This compound belongs to the class of organic compounds known as catechols. These are compounds containing a 1,2-benzenediol 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.
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
153.140 g/mol
XLogP3
0.900
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Exact Mass
153.043 Da
Monoisotopic Mass
153.043 Da
Topological Polar Surface Area
73.100 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
149.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
1
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
1
Covalently-Bonded Unit Count
1
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Recensioni
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Application Protocols
Not applicable. No tested bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent in the Product Data. For synthetic or coordination chemistry uses, refer to the Reaction Conditions and Synthetic Utility sections for general guidance.
Biological Roles
Item is for research use only. No clinical or therapeutic claims are made.
General biochemical context (literature/general):
Metal chelation: Catechol-containing aromatics are well-known for their ability to chelate Fe(III) and other transition metals through o-diphenolate coordination. The additional oxime functionality introduces N/O coordination possibilities, potentially altering redox behavior and binding geometries in model systems.
Redox chemistry: Ortho-dihydroxybenzenes can undergo reversible redox between catechol and o-quinone, which is relevant in studies of oxidative stress and electron-transfer processes in model systems. The presence of an oxime can affect oxidation potentials via intramolecular hydrogen bonding and resonance effects.
Hydrogen bonding and supramolecular assembly: Multiple donor/acceptor sites support intramolecular and intermolecular H-bonds, influencing crystallinity, polymorphism, and self-assembly—useful in host–guest or crystal engineering research.
Reactivity probes: Aldoxime groups can serve as handles for bioconjugation after suitable derivatization (e.g., conversion to nitrile or amine, then coupling), though this specific compound is not typically used in biological buffer systems.
Note: Any biological testing should be designed and interpreted within appropriate lab safety and ethical frameworks. This product is supplied strictly for laboratory research use.
Buffer Applications
This compound is not a buffering reagent and is not typically used to prepare biological buffers. Its limited aqueous solubility and multiple reactive sites (phenols, oxime) make it unsuitable as a primary pH buffer.
Practical note: If dissolution in aqueous systems is required for spectroscopic or binding studies, use a small fraction of a miscible organic co-solvent (e.g., DMSO, EtOH) and adjust pH to modest basicity to increase solubility via phenolate formation, monitoring for oxidation of the catechol (literature guidance).
Green Alternatives
This product is a solid building block/ligand rather than a process solvent. Greener considerations therefore focus on solvent choice and reagent selection during its use (literature/general guidance):
Solvent selection:
Prefer bio-based or lower-toxicity solvents (EtOH, i-PrOH, Me-THF, water/co-solvent systems) over high-toxicity or problematic solvents (DMF, NMP) when solubility allows.
For recrystallization, ethanol–water mixtures often provide good performance with reduced environmental impact compared to chlorinated solvents.
Reagent alternatives for key transformations:
Oxime → nitrile dehydration: Replace POCl3/SOCl2 with greener dehydrations, e.g., catalytic PPh3/I2 in MeCN under mild conditions, or solvent-free microwave-assisted dehydrations (literature). Solid acid catalysts (e.g., sulfated zirconia) have been reported to reduce waste.
Oxime reduction: Consider catalytic hydrogenation in ethanol over stoichiometric metal hydrides. Transfer hydrogenation (e.g., Pd/C with formate) can avoid compressed H2 in small-scale labs.
Energy and workup:
Employ room-temperature or flow methods where feasible; use minimal solvent and telescoped steps (e.g., in situ oxime formation from 2,3-dihydroxybenzaldehyde followed by direct use) to limit solvent exchanges.
Tradeoffs:
Greener solvents may reduce solubility, requiring higher volumes or temperature. Avoid base-promoted air oxidation of catechol in aqueous media by working under inert gas and minimizing residence time.
Pharmaceutical Uses
No excipient or pharmacopeial status is specified for this item; it is offered for research use only.
General formulation context (literature/general):
Phenolic oximes are not common pharmaceutical excipients due to reactivity (oxidation, dehydration) and limited aqueous solubility. If incorporated into research formulations (e.g., as a ligand or probe), they are typically dissolved in organic vehicles (EtOH, propylene glycol) or delivered as DMSO stock solutions for in vitro assays.
Stability considerations: Protect from strong oxidants and high temperatures; avoid strong dehydrating conditions that can convert aldoximes to nitriles. Inclusion of antioxidants (e.g., ascorbate) and oxygen exclusion may be considered in sensitive studies, but such measures are application-specific and should be validated by the user.
