This compound belongs to the class of organic compounds known as dinitrotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and exactly two 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
207.140 g/mol
XLogP3
1.700
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
0
Exact Mass
207.028 Da
Monoisotopic Mass
207.028 Da
Topological Polar Surface Area
115.000 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
323.000
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
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Recensioni
Recensioni dei clienti
Application Protocols
No standardized bioassay or immunoassay protocols apply to this small-molecule reagent. For synthetic applications, consider the following general laboratory protocols (illustrative; adjust to your needs):
Stock solution preparation (analytical studies):
Dissolve in DMSO at 10–100 mM; sonicate gently or warm to 40 °C if needed. Filter (PTFE, 0.2 µm) before use.
Reduction to diamine (screening protocol):
Charge autoclave vial with substrate (1.0 equiv), 10 wt% Pd/C (5–10 mol% Pd), EtOH (0.05–0.2 M). Purge with N2 then H2, pressurize to 3 bar, stir at 25–35 °C until complete (LC–MS). Filter over celite, wash, and concentrate. Crystallize from EtOAc/hexanes.
Nitrile hydrolysis (amide):
Substrate (1.0 equiv), K2CO3 or KOH (2–3 equiv), EtOH/H2O (4:1), 70–80 °C, 2–6 h. Neutralize, extract with EtOAc, and purify by crystallization.
These examples are general literature-style methods and not validated specifications for this catalog item. Always perform appropriate safety and feasibility assessments.
Biological Roles
This compound is a synthetic, highly substituted aromatic nitrile and is not known to occur in biological systems.
General context (not specific to this item):
Nitroaromatics can display bioactivity due to their redox properties, though such effects are highly structure-dependent and outside the scope of research-use products.
Aromatic nitriles lack intrinsic buffering capacity or known metabolic roles; nitriles can undergo biotransformation in vivo (e.g., via nitrilases or oxidative pathways) but these pathways are substrate-specific and typically studied under controlled research settings.
Research relevance:
The electron-deficient ring can serve as a probe substrate for studying reduction mechanisms (e.g., microbial nitroreductases) or abiotic redox chemistry in environmental or mechanistic studies.
Important limitation:
No medical, diagnostic, or therapeutic use is implied. Any biological testing should be conducted under appropriate approvals and safety protocols.
Summary:
No established physiological role. Treat as a specialized organic building block that may be evaluated for biochemical interactions solely in a research context.
Buffer Applications
Not typically applicable. 3-Methyl-2,6-dinitrobenzonitrile is a neutral organic building block without acid/base functionality suitable for buffering. For aqueous experimental setups, select an appropriate external buffer system (e.g., phosphate, HEPES) independent of this compound. Solubilization, if required for assays, should be achieved with water-miscible organic cosolvents (e.g., DMSO) before dilution into the buffered medium.
Green Alternatives
While the molecule itself is a fixed building block, greener choices can be made in its processing.
Solvent selection (comparative, general guidance):
Replace chlorinated solvents and DMF where possible with greener media while maintaining performance.
Favor catalytic hydrogenation over stoichiometric tin or iron salts when feasible to minimize metal-containing waste.
For nitrile reductions to aldehydes, consider DIBAL-H alternatives like catalytic hydrogenation with poison-modified catalysts if selectivity allows.
Energy and safety:
Employ continuous flow for exothermic nitro reductions to improve heat transfer and reduce inventory.
Optimize crystallization-based purifications to reduce chromatographic solvent usage.
Pharmaceutical Uses
No excipient or pharmacopoeial status is specified for this item. It is provided strictly for research use.
Potential roles in pharma R&D (general, non-clinical):
Synthetic intermediate: The 2,6-dinitro pattern enables access to 2,6-diamino- or other difunctionalized benzonitriles after reduction/diazotization, useful in constructing rigid aryl linkers in small-molecule libraries.
Scaffold diversification: The nitrile can be orthogonally transformed (to amide/acid/amine), enabling rapid SAR exploration during lead discovery.
Formulation context:
As a hydrophobic, neutral solid, it is not a typical excipient. If used as a reference or impurity standard in QC/analytical development, ensure traceability with an authenticated CoA and verify purity by orthogonal techniques (NMR, LC–MS, qNMR).
Compliance note:
No clinical or therapeutic claims are made. For any GMP-relevant application, suitability, impurity limits, and trace metals must be established with process-specific controls and documentation.
