This compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Sensibilité
Air sensitive
Point de fusion (°C)
152 °C
Poids moléculaire
168.150 g/mol
XLogP3
1.200
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
2
Exact Mass
168.042 Da
Monoisotopic Mass
168.042 Da
Topological Polar Surface Area
66.800 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
159.000
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
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Application Protocols
No assay-validated biological application protocols are provided for this item. For synthetic applications, general procedures include:
Preparation of a 0.5–1.0 M stock solution in ethanol, methanol, acetonitrile, or DMSO; filter through a 0.2 µm PTFE membrane prior to use in moisture-sensitive steps.
For imine formation: Combine aldehyde (1.0 eq) and amine (1.05 eq) in EtOH with 3 Å sieves; stir at RT 2–6 h; monitor by TLC. Concentrate and recrystallize from EtOH/EtOAc.
For oxime: Dissolve aldehyde and hydroxylamine·HCl (1.1 eq) with NaOAc (1.2 eq) in EtOH/H2O (1:1); stir at 40 °C 3 h; cool and filter precipitated product.
These are general, literature-style procedures and should be optimized for each use case. Always consult the CoA/SDS and perform small-scale trials.
Biological Roles
Item-specific biological data were not provided. The following is general context for substituted phenolic benzaldehydes and should not be construed as claims about this specific product.
Phenolic aromatic aldehydes are common motifs in plant secondary metabolites, contributing to aroma, flavor, and defense chemistry (e.g., vanillin-related structures). Their phenolic OH groups enable antioxidant/redox behavior, while the aldehyde confers reactivity toward amino functionality in biomolecules.
The 2-hydroxybenzaldehyde (salicylaldehyde) motif is widely used to prepare Schiff base ligands that model enzymatic metal-binding sites. Such ligands are studied for metalloenzyme mimics and as probes in bioinorganic chemistry.
In biochemical assays, aldehydes can form reversible imines with lysine residues or small-molecule amines; this underlies applications in enzyme labeling or reversible covalent probe design (general principle).
Phenolic acidity (pKa ~9–10, literature) allows ionization at alkaline pH, influencing membrane partitioning and protein binding in vitro. Methoxy substitution modulates both electron density and lipophilicity compared with catecholic systems.
No evidence is asserted here regarding endogenous occurrence, metabolic pathways, or bioactivity of 2,4-dihydroxy-5-methoxybenzaldehyde specifically. For biological testing, use appropriate controls and consult primary literature.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare biochemical buffers. The phenolic groups do show weak acidity (phenol pKa range ~9–10, literature), but this is unsuitable for stable buffering in common physiological ranges. For experimental use, dissolve in a suitable solvent (e.g., ethanol, DMSO) before dosing into pre-made buffers, and control pH separately with a dedicated buffer system (e.g., phosphate, Tris, HEPES).
Green Alternatives
Because this product is a solid aromatic building block rather than a solvent, greenness considerations focus on solvent choice and process conditions during its use.
Prefer greener solvents (literature guidance):
Replace chlorinated solvents (DCM) with ethyl acetate or 2-methyltetrahydrofuran (2-MeTHF) when reaction scope allows.
Use bio-based alcohols (ethanol, isopropanol) for imine/oxime/hydrazone formation.
Implement water or water–ethanol systems for oxime formation and some Knoevenagel condensations using organocatalysts (e.g., L-proline, ammonium acetate).
Energy and waste minimization:
Conduct condensations under solvent-free or mechanochemical conditions (ball milling) where feasible—numerous benzaldehyde derivatives show high conversions without solvents (literature reports).
Employ microwave or flow conditions to shorten reaction times and improve space–time yields.
Comparison snapshot (general):
DCM vs EtOAc: EtOAc offers lower toxicity and better environmental profile; slightly higher boiling point may lengthen evaporation.
THF vs 2-MeTHF: 2-MeTHF is from renewable feedstocks and has improved safety profile; water miscibility differs—affects workups.
Feedstock considerations:
Phenolic benzaldehydes like vanillin (4-hydroxy-3-methoxybenzaldehyde) are bio-derived; when substitution patterns permit, such analogs may serve as greener alternatives or starting points for route design. Tradeoff: additional steps may be required to achieve the 2,4-dihydroxy-5-methoxy substitution pattern.
Always validate that greener substitutions preserve reaction performance and product quality.
Pharmaceutical Uses
Item-specific pharmacopeial status and excipient roles: Not specified for this item; refer to CoA/Spec Sheet.
