This compound belongs to the class of organic compounds known as nitronaphthalenes. These are polycyclic aromatic compounds containing a naphthalene moiety substituted by one or more nitro 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
275.260 g/mol
XLogP3
3.300
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
5
Exact Mass
275.079 Da
Monoisotopic Mass
275.079 Da
Topological Polar Surface Area
81.400 Ų
Heavy Atom Count
20
Formal Charge
0
Complexity
354.000
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
Calcolatori di soluzioni
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Recensioni
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Application Protocols
Item-specific, tested biological application protocols (e.g., WB, IHC, IF, FC) and recommended dilutions: Not applicable for this small-molecule reagent.
General laboratory usage (guidance only):
Stock solutions: Prepare in dry MeCN, DMSO, or DCM at a convenient concentration (e.g., 10–100 mM) for screening or photolysis tests. Filter (PTFE, 0.2 µm) if particulate is present.
Photochemical evaluation: Determine absorption spectrum (200–450 nm) and carry out small-scale irradiation trials with actinometry to establish kinetics before scaling.
Synthetic transformations: For hydrolysis/coupling/reduction workflows, see the Reaction Conditions tab for starting parameters; optimize for your substrate and equipment.
Note: Always consult the product’s SDS and CoA for authoritative handling and quality information.
Biological Roles
Item-specific biological function: Not applicable; this product is supplied for research use only.
General context (no clinical/therapeutic claims):
Nitro-naphthyl motifs have been extensively used as photolabile protecting groups (“caging groups”) in chemical biology to temporally control the availability of small molecules and biomolecule functionalities under defined irradiation. The compound here embodies the nitro-naphthyl ether linkage with an oxyacetic ethyl ester handle, making it suitable as a precursor to research probes after further derivatization.
The molecule itself is not a buffer, nutrient, or signaling molecule. Any interactions in biological systems arise from designed conjugates prepared from it (e.g., after converting the ester to other linkages), and must be validated case by case.
Good laboratory practice:
If used in bio-adjacent experiments (e.g., photolysis studies in aqueous media), confirm solvent compatibility, cytocompatibility of byproducts, and photoproduct identities independently. Avoid extrapolating literature behavior from related nitroaryl systems without direct verification on this exact structure.
Always adhere to the Research Use Only designation: not for diagnostic, therapeutic, or clinical applications.
Buffer Applications
Not typically applicable. Ethyl [(1-nitro-2-naphthyl)oxy]acetate is a neutral organic building block, not a buffering agent and not intended for preparing biological buffers.
Practical note:
If handling in buffered aqueous systems for photochemical tests, use an external co-solvent (e.g., MeCN, DMSO) and select buffers that are optically compatible with the intended irradiation wavelength (minimal absorbance in near-UV). Verify that the buffer pH and ionic strength do not promote ester hydrolysis.
Green Alternatives
Considerations: Nitroaromatic scaffolds and chlorinated solvents can carry environmental burdens. Where feasible, adjust chemistry to reduce hazard and waste while meeting research goals.
Potential greener choices (general guidance; balance with performance):
Alternative photocages: Coumarin- or BODIPY-based photolabile groups often permit longer-wavelength excitation (blue/green light), improving energy efficiency and reducing UV exposure. Tradeoff: synthesis complexity and cost can be higher; photoproducts and biological compatibility differ.
Solvent selection: Prefer ethyl acetate, 2-MeTHF, or MeCN over chlorinated solvents (DCM/CHCl3) when solubility and reaction scope allow. 2-MeTHF offers biomass origin and easier solvent recovery; watch for peroxide formation and water content.
Workup minimization: Use solid-supported reagents/ scavengers to reduce aqueous waste. Implement in-line chromatography or crystallization-based purifications when practicable.
Comparison snapshot (general):
DCM (benchmark) vs EtOAc: EtOAc is less toxic and derived partly from bio-ethanol; polarity is comparable for many extractions, though DCM dissolves dense aromatics more readily.
Nitro-naphthyl vs o-nitrobenzyl: Nitro-naphthyl groups can show red-shifted absorption and different photoproducts; o-nitrobenzyl derivatives are more common with extensive data. Selection depends on wavelength requirements and downstream compatibility.
Implementation tips:
Evaluate life-cycle impact of solvent volume; work at higher concentrations or continuous flow to reduce solvent use.