Physical Properties
Item-specific data (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.
Other specs (mp, bp, density, UV cutoff, residuals): Not specified for this item; refer to CoA/Spec Sheet.
Literature/typical expectations for this structure (not item specifications):
Physical state: Typically a crystalline solid for dinitro-substituted benzonitriles.
Formula (literature): C8H5N3O4; FW (calc.): ~207.14 g/mol.
Polarity: Moderately polar aromatic due to –NO2 and –C≡N; substantially less polar than ionic species.
Solubility (qualitative):
Sparingly soluble in water (nitroaromatics and benzonitriles are generally water-insoluble).
Soluble in polar aprotic organic solvents (e.g., DMSO, DMF, NMP, acetone, acetonitrile) and in chlorinated solvents (e.g., dichloromethane, chloroform); solubility can improve with gentle warming.
Acid/base properties: No protic functionality; nitrile is weakly basic at nitrogen but typically non-ionizable under neutral conditions. Nitro groups are strongly deactivating/electron-withdrawing.
Partitioning: Expect a positive logP consistent with nitroaromatics; exact value not established here.
Practical notes:
For analytical characterization, 1H/13C NMR in DMSO-d6 or CDCl3 is typical; nitro substitution induces downfield aromatic shifts.
IR shows a strong C≡N stretch typically near 2220–2240 cm−1 (literature), and strong NO2 asymmetric/symmetric bands (~1520–1550 and ~1340–1370 cm−1, literature). Values will vary—confirm by your own data.
Quality and Grades
Item-specific grade/purity (Product Data):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting common grades (general guidance):
Research grade: Suitable for most synthetic and exploratory work. Impurity profiles vary; check CoA for assay and key impurities (e.g., unreacted isomers, reduced/oxidized byproducts).
Analytical/AR grade: Tighter control of inorganic/organic contaminants; useful where trace metals or UV background must be minimized.
HPLC grade (solids rarely so designated): Emphasis on low UV background and absence of fluorescent impurities; pertinent when the compound is used as a standard or in trace analysis.
Stabilizers/inhibitors:
None are typically required for nitroaromatic benzonitriles; if any stabilizer or anti-caking agent is used, it will be stated on the CoA/Spec Sheet. Absent such note, no stabilizer is implied.
What to check on receipt:
Identity/assay: 1H/13C NMR, IR (C≡N and NO2 bands), HRMS, melting point where applicable.
Residual solvents/volatiles: If critical, request GC headspace data.
Inorganic residues: Ash/metal content may matter for catalysis—request ICP data if relevant.
Always rely on the lot-specific CoA for definitive specifications.
Reaction and Applications
This scaffold is an electron-deficient benzonitrile suitable for divergent functionalization via the nitro groups and the nitrile.
Transformations of the nitro groups (general, literature):
Reduction to diamines: 2,6-dinitro → 2,6-diamino variants using catalytic hydrogenation (H2/Pd–C or Raney Ni), transfer hydrogenation, or metal/acid systems (Fe/HCl, Sn/HCl). The adjacent methyl can be preserved under mild conditions.
Selective mono-reductions: Achievable with stoichiometric hydride donors or controlled catalytic systems; facilitates orthogonal elaboration.
Nucleophilic aromatic substitution (SNAr): Nitro groups activate the ring; however, a leaving group is typically required at the site of substitution. Post-reduction/diazotization enables installation of halides or other groups (Sandmeyer-type).
Nitrile group chemistry (literature):
Hydrolysis: To amide (mild) or acid (stronger aqueous acid/base, elevated temp; dehydrating workup yields amide/acid derivatives).
Reduction: To primary amine (e.g., LiAlH4, catalytic hydrogenation) or to aldehyde (DIBAL-H at low temperature).
Cycloadditions/annulations: Nitriles can participate in heterocycle formation (e.g., imidates/imididates en route to 1,2,4-oxadiazoles with amidoximes).
Applications domains (non-clinical):
Building block for polyfunctional arenes used in materials, pigments/dyes precursors, and ligand frameworks where meta/ortho relationships are required.
Maintain inert atmosphere when employing moisture-sensitive reductants (LiAlH4, DIBAL-H).
For hydrogenations, degas solvents and monitor exotherm; nitro reductions can be strongly exothermic.
Confirm substitution pattern by 2D NMR after multistep elaborations.
