Moxnidazole - ≥95% , CAS No.52279-59-1

CAS: 52279-59-1 Cat. No.: M961529 Fórmula: C₁₃H₁₈N₆O₅ Peso molecular: 338.320

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥95%

Nomes e identificadores

Sorrisos canónicos

CN1C(=CN=C1/C=N/N2CC(OC2=O)CN3CCOCC3)[N+](=O)[O-]

IUPAC Name

3-[(E)-(1-methyl-5-nitroimidazol-2-yl)methylideneamino]-5-(morpholin-4-ylmethyl)-1,3-oxazolidin-2-one

InChIKey

RILWUTQZRXWBOB-GIDUJCDVSA-N

INCHI

1S/C13H18N6O5/c1-16-11(14-7-12(16)19(21)22)6-15-18-9-10(24-13(18)20)8-17-2-4-23-5-3-17/h6-7,10H,2-5,8-9H2,1H3/b15-6+

Peso molecular

338.320

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Azoles
      • Subclass Imidazoles
        • Level5 Substituted imidazoles
          • Level6 Nitroimidazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Azoles
• Subclass: Imidazoles
• Intermediate Tree Nodes: Substituted imidazoles
• Direct Parent: Nitroimidazoles
• Alternative Parents: 1,2,5-trisubstituted imidazoles Nitroaromatic compounds Morpholines Oxazolidinones N-substituted imidazoles Heteroaromatic compounds Organic carbonic acids and derivatives Trialkylamines Oxacyclic compounds Propargyl-type 1,3-dipolar organic compounds Dialkyl ethers Azacyclic compounds Organic oxoazanium compounds Organic oxides Organopnictogen compounds Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 1,2,5-trisubstituted-imidazole - Nitroaromatic compound - Nitroimidazole - Trisubstituted imidazole - Morpholine - N-substituted imidazole - Oxazinane - Oxazolidinone - Heteroaromatic compound - Oxazolidine - C-nitro compound - Carbonic acid derivative - Tertiary amine - Tertiary aliphatic amine - Organic nitro compound - Organic 1,3-dipolar compound - Azacycle - Oxacycle - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Dialkyl ether - Organic oxoazanium - Ether - Hydrocarbon derivative - Organic oxide - Organic nitrogen compound - Organopnictogen compound - Organic oxygen compound - Amine - Carbonyl group - Organonitrogen compound - Organooxygen compound - Aromatic heteromonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as nitroimidazoles. These are compounds containing an imidazole ring which bears a nitro group.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Propriedades químicas e físicas

• Peso molecular: 338.320 g/mol
• XLogP3: -0.100
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 338.134 Da
• Monoisotopic Mass: 338.134 Da
• Topological Polar Surface Area: 118.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 506.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Application Protocols

No tested biological assay protocols are provided for this item. For general small-molecule use in research settings:

• Stock solution preparation (analytical/biochemical screens): Dissolve in DMSO to 10–50 mM; vortex and, if needed, sonicate briefly. Filter through 0.22 µm PTFE for analytical work. Record exact concentration by weight-in/volume or by UV if an extinction coefficient is established for your solvent.
• Serial dilution: Prepare intermediate DMSO dilutions to maintain consistent final DMSO content (e.g., 0.1–0.5% v/v) in assays. Check for precipitation upon dilution into aqueous buffers.
• LC–MS method check: Optimize cone/fragmentor voltages and collision energies for stable parent/product ions. Evaluate short- and long-term solution stability at bench and autosampler conditions.

These are general suggestions only; tailor to your system and consult the item’s CoA for purity/identity confirmation before use.

Biological Roles

No biological role is specified for this item. The following notes are general, literature-based context for nitroimidazole chemotypes and are not specific to this catalog entry, which is provided strictly for research use only.

• Bioreductive behavior: Nitroimidazoles can undergo enzymatic or chemical one-electron reductions generating nitro radical anions that may further react under low-oxygen conditions. This behavior underlies their frequent use as hypoxia indicators in biochemical systems (literature).
• Macromolecular interactions: The imidazole ring can participate in hydrogen bonding and π–stacking with biomolecules. Substituent polarity influences membrane permeability and distribution.
• Metabolism (general): Typical pathways include nitro reduction (to hydroxylamine/amine), N-dealkylation, and phase II conjugation (glucuronidation/sulfation) depending on substituents.
• Analytical biochemistry: Nitroimidazole scaffolds are used as reporter tags for hypoxic adduct formation or as internal standards for LC–MS workflows quantifying related analytes.

