This compound belongs to the class of organic compounds known as nitrophenyl ethers. These are aromatic compounds containing a nitrobenzene moiety that carries an ether group on the benzene ring.
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.
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Recensioni
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Application Protocols
No application protocols are predefined for this small-molecule building block.
Typical lab use (general)
Weigh and transfer under ambient conditions; use dry glassware for moisture-sensitive reactions (e.g., with Lewis acids).
Prepare stock solutions in suitable organic solvents (e.g., DMSO, acetonitrile, DCM, THF) depending on the intended reaction or assay.
Analytical setup (general)
TLC: silica gel, visualize at 254 nm; elute with hexanes/EtOAc gradients.
HPLC: C18 reversed-phase with acetonitrile/water (with 0.1% acid modifier) often gives good retention due to aromaticity; detection at 220–280 nm.
Item-specific tested applications or dilutions: Not specified for this item; refer to CoA/Spec Sheet.
Biological Roles
This product is intended for research and laboratory use only. No medical or clinical claims are made.
General biochemistry context (literature/general)
Nitroaromatic ethers like 5-methyl-2-nitroanisole do not have known endogenous biological roles; they are typically synthetic intermediates.
Nitro groups can undergo enzymatic bioreduction in some organisms, generating anilines or hydroxylamines; this property underlies their use in studying reductive metabolism or in designing pro-fragments for bioconjugation research.
The anisole ether can be cleaved to the phenol under strongly acidic or oxidative conditions; in biological systems, O-demethylation is usually mediated by oxidative enzymes on certain aryl methyl ethers, though substrate specificity varies widely.
Research relevance
May serve as a model substrate in studies of nitroaromatic reduction, aryl-O demethylation, or phase I/II metabolism in microsomal or microbial systems (literature use-cases).
Item-specific biological data (targets, ADME, toxicity parameters): Not specified for this item; refer to primary literature or generate in-house.
Buffer Applications
This compound is a hydrophobic aromatic building block and is not used as a buffering agent. It has no defined acid/base pair suitable for preparing aqueous buffers.
Practical note: If handling in aqueous systems (e.g., biotransformations), dissolve first in a miscible co-solvent (DMSO, acetonitrile, ethanol) at low percentage to avoid precipitation and ensure consistent dosing.
Green Alternatives
Greener choices relate to solvent and reagent selection rather than substitution of the substrate itself.
Solvent choices (general guidance)
Prefer ethyl acetate or 2-MeTHF over chlorinated solvents (DCM, CHCl3) for extractions/chromatography when compatible with the transformation.
For hydrogenations, ethanol or isopropanol are greener media than DMF/DMAC or halogenated solvents.
Reagent choices for key transformations (literature)
O-Demethylation: BBr3 is effective but corrosive and generates hazardous waste. Greener alternatives include aqueous AlCl3 under phase-transfer, ionic liquids with nucleophiles, or oxidative demethylation with ceric ammonium nitrate under carefully controlled conditions. Trade-offs include lower chemoselectivity and narrower substrate scope.
Nitro reduction: Catalytic hydrogenation with H2/Pd in ethanol or water/ethanol mixtures is generally greener than stoichiometric metal reductions (SnCl2, Fe/HCl) that produce heavy-metal/iron salt waste.
Brief comparison (general)
DCM vs EtOAc: EtOAc has lower toxicity and better environmental profile; however, DCM often provides superior solubility and phase separation.
BBr3 vs alternative demethylations: BBr3 offers high yields at low temperature but is moisture sensitive and hazardous; alternative methods may require longer times/higher temps and can impact the nitro group.
Item-specific environmental certifications or green grade: Not specified for this item; refer to CoA/Spec Sheet.
Pharmaceutical Uses
No therapeutic claims are made. This product is for research use only.
General formulation/manufacturing context (literature/general)
5-methyl-2-nitroanisole may be employed as a synthetic intermediate toward drug-like molecules, enabling downstream conversion to aminophenols/anilines or ether variations.
Not typically used as an excipient. No pharmacopeial monograph is known for this specific isomer.
Regulatory/quality note
If the material is used in GMP-related development, establish impurity profiles (including positional isomers and residual catalysts) and confirm identity with orthogonal methods per ICH Q6A/Q3A/B.
