2-Ethyl-4-nitrobenzonitrile - ≥95% , CAS No.1312008-58-4

CAS: 1312008-58-4 Cat. No.: E1037469 Formula: C₉H₈N₂O₂ Peso molecolare: 176.170 Numero EC: 980-897-1

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: CCC1=C(C=CC(=C1)[N+](=O)[O-])C#N
• IUPAC Name: 2-ethyl-4-nitrobenzonitrile
• InChIKey: QPCCFSXLLQTEDD-UHFFFAOYSA-N
• INCHI: 1S/C9H8N2O2/c1-2-7-5-9(11(12)13)4-3-8(7)6-10/h3-5H,2H2,1H3
• Peso molecolare: 176.170

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Nitrobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Nitrobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Nitrobenzenes
• Alternative Parents: Nitroaromatic compounds Benzonitriles Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Nitriles Organic salts Organic oxides Hydrocarbon derivatives Organic cations
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Nitrobenzene - Benzonitrile - Nitroaromatic compound - C-nitro compound - Organic nitro compound - Carbonitrile - Nitrile - Organic oxoazanium - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organonitrogen compound - Organic nitrogen compound - Organic oxygen compound - Cyanide - Organic salt - Organic oxide - Hydrocarbon derivative - Organic cation - Aromatic homomonocyclic compound
• Descrizione: 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

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

Proprietà chimiche e fisiche

• Peso molecolare: 176.170 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 176.059 Da
• Monoisotopic Mass: 176.059 Da
• Topological Polar Surface Area: 69.600 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 238.000
• 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

Application Protocols

Not applicable. No validated bioassay/diagnostic protocols (e.g., WB, IHC, FC) are associated with this small-molecule reagent. For synthetic use, follow standard organic laboratory procedures and consult literature methods under “Reaction Conditions.”

Biological Roles

• Item-specific biological information: Not specified for this item; refer to CoA/Spec Sheet.

• General context (for substituted benzonitriles; no clinical/therapeutic claims)

  • 2-Ethyl-4-nitrobenzonitrile is a synthetic organic intermediate without known intrinsic biological role in natural systems.
  • Nitroaromatics and benzonitriles may interact with biological targets in discovery screening; however, any activities are context-specific to derivatives and not generalizable to this compound.
  • In biochemical workflows, compounds of this class may serve as reference substrates for testing reduction/hydration catalysts (e.g., nitroreductases, nitrile hydratases) in vitro.

• Environmental/biotransformation notes (literature)

  • Nitro groups can undergo microbial reduction to anilines; nitriles can be enzymatically hydrated to amides/acids by specialized microbes/enzymes. Such pathways are used in biocatalysis research rather than indicating any physiological role.

Buffer Applications

This compound is a neutral organic building block and is not used as a buffer component. It does not provide useful acid/base equilibria in the biological pH range.

• For aqueous work, choose an appropriate buffer system (e.g., phosphate, HEPES, acetate) separate from the use of this reagent.
• If dissolution in buffer is required for assays, employ a water-miscible co-solvent (e.g., DMSO) and keep final organic content low to avoid perturbing the buffer system.

Green Alternatives

• Greener solvent choices (general guidance)

  • Replace DMF/DMAc/NMP with 2-MeTHF, CPME, EtOAc, or propylene carbonate where catalyst/substrate compatibility permits.
  • Prefer ethanol or isopropanol as hydrogenation solvents over chlorinated media when feasible.

• Greener transformations (literature)

  • Nitrile hydration: Use water-tolerant catalysts (e.g., Ru, Pd, or metal–organic frameworks) or biocatalytic nitrile hydratases to form amides under milder, aqueous conditions.
  • Nitro reduction: Employ catalytic hydrogenation with H2 over Pd/C, Raney Ni, or supported non-precious metals under low pressure; avoid stoichiometric SnCl2/Fe to minimize inorganic waste.
  • Side-chain oxidation: Use aerobic oxidation (O2/air) with cobalt/manganese catalysts instead of KMnO4/Cr(VI) oxidants.

• Trade-offs

  • Polar green solvents may alter solubility and reaction rates; optimization of temperature and catalyst loading is often required.
  • Catalytic aqueous methods can challenge isolation; consider in situ extraction or solvent switching.

