This compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
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
180.160 g/mol
XLogP3
0.200
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
180.053 Da
Monoisotopic Mass
180.053 Da
Topological Polar Surface Area
88.900 Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
224.000
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
No item-specific, tested application protocols are provided for this SKU.
General laboratory practices for this compound type:
Stock solution preparation: dissolve in dry DMSO (e.g., 10–100 mM), vortex/sonicate gently. Filter through 0.2 µm PTFE if needed.
Weighing/dispensing: minimize dust; use antistatic tools. For microgram dosing, prepare intermediate concentrates for accuracy.
Reaction setup: for hydrogenations, pre-wet Pd/C, inert the system, and control temperature. For metal-mediated reductions, add metal in portions to manage exotherms.
Analytical QC: verify identity/purity by 1H/13C NMR, LC–MS, and HPLC. Typical LC gradients: water/acetonitrile with 0.1% formic acid, 5–95% ACN over 10–20 min on C18.
For detailed, validated protocols, consult primary literature or develop method-specific SOPs.
Biological Roles
This product is intended for research and synthetic chemistry use rather than as a biological reagent. No item-specific biological activity data are provided for this SKU.
General context (literature; not specific to this item):
Aromatic amides such as substituted 2-nitrobenzamides can serve as intermediates in the preparation of bioactive scaffolds (e.g., benzoxazoles, anthranilamide derivatives), but the parent nitrobenzamide itself is typically a synthetic precursor rather than a probe.
The nitro group is strongly electron-withdrawing and can modulate hydrogen-bonding capacity and lipophilicity when embedded in larger molecules. Upon reduction to the aniline, the resulting ortho-aminobenzamide motif can engage in intramolecular H-bonding and serve as a bidentate pharmacophore in medicinal chemistry programs.
Metabolism considerations for nitroaromatics (in general) include potential nitroreduction pathways and conjugation after aniline formation; such discussions pertain to final compounds, not this intermediate.
If a biological assay or screening use is planned, confirm purity, residual solvent levels, and stability in your assay medium. No claims of biological efficacy or safety are made for this material.
Buffer Applications
Not typically applicable. 5-Methyl-2-nitrobenzamide is a neutral, poorly water-soluble aromatic amide and is not used as a buffering reagent. For aqueous work, dissolve in a minimal amount of DMSO or DMF and dilute into assay buffer if necessary, staying below solvent tolerance limits.
If you require buffering capacity near physiological pH, consider dedicated buffers (HEPES, MOPS, phosphate) and verify compound solubility/compatibility in those media.
Green Alternatives
Because this product is a solid building block rather than a process solvent, greener considerations focus on transformation choices and media surrounding its use.
Greener strategies (literature guidance):
Nitro reduction:
Prefer catalytic hydrogenation with H2 over stoichiometric tin or iron salts to reduce inorganic waste. Use ethanol or isopropanol as solvent; consider flow hydrogenation for enhanced safety and atom economy.
Transfer hydrogenation with formate (HCO2Na/HCO2H) in ethanol/water under Pd/C can avoid compressed gas handling.
Heterocycle formation:
Reductive cyclization to benzoxazoles in ethanol or water–ethanol with Fe/NH4Cl or catalytic Pd and a benign reductant has been reported, avoiding POCl3 or PPA.
Workup and purification:
Favor crystallization over column chromatography when feasible. If chromatography is needed, use heptane/ethyl acetate over dichloromethane.
Solvent selection:
Replace DMF/NMP with safer polar alternatives when possible (e.g., Cyrene, propylene carbonate, or 2-MeTHF/EtOAc blends) acknowledging solubility tradeoffs.
Comparison (illustrative):
Tin(II) chloride in HCl (classical): high hazardous waste, aqueous heavy metal stream.
H2/Pd in EtOH (greener): low E-factor for reductive step; flammability and catalyst recovery must be managed.
Transfer hydrogenation (formate/iPrOH): avoids cylinders, mild conditions; potentially slower kinetics.
Always evaluate solvent selection via solvent guides (e.g., CHEM21, Pfizer) and perform small-scale trials to confirm performance.
Pharmaceutical Uses
No item-specific pharmacopeial status or excipient use is provided for this SKU.
General formulation context (literature; not specific to this item):
Substituted benzamides are common synthetic intermediates in discovery chemistry. The nitrobenzamide here is primarily a precursor to more elaborated structures (e.g., via nitro reduction to anilide motifs or cyclizations to benzoxazoles) rather than a formulated component.