Physical Properties
Item-specific specifications (from Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed properties (reference, not product specifications):
Approximate molecular weight: ~155.15 g/mol (computed from literature formula)
Acid–base behavior: two phenolic OH groups (typical phenol pKa ~9–10, literature); oxime OH is typically more acidic than alcohols but less than phenols (pKa ~10–11, literature). Actual values depend on substitution and solvent.
Polarity: polar, hydrogen-bonding solid; expected to be sparingly soluble in water and soluble in polar organic solvents (ethanol, methanol, DMSO, DMF) (literature).
LogP: phenolic oximes typically show low-to-moderate logP due to multiple HBD/HBA sites (literature qualitative assessment).
Melting/boiling: aromatic aldoximes are generally crystalline solids with melting points often in the 120–200 °C range; thermal dehydration to the corresponding nitrile can occur under strong dehydrating conditions (literature). Specific MP/BP for this compound is not established here.
UV–Vis: catechol-containing aromatics absorb in the UV (near 280 nm) with possible bathochromic shifts upon deprotonation or metal complexation (literature, qualitative).
Note: The values above are provided as general literature guidance for chemists. For procurement, release testing, or analytical work, consult the item’s CoA/Specification Sheet.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general information):
Research grade: Suitable for most synthetic and analytical research tasks. Purity typically >95% but varies; review CoA for exact assay, residual solvents, and impurity profile.
Analytical/AR grade: Tighter control of inorganic/organic impurities; used where background signals (e.g., metals) need to be minimized.
HPLC grade (for solvents): Defined by low UV cutoffs and particulate levels; not applicable to this solid reagent.
Stabilizers: None specified for this item; if stabilizers or inhibitors are used, they will be declared on the CoA/label because they can affect reactivity (e.g., metal chelation, O-alkylation).
What to check on receipt (practical tips):
Verify identity by NMR/HRMS/IR against literature spectra for 2,3-dihydroxybenzaldoxime (distinct oxime C=N stretch ~1650–1600 cm−1 and O–H stretches; phenolic resonances in 1H NMR, and oxime =CH near 7–9 ppm depending on E/Z, literature).
Examine water content and residual inorganic salts if prepared via hydroxylamine salts; presence of chloride/sulfate may be detectable by ion chromatography (method selection per lab SOP).
If metal content matters (e.g., for coordination studies), request a metals screen on the CoA.
Reaction and Applications
Use domains (literature/general for phenolic aldoximes with catechol motif):
Ligand/chelator chemistry: The 2,3-dihydroxy (catechol) and oxime functionalities together provide an O,N,O donor set. Upon deprotonation, the ligand can chelate transition metals (e.g., Fe, Cu, Ni), useful in coordination chemistry, redox studies, or as precatalyst scaffolds. Intramolecular H-bonding can preorganize the binding pocket.
Oxime transformations:
Dehydration to nitriles (aldoxime → nitrile) using dehydrating agents such as SOCl2, POCl3, P2O5, or Burgess reagent (literature). The product would be 2,3-dihydroxybenzonitrile.
Reduction to amines (via oxime → amine) employing catalytic hydrogenation (Pd/C, H2), or metal hydrides (e.g., NaBH3CN under appropriate activation), giving 2,3-dihydroxybenzylamine.
O-/N-alkylation or acylation to form oxime ethers/esters, tuning lipophilicity and stability.
Aromatic functionalization:
Electrophilic substitution directed by the catechol/oxime array; protection of phenolic OH (e.g., as methyl/benzyl ethers or carbonates) facilitates cross-coupling on the ring after halogenation.
Oxidation of catechol to o-quinone followed by cycloadditions or conjugate additions (literature context for catechol systems).
Schiff-base and heterocycle synthesis: Condensation of the oxime or further derivatization can lead to imidates, isoxazoles (via cycloaddition from oxime derivatives), or ligands for salen/salophen-like frameworks after appropriate modification.
Practical tips:
Maintain anhydrous conditions for dehydration to nitriles; trace water suppresses conversion.
Control pH during metal-binding experiments; phenolate formation (pH > ~9, literature) enhances chelation but may induce competing oxidation of catechol—use inert atmosphere as needed.
Reaction Conditions
The following are literature-general conditions for reactions relevant to 2,3-dihydroxybenzaldehyde oxime. They are provided for planning purposes only and are not product specifications.
Oxime formation (context): 2,3-dihydroxybenzaldehyde + NH2OH·HCl, EtOH/H2O, NaOAc or pyridine base, 0–25 °C to rt, 1–4 h; isolate by filtration/recrystallization (typical for salicyl/benzaldoximes).