This information is provided to aid experimental design in biochemical research; it does not imply any biological efficacy or safety for therapeutic, diagnostic, or clinical use.

Buffer Applications

This compound is not a buffering agent and is not typically used to set or maintain pH. Accordingly:

• No item-specific buffer system or pKa data are provided. For any bioassay use, prepare stock solutions in DMSO or a suitable organic cosolvent and dilute into your target buffer (e.g., PBS, HEPES) while monitoring for precipitation.
• If ionizable groups are present in your sample, apparent solubility may improve in mildly acidic or basic buffers; verify experimentally at small scale.

For preparing assay buffers and mobile phases, consult appropriate buffer components (phosphate, HEPES, acetate, formate) rather than this compound.

Green Alternatives

This item is an individual organic compound, not a process solvent. Green considerations relate to its handling and the solvents/reagents you choose around it.

• Prefer safer solvents where feasible:
  • Replace DMF/DMAc with acetonitrile, ethanol, isopropanol, or 2‑MeTHF when solubility and reactivity permit.
  • For extractions, consider ethyl acetate or MTBE over chlorinated solvents.
• Workup minimization:
  • Use microscale reactions and high‑solids crystallizations to reduce solvent volumes.
  • Apply direct-injection LC–MS or SPME to cut sample prep waste.
• Energy and safety:
  • Room‑temperature methods (e.g., electrochemical or catalytic hydrogenation) can be favored over stoichiometric metal reductions when compatible with the nitroimidazole scaffold (literature-dependent).
• Comparison (general, literature-based):
  • DMF vs ACN: ACN is more volatile and less problematic in waste streams; DMF has reproductive toxicity concerns.
  • DCM vs EtOAc: EtOAc is biodegradable with lower toxicity; DCM is a suspected carcinogen and ozone-depleting when released.

Because item-specific solvent preferences are not specified, evaluate greener substitutions via a solubility screen and DoE, ensuring assay performance and stability remain acceptable.

Pharmaceutical Uses

No pharmacopeial status or excipient role is specified for this item. Aladdin supplies this material strictly for research use only (not for human or veterinary use, diagnostic, or therapeutic applications).

General formulation considerations for small-molecule research compounds (not item-specific):

• Solubility enabling: Use cosolvents (DMSO, PEG 400), cyclodextrins, or lipidic vehicles for in vitro and preclinical exploratory work; confirm chemical stability in chosen vehicles.
• Analytical reference: Can serve as a non-compendial reference for method development (HPLC/LC–MS) with appropriate in-house qualification (assay, identity, impurity profile, water content).
• Solid form: If multiple polymorphs or solvates are possible for a given nitroimidazole derivative (literature), confirm solid-state form by PXRD/DSC as it affects dissolution rates.

This section provides general R&D formulation context only; no clinical or therapeutic claims are made or implied for this item.

Physical Properties

Item-specific physico-chemical data

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point (MP): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point (BP): Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• LogP / pKa / refractive index: Not specified for this item; refer to CoA/Spec Sheet.

General literature context for nitroimidazole chemotype (not item-specific; verify experimentally)

• Nitroimidazoles are often crystalline solids with moderate polarity; many exhibit limited aqueous solubility at neutral pH but are readily soluble in DMSO, DMF, acetonitrile, and alcohols.
• The imidazole N–H can display weak basicity/acidicity depending on substitution; pKa values vary widely among derivatives, typically rendering them partially ionizable under strongly acidic/basic conditions only.
• The nitro group strongly withdraws electron density, affecting UV absorbance in the near‑UV region; in practice, many nitroimidazoles show UV bands ~270–320 nm (literature, compound-dependent) useful for analytical detection.

Because exact values depend on substitution pattern, rely on the item’s CoA/Spec Sheet for precise constants and analytical control limits relevant to your application.

Quality and Grades

Item-specific quality information

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.

How to interpret grades and specs (general guidance)

• For small-molecule library members, suppliers typically control identity and purity by NMR/LC–MS/HPLC. Purity descriptors (e.g., ≥95% or ≥98% by HPLC) indicate the main component area percent; water/peroxide/metal limits are usually not defined unless the material is a solvent or catalyst. If UV cutoff or LC baseline suitability is relevant (e.g., for analytical reference use), check the CoA.
• If provided, “research grade” confirms suitability for laboratory R&D but is not intended for clinical or GMP manufacturing uses. For method development or quantitation, request a reference standard grade with a full characterization package (qNMR, residual solvent profile, assay uncertainty).
• Stabilizers are generally unnecessary for heteroaromatic nitro compounds; however, if the CoA lists any antioxidant or processing aid, evaluate its impact on your assay (chromatographic interference, mass ions).