If used in discovery screening, typical practice is to prepare DMSO stock solutions (e.g., 10–50 mM) and dilute into assay media. Assess solubility limits and adsorption to plastics.
No claims are made regarding suitability as an API, excipient, or compliance with USP/EP/JP. This product is supplied strictly for research use only.
Physical Properties
Item-specific specifications (this lot):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Water content, metals, UV cutoff, residual solvents: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general reference values (non-binding; for planning only):
Phase at ambient conditions: typically a solid aromatic amide.
Solubility profile (qualitative, literature): sparingly soluble in water; soluble in polar aprotic organics (DMSO, DMF, NMP) and moderately soluble in alcohols and ethyl acetate. Limited solubility in hexanes/aliphatic hydrocarbons.
Acid–base: neutral primary amide; amide N–H weakly acidic (pKa of conjugate acid typically ~–1 to 1; deprotonation of amide N requires strong base). Nitro group is strongly deactivating/−M.
Polarity: moderate polarity due to amide and nitro functionality; expected cLogP in the low-to-moderate range for substituted benzamides (literature, qualitative).
Thermal behavior: aromatic amides generally exhibit well-defined melting points; decomposition may occur on prolonged heating above mp, especially in the presence of bases or reducing agents.
Hygroscopicity: typically low for nitrobenzamides; handle in dry conditions for reproducible weighing.
Measurement guidance:
Prepare analytical or preparative solutions in DMSO or DMF for highest solubility; for LC, dilute into acetonitrile/water with 0.1% formic acid as needed.
Verify exact mp, density, and refractive index from the CoA for this specific SKU prior to method validation.
Quality and Grades
Item-specific grade/purity and stabilizers:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
General guidance for this compound class:
Research-grade aromatic amides are typically supplied at high assay purity suitable for synthesis, method development, and structure–activity studies. Trace impurities can include regioisomers (other nitro positions), residual nitration byproducts, or solvent residues.
If HPLC/LC–MS analysis is intended, preference is given to lots with low non-volatile residue and minimal UV-absorbing impurities. For photometric or QC methods, check the UV spectrum in your matrix.
Metal content is usually not a primary concern for downstream use unless employing metal-catalyzed couplings after nitro reduction; if so, confirm low halide/metal residue from prior steps.
If your workflow requires specific impurity profiles (e.g., total unknowns <0.5%, water content <0.2%), request the lot-specific CoA and, if needed, a method validation package (chromatograms, residual solvent analysis, Karl Fischer).
Practical tips:
Record lot numbers in notebooks for reproducibility.
If polymorphism affects your application (crystallization/seeding), perform DSC/XRD screening on receipt.
For solid dispensing automation, ask for particle size distribution if critical.
Reaction and Applications
This substituted ortho-nitro benzamide is a versatile synthetic intermediate. Typical applications (literature) include:
Nitro group manipulation:
Catalytic hydrogenation (H2/Pd-C, PtO2, or Raney Ni) to 5-methyl-2-aminobenzamide, a handle for subsequent acylations, sulfonylations, urea/carbamate formation, or diazotization chemistry.
Chemoselective reductions (Fe/AcOH, SnCl2, Zn/NH4Cl, transfer hydrogenation) when hydrogenation-sensitive moieties are present.
Heterocycle construction:
Reductive cyclization to 2-substituted benzoxazoles from o-nitrobenzamides under Zn/AcOH, Fe/NH4Cl, or Pd-catalyzed conditions; the 5-methyl substituent modulates electronics and regiochemistry.
Conversion to benzimidazoles/quinazolinones after nitro-to-aniline reduction followed by intramolecular condensations.
Cross-coupling from the aniline stage:
After reduction, formation of aryl diazonium salts (from the aniline) enabling Sandmeyer-type substitutions (Cl, Br, CN) or Meerwein arylations, while retaining the amide.
Late-stage diversification:
Directed ortho metalation (DoM) adjacent to the amide on suitably protected derivatives for further functionalization.
Practical tips:
Maintain temperatures ≤25–40 C during hydrogenations to minimize over-reduction or amide hydrogenolysis.
Use buffered acidic conditions (e.g., NH4Cl) for metal-mediated reductions to suppress hydrolysis of the amide.