Dehydration to nitrile:
POCl3 (2–4 equiv) in dry MeCN or DCM, 0 °C to reflux, 1–6 h; or SOCl2 (excess) with catalytic DMF, reflux 1–3 h. Typical literature yields for analogous aldoximes: 70–90%.
Greener alternative: PPh3/I2 (1.2–1.5 equiv each) in MeCN, rt to 60 °C, 2–8 h (literature reports good yields for aldoximes), reduced corrosive waste.
Reduction to amine:
H2 (1–5 bar), Pd/C (5–10 wt%), EtOH or EtOH/EtOAc, rt to 50 °C, 2–16 h; or Raney Ni under similar conditions. Workup with filtration and concentration. Reported yields for related systems: 60–90%.
Alternative: Zn/AcOH or Fe/AcOH reductions for oximes at reflux (literature).
Metal complexation studies:
Dissolve ligand in MeOH or MeOH/H2O; add metal salt solution (e.g., FeCl3, Cu(OAc)2) under controlled pH (8–10 for phenolate formation); stir at rt to 50 °C, 0.5–4 h. Isolate complexes by precipitation or slow evaporation (literature practice).
Notes:
Protect catechol from air oxidation in basic media (inert atmosphere recommended).
Control E/Z oxime isomer ratio by crystallization or via derivatization if necessary for spectroscopy.
Safety and Handling
Authoritative safety information:
GHS classification, signal word, hazard statements, and pictograms (item-specific): Not specified for this item; refer to the product SDS for definitive information.
General laboratory safety guidance for phenolic aldoximes (literature/general):
Hazards: May cause skin/eye irritation and respiratory irritation. Phenolic compounds can be harmful if swallowed; oximes may cause methemoglobinemia at high exposure in some cases (class-level observation). Avoid dust and aerosols.
PPE: Wear lab coat, safety goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of dust or vapors.
Incompatibilities: Strong oxidizers (risk of exothermic reaction); strong bases may cause rapid deprotonation and enhanced reactivity; strong dehydrating agents (SOCl2, POCl3, P2O5) can convert aldoximes to nitriles.
Special risks: Aromatic oximes may isomerize (E/Z) and can dehydrate under harsh conditions. Phenolic moieties can undergo oxidation to quinonoid species; minimize exposure to air/heat if purity is critical.
First aid (overview): If inhaled—move to fresh air; if on skin—wash with soap/water; if in eyes—rinse cautiously with water for several minutes; if ingested—rinse mouth, seek medical advice. Always follow the SDS.
Spill/cleanup: Avoid dust formation; collect solids by damp wiping or HEPA vacuum; dispose according to institutional and local regulations.
Storage per Product Data: Store at room temperature. Keep container tightly closed in a dry, well-ventilated place. Consult SDS for detailed stability and incompatibility data.
Solvent Selection
This compound is a polar, hydrogen-bonding aromatic solid with three protic sites (two phenols, one oxime OH). Practical solvent considerations (literature/general):
Expected solubility profile: Good in DMSO, DMF, NMP, and alcohols (MeOH, EtOH); moderate in acetone and acetonitrile; poor to very low in nonpolar solvents (hexanes, toluene) unless deprotonated or derivatized.
Water solubility: Typically low for neutral phenolic oximes; increases at basic pH via phenolate formation (literature).
Dielectric considerations: Polar aprotic media (DMSO, DMF) enhance solubility without protonating the oxime; choose protic alcohols when hydrogen bonding is desired (e.g., for crystallization from EtOH/water).
Purification: Recrystallization from alcohol–water mixtures is common for phenolic oximes; avoid strong base during workup to minimize rearrangement/dehydration.
When to choose alternatives:
If water compatibility is required, consider making a salt (phenolate) transiently or using co-solvent systems (e.g., 10–30% DMSO or EtOH in buffer) for spectroscopic studies.
For metal complexation studies, use alcohols or mixed MeOH/H2O to foster ligand deprotonation under controlled basicity; avoid coordinating solvents (e.g., pyridine) if they could compete with O,N,O binding.
Small comparison (literature tendencies):
DMSO: maximal solubility; best for NMR/stock solutions; high boiling point complicates removal.
EtOH/MeOH: good solubility; convenient crystallizations; may engage in H-bonding networks affecting polymorphs.
Acetonitrile: moderate solubility; useful for dehydration reactions to nitriles in presence of SOCl2/POCl3 (literature).
