/acetals in alcohols under acid), acylating/chlorinating agents (may react with phenol). Avoid prolonged exposure to air, light, and moisture to limit oxidation/polymerization.
Safe handling: Work in fume hood. Wear safety glasses, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Avoid dust formation; use weigh boats and antistatic measures.
First aid (overview; consult SDS): Eye/skin contact—rinse with water for ≥15 minutes and remove contaminated clothing; Inhalation—move to fresh air; Ingestion—rinse mouth, seek medical advice. Provide SDS to responders.
Thermal/chemical stability: Aldehydes can oxidize to acids on air exposure; phenolic compounds may darken under light. Store tightly closed, protected from light and moisture when possible.
Defer to the official SDS for authoritative hazard classification, exposure limits, and spill/cleanup procedures.
Solvent Selection
This compound is a polar, π-conjugated aromatic aldehyde with a phenolic OH and a tertiary anilino donor.
Polarity and miscibility (literature/general)
Expected to dissolve well in polar aprotic solvents (DMF, DMSO, acetone, acetonitrile) and polar protic solvents (methanol, ethanol). Limited solubility in nonpolar solvents (hexanes) but often soluble in chlorinated solvents (DCM, chloroform) and ethyl acetate.
For aqueous work, co-solvents (DMSO, ethanol) or pH modulation (deprotonation of phenol) may aid dissolution, noting potential reactivity under basic conditions.
Choosing solvents by application
Imine (Schiff base) formation: ethanol, methanol, or toluene (with Dean–Stark) are common; addition of 3Å molecular sieves in MeOH/EtOH can improve conversion.
Knoevenagel condensations: ethanol, acetonitrile, or toluene with weak base catalysts (piperidine) are typical; greener option: water/ethanol mixtures with L-proline or ammonium acetate.
O-alkylation (phenol protection/derivatization): acetone or acetonitrile with K2CO3/Na2CO3; phase-transfer catalysis enables use of less polar solvents.
Practical tips
Dry solvents for reactions consuming water (imine, acetal/ketal formations).
Avoid strong basic media if aldehyde integrity is critical; strong base can induce side reactions (Cannizzaro under certain conditions, though less common for aromatic aldehydes without α-H).
Comparison (general):
Ethanol vs toluene: ethanol is greener and often adequate for imine formation; toluene with Dean–Stark can drive water removal when equilibrium is sluggish.
Storage and Reconstitution
Item-specific (from Product Data)
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Appearance at receipt: Not specified for this item; refer to CoA/Spec Sheet.
General handling and storage (literature/practice; not product specification)
Store in a tightly closed container, preferably under inert gas if long-term storage is planned, to minimize aerial oxidation of the aldehyde to the corresponding acid.
Protect from light and moisture to preserve color and photophysical integrity; consider amber glass.
If solid cakes or discolors slightly over time, verify purity by NMR/HPLC before critical applications; simple recrystallization from ethanol or ethyl acetate/hexanes often restores purity for salicylaldehyde derivatives (optimize solvent system experimentally).
Solution stability (general)
Prepare stock solutions in dry solvents (e.g., DMSO, ethanol, acetonitrile). Store aliquots at 2–8 C, protected from light, and use within days to weeks depending on solvent and application. Avoid repeated freeze–thaw of solutions.
For definitive shelf-life, container compatibility, and reconstitution instructions specific to this lot, refer to the product CoA and SDS.
Structure and Identity
Brief: 5-(Dimethylamino)-2-hydroxybenzaldehyde is an ortho-hydroxybenzaldehyde bearing a para-to-CHO dimethylamino donor, forming a classic push–pull salicylaldehyde scaffold useful for Schiff bases and fluorescent dyes.
A salicylaldehyde framework: starting from the aldehyde carbon as C1, the OH at C2 (ortho), and an N,N-dimethylamino group at C5 (meta to CHO, para to OH). The dimethylamino nitrogen is bonded to two methyl groups and the aromatic C5.
Synthetic Utility
Key functional elements and their reactivity enable broad synthetic leverage:
Functional group leverage (general)
Aldehyde (Ar–CHO): engages in imine formation (with RNH2), oxime/hydrazone formation, Wittig and Horner–Wadsworth–Emmons olefinations, and selective reductions (NaBH4 to benzyl alcohols, oxazolidines with amino alcohols).
Phenol (Ar–OH): O-alkylation/acylation for protection or electronic modulation; can participate in intramolecular H-bonding stabilizing imine tautomers.
Anilino donor (Ar–NMe2): enhances electrophilicity of the aldehyde via push–pull effects in conjugated extensions; improves fluorescence in resulting dyes.
Retrosynthetic roles
D–π–A dye precursors: Combine with malononitrile/cyanoacetates (Knoevenagel) to access highly polarizable chromophores.
Salen-type ligands: Condense with diamines (e.g., ethylenediamine) to form bis-imines for metal complexation.
Probe scaffolds: Derivatize to hydrazones with target-responsive moieties for sensing (pH, metal ions), exploiting ESIPT.
Selectivity and control
The ortho-OH often forms intramolecular H-bonds that can direct reactivity and stabilize E/Z isomers in condensations.
Electronic activation by NMe2 can bias substitution patterns in subsequent electrophilic aromatic substitutions on the ring (if pursued), though the presence of CHO/OH modulates regioselectivity.
This multifaceted handle allows concise routes to ligands, chromophores, and functional materials.
Target Specificity
Not applicable. This product is a small-molecule building block and not an antibody, enzyme, or targeted biological reagent.
Item-specific
No antigen/epitope, clone, isotype, or species reactivity information is provided or relevant to this compound.
Perguntas frequentes
What is the purity of this product?
This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 67868-63-7, the molecular formula is C9H11NO2, and the molecular weight is 165.19 g/mol. InChIKey FXHYHSHSEXIDFE-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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