This compound belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
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
196.200 g/mol
XLogP3
1.000
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Exact Mass
196.085 Da
Monoisotopic Mass
196.085 Da
Topological Polar Surface Area
77.100 Ų
Heavy Atom Count
14
Formal Charge
0
Complexity
208.000
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
Calcolatori di soluzioni
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Recensioni
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Application Protocols
No tested bioassay or immunoassay protocols are provided for this item.
General laboratory handling examples (literature/general; not item-specific specifications):
Preparing a DMSO stock: Weigh the solid quickly in a dry environment. Prepare a 100 mM stock in anhydrous DMSO, vortex to dissolve, aliquot, and store tightly sealed; warm to rt before opening to limit moisture condensation.
Oxadiazole coupling (CDI method, sketch): Dissolve amidoxime (1.0 equiv) and carboxylic acid (1.0–1.2 equiv) in DMF (0.1–0.5 M). Add CDI (1.2–1.5 equiv) at 0–25 C, stir 30–60 min, then heat to 80–110 C for 2–6 h. Quench with water, extract or precipitate, and purify by chromatography or crystallization.
Reductive conversion to amidine (sketch): Charge MeOH with the amidoxime (1.0 equiv) and Pd/C (5–10 wt%). Stir under H2 (1–3 bar) at rt–40 C until completion (LC–MS). Filter through Celite, concentrate, and convert amidine to its HCl salt if desired.
For any regulated or scaled operations, develop full SOPs and confirm parameters for your specific batch (refer to CoA/Spec Sheet for item-specific details).
Biological Roles
No biological activity data or functional roles are provided for this specific catalog item.
General biochemistry (literature, non-clinical):
Amidoxime motif as a bioreductive handle: Aromatic amidoximes are known to be reduced in cells by the mARC–cytochrome b5–cytochrome b5 reductase system to afford amidines. This transformation is exploited in medicinal chemistry to mask strongly basic amidines as pro-moieties with improved permeability. This is a general chemical concept, not a claim for this item.
Metal binding: The N–O and –NH2 donors can chelate metal ions; amidoxime-functional materials are studied for metal ion capture (e.g., U(VI), Cu(II)). Such interactions may inspire coordination studies with this small molecule analogue.
Physicochemical context: The 2,4-dimethoxyphenyl substituent increases lipophilicity and can influence membrane affinity and protein binding in model systems; however, no specific ADME data exist here.
Use limitations:
For research use only (per Product Data). Not intended for food, drug, household, or cosmetic use.
No medical or therapeutic claims are made for this product. Any biological experiments should be hypothesis-generating and properly controlled.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare defined pH buffer systems.
Practical note: If aqueous work is required (e.g., enzymatic reductions or binding assays), dissolve first in DMSO or EtOH and dilute into a pre-made buffer (e.g., phosphate, acetate). Slight acidification (e.g., pH 5–6) can enhance solubility via protonation of the imine nitrogen (literature behavior of amidoximes).
For pH control, select classical buffers (PBS, acetate, citrate, HEPES) appropriate to your assay. This product does not substitute for those reagents.
Green Alternatives
Because this product is a solid building block/reagent rather than a volatile solvent, “greener” considerations focus on solvent and reagent choices during its use rather than replacing the molecule itself.
Greener choices (literature/general):
Solvents:
Prefer EtOH, i-PrOH, MeCN (ACS green tier dependent on process) or 2-MeTHF/CPME for workups over halogenated solvents where feasible.
For high-temperature cyclodehydrations, propylene carbonate or Cyrene (dihydrolevoglucosenone) can substitute for DMF/DMSO in some cases; verify solubility and stability.
Coupling agents/dehydrating systems:
Use EDC·HCl in water/EtOH where possible instead of DCC (reduces urea waste handling). CDI in greener solvents can also be effective.
Energy and workup:
Employ microwave or flow heating to shorten reaction times and improve energy efficiency.
Replace silica-intensive purifications with crystallization or aqueous workups when the product profile permits.
Trade-offs:
Polar aprotic replacements (e.g., Cyrene) may alter O- vs N- selectivity in amidoxime reactions.
Greener solvents can reduce solubility for highly polar intermediates; co-solvent strategies (EtOH/H2O, MeCN/H2O) may be needed.
Note: No stabilizers or inhibitors are listed for this item (Not specified). Greenness of the supplied solid itself is not typically rated; optimization lies in the process design using the reagent.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or formulation grade is provided for this item.