Item-specific pharmacopeial status or compliance: Not specified for this item; refer to CoA/Spec Sheet.
Physical Properties
Only item-specific specifications should be taken from the CoA/Spec Sheet. No item-specific physical property values are provided in the Product Data.
Item-specific specs
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Any numeric specs (bp, mp, density, water/peroxide/metal/UV): Not specified for this item; refer to CoA/Spec Sheet.
Typical properties (literature/general; for reference only, not item specifications)
Phase/appearance (literature): often isolated as a pale yellow solid or low-melting solid/liquid depending on sample purity and isomer content.
Solubility (literature): sparingly soluble in water; soluble in common organic solvents (e.g., dichloromethane, toluene, ethyl acetate, acetone, THF, acetonitrile).
Polarity: moderately polar aromatic ether with a strongly polar nitro group; expected logP in the 1–2.5 range (literature, varies by source; consult specific database for exact value).
UV characteristics: aromatic chromophore with nitro-aryl charge-transfer band; strong absorption in near-UV (literature). Exact cutoffs Not specified for this item; refer to CoA/Spec Sheet.
Note: For method development, determine actual values (mp/bp, purity profile, residual solvents, water content) by reference to the product’s CoA/Spec Sheet.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile (including positional isomers), and residual solvents.
Guidance on interpreting grades (general information)
Research or laboratory grade: suitable for routine synthesis and method development; impurity levels are managed for general chemical use.
High-purity/synthetic intermediate grade (if applicable): focuses on low inorganic/ionic contaminants and controlled organic impurity profile, often important for catalysis or downstream transformations.
HPLC/UV grade (not indicated here): ensures low UV background and minimal fluorescence—relevant if used as a chromatographic standard.
Batch documentation and verification
CoA typically includes identity confirmation (e.g., 1H NMR, GC/LC purity, MS), and may include water content (KF), residual solvent, and isomeric purity when relevant. For this aromatic isomer, verification of the 1,2,5-substitution pattern is often performed by NMR coupling patterns and NOE/2D correlations.
Stabilizers/inhibitors
Not typically required for nitroanisoles; any use of stabilizer would be stated on the CoA. For this item: Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
As a functionalized anisole, 5-methyl-2-nitroanisole is a versatile intermediate in aromatic synthesis, enabling orthogonal transformations at OMe, NO2, and benzylic positions.
O-Demethylation to 5-methyl-2-nitrophenol using Lewis acids (e.g., BBr3, BCl3) or nucleophilic reagents (e.g., AlCl3/thiols), enabling subsequent etherification/esterification.
Nitro group transformations: reduction to 5-methyl-2-anisidine (or to the corresponding aminophenol after sequential demethylation) via catalytic hydrogenation (Pd/C, H2) or transfer hydrogenation/metal reductions (Fe/AcOH, SnCl2, Zn/NH4Cl).
Electrophilic aromatic substitution (EAS): the methoxy activator (ortho/para directing) is tempered by the ortho nitro deactivation; remaining unsubstituted positions can be addressed with carefully tuned conditions (e.g., halogenation, sulfonylation) to control regioselectivity.
Nucleophilic aromatic substitution (SNAr): not favored at the anisole ipso position without activation (–OMe is a poor leaving group), but feasible after converting –OMe to a better leaving group (e.g., –OTf from the phenol) following demethylation.
Cross-coupling after prefunctionalization: halogenation of the ring enables Suzuki–Miyaura, Buchwald–Hartwig (after nitro reduction), or Ullmann couplings to elaborate the scaffold.
Benzylic functionalization: oxidation of the 5-methyl to aldehyde/acid (e.g., SeO2 or KMnO4 under controlled conditions) expands diversity.
Practical notes
Orthogonal protection: the nitro can mask an aniline and be reduced late-stage; demethylation conditions should avoid nitro reduction unless desired.
Analytical: strong UV absorption aids HPLC monitoring; 1H NMR offers diagnostic ortho coupling confirming the 1,2,5 substitution pattern.