Reaction Conditions
General literature guidance for typical transformations of 3-methyl-2,6-dinitrobenzonitrile and close analogs. Adjust based on your substrate, scale, and safety assessment.
Nitro → amino (catalytic hydrogenation):
Catalyst/solvent: 5–10 wt% Pd/C (2–10 mol% Pd rel. to Ar–NO2) in EtOH, iPrOH, or EtOAc; H2 at 1–5 bar; 20–40 °C.
Notes: Exothermic; add substrate gradually or operate in flow. Monitor by TLC/LC-MS; avoid over-reduction of the nitrile by moderating pressure and catalyst loading.
Nitro → amino (iron reduction):
Conditions: Fe powder (4–6 equiv), AcOH or HCl (aqueous), 50–80 °C.
Notes: Robust and scalable; generates significant iron salts—plan for waste treatment.
Nitrile → amide/acid (hydrolysis):
Basic: KOH/NaOH in aqueous ethanol or dioxane/H2O, 50–100 °C; amide at shorter times, acid upon extended reflux and workup.
Acidic: H2SO4 or HCl (conc.) in H2O/AcOH, 80–120 °C.
Nitrile → aldehyde (partial reduction):
DIBAL-H: 1.2–1.5 equiv in toluene or THF, −78 to −20 °C; quench carefully at low temperature to suppress over-reduction.
Diazotization/Sandmeyer (after nitro reduction to anilines):
Diazotization: NaNO2, HX (HCl/HBF4) at 0–5 °C, then CuX for halogenation/cyanation.
Workup/purification:
Crystallization from EtOAc/hexanes or EtOH/H2O is often effective for nitroaromatics. Silica gel chromatography with DCM/EtOAc or hexanes/EtOAc mixtures is common.
All parameters above are general literature ranges and not specifications for this item.
Safety and Handling
Item-specific hazard information (Product Data):
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 guidance for nitroaromatic benzonitriles (informational; not a substitute for SDS):
Toxicological profile: Nitroaromatics can present acute toxicity, methemoglobin-forming potential, and organ-specific hazards upon significant exposure; nitriles may be harmful if ingested or inhaled. Treat as harmful/irritant unless otherwise classified.
PPE: Lab coat, safety glasses or chemical splash goggles, and suitable chemical-resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dust or vapors.
Engineering controls: Handle solids to minimize dust; employ local exhaust ventilation. Avoid aerosol generation during weighing or transfers.
Incompatibilities: Strong reducing agents (risk with nitro groups), strong bases under forcing conditions (possible Meisenheimer formation after activation), and strong oxidizers (general precaution). Avoid high temperatures and ignition sources; although not a classic explosive, nitroaromatics warrant prudent handling away from energetic reagents.
First aid (overview):
Skin/eye contact: Rinse with water for ≥15 min; remove contaminated clothing; seek medical attention as needed.
Inhalation: Move to fresh air; seek medical attention if symptoms develop.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Waste: Collect as hazardous organic waste. Do not release to the environment. Follow institutional and local regulations.
Always consult the product’s SDS for authoritative, item-specific safety information.
Solvent Selection
As an electron-poor aromatic nitrile with two nitro groups, this compound is a neutral, moderately polar organic solid.
Polarity/miscibility (general):
Water: Expected to be sparingly soluble to insoluble.
Polar aprotic solvents: Good solubility in DMSO, DMF, NMP, and acetonitrile; suitable for reactions and analytics.
Ethers/ketones/esters: Acetone, MEK, ethyl acetate, and 2-MeTHF can dissolve it moderately, depending on temperature.
Chlorinated solvents: CH2Cl2 and CHCl3 often dissolve nitroaromatics effectively.
Selection by application:
Reductions (e.g., nitro → amino): Ethanol, isopropanol, EtOAc, or THF in combination with catalysts (Pd/C, Raney Ni, Fe/AcOH) are common; for catalytic hydrogenation, protic solvents or alcohols are typical, whereas metal/acid reductions may prefer EtOH/AcOH or EtOH/H2O.
Nitrile transformations (hydrolysis/reduction): Aqueous-organic systems (e.g., dioxane/H2O, MeOH/H2O) for hydrolysis; polar aprotics (THF, MeCN, DME) for DIBAL or borohydride variants.
Cross-couplings after amine installation: DMF, dioxane, or toluene under Pd catalysis (post-reduction to aryl amines and diazotization if needed).