Recycle high-purity solvents where institutional infrastructure allows.
Pharmaceutical Uses
Not for human or veterinary use. No pharmacopeial status is stated for this item.
Role: This compound is best viewed as a synthetic intermediate or specialty building block to install a 1-nitro-2-naphthyl-oxyacetic motif. It is not an excipient and has no established role in dosage form performance.
Downstream transformations (research/manufacturing development): Hydrolysis to the corresponding acid enables coupling into more complex APIs or probes during route scouting; the nitro group offers orthogonal manipulation to tune physicochemical properties (e.g., reduction to aniline followed by acylation). Any such use requires rigorous impurity and residual solvent control.
Quality considerations:
If used in regulated development (preclinical chemistry only), ensure traceability with lot-specific CoA, and establish impurity fate maps when converting to subsequent intermediates.
Photochemical sensitivity of nitro-naphthyl groups suggests protecting from light during processing and packaging to avoid off-target photoproducts.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Density, melting point, boiling point, refractive index, UV cutoff, water content, residual solvents, metal content: Not specified for this item; refer to CoA/Spec Sheet.
Literature/structure-based expectations (informational, not product specifications):
Phase: Many nitroaryl esters are crystalline solids or low-melting solids; actual state for this item is not specified.
Solubility profile (qualitative): Expected good solubility in moderately polar organic solvents (e.g., dichloromethane, ethyl acetate, THF, acetone); low solubility in water due to aromatic core and neutral functionality.
Polarity: Contains one nitro and one ester group; overall moderately polar aprotic character with an aromatic framework.
UV behavior: Nitroaryl chromophores typically show strong π→π* absorption in the near-UV; actual spectrum and cutoffs for this item are not specified.
Notes for practitioners:
If purity assessment by HPLC/UPLC is needed, choose eluents compatible with nitroaromatics (e.g., ACN/water with acid modifier) and monitor at 254–320 nm; exact λmax should be determined experimentally.
Drying: Esters and aryl ethers are generally stable to standard vacuum drying conditions; avoid excessive heat until the actual melting point/specification is known.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Additives: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting typical grades (general guidance):
Research grade: Suitable for most synthesis and discovery workflows. Purity is commonly reported by HPLC/GC or NMR; check CoA for assay, residual solvent, and impurity profile.
Analytical/HPLC grade solvents/reagents: Minimized UV absorbance and trace contaminants; chosen when spectroscopic or chromatographic sensitivity is critical.
Low water/peroxide specifications: Often required for moisture- or radical-sensitive transformations; if needed for your use case, verify the exact specification on the CoA.
Recommendations for this item:
Verify purity (e.g., 1H/13C NMR, LC–MS) upon receipt if it will be used in photochemistry or surface-sensitive applications, where trace chromophores can interfere.
If chromatographic use is planned (e.g., as a standard), confirm UV background and any stabilizers on the Spec Sheet.
Batch-to-batch consistency: Reference the provided CAS (893774-43-1) and CID (5306903) alongside the CoA lot number to ensure traceability.
Reaction and Applications
Context: Ethyl [(1-nitro-2-naphthyl)oxy]acetate combines a nitro-naphthyl chromophore with an oxyacetic ethyl ester, providing both a photoreactive aryl-ether linkage and a transformable ester handle.
Representative research uses (literature/general; expand/adapt to your workflow):
Photochemistry: Nitro-naphthyl ethers are widely explored as photolabile motifs. The aryl–O–CH2–CO– fragment supports studies of UV-triggered cleavage and chromophore optimization. Establish your own photolysis profile (action spectrum, quantum yield) for this exact structure.
Building block for “caged” constructs: Hydrolysis to the corresponding acid (1-nitro-2-naphthyl)oxyacetic acid, followed by coupling to alcohols/amines (via EDC/DMAP or mixed anhydrides), provides access to nitro-naphthyl–linked esters/amides for chemical biology probes (research use only).
Orthogonal derivatization: The nitro group can be chemoselectively transformed (e.g., reduced to amine, then diazotized or used in coupling), while retaining the oxyacetic ester pending subsequent hydrolysis.