To ensure method suitability, align your assay requirements (purity threshold, residual solvent limits, identification tests) with the item’s CoA prior to use.

Reaction and Applications

Manufacturer listing places this compound in a small-molecule and compound library category. No specific reaction use is claimed for this exact item. The following are general research uses for nitroimidazole-class molecules (not item-specific; verify suitability):

• Analytical controls and standards: Use as a reference analyte for developing LC–MS/MS or HPLC-UV methods for nitroimidazoles in complex matrices; optimize MRM transitions and retention behavior on C18 or phenyl-hexyl phases.
• Probe development: Nitroimidazole cores are commonly used as bioreductive motifs in hypoxia‑responsive probes (literature). Derivatization at N1/C2 side chains enables conjugation to fluorophores or affinity tags.
• SAR studies: Evaluate how side-chain polarity and steric bulk modulate reduction potential and cellular uptake across nitroimidazole analog libraries.
• Electrochemical studies: Characterize reduction waves (cyclic voltammetry) associated with the nitro group to correlate with reactivity and stability.
• Derivatization chemistry: The nitro group can be transformed under controlled conditions (e.g., stepwise reduction to hydroxylamine/aniline; literature) to access a suite of analogs for property tuning.

Tip: When using as an analytical standard, confirm purity and identity by independent methods (qNMR, HRMS) and document solution stability (freeze–thaw and bench stability) for your method validation file.

Reaction Conditions

No reaction conditions are specified for this catalog item. The following are general, literature-based conditions for common transformations on nitroimidazole scaffolds; confirm suitability for your substrate and scale:

• Nitro reduction:
  • Catalytic hydrogenation (H2, 1–5 atm) over Pd/C (5–10%) in EtOH/EtOAc/MeOH at 20–40°C; monitor to avoid over-reduction of other functionalities.
  • Chemoselective reductions: Fe/AcOH or Zn/NH4Cl in EtOH/H2O mixtures at RT–60°C for partial reduction to hydroxylamine.
• N‑Alkylation:
  • Base (e.g., K2CO3, Cs2CO3) in DMF/ACN with alkyl halides at 20–60°C; consider phase-transfer catalysis to improve selectivity.
• Linker installation / Click handles:
  • Alkylation with haloalkyl azides followed by CuAAC (CuSO4/sodium ascorbate) in t‑BuOH/H2O or DMSO/H2O at RT.
• Analytical method development:
  • LC–MS: ESI+ or ESI− depending on substituents; mobile phases of ACN/H2O + 0.1% FA; start with C18, 5–30% ACN gradients, detect at 280–320 nm (compound-dependent UV).

Always run small-scale trials and consult the CoA for this item’s exact structure to anticipate chemoselectivity and stability under these conditions.

Safety and Handling

Regulatory and GHS details for this item

• Signal word / GHS classification / H-statements / pictograms: Not specified for this item; refer to SDS.

General laboratory safety guidance (non-authoritative; defer to SDS)

• Handle in a fume hood to minimize inhalation exposure to fine powders and organic solids. Avoid dust generation.
• Wear appropriate PPE: lab coat, safety glasses, and chemically resistant gloves (e.g., nitrile). Wash hands and exposed skin after handling.
• Avoid contact with strong oxidizers and strong bases/acids unless such conditions are part of a controlled procedure; nitro-containing heteroaromatics can undergo redox chemistry under forcing conditions.
• Prevent environmental release; collect waste in labeled organic‑solid or halogen‑free organic liquid waste streams per local regulations.
• First aid (overview; follow institutional procedures): eye/skin contact—rinse with water for at least 15 minutes; inhalation—move to fresh air; ingestion—rinse mouth and seek medical advice. Provide SDS to medical personnel.
• Thermal stability: store away from excessive heat and direct sunlight. No data on self-reactivity is provided for this item; avoid grinding with strong oxidants or metals.

Always consult the Aladdin SDS for Moxnidazole (CAS 52279‑59‑1) for authoritative hazard classification, exposure limits, and emergency measures.

Solvent Selection

This product is a discrete organic small molecule (not supplied as a solvent). Selection of media pertains to dissolving, handling, and processing.