General considerations (non-clinical, research/manufacturing context only):
Aromatic aldehydes with phenolic functionality are primarily used as synthetic intermediates for discovery chemistry, including preparation of imines, hydrazones, oximes, and subsequent heterocycle formation (e.g., benzoxazoles, benzoxazines).
The salicylidene motif derived from o-hydroxybenzaldehydes is a classic handle to generate chelating ligands for metal complexes that can serve as catalysts or analytical standards in pharmaceutical process development.
In formulation science, aldehydes are generally avoided as excipients due to reactivity with amines; instead, they are treated as reactive reagents in API intermediate synthesis. Any use near regulated environments would require rigorous impurity control and residual limits.
No therapeutic or clinical claims are made for this product. It is supplied strictly for research use only.
Physical Properties
Item-specific physico-chemical specifications were not provided in the Product Data. Values below are general literature descriptors for this structure and should not be treated as specifications for this lot.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
State at ambient: typically a crystalline solid for analogous tri-oxygenated benzaldehydes (literature, indicative only).
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not meaningful for aromatic aldehydes that decompose or oxidize before boiling; literature values for analogs often report decomposition (literature, general).
Density: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (qualitative, literature):
Water: low to moderate due to two phenolic OH plus one methoxy; expect limited aqueous solubility that increases in basic media via phenolate formation.
Organic solvents: good solubility in polar organics (MeOH, EtOH, acetone, acetonitrile, ethyl acetate, DMSO, DMF); lower in nonpolar solvents (hexanes, toluene) unless warmed.
pKa (phenolic OH, literature): phenolic sites typically pKa ~9–10; ortho-OH adjacent to aldehyde may be slightly more acidic due to intramolecular H-bonding and resonance stabilization (qualitative guidance).
LogP/logD: Not specified for this item; refer to CoA/Spec Sheet (vanillin analogs often logP ~1, literature).
UV-Vis: Aromatic π–π* absorption in the near-UV; phenoxide formation bathochromically shifts bands (literature, general).
Always consult the CoA/SDS for item-specific physical data.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on typical grades for aromatic building blocks (general information):
Research/technical grade: Suitable for most synthetic applications. Trace impurities (unreacted precursors, oxidized acid, water) may be present. Often adequate for ligand synthesis, screening, and general organic transformations.
High-purity/assay grade: Tighter controls on organic impurities, residual solvents, and moisture—preferred for analytical method development or where impurity profiles affect downstream catalysis or bioassays.
Stabilizers: Phenolic aldehydes are sometimes packaged under inert gas or with desiccants to slow oxidation to acids or polymerization; absence/presence of stabilizers should be confirmed on the CoA.
What to review on the CoA for this item:
Identity confirmation: NMR (1H/13C), IR (aldehyde C=O ~1680–1710 cm−1; phenolic O–H), MS, and HPLC purity.
Impurity profile: Limits for related benzaldehyde acids (carboxylic acid oxidized form), anisolic isomers, water content (via KF), and residual solvents.
Metals: Generally not applicable unless produced via catalytic processes; if relevant, metal limits will appear on the CoA.
Research Use Note: For research use only.
Reaction and Applications
As a dihydroxy-methoxybenzaldehyde, this reagent is a versatile electrophile and ligand precursor in synthetic and coordination chemistry.
Condensation chemistry:
Schiff bases/iminates: Rapid condensation with primary amines to give salicylidene-type imines; the ortho-phenol can chelate, stabilizing imine formation and enabling bidentate O,N ligation to metals (e.g., Cu, Ni, Zn). Hydrazides and hydroxylamine provide hydrazones and oximes for analytical derivatization or materials applications.
Knoevenagel reactions: Activated by the formyl group; condenses with active methylene compounds (malononitrile, ethyl cyanoacetate) under base or ammonium acetate catalysis, often in ethanol or acetonitrile.
Aldol-type additions: Soft nucleophiles (enolates) add under basic conditions; protection of phenols may be required to avoid side reactions.
Organometallic transformations:
Wittig/Still–Gennari/HWE olefinations to introduce vinyl groups; typical solvents THF/DCM, −78 to 25 °C, under inert gas.
Reduction: Selective reduction of aldehyde to benzylic alcohol (NaBH4 mild in alcohols) or to methyl group (Wolff–Kishner, Clemmensen). Chemoselectivity must consider phenolic functions.