Reaction Conditions
General literature guidance for common transformations of 5-methyl-2-nitroanisole (not item-specific specifications):
O-Demethylation to 5-methyl-2-nitrophenol
Reagents: BBr3 (1.2–3.0 equiv) in dry DCM, –78 to 0 °C, then warm to rt; quench with MeOH/H2O. Typical times: 1–16 h. Alternative: BCl3 or AlCl3/thiol systems. Monitor to avoid nitro reduction.
Nitro reduction to 5-methyl-2-anisidine
Catalytic hydrogenation: H2 (1–5 bar) with 5–10 wt% Pd/C in EtOH or EtOAc at rt–40 °C; 2–12 h. Alternative metal reductions: Fe/AcOH or SnCl2/HCl at reflux (generates inorganic waste). Protect OMe if conditions risk demethylation.
Benzylic oxidation (methyl → aldehyde/acid)
MnO2 (activated) in DCM/toluene at rt–reflux to aldehyde (hours to overnight). Stronger oxidants (KMnO4, Na2Cr2O7) convert to acid; ensure compatibility with nitro group.
Electrophilic aromatic substitution
Halogenation (e.g., NBS for benzylic bromination vs NCS/NBS for ring halogenation under Lewis acid): conditions must be tuned to control site selectivity due to competing directing effects of –OMe and –NO2.
Cross-coupling (after prefunctionalization)
Following halogenation, employ Pd-catalyzed Suzuki–Miyaura (aryl–B(OH)2), Buchwald–Hartwig (after nitro→aniline), or Ullmann couplings in toluene/1,4-dioxane/DMF with bases such as K3PO4, Cs2CO3 at 60–110 °C.
Notes
Dry, oxygen-free conditions are recommended for moisture-sensitive steps (e.g., BBr3 demethylation).
Always perform small-scale trials to optimize equivalents, temperature, and time; monitor by TLC/HPLC/GC.
Safety and Handling
Always consult the product SDS for authoritative safety information. The following is general guidance for substituted nitroanisoles.
GHS/Hazard (item-specific): Not specified for this item; refer to SDS.
Likely hazards (general for nitroaromatics and anisole ethers)
Combustible organic compound; may cause irritation to eyes/skin/respiratory tract.
Nitroaromatics can present methemoglobinemia risk upon significant exposure; avoid inhalation/ingestion (general toxicology note).
Recommended PPE/practices
Use in a chemical fume hood; avoid dust or vapor generation.
Wear lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Consider double-gloving for extended contact.
Prevent contact with oxidizing agents and strong reducing agents; avoid strong bases/acids for extended periods (may promote O-demethylation or nitration side reactions).
First aid (general overview; defer to SDS)
Eye/skin contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; monitor for respiratory discomfort; seek medical attention if symptoms develop.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire fighting
Use CO2, dry chemical, or alcohol-resistant foam. Combustion may produce CO/CO2 and nitrogen oxides.
Stability and incompatibilities (general)
Stable under normal lab conditions. Avoid prolonged exposure to strong oxidizers, strong bases, and strong acids. Protect from excessive heat and direct sunlight.
Item-specific signal word, H-statements, pictograms: Not specified for this item; refer to SDS.
Solvent Selection
This product is an aromatic ether bearing a nitro group, with low aqueous solubility and good solubility in common organic media.
Polarity/miscibility (literature/general)
Expected to dissolve readily in dichloromethane, chloroform, ethyl acetate, acetone, acetonitrile, toluene, and THF; limited solubility in hexanes depending on temperature.
Poorly soluble in water due to hydrophobic aromatic core; nitro group imparts some polarity for moderately polar organics.
Selection guidance by use case
Workup/extraction: DCM or EtOAc commonly provide efficient partitioning from aqueous phases; select based on density and downstream chromatography.
Chromatography: Normal-phase silica with hexanes/EtOAc gradients is typical. The nitro group improves UV detectability at 254 nm.
Reactions involving demethylation: Non-nucleophilic, chlorinated aromatics (DCM) or neat BBr3 often used; strictly anhydrous conditions are critical.
Catalytic hydrogenation (nitro reduction): Alcohols (EtOH, i-PrOH) or ethyl acetate/toluene under H2 with Pd/C are common choices.