Purify products by crystallization when possible; nitro/amide combinations often yield crystalline solids amenable to trituration.
Reaction Conditions
General literature conditions (illustrative; adjust per substrate and scale):
Nitro reduction to aniline:
H2/Pd-C (5–10 wt% Pd, 5–10 mol% Pd): EtOH or MeOH, 1–5 bar H2, 20–40 C, 1–6 h. Monitor by TLC/LC–MS. Work up by filtering catalyst, concentrating, and basifying if necessary before extraction.
Fe (3–6 eq) / AcOH or NH4Cl in EtOH/H2O: reflux 2–8 h; filter off iron salts. Good for avoiding hydrogen.
Zn (3–5 eq) / NH4Cl in MeOH/H2O: rt–reflux, 2–6 h; milder, compatible with sensitive groups.
Benzoxazole formation from o-nitrobenzamide (one-pot reductive cyclization):
Zn/NH4Cl, EtOH or EtOH/H2O, 60–80 C, 4–16 h; air or inert. Produces 2-substituted benzoxazoles after intramolecular condensation.
Fe/AcOH or catalytic Pd with formate donors: similar temperatures and times; greener solvent systems possible.
Electrophilic halogenation (post-reduction to aniline):
NBS/NCS in DMF/AcOH, 0–25 C, 1–3 h; regioselectivity governed by amide directing effects and existing methyl.
Diazotization/Sandmeyer (from aniline):
NaNO2, HCl (0–5 C) to form diazonium; then CuX for halogenation or CuCN for cyanation; maintain low temperatures during formation.
Expected outcomes:
Yields commonly range from moderate to excellent (50–95%) depending on substitution and workup efficiency. Verify with small-scale trials.
Note: Conditions above are general literature guidance and not product-specific specifications.
Safety and Handling
Item-specific hazard classification (for this SKU):
Signal Word / H-Statements / GHS Classification / Pictograms: Not specified for this item; refer to SDS.
General safety information for nitro-substituted benzamides (literature; not a substitute for SDS):
Likely hazards: may cause irritation to skin/eyes/respiratory tract. Dust may be harmful if inhaled. Nitroaromatics can present risk of methemoglobinemia upon significant exposure—avoid inhalation/ingestion.
PPE: lab coat, safety glasses, and suitable gloves (e.g., nitrile). Use in a chemical fume hood to avoid dust exposure and when handling reagents for reductions (H2/Pd, metal acids).
Incompatibilities: strong reducing agents (especially at elevated temperature), strong bases (amide hydrolysis), and strong oxidizers (nitro functionality). Avoid contact with reactive metals in the presence of acids/bases.
Special risks: during catalytic hydrogenation of the nitro group, manage flammable hydrogen and Pd/C pyrophoricity—wet catalyst, inert atmosphere, control exotherms. Filtration of Pd/C must be done with care; keep catalyst wet.
First aid (overview): move to fresh air after inhalation; rinse skin with soap/water upon contact; flush eyes with water for 15+ minutes; seek medical attention if symptoms persist. If swallowed, rinse mouth—do not induce vomiting; seek medical advice.
Always consult the official SDS for authoritative hazard, exposure limits, and emergency procedures before use.
Solvent Selection
Applicability: This product is a solid aromatic amide building block, not a laboratory solvent. Solvent selection guidance below pertains to dissolving/processing this compound in reactions and analyses.
General solvent considerations:
Highest solubility: DMSO, DMF, NMP (polar aprotic). Useful for stock solutions (10–100 mM) and for coupling or cyclization chemistry.
Low solubility: water and nonpolar hydrocarbons (hexanes, heptane, toluene shows limited but sometimes workable solubility when heated).
Selection by use case:
LC/LC–MS: prepare concentrated DMSO stock, dilute into acetonitrile/water with 0.1% formic or ammonium formate as needed. Filter through 0.2 µm PTFE/nylon to remove particulates.
Reductive transformations (nitro → amine): ethanol, methanol, ethyl acetate, or THF under H2/Pd; for transfer hydrogenation, use iPrOH or formate in MeOH/EtOH. DMF/DMSO are also viable but complicate workup.
Cyclodehydrations to benzoxazoles: acetic acid, POCl3 (reagent/medium), or polyphosphoric acid; greener variants employ AcOH or catalytic acid in ethanol under reductive conditions.