Electrophilic aromatic substitution (EAS): Phenolic and methoxy groups activate the ring ortho/para; however, the aldehyde deactivates and directs meta. Net substitution patterns can be managed via protecting groups (e.g., methylation/silylation of phenols) and temperature control.
Metal–ligand frameworks: The 2-hydroxy-iminobenzyl motif from this aldehyde gives classic salen/salophen-type chelates upon condensation with diamines, enabling catalysis or magnetic/optical materials.
Practical notes:
Drying: If required, dry under vacuum over P2O5 or in a desiccator; avoid heating to prevent oxidation.
Antioxidants/inerting: Working under nitrogen/argon and minimizing air/light exposure reduces formation of the corresponding carboxylic acid.
Reaction Conditions
General conditions below are literature-style guidance for benzaldehyde derivatives; they are not specifications for this product.
Schiff base (imine) formation:
Reagents: primary amine (1.0–1.2 eq), catalytic acid (acetic acid, 0.1 eq) or 3 Å molecular sieves.
Solvent: ethanol or toluene; Dean–Stark in toluene for water removal.
Temperature/time: RT to reflux, 1–12 h, monitor by TLC/HPLC. Or use MeOH at RT with sieves for sensitive amines.
Notes: Ortho-phenol facilitates imine formation via intramolecular H-bonding; products often crystallize from alcohols.
Oxime/hydrazone formation:
Reagents: hydroxylamine·HCl (1.1 eq) with NaOAc buffer; or hydrazine derivatives (1.0–1.2 eq).
Solvent: EtOH/H2O (1:1) or MeOH; pH ~4.5–5.5 favors oxime formation.
Temperature: RT to 60 °C, 1–6 h.
Knoevenagel condensation:
Reagents: malononitrile or ethyl cyanoacetate (1.0–1.2 eq), base catalyst (piperidine 10 mol%, ammonium acetate 1.5 eq).
Solvent: EtOH or MeCN; can be solvent-free under grinding.
Temperature: RT to 60 °C, 0.5–4 h; typical isolated yields for benzaldehydes 70–95% (literature range).
Temperature: 0 °C to RT, 0.5–2 h; quench with aqueous NH4Cl.
Workup/purification:
Avoid strong base during aqueous workup to minimize Cannizzaro in highly basic media; use buffered or mildly acidic washes. Purify by recrystallization from alcohol/EtOAc or by silica gel chromatography (hexanes/EtOAc gradient).
Safety and Handling
Item-specific hazard classifications (GHS, signal word, pictograms, H-statements): Not specified for this item; refer to SDS.
General laboratory safety guidance for aromatic phenolic aldehydes (literature/practice; not product-specific):
Primary hazards:
Irritation: Aldehydes and phenols can be skin/eye irritants; avoid contact and inhalation of dust.
Sensitization: Some substituted benzaldehydes may cause skin sensitization in susceptible individuals.
Reactivity: Susceptible to air oxidation (to carboxylic acids/quinonoid species) and to condensation with nucleophiles (amines, hydrazines). Not prone to peroxide formation.
PPE and controls:
Wear lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle solids to minimize dust. Use a fume hood when weighing and preparing solutions.
Storage incompatibilities:
Avoid strong oxidizers (risk of rapid oxidation), strong bases/acids (uncontrolled condensation/ionization), and reactive amines/hydrazines unless intended.
Keep desiccated to limit hydrolysis/oxidation; minimize light exposure to reduce photo-oxidation.
First-aid overview (defer to SDS for details):
Skin/eye contact: Rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; obtain medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire-fighting notes:
Use dry chemical, CO2, or alcohol-resistant foam. Combustion may produce CO/CO2 and phenolic/aldehydic vapors.
Always consult the specific SDS for authoritative safety data for this SKU.
Solvent Selection
This compound is a polar, hydrogen-bonding aromatic aldehyde with two phenolic OH groups and one methoxy. It dissolves best in polar protic and aprotic organic solvents.
Low: alkanes (hexanes, heptane), toluene at room temperature.
Water: limited; solubility increases in basic aqueous media (phenolate formation). For aqueous work, prepare concentrated DMSO or ethanol stock, then dilute.
Selection guidance by application:
Imine/Schiff base formation: ethanol, methanol, or toluene with azeotropic water removal (Dean–Stark) when using less polar amines; MeOH/EtOH with catalytic acid/base for anilines or alkylamines.
Knoevenagel condensations: ethanol, acetonitrile, or ionic liquids; weak base catalysts (piperidine, ammonium acetate) or L-proline.