Small comparison (general)
DCM vs EtOAc: DCM offers better solubility and heavier phase for extractions; EtOAc is greener and easier to remove but may participate in hydrogenations.
Toluene vs THF: Toluene is non-protic and high-boiling for elevated-temperature reactions; THF is polar and coordinates metals but requires peroxide monitoring.
Item-specific solvent specs/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Storage and Reconstitution
Storage (item-specific from Product Data)
Store at room temperature. Shipped under normal conditions.
General storage guidance (small organic molecules)
Keep container tightly closed in a dry, well-ventilated place. Protect from direct sunlight and heat sources.
For long-term storage, consider using an inert gas blanket (N2/Ar) after opening to minimize oxidation of sensitive impurities; store away from strong oxidizers and strong acids/bases.
Reconstitution/solution preparation (general)
Prepare solutions in suitable organic solvents (e.g., DMSO, acetonitrile, methanol, ethanol, ethyl acetate, dichloromethane, toluene) according to the needs of the procedure.
Filter stock solutions (0.2 µm PTFE) for analytical applications if particulate is present.
Avoid prolonged storage of solutions, particularly in protic/oxidizing media; prepare fresh when possible or store at 2–8 °C in amber vials to limit photodegradation.
Stability notes
No stabilizer information is provided for this item; refer to the CoA/Spec Sheet. Under normal laboratory conditions, substituted nitroanisoles are generally stable.
Structure and Identity
Brief description: 5-methyl-2-nitroanisole is a substituted anisole bearing an ortho nitro group relative to methoxy and a meta (5-) methyl substituent; an electron-rich methoxy and electron-withdrawing nitro create a polarized aromatic system useful as a building block.
Item-specific identifiers (from Product Data)
SKU: M134141
Product name: 5-methyl-2-nitroanisole
CAS: 38512-82-2
InChIKey: 414437 (as provided)
Storage conditions: Room temperature; shipped under normal conditions
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Core identity (literature/computed; for reference only)
SMILES (literature): a representative form is COc1c(N+[O-])ccc(c1)C (note: canonical forms vary by source)
Structural features (general chemistry)
Aromatic ring bearing three substituents: methoxy (–OCH3) at C1, nitro (–NO2) at C2 (ortho to methoxy), and methyl (–CH3) at C5 (meta to methoxy, para to nitro in the 1,2,5-arrangement).
Reactivity implications: the ring experiences opposing directing/activation effects (–OMe activator/ortho–para director vs –NO2 deactivator/meta director), enabling selective transformations when conditions are tuned.
Synthetic Utility
Key functional handles and their synthetic leverage (literature/general):
Methoxy group (anisole ether)
Protecting-group-like behavior for phenols: robust under many conditions; can be unveiled by BBr3 or other demethylations to give the phenol for further diversification (e.g., O-alkylation, O-acylation, Mitsunobu couplings from the phenol stage).
Direct metalation/ortholithiation adjacent to methoxy is attenuated by the ortho nitro, but directed metalation strategies may be adapted at remaining positions with strong bases and protecting tactics.
Nitro group
Versatile convertible functionality: reduction to aniline enables diazotization/Sandmeyer, Buchwald–Hartwig amination variants, or formation of ureas/carbamates.
Used in N-oxide rearrangements and as a directing group in certain radical or photoredox protocols after partial reduction (literature-dependent).
Benzylic methyl
Oxidation to aldehyde/acid (e.g., with MnO2 for selective benzylic oxidation to the aldehyde, or KMnO4 for deeper oxidation) provides handle for further C–C or C–X formation (e.g., Horner–Wadsworth–Emmons from aldehyde).
Strategic value
Orthogonal manipulation sequence options: (1) demethylate → phenol chemistry; (2) reduce nitro → aniline chemistry; (3) benzylic oxidation → carbonyl chemistry. Order can be chosen to protect sensitive motifs and maximize selectivity.
Retrosynthetic role
Serves as a convergent point to access substituted catechol/aniline derivatives after sequential transformations, valuable in agrochemicals and medicinal chemistry libraries.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological targeting reagent, antibody, or probe.
Item-specific biological target data: Not specified for this item; refer to CoA/Spec Sheet.
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