Comparison snapshot (general):

• DMF → 2-MeTHF: Lower toxicity and easier removal, but potentially reduced solubility.
• DCM → EtOAc: Greener and biodegradable, with higher boiling point that may aid certain reductions.
• SnCl2 reduction → H2/Pd: Dramatically less waste, requires pressure equipment and selectivity control (to avoid over-reduction of –CN).

Pharmaceutical Uses

• Item-specific pharmacopeial/excipient status: Not specified for this item; refer to CoA/Spec Sheet.

• General context (no therapeutic claims)

  • 2-Ethyl-4-nitrobenzonitrile may serve as a synthetic intermediate in pharmaceutical process development or medicinal chemistry campaigns due to its convertible –CN and –NO2 groups.
  • Potential roles include building block for API precursors after functional-group interconversions (e.g., aniline via nitro reduction, carboxamide/acid via nitrile hydrolysis).
  • Not used as an excipient. Any GMP relevance would require specification, validation of impurities, and alignment with ICH guidelines; such controls are batch- and process-dependent.

Physical Properties

• Item-specific specifications (this product)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Density, refractive index, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general expectations for this class of compounds (non-binding guidance)

  • Phase at ambient conditions: Many nitrobenzonitriles are crystalline solids; ortho-alkyl substitution can lower melting point, so low-melting solid or high-boiling liquid is possible (literature trend, not a spec).
  • Solubility (qualitative): Typically sparingly soluble in water; soluble in polar aprotic organic solvents (e.g., acetonitrile, DMF, DMSO) and in moderately polar organics (ethyl acetate, THF), and often in chlorinated and aromatic solvents (DCM, toluene) (literature trends).
  • Polarity: Moderate polarity due to –CN and –NO2; logP expected in the low-to-moderate range for substituted benzonitriles (literature expectation).
  • Acid/base behavior: No Brønsted acidity/basicity; nitrile nitrogen is weakly basic only under strong conditions. Nitro group is non-basic.
  • Thermal behavior: Aromatic nitriles and nitroarenes generally have good thermal stability below decomposition; avoid strong heat to prevent decomposition (literature guidance).

Note: Exact numerical BP/MP/density for this SKU are not specified; consult the CoA/Spec Sheet for authoritative values.

Quality and Grades

• Item-specific 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.

• Guidance on grades (general, for context)

  • Research-grade or analytical-grade substituted benzonitriles are typically suitable for synthesis and method development. HPLC-grade relevance is minimal for a solid reagent but can matter if used as a chromatographic standard.
  • If sold as “high-purity” or “≥98%,” typical implications include tight control of regioisomers and starting-material residues; verify by NMR/GC/LC as needed in regulated environments.
  • Low UV absorbance requirements (for solvent grades) are not applicable here; for solid reagents, attention focuses on assay purity, isomeric purity, and residual solvents.

• Documentation

  • For assay method, residual solvent profile, and impurity limits, consult the CoA/Spec Sheet. Batch-specific parameters supersede general statements.

Reaction and Applications

This molecule is a versatile aromatic building block combining a nitrile and a nitro group with an ortho ethyl substituent. Typical research uses include multi-step synthesis toward heterocycles, anilines, carboxamides/acids, and further elaborated arenes.

• Transformations of the nitrile (literature)

  • Hydrolysis: Controlled conversion to the primary amide (partial) or carboxylic acid (complete) under acidic or basic conditions. Dehydrative/one-pot variants allow tuning of chemoselectivity in the presence of nitro.
  • Reduction to amine: Catalytic hydrogenation (Pd/C, Raney Ni) or borane/hydride systems to yield the benzylamine analogue; take care to chemoselectively reduce –CN vs –NO2.
  • Pinner reaction: Alcohol/HCl converts –CN to imidate esters, enabling subsequent amidine/amide synthesis.
  • Nucleophilic additions: Under strong nucleophiles (e.g., Grignard, organolithium), the nitrile can furnish imines/ketimines followed by hydrolysis to ketones (after careful protection of –NO2).

• Transformations of the nitro group (literature)

  • Reduction to aniline: H2 (Pd/C), Fe/HCl, SnCl2/HCl, or transfer hydrogenation; the resulting aniline enables diazotization/Sandmeyer or coupling to form C–N/C–O/C–S bonds.
  • N–O bond manipulations: Chemoselective partial reductions or conversion to nitroso for further elaboration.