Practical tips:
Begin with DMSO or DMF to prepare concentrated stock solutions for screening; switch to greener or volatile solvents for scale-up and isolation.
Warm to 40–60 °C to improve solubility, avoiding decomposition.
Filter warm solutions through PTFE or glass microfiber to remove insolubles before crystallization.
Storage and Reconstitution
Item-specific instructions (Product Data):
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General handling for solid nitroaromatic nitriles:
Store tightly closed in a dry, well-ventilated place, away from strong reducing agents and sources of ignition.
Protect from moisture to preserve integrity, particularly if long-term storage is anticipated.
For multi-month storage, consider an inert atmosphere (nitrogen/argon) in amber glass to minimize slow oxidative changes.
Reconstitution/solution preparation:
Prepare stock solutions in dry DMSO, DMF, or acetonitrile. If using protic solvents, confirm stability by test aliquots.
Filter solutions through 0.2 µm PTFE prior to sensitive applications. Store solutions refrigerated (2–8 °C) if compatible, and use within days to weeks depending on solvent and concentration.
Avoid repeated freeze–thaw of solutions; aliquot as needed.
Shelf-life considerations:
Monitor by NMR/LC–MS for any degradation during prolonged storage. Refer to the lot-specific CoA for recommended retest/expiry, if provided.
Research use note:
For research use only.
Structure and Identity
A highly electron-deficient, substituted benzonitrile featuring two nitro groups and one methyl group, arranged on a single aromatic ring.
Item-specific identifiers (Product Data):
Product Name: 3-Methyl-2,6-dinitrobenzonitrile
SKU: M943245
CAS: 948-30-1
CID: 53216176
InChIKey (as provided): 113201
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/computed identity (for context; not item specification):
Typical molecular formula (literature): C8H5N3O4
Calculated formula weight (literature): ~207.14 g/mol
Structural features (general description):
Core: Benzene ring bearing a nitrile (–C≡N) at ring position 1.
Substituents: Nitro groups (–NO2) at the 2- and 6-positions (ortho to the nitrile), and a methyl (–CH3) at the 3-position (meta to the nitrile; ortho to one nitro, meta to the other).
Electronic character: Strongly electron-withdrawing –NO2 and –C≡N groups render the ring deactivated toward electrophilic aromatic substitution and more susceptible to certain nucleophilic processes after appropriate activation.
Stereochemistry: None (achiral, planar aromatic system). The nitrile is linear; nitro groups are conjugated with the ring via the nitro N–C bond.
2D description: A six-membered aromatic ring with four substituted positions: C1 = –C≡N, C2 = –NO2, C3 = –CH3, C6 = –NO2; ring hydrogens remain at C4 and C5.
Synthetic Utility
This molecule combines three orthogonal handles: a nitrile and two nitro groups, plus a benign methyl substituent that can modulate sterics/electronics.
Nitro group reactivity (literature):
Reductions to anilines: Enables access to 2,6-diamino-3-methylbenzonitrile. Subsequent transformations include acylation, sulfonylation, or diazotization/Sandmeyer to introduce halides, CN, or other substituents.
N–O bond chemistry: Partial reductions can produce hydroxylamines or azoxy/azo derivatives, providing entry to dyes/push–pull systems after further elaboration.
Nitrile reactivity:
Hydrolysis: Stepwise to amide then acid; the 2,6-disubstitution can influence rates and selectivity.
Reduction: To primary amine (LiAlH4, catalytic hydrogenation) or to aldehyde (DIBAL-H, low temperature), furnishing benzylic aldehyde derivatives after further manipulations.
Cyclization: Formation of heterocycles (e.g., 1,2,4-oxadiazoles via amidoximes; tetrazoles via [3+2] cycloaddition with azide under activating conditions).
Strategic features:
Electronic tuning: The nitrile and nitro groups markedly decrease ring electron density, suppressing electrophilic aromatic substitution but enabling strategic SNAr upon installation of a leaving group via diazotization.
Regiochemical control: The 2,6-pattern enforces ortho-substitution, valuable for constructing sterically encumbered, conformationally constrained scaffolds.
Late-stage diversification: Orthogonal conversions allow route scouting with minimal protecting group burden.
Target Specificity
Not applicable. This product is a small-molecule organic building block and does not possess biological target specificity, epitopes, or immunochemical attributes. No antibody/biologic metadata (clone, isotype, species reactivity) apply.
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