General R&D context (literature, non-clinical):
Medicinal chemistry building block: Aromatic amidoximes are frequently used as precursors to amidines (via reduction) or to 1,2,4-oxadiazoles (via cyclodehydration with carboxylic acid derivatives). The 2,4-dimethoxyphenyl motif is a common aryl fragment in SAR exploration.
Salt formation: The amidoxime can be protonated, allowing exploration of salt forms for intermediate handling; however, no specific salt form is supplied or specified for this item.
Formulation screening: For in vitro assays, stock solutions are commonly prepared in DMSO and diluted into assay media. Verify compatibility with plastics and assay components.
Compliance note:
For research use only (per Product Data). Not for human or animal therapeutic or diagnostic use.
Any cGMP, residual solvents, or impurity profiles required for clinical manufacture are not specified for this item; consult CoA/Spec Sheet if regulatory use is contemplated.
Physical Properties
Item-specific specifications have not been provided for this catalog entry. Do not treat any values below as product 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/estimated (non-spec) properties for N-hydroxy-2,4-dimethoxy-benzamidine (amidoxime of a dimethoxybenzamide):
Formula (literature): C9H12N2O3
Formula weight (literature): ~196.20 g/mol
Physical state: typically a solid for aromatic amidoximes with methoxy substitution (literature trend).
Solubility: generally soluble in polar organic solvents (DMSO, DMF, MeOH, EtOH) and in aqueous media under acidic or basic conditions due to ionization of the amidoxime functionality (literature). Limited solubility expected in nonpolar solvents (hexanes, toluene).
Acid–base behavior: amidoximes are amphiprotic; literature pKa values commonly fall around pKa1 ~ 4–6 (protonation of imine N) and pKa2 ~ 10–12 (deprotonation of N–OH), enabling pH-tunable solubility. Exact pKa for this compound not located.
LogP: aromatic dimethoxy substitution increases lipophilicity vs unsubstituted benzamidoxime; experimental logP not located (literature expectation: moderate polarity due to N–O and –NH2).
Melting point, boiling point, density, refractive index: Not located in primary literature for this exact compound.
Always verify critical physical data on the item’s CoA/Spec Sheet or SDS before process design.
Quality and Grades
From Product Data (item-specific):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance:
Without an explicit grade (e.g., AR, Reagent, Puriss., HPLC), end-users should verify assay, residual solvent, and chromatographic purity on the CoA.
For chromatographic or medicinal chemistry uses, low UV background and low nonvolatile residue are typically desirable; confirm UV cutoff and absorbance, if relevant, on the CoA (Not specified for this item).
Trace impurities (metals, peroxides, water): Not specified for this item; refer to CoA/Spec Sheet. If metal-catalyzed reactions are planned (e.g., Pd, Cu), consider pre-rinsing or recrystallization to minimize adventitious inhibitors.
Stabilizers/inhibitors: None stated. Amidoximes generally do not require polymerization inhibitors. If any stabilizer is present, it will be listed on the CoA (Not specified for this item).
Recommended incoming QC (user practice):
Verify identity by 1H/13C NMR and HRMS; amidoximes show characteristic NOH and NH2 resonances and downfield shifts from H-bonding.
Check purity by HPLC/UPLC with PDA and/or LC–MS. Record water content by Karl Fischer if moisture sensitivity matters for your application.
Document batch-specific melting range if solid (Not specified for this item).
Reaction and Applications
Amidoximes are versatile N,O-bifunctional synthons. The 2,4-dimethoxyphenyl group tunes electronics and solubility, often enhancing reactivity toward cyclodehydrations and N-/O-derivatizations.
Key application families (literature/general):
Heterocycle construction:
1,2,4-Oxadiazoles from amidoximes and carboxylic acid derivatives via activation (CDI, DCC, acid chlorides) then cyclodehydration. The electron-rich aryl increases nucleophilicity of the amidoxime carbon, aiding ring closure.
1,2,4-Oxadiazolin-5-ones via reaction with carbonyl diimidazole or carbonates, then cyclization under heat.
N-/O-Functionalization:
Selective O-alkylation/acylation to imidates or O-acyl amidoximes under basic conditions; N-alkylation favored with stronger bases/phase-transfer or via protection strategies.
Sulfonylation (e.g., with MsCl/TsCl) generates O-sulfonyl intermediates for subsequent rearrangements.
Reductive conversions:
Conversion of amidoximes to amidines by reduction (e.g., Zn/AcOH, catalytic hydrogenation, or TiCl3/NaBH4 systems), useful for accessing cationic amidine targets when direct amidination is challenging.