Wittig/Still–Gennari: dry THF, DCM, or toluene under inert atmosphere.
Oxime/hydrazone formation: ethanol, methanol, or aqueous ethanol with buffered pH ~4–5 for oximes; slightly acidic conditions accelerate.
Small comparison (literature, qualitative):
Ethanol vs DMSO: ethanol simplifies workup and is greener; DMSO maximizes solubility for high-concentration stock solutions.
Acetonitrile vs THF: MeCN offers higher polarity and ease of removal; THF beneficial for organometallic steps but demands rigorous drying.
Storage and Reconstitution
Item-specific storage: Room temperature, desiccated (from Product Data). Shipped under normal conditions.
Additional handling guidance (general best practice for phenolic aldehydes):
Keep tightly closed in the original container with a desiccant. Minimize exposure to air and light to reduce oxidation to the corresponding carboxylic acid or quinonoid byproducts.
If extended storage is anticipated, consider inert headspace (nitrogen/argon) after each use.
Solution preparation/reconstitution:
Solubility: Readily prepares concentrated stock solutions in ethanol, methanol, acetonitrile, DMSO, DMF (literature, qualitative). For aqueous applications, dissolve in an organic cosolvent first, then dilute into buffer with vigorous mixing.
Typical stock concentrations: 10–100 mM in DMSO or MeOH for screening workflows; verify solubility at intended temperature.
Filtration: Pass through 0.2 µm PTFE syringe filter to remove particulates prior to sensitive reactions or analysis.
Stability of solutions (general):
Alcoholic or aprotic solutions are stable for days at ambient if protected from air/light; for longer-term storage, keep aliquots at 2–8 °C or −20 °C in amber vials. Avoid repeated freeze–thaw; prepare single-use aliquots.
Refer to the product’s CoA and SDS for definitive storage limits and stability information for this specific lot.
Structure and Identity
A tri-oxygenated benzaldehyde bearing two phenolic OH groups and one methoxy substituent on the aromatic ring.
Item-specific (from Product Data):
Product name: 2,4-Dihydroxy-5-methoxybenzaldehyde
CAS: 51061-83-7
SKU: D469286
CID: 11194554
InChIKey: 455958 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers and descriptors (for reference; not product specifications):
Structural features: electron-rich ring due to phenolic/methoxy donors; ortho-phenol (2-OH) can engage in intramolecular H-bonding to the aldehyde oxygen, favoring a planar, chelated quasi-six-membered ring; the 4-OH provides an additional H-bond donor site.
2D structure, described:
A benzene ring bearing at C1 a formyl group; at C2 an OH (ortho to –CHO); at C4 an OH (para to –CHO); at C5 a methoxy group (meta to –CHO). No stereocenters; fully aromatic.
Synthetic Utility
This tri-oxygenated benzaldehyde offers multiple orthogonal handles enabling diverse transformations.
Protection: Methylation (MeI/Me2SO4), benzylation (BnBr), or silylation (TBSCl) to control chemoselectivity. Differential protection can exploit varying acidity/reactivity of the ortho vs para OH.
Coupling: Aryl O-alkylation/arylation (Ullmann-type or Buchwald–Hartwig O-arylation) to access diaryl ethers.
Electrophile activation: Phenoxide formation enhances ring nucleophilicity, enabling directed ortho metalation or intramolecular cyclization.
Directed assembly:
Salen-type frameworks: Condense with diamines (e.g., ethylenediamine) to form bis-Schiff bases; subsequent metalation affords robust catalysts and materials.
Heterocycle synthesis: Via o-aminophenol-type strategies after appropriate functional interconversions; benzoxazole/benzoxazine formation from imine–phenol precursors.
Retrosynthetic value:
Acts as a masked catechol equivalent (after demethylation of methoxy and/or selective O-functionalization), allowing entry to diverse substitution patterns on the anisaldehyde/catechol axes.
Practical tips:
Control oxidation: Work under inert gas when prolonged reactions are required.
Use mild bases for condensations to avoid over-alkylation or Cannizzaro-type side reactions in strongly basic, non-enolizable systems.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological targeting agent or antibody. No antigen, epitope, clone, isotype, or species reactivity applies.
Foire aux questions
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, desiccated. Keep the container tightly closed with desiccant — the material is moisture-sensitive.
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 51061-83-7, the molecular formula is C8H8O4, and the molecular weight is 168.15 g/mol. InChIKey ZFZAFNQYRZGWNK-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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