• Benzylic/side-chain chemistry (literature)

  • Oxidation of the ethyl side chain to the corresponding benzoic acid (KMnO4, Co/Mn-catalyzed aerobic) can be feasible on deactivated rings.
  • Radical halogenation at the benzylic position provides handles for subsequent substitution.

• Application contexts

  • Intermediate toward agrochemical/pharma discovery scaffolds (library synthesis; no clinical claims).
  • Precursor for isosteric replacements where –CN serves as a carboxylate or carbonyl bioisostere in SAR studies.

Reaction Conditions

The following are literature-style general conditions for functional groups present; they are not specifications for this SKU.

• Nitro reduction to aniline (literature)

  • H2, Pd/C (5–10 wt%), EtOH or EtOAc, rt–50 °C, 1–6 h; monitor for over-reduction of –CN. Alternatively, Fe/AcOH or SnCl2/HCl at reflux affords anilines but generates inorganic waste.
  • Transfer hydrogenation: ammonium formate or hydrazine with Pd/C in EtOH, 25–60 °C.

• Nitrile hydrolysis/hydration (literature)

  • To primary amide: H2O with catalytic acids/bases or metal catalysts (e.g., Cu, Ru) at 60–120 °C; or enzymatic nitrile hydratases in aqueous buffer (pH 7–8) at ambient–40 °C.
  • To carboxylic acid: Aqueous H2SO4 or NaOH, 80–120 °C; times 2–16 h depending on solvent and substitution.

• Nitrile reduction to amine (literature)

  • H2, Raney Ni or Pd/C in EtOH/MeOH, 25–80 °C; or BH3·THF at 0–25 °C followed by quench. Selectivity control required to avoid reducing –NO2; consider protecting –NO2 or stepwise sequences.

• Benzylic functionalization (literature)

  • Radical bromination: NBS, AIBN, CCl4 or greener solvents, reflux; follow with SN2 to install heteroatoms.
  • Side-chain oxidation: Co/Mn/Br-catalyzed aerobic oxidation in acetic acid or neat, 80–120 °C; or KMnO4 under controlled conditions.

• Workup and purification

  • Typical extractions with EtOAc or DCM; wash acidic/basic depending on route. Purify by column chromatography on silica; crystallization possible depending on derivative.

Note: Reaction times, temperatures, and yields vary with substitution pattern and scale; conduct small-scale optimization.

Safety and Handling

• Regulatory/GHS for this item

  • Signal Word, H-Statements, GHS Classification, Pictograms: Not specified for this item; refer to the SDS for authoritative safety information.

• General hazards of nitroaromatic nitriles (literature-based, not product-specific classification)

  • May cause irritation to skin, eyes, and respiratory tract upon contact or inhalation.
  • Nitroaromatics can exhibit methemoglobin-forming potential upon significant exposure; handle to minimize inhalation/ingestion (general toxicological consideration).
  • Combustible organic solid/liquid; can burn if ignited.

• Handling and PPE

  • Use in a chemical fume hood. Wear lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid inhalation of dust/vapor and contact with skin/eyes.
  • Prevent dust generation; use closed transfers when feasible.

• Incompatibilities and reactivity (general)

  • Strong reducing agents may reduce the nitro group; strong oxidizers may react exothermically with organics.
  • Avoid strong acids/bases if undesired hydrolysis or side reactions of the nitrile would be problematic.

• First-aid overview (general)

  • Skin/eyes: Rinse with water for at least 15 minutes; remove contaminated clothing. Seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Always defer to the product SDS for definitive hazard classification, exposure limits, and spill/firefighting procedures.

Solvent Selection

• Solubility/miscibility (general expectations)

  • Poorly soluble in water; readily soluble in polar aprotic solvents (DMF, DMSO, NMP, acetonitrile), moderately soluble in esters/ethers (EtOAc, THF), and typically soluble in chlorinated or aromatic solvents (DCM, toluene) — literature trends for nitrobenzonitriles.

• Polarity and dielectric considerations

  • The presence of –CN and –NO2 confers moderate polarity and significant dipole moment; polar aprotic solvents enhance rates in nucleophilic or polar mechanisms involving these groups.