Metal coordination and materials uses:
N,O-chelation to transition metals (Cu, Ni, Fe) for complex synthesis and sorbent/ligand studies; methoxy substituents modulate donor properties of the aryl.
Practical notes:
Control moisture; protic media can shift O-/N-selectivity.
For cyclizations, 80–150 C in polar aprotics is common; azeotropic removal of water (e.g., toluene with Dean–Stark) can drive dehydrations.
Monitor by LC–MS; amidoximes often show characteristic [M+H]+ and dehydration fragments.
Reaction Conditions
General literature guidance for amidoximes; verify and optimize for your substrate. Values below are not product specifications.
1,2,4-Oxadiazole formation:
Activation: convert carboxylic acid partner to acid chloride (SOCl2, oxalyl chloride) or use CDI/DCC in situ.
Solvent: DMF, DCM, or toluene; CDI-mediated couplings often run in DMF or MeCN.
Base: DIPEA or pyridine (0.5–2.0 equiv) to scavenge HCl/activate.
Temperature/time: 60–120 C, 2–16 h (microwave heating can reduce time to 10–60 min).
Typical isolated yields: 50–85% depending on substitution pattern (literature range).
Reduction to amidine:
Catalytic hydrogenation (H2, Pd/C 5–10 wt%) in MeOH/EtOH at rt–50 C for 2–8 h.
Alternative: Zn/AcOH or Fe/AcOH at 25–60 C; or TiCl3/NaBH4 in THF/MeOH at 0–25 C.
Workup: neutralize, filter catalyst, extract; avoid strong base to prevent N–O cleavage side products.
Base/solvent: K2CO3/DMF for O-alkylation bias; NaH/THF or PTC (Bu4NBr) for increased N-alkylation.
0–25 C for selectivity control; monitor by LC–MS and 1H NMR (diagnostic NOH vs N-alkyl signals).
Metal complexation:
Combine ligand with metal salt in EtOH/H2O or MeOH at rt–reflux; pH 6–8 can promote chelation while limiting hydrolysis.
Note: The 2,4-dimethoxy aryl ring generally tolerates these conditions; avoid prolonged strong acid or BBr3 unless demethylation is desired.
Safety and Handling
From Product Data (item-specific):
GHS classification: Not specified for this item; refer to SDS.
Signal word: Not specified for this item; refer to SDS.
Hazard (H) statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety guidance for amidoxime-bearing aromatic compounds (literature/general knowledge):
Likely hazards: May cause skin/eye irritation and respiratory irritation upon dust formation. Avoid inhalation of particulates and contact with skin/eyes.
PPE: lab coat, safety glasses or face shield, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to control dust/aerosols.
Incompatibilities: Strong oxidizers (due to aromatic/oxime functionality), strong acids/bases may induce decomposition or hydrolysis; acylating/alkylating agents may react with the N–O/NH2 sites.
Thermal decomposition: Nitrogen oxides may form on burning (general for N–O compounds). Avoid open flames and excessive heat.
First aid (overview; defer to SDS):
Inhalation: move to fresh air, seek medical attention if symptoms persist.
Skin/eyes: rinse with water for 15 minutes; remove contaminated clothing; seek medical attention for persistent irritation.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Handling tips: Minimize moisture uptake; the amidoxime functionality can engage in hydrogen bonding and may cake under humid conditions. Use clean, dry tools; close cap promptly after use.
For authoritative hazard classification and exposure limits, consult the product-specific SDS.
Solvent Selection
This compound is a polar aromatic amidoxime with hydrogen-bond donor and acceptor sites.
Polarity class and miscibility (literature/general):
Limited solubility in nonpolar media (hexanes, cyclohexane) and modest in moderately polar aromatics (toluene) due to H-bonding.
Practical selection by use-case:
Stock solutions for screening: DMSO (100 mM typical), then dilute into aqueous buffers; for higher aqueous solubility, acidify slightly (e.g., 0.1% AcOH) to protonate the imine N (literature guidance).
Couplings/cyclizations to 1,2,4-oxadiazoles: polar aprotics (DMF, DMAc, NMP) support carbonyldiimidazole or acid chloride activation; include mild base (DIPEA) as needed.
O-/N-alkylation chemistry: acetone, MeCN, or DMF with alkyl halides/mesylates, base-tuned to control O- vs N-selectivity (literature trend for amidoximes).