O–C bond lability tuning: The benzylic-like methylene next to carbonyl can participate in SN1/SN2-type displacements after activation (e.g., halogenation to –CHX–COOEt), enabling introduction of the 1-nitro-2-naphthyl-oxy motif into other frameworks.
Practical tips:
Maintain neutral to mildly acidic conditions to preserve the ethyl ester when undesired hydrolysis must be avoided.
For photolysis studies, degas solutions to minimize radical/oxygen quenching pathways and work under controlled illumination (e.g., 320–400 nm bandpass as appropriate; establish conditions experimentally).
Reaction Conditions
General literature guidance (not product specifications):
Ester hydrolysis: Basic saponification (NaOH or K2CO3, MeOH/H2O, 0–25 °C) to give the acid; acid-catalyzed hydrolysis (HCl, refluxing MeOH/H2O) is also feasible. Monitor by TLC/LC–MS; quench carefully to avoid aryl–O cleavage.
Coupling to alcohols/amines: EDC·HCl/DMAP in DCM or MeCN (0–25 °C, 2–16 h) to form esters/amides from the corresponding acid. DIC/DMAP or NHS esters are alternatives.
Nitro reduction: Pd/C (5–10 wt%) H2 (1 atm), EtOAc/EtOH at 20–25 °C, 1–6 h, or Fe/AcOH (reflux) as a non-catalytic method. Protect the ester if harsh acidic conditions are used.
Benzylic activation: Formation of the chloromethyl ester (–CH2Cl–COOEt) via SOCl2 (catalytic DMF) in DCM, 0 °C to rt, can enable subsequent SN2 with soft nucleophiles; confirm compatibility with the nitro group.
Photolysis studies: Nitro-naphthyl chromophores are typically excited in the 320–380 nm range; solvent choices like MeCN, MeOH, or buffered MeCN/H2O are common. Determine wavelength, intensity, and quantum yield empirically for this exact structure.
Monitoring and workup:
TLC visualization: UV 254 nm; staining with KMnO4 or phosphomolybdic acid often reveals nitroaryl esters.
Extraction: DCM/EtOAc against brine; dry over Na2SO4 or MgSO4. Minimize exposure to strong base during workup to preserve the ethyl ester.
Expected outcomes: Yields and selectivities are substrate- and setup-dependent; consult primary literature and run small-scale scouts to identify optimal conditions.
Safety and Handling
Item-specific GHS/SDS fields: Not specified for this item; refer to SDS.
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification/Pictograms: Not specified for this item; refer to SDS.
General safety considerations for nitroaryl ethers and esters (informational; defer to SDS):
Potential hazards: Nitroaromatic compounds may cause irritation and can be harmful if ingested or inhaled. Some nitroaromatics are light-sensitive. Avoid dust/aerosol formation.
PPE: Use lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to minimize inhalation exposure.
Incompatibilities: Avoid strong reducing agents (risk of nitro reduction), strong bases for prolonged periods (risk of ester cleavage/transesterification), and strong oxidizers. Separate from alkali metals and powerful nucleophiles that may attack the benzylic-like methylene.
Light sensitivity: Nitro-naphthyl motifs can undergo photochemical reactions; handle and store protected from intense light until photostability is confirmed.
First-aid overview: In case of skin contact, wash with soap and water. If in eyes, rinse cautiously with water for several minutes and seek medical attention if irritation persists. If inhaled, move to fresh air. If swallowed, rinse mouth; seek medical advice. Always consult the SDS for authoritative instructions.
Spills/waste: Absorb small spills with inert material, collect in compatible waste containers. Dispose of as organic hazardous waste per institutional and local regulations.
Storage per Product Data: Room temperature. Store tightly closed in a dry, well-ventilated place; keep container protected from light as a precaution.
Solvent Selection
Applicability: This is a neutral, moderately polar, aromatic nitro ether/ester. It is typically handled and processed in organic media.
Polar aprotic: Good solubility expected in DMF, DMSO, acetonitrile; useful for reactions or stock solutions for screening.
Chlorinated: Dichloromethane and chloroform often dissolve nitroaryl esters well; useful for extractions and chromatography.
Ethers/esters: THF and ethyl acetate are typically good; EtOAc is especially convenient for workups and crystallizations.
Alcohols: Methanol/ethanol can be used, but caution with base or heat to avoid transesterification/saponification.