• Choosing a medium

  • For nitrile hydrolysis or hydration: aqueous mineral acid/base, or homogeneous catalysts in polar aprotic co-solvents.
  • For nitro reduction: alcoholic solvents (EtOH, iPrOH), ethyl acetate, or THF under hydrogenation; avoid strongly basic media if undesired nitrile reactions are a concern.
  • For metal-catalyzed coupling on the ring (if applicable after functional-group interconversion): high-boiling polar aprotics (DMF, DMAc, NMP) or greener ethers (2-MeTHF) depending on catalyst system.

• Comparison notes (general)

  • DMSO/DMF maximize solubility but complicate workup; EtOAc/2-MeTHF balance solubility and ease of removal; toluene provides thermal headroom for elevated temperatures.

Storage and Reconstitution

• Item-specific storage/shipping

  • Storage Conditions: Room temperature (per Product Data). Keep container tightly closed in a dry, well-ventilated place.
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General guidance for this class of compounds

  • Protect from moisture and prolonged exposure to light and heat. Although aromatic nitriles/nitroarenes are typically stable, store under ambient inert atmosphere (e.g., nitrogen) if long-term stability is critical.
  • Avoid contact with strong oxidizers or reducing agents during storage.
  • If hygroscopicity or caking is observed (rare for this class), gently warm and triturate under dry conditions before use.

• Reconstitution/dissolution

  • Readily dissolved for use in dry organic solvents such as DMSO, DMF, acetonitrile, ethyl acetate, THF, toluene, or DCM depending on downstream chemistry (select solvent consistent with your reaction and safety requirements).
  • For assay stock solutions, prepare concentrated solutions in anhydrous DMSO or acetonitrile; store aliquots at 2–8 °C or −20 °C if needed to minimize freeze–thaw cycles (general practice). Verify stability experimentally for your application.

Research Use Note: For research use only.

Structure and Identity

Brief description: 2-Ethyl-4-nitrobenzonitrile is a substituted benzonitrile bearing an ortho ethyl group and a para nitro group relative to the cyano functionality, offering two orthogonal handles (–CN and –NO2) for divergent synthesis.

• Item-specific (Product Data)

  • CAS: 1312008-58-4
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • 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.

• Computed/Literature (structure-based, non-spec)

  • Approximate empirical formula (from name-based structural accounting): C9H8N2O2 (literature/calculated)
  • Approximate formula weight: ~176.17 g/mol (literature/calculated)
  • Functional groups: aromatic nitrile (–C≡N), nitro (–NO2), alkyl (ethyl) substituent on benzene.
  • 2D structural description: A benzene ring bearing three substituents: a cyano (–C≡N) at the reference position, an ethyl (–CH2CH3) ortho (2-position) to the nitrile, and a nitro (–NO2) para (4-position) to the nitrile. The ring is deactivated toward electrophilic substitution by the –CN and –NO2 groups; the ethyl group is weakly activating but overridden in directing power by the strong deactivators.

• Stereochemistry: None; molecule is achiral and contains no stereocenters or geometric isomerism.

Synthetic Utility

• Orthogonal handles for divergence

  • Nitrile (–C≡N): convertible to amide, acid, amine, ketone (via organometallic addition), imidate (Pinner), amidine/ester derivatives; participates in metal-catalyzed C–CN bond activation in specialized systems.
  • Nitro (–NO2): precursor to aniline (reduction), nitroso (partial reduction), or leaving group equivalents in nucleophilic aromatic substitution after conversion; enables diazotization chemistry post-reduction.

• Regiochemical features

  • The nitrile and nitro groups are both strong meta directors; their presence modulates further electrophilic/aromatic functionalization and can stabilize Meisenheimer intermediates in SNAr after appropriate activation.
  • The ortho ethyl substituent enables benzylic functionalization (radical halogenation, oxidation to carboxyl group) opening additional pathways.

• Retrosynthetic value

  • Serves as a branch point for two-directional diversification: maintain one handle while transforming the other, then interconvert.
  • Useful in library synthesis for SAR, enabling rapid access to anilide, aniline, or benzoic-acid series from a single starting scaffold.

• Practical notes

  • Protecting-group strategies may be required to achieve chemoselectivity between –CN and –NO2 during reductions or nucleophilic additions.
  • Catalytic hydrogenation conditions can be tuned (pressure, catalyst) to favor nitro vs nitrile reduction selectively.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and is not an antibody, enzyme, or biological probe with defined target specificity. No antigen/epitope, species reactivity, clone, or isotype information applies.