Metal chelation/coordination studies: aqueous ethanol or MeOH/H2O mixtures facilitate complexation while maintaining solubility.
Small comparison (literature/general):
DMSO: highest solvating power; miscible with water; easy stock prep; consider odor and removal.
DMF/NMP: excellent for thermal cyclizations; higher boiling; ensure rigorous drying.
MeOH/EtOH: greener, easy workup; may participate in H-bonding that affects selectivity.
Always verify actual solubility and compatibility empirically for your lot (item-specific solubility Not specified).
Storage and Reconstitution
From Product Data (item-specific):
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature/practice):
Keep container tightly closed in a dry, well-ventilated place. Protect from prolonged exposure to moisture and strong light to minimize potential degradation or caking.
If preparing solutions, use anhydrous solvents (e.g., DMSO, DMF, MeOH). For long-term solution storage, prefer aliquots at ≤ –20 C, protected from moisture; avoid repeated freeze–thaw cycles.
Typical reconstitution: For screening stocks, dissolve to 10–100 mM in DMSO; for synthetic use, dissolve to 0.1–0.5 M in an appropriate solvent (see Solvent Selection). Filter if particulates persist.
Stability/shelf-life: Not specified for this item; refer to CoA/Spec Sheet. As a general rule, check integrity by NMR/LC–MS periodically, especially after 12–24 months or if the container has been opened frequently.
Note: For research use only (per Product Data). Always consult the product label and SDS for definitive storage and handling instructions.
Structure and Identity
N-Hydroxy-2,4-dimethoxy-benzamidine is an aromatic amidoxime bearing two methoxy substituents at the 2- and 4-positions of the phenyl ring.
Item-specific identifiers from Product Data:
CAS: 500024-82-8
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
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 interpretation (non-spec):
Expected molecular formula (literature, based on name): C9H12N2O3
Calculated formula weight (literature): ~196.20 g/mol
Core functionality: amidoxime (C(=NOH)–NH2) conjugated to a 2,4-dimethoxyphenyl ring.
Functional groups: aromatic ring, two anisole-type methoxy groups (–OCH3), amidoxime bearing both oxime hydroxyl (–NOH) and amino (–NH2) donors.
2D description: a benzene ring with methoxy at ortho (2-) and para (4-) positions relative to the benzamidoxime substituent at position 1. The amidoxime carbon is directly bonded to the ring; one side is =N–OH, the other is –NH2.
Stereochemistry: none (achiral, E/Z isomerism does not apply to the C=N–OH when embedded as amidoxime in this context; oxime-like syn/anti rotamers may exist in solution, literature).
Synthetic Utility
Functional group reactivity (literature/general):
Ambident nucleophile: The amidoxime (–C(=NOH)–NH2) features both O- and N-centered nucleophilicity. Reaction conditions can be tuned to favor O-alkylation/acylation (weaker bases, polar aprotics) vs N-alkylation/acylation (stronger bases, phase-transfer, or protecting-group strategies).
Cyclodehydration manifold: Readily forms 1,2,4-oxadiazoles upon coupling with carboxylic acids or their derivatives, typically via activation (CDI, EDC, acid chlorides) followed by thermal closure.
Reductive conversion to amidines: Chemoselective reduction (e.g., catalytic hydrogenation, metal/acid systems) affords benzamidines that may be otherwise challenging to prepare directly from anilides.
Electrophile capture: Reaction with isothiocyanates or carbon disulfide can provide thiourea/thiocarbonyl-linked intermediates and access to thio-oxadiazoles in some protocols.
Coordination chemistry: N,O-chelation to metals enables complex synthesis and can mediate catalytic transformations or materials assembly.
Strategic advantages of the 2,4-dimethoxy aryl:
Electron donation increases the nucleophilicity at the amidoxime carbon and can facilitate cyclizations.
Methoxy groups serve as handles for further diversification (e.g., demethylation to phenols, cross-coupling after halogen introduction).
Workup and purification tips:
Amidoximes often crystallize well from EtOH/EtOAc or MeOH/MTBE mixtures.
Avoid strong acid during chromatography to prevent N–O bond cleavage; add 0.1–0.5% NH4OH or Et3N to silica eluents if tailing occurs.
Target Specificity
This product is a small-molecule reagent, not a biological targeting agent. No antigen/epitope, clone, isotype, or species-reactivity information is applicable.
From Product Data: No target-specific information is provided.
Use-case guidance: Consider this tab not applicable; see Reaction & Applications and Synthetic Utility for relevant details.
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