Crystallization/purification: ethyl acetate/hexanes or EtOAc/toluene gradients; hot MeOH or EtOH for recrystallization when feasible.
Compatibility notes:
Avoid strong bases in protic solvents to limit amide hydrolysis.
For metal-catalyzed steps, pre-dry polar aprotics and degas as needed to improve reproducibility.
Storage and Reconstitution
Item-specific storage and shipping:
Storage Conditions: Room temperature (per Product Data). Avoid direct light and moisture for best stability.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General handling and reconstitution (guidance):
Solid storage: keep tightly closed in the original container with desiccant. If long-term storage is planned, consider inert atmosphere (N2/Ar) and a cool, dry cabinet to minimize hydrolysis or discoloration over time.
Reconstitution for working solutions:
Analytical stocks: dissolve in anhydrous DMSO to 10–100 mM; store aliquots at −20 C to minimize freeze–thaw. Protect from light.
Synthetic use: dissolve in DMF/DMSO/EtOH as required by the reaction. For hydrogenations, pre-dissolve in EtOH or MeOH and filter particulates before charging reactors.
Stability notes (general): aromatic amides are typically stable at room temperature; nitro functionality is robust under neutral conditions. Avoid prolonged exposure to strong bases or reducing environments during storage.
Always refer to the lot-specific CoA/SDS for definitive guidance on storage limits, stability, and any reconstitution constraints.
Structure and Identity
Overview: 5-Methyl-2-nitrobenzamide is a methyl-substituted, ortho-nitro benzamide scaffold useful as an aromatic amide building block and precursor to 2-aminobenzamide derivatives.
From Product Data (item-specific):
Product Name: 5-Methyl-2-nitrobenzamide
CAS: 4315-12-2
CID: 13244367
InChIKey: 184644 (as provided)
Storage Conditions: Room temperature
Research Use Note: For research use only
Literature/Computed (general reference; not item-specific specs):
Molecular formula (literature): C8H8N2O3
Molecular weight (literature): ~180.16 g/mol
Core structural features: benzamide (–CONH2) on a substituted phenyl ring; nitro group (–NO2) at the 2-position (ortho to the amide), and a methyl substituent at the 5-position (meta to the amide, para to the nitro).
2D description: A benzene ring bearing adjacent amide carbonyl (benzamide) and ortho nitro substituent; a methyl group resides two carbons away from the nitro (para to NO2, meta to the amide).
SMILES/InChIKey (literature): Not specified here to avoid inconsistency with item data; refer to public databases if needed.
Notes:
The ortho nitro relative to the amide enables reductive cyclizations to benzoxazoles and facile nitro-to-aniline transformations, enhancing synthetic versatility.
Synthetic Utility
Key reactive elements:
Nitro group (ortho to amide): gateway to aniline via reduction; enables reductive cyclizations to benzoxazoles; strongly deactivating/−M, influencing electrophilic/nucleophilic aromatic substitution patterns.
Primary amide: robust under many conditions; can be converted to more reactive derivatives (acid chloride via activation after hydrolysis to acid, or via Hofmann/Curtius pathways from suitable precursors post-reduction/derivatization). Amide N can be protected or acylated to modulate directing effects.
Strategic uses (literature):
Reductive unmasking: H2/Pd reduces NO2 to NH2 giving 5-methyl-2-aminobenzamide—an anchoring point for ureas, sulfonamides, diazotization, and cross-coupling (via diazonium or subsequent halogenation).
Heterocycle synthesis: o-nitrobenzamides cyclodehydrate to benzoxazoles under reductive or dehydrative conditions; the 5-methyl group tunes electronics and solubility of products.
Late-stage diversification: Electrophilic substitutions (e.g., bromination) are directed by the amide; DoM on protected amide derivatives allows introduction of substituents adjacent to the amide.
Linker/scaffold role: Serves as a rigid aromatic spacer bearing H-bond donor/acceptor (amide) that can be incorporated into peptidomimetic or fragment-like libraries after nitro manipulation.
Practical considerations:
Control chemoselectivity during reductions to avoid amide hydrogenolysis; choose catalyst/solvent accordingly.
Purification is often amenable by crystallization; use polar/nonpolar solvent pairs to exploit the amide’s polarity.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biological targeting reagent (e.g., antibody, enzyme inhibitor with validated target), and no target specificity data are provided in the Product Data.
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