Storage and Reconstitution
Storage conditions (item-specific): Room temperature (per Product Data). Ship under normal conditions.
Container: Keep tightly closed in a dry, well-ventilated place. Use amber glass if prolonged light exposure is expected (general good practice for phenolic compounds).
Stability notes (general): Phenolic oximes are typically stable as solids at ambient temperature. Avoid strong oxidants and dehydrating agents. Minimize exposure to basic conditions and air if long-term purity is critical.
Reconstitution and solution handling (general guidance for research use):
Solvents: Prepare stock solutions in DMSO, DMF, methanol, or ethanol. Typical stock concentrations: 10–100 mM depending on solubility.
Aqueous use: Employ co-solvents (e.g., 1–10% DMSO or EtOH v/v). Adjust pH cautiously if enhanced solubility via phenolate formation is desired; work under inert gas to limit catechol oxidation.
Filtration: If particulates are present, filter solutions through 0.22–0.45 µm PTFE/nylon filters.
Aliquoting: For multi-use solutions, aliquot and store tightly capped to minimize air and moisture uptake. Avoid repeated freeze–thaw if refrigerated or frozen solutions are prepared.
Always consult the product’s CoA and SDS for definitive stability, purity, and safety information. Research Use Only.
Structure and Identity
Brief description: 2,3-Dihydroxybenzaldehyde oxime (also called 2,3-dihydroxybenzaldoxime) is an aromatic aldoxime bearing an ortho-dihydroxy (catechol) motif on the ring.
SKU: D1240151
Product name: 2,3-Dihydroxybenzaldehyde oxime
CAS: 110827-84-4
PubChem CID: 135455564
InChIKey (from Product Data): 354707 (note: this appears non-standard in length; verify against CoA/Spec Sheet)
SMILES (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Likely molecular formula (literature/computed): C7H9NO3 for an ortho-dihydroxy benzaldoxime isomer
Approx. formula mass (literature/computed): ~155.15 g/mol
Representative SMILES (literature): ON=CHc1c(O)cccc1O (one of several equivalent aromatic depictions)
Structural features (general chemistry description):
Functional groups: one aldoxime (C=NOH), two phenolic hydroxyls (catechol, 1,2-dihydroxy) on a benzene ring.
Donor set: O,N,O tridentate potential upon deprotonation/coordination (phenolates plus oxime N/O), enabling chelation to transition metals.
2D structure description: a benzene ring with adjacent hydroxyl groups at positions 2 and 3; the formyl carbon (position 1) is converted to an oxime (C=NOH). The oxime can exist as E/Z geometric isomers around the C=N bond (literature). No stereogenic centers in the ring.
Electronic character: strongly electron-rich ring due to two ortho phenols; oxime is both hydrogen-bond donor and acceptor, facilitating intramolecular H-bonding.
Synthetic Utility
Functional group leverage (literature/general):
Oxime handle:
Dehydration to nitrile (aldoxime → nitrile) with POCl3, SOCl2, P2O5, or milder catalytic systems. The nitrile can be further transformed to amide, acid, or amine (via hydration, hydrolysis, or reduction).
Reduction to primary amine (via oxime → amine) by catalytic hydrogenation (Pd/C, Pt/C, Raney Ni) or metal/acid protocols, giving 2,3-dihydroxybenzylamine for downstream coupling (amide formation, urea synthesis, etc.).
O-/N-derivatization to tune electronic and steric properties (oxime ethers, esters), enabling cycloadditions or radical chemistry.
Catechol (2,3-dihydroxy) manifold:
Temporary protection as methyl/benzyl ethers permits selective electrophilic substitutions and cross-couplings (e.g., halogenation → Suzuki/Miyaura, Buchwald–Hartwig on appropriately functionalized derivatives).
Oxidation to o-quinone provides entry to Michael acceptors and Diels–Alder partners; careful control prevents over-oxidation.
Coordination chemistry:
The O,N,O donor set forms stable chelates; metalated complexes can serve as catalysts or model systems for redox and magnetism studies.
Retrosynthetic value:
Starting from 2,3-dihydroxybenzaldehyde, the oxime is formed via condensation with hydroxylamine (typically NH2OH·HCl, base). Having the oxime pre-installed can streamline routes where nitrile or amine derivatives are targeted, avoiding handling of more volatile aldehydes.
Target Specificity
Not applicable. This product is a small-molecule reagent/ligand, not an antibody or biologic. No antigen/epitope specificity, clone, isotype, or species reactivity information applies.
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