• Polarity and miscibility (general nitroimidazole context; verify for this item):
  • Often readily soluble in DMSO, DMF, and acetonitrile; frequently soluble in ethanol/methanol; water solubility may be limited at neutral pH but can increase with pH adjustment (if ionizable groups are present).
• Practical choices by application:
  • Bioassays/stock solutions: DMSO is typical for 10–50 mM stocks; dilute into aqueous buffers with vigorous mixing to minimize precipitation.
  • Chromatography/analytical: ACN/H2O with 0.1% FA or MeOH/H2O systems often provide good peak shape; confirm UV response near 280–320 nm (compound-dependent).
  • Synthetic manipulations: Polar aprotic solvents support nucleophilic substitutions and reductions on nitro-heteroaromatics; dry conditions help if base-sensitive motifs are present.
• Comparison (general):
  • DMSO: highest solvent power, low volatility; may interfere with some bioassays at >0.5–1% v/v.
  • ACN: volatile, LC‑MS friendly; lower solvating power vs DMSO.
  • MeOH/EtOH: protic, facilitate some ionization; may engage in hydrogen bonding with imidazole nitrogens.

Because exact solubility of Moxnidazole is not specified for this item, perform a small‑scale solubility screen under your intended conditions.

Storage and Reconstitution

Item-specific storage

• Storage conditions: Room temperature (per Product Data). Protect from moisture and direct sunlight. Keep container tightly closed.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance on receipt: Not specified for this item; refer to CoA/Spec Sheet.

General reconstitution and solution handling (research use; not item-specific)

• Prepare concentrated DMSO or ACN stock solutions (e.g., 10–50 mM) based on solubility screening. If aqueous use is required, add stocks slowly to buffer with vigorous mixing to avoid precipitation.
• For long-term solution storage, aliquot and store at −20°C or −80°C (away from light) to minimize degradation and freeze–thaw. Document stability experimentally (e.g., periodic LC–MS assay).
• Avoid repeated freeze–thaw of solid or solution. Let vials equilibrate to room temperature in a desiccator before opening to prevent moisture uptake.

For definitive guidance on solid-state stability, recommended solvents, and solution shelf life for this specific lot, consult the product’s CoA and Safety Data Sheet.

Structure and Identity

Item-specific identifiers (from Product Data)

• Product Name: Moxnidazole (SKU: M961529)
• CAS: 52279-59-1
• PubChem CID: 9571039
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: 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.

Structural features (general literature context for nitroimidazoles; not item-specific)

• Nitroimidazoles typically feature a 1H-imidazole ring bearing a nitro group (–NO2), most commonly at the 5-position, and various N- or C-substituents that tune polarity and metabolic stability.
• The 2D structure is characterized by an imidazole diazole ring (two nitrogens within a five‑membered aromatic system). The nitro substituent is a strongly electron‑withdrawing group that modulates the ring’s electronics and reduction potential.
• Substituents on the imidazole (e.g., alkyl, hydroxyethyl, haloalkyl, or ether chains in the nitroimidazole chemotype) influence solubility and logP; many members are moderately polar with good solubility in polar aprotic media (DMSO, DMF) and limited water solubility.

Note: For definitive structural representation (SMILES/InChI), and to confirm positional substitution and stereochemistry (if any), consult the Certificate of Analysis or Specification Sheet for this specific catalog item.

Synthetic Utility

Although sold as a finished small molecule for screening and analytical work, nitroimidazole scaffolds provide useful synthetic handles (general, literature-based):

• Nitro group transformations:
  • Stepwise reduction (e.g., catalytic hydrogenation, Fe/AcOH, SnCl2/HCl) to hydroxylamine or aniline equivalents allows access to aminoimidazole derivatives for further diversification (acylation, sulfonylation, urea formation).
• N1/C2 functionalization of imidazole:
  • Deprotonation at N1 under basic conditions enables N‑alkylation/etherification with suitable electrophiles (careful control to avoid O- vs N-alkylation in multifunctional substrates).
  • C2 substitution patterns, when activated, engage in cross-couplings or nucleophilic displacements (substrate-dependent).
• Conjugation chemistry:
  • Installation of linkers (e.g., azide/alkyne handles) on the side chain enables click chemistry to fluorophores or affinity tags, common in probe/sensor development for hypoxia studies.
• Retrosynthetic value: The nitro group serves as a masked amine while tuning electronics of the ring, enabling late-stage diversification after core assembly.

Note: Specific reactivity and selectivity depend strongly on the substitution pattern of Moxnidazole. Consult the item’s structural data (CoA/Spec) before planning transformations.

Target Specificity

Not applicable. This product is not an antibody, enzyme, or biological targeting reagent. No antigen, epitope, species reactivity, clone, or isotype information applies.