Water: Poor solubility anticipated; use biphasic systems (e.g., DCM/water) for extractions.
Selection tips:
For photochemical studies, choose solvents with low absorbance at the intended irradiation wavelength and minimal photoreactivity (e.g., acetonitrile, MeCN/water blends); confirm empirically.
For base- or nucleophile-sensitive steps (to retain the ester), favor neutral, aprotic solvents and mild conditions.
Small qualitative comparison (general):
DCM vs EtOAc: DCM offers faster phase separation and broader solubility; EtOAc is greener and less dense, with slightly lower capacity for highly aromatic solutes.
THF vs MeCN: THF offers better solubility for many aromatics; MeCN is superior for photolysis monitoring (transparent deeper into UV) and LC compatibility.
Storage and Reconstitution
Storage conditions (from Product Data):
Storage: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance for nitroaryl esters/ethers:
Keep tightly closed in the original container, in a dry place with desiccation if possible.
Protect from direct light to mitigate potential photochemical degradation of the nitro-naphthyl chromophore.
Avoid prolonged exposure to basic vapors and moisture which can promote ester hydrolysis.
Reconstitution/solution preparation (general):
Solvents: Use dry, oxygen-free organic solvents (e.g., MeCN, DCM, THF, DMSO) as appropriate for your application.
Concentration: Prepare stock solutions at convenient levels (e.g., 10–100 mM) and store aliquots to minimize repeated freeze–thaw or light exposure.
Storage of solutions: For photosensitive work, use amber vials, purge with inert gas, and refrigerate if compatible with your protocol. Determine solution stability empirically; no item-specific stability data are provided.
Specifications not provided: Any item-specific stabilizers, water content, or shelf-life claims are not specified for this item; refer to the CoA/Spec Sheet.
Structure and Identity
Intro: Ethyl [(1-nitro-2-naphthyl)oxy]acetate is an aryl nitro ether bearing an oxyacetic ethyl ester, derived from 1-nitro-2-naphthol.
Stereochemistry: none (achiral as named; no defined stereocenters).
2D verbal description (general): A fused bicyclic naphthalene ring bears a nitro substituent ortho to an aryloxy linkage. The phenoxy oxygen is tethered to a two-atom oxyacetic spacer terminating in an ethyl ester. The electron-withdrawing nitro and ester groups modulate the electron density of the aryl ether linkage.
Synthetic Utility
Key reactive elements:
Aryl nitro group: Can be chemoselectively reduced (e.g., catalytic hydrogenation, Fe/AcOH, SnCl2/HCl) to afford the corresponding 1-amino-2-naphthyl ether, unlocking diazotization, Sandmeyer-type substitutions, or amide/urea formation.
Aryl–O–CH2–COOEt fragment: The ester can be hydrolyzed (acidic or basic) to the acid for further coupling (EDC/HOBt/DMAP; mixed anhydride) to install the (1-nitro-2-naphthyl)oxyacetyl unit onto nucleophiles (alcohols/amines) as esters or amides.
Benzylic-like methylene: After halogenation/activation (e.g., Appel-type or SOCl2/DMF to form –CH2Cl–COOEt), nucleophilic substitution allows introduction of diverse heteroatoms while retaining the aryl–O linkage.
Retrosynthetic/forward use cases (general):
Access to caged constructs: Convert ester to acid chloride or activated ester; couple to sensitive alcohols/phenols under mild conditions to assemble photolabile linkers.
Divergent synthesis: Nitro reduction first, then ester manipulations to generate libraries varying at the nitrogen without disturbing the ether.
Late-stage functionalization: The aryl nitro group deactivates the ring toward electrophilic substitution, aiding selectivity in certain cross-couplings after nitro-to-amino conversion (e.g., Buchwald–Hartwig on anilines derived thereof).
Practical guidance:
Sequence planning: If both the ester and nitro will be transformed, reduce the nitro under conditions that do not saponify the ester (e.g., catalytic hydrogenation at ambient temperature/neutral solvent).
Purification: Aromatic nitro/ester compounds often elute mid-polarity on silica (e.g., 10–30% EtOAc in hexanes); confirm and optimize for your matrix.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological antibody/enzyme/ligand with defined target specificity.
Item-specific data such as antigen, epitope, clone, isotype, or species reactivity: Not applicable for this item.
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