2-[(E)-2-(4-nitrophenyl)vinyl]pyridine - ≥98% , CAS No.24470-06-2

CAS: 24470-06-2 Cat. No.: E1349819 EC Number: 118-994-0 PubChem CID: 5376482

GRADE & PURITY ≥98%

Storage

Room temperature

Shipped In

Normal

Specifications

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

Canonical Smiles

C1=CC=NC(=C1)C=CC2=CC=C(C=C2)[N+](=O)[O-]

IUPAC Name

2-[(E)-2-(4-nitrophenyl)ethenyl]pyridine

InChIKey

RBWIGCZMJZUUCB-QPJJXVBHSA-N

INCHI

1S/C13H10N2O2/c16-15(17)13-8-5-11(6-9-13)4-7-12-3-1-2-10-14-12/h1-10H/b7-4+

Isomeric SMILES

C1=CC=NC(=C1)/C=C/C2=CC=C(C=C2)[N+](=O)[O-]

Alternate CAS

1023-67-2,24470-06-2

PubChem CID

5376482

NSC Number

42663

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Nitrobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Nitrobenzenes
• Alternative Parents: Styrenes Nitroaromatic compounds Pyridines and derivatives Heteroaromatic compounds Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Nitrobenzene - Nitroaromatic compound - Styrene - Pyridine - Heteroaromatic compound - C-nitro compound - Organic nitro compound - Organic oxoazanium - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organoheterocyclic compound - Azacycle - Organic oxide - Organic nitrogen compound - Organic oxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Aromatic heteromonocyclic compound
• Description: 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

Chemical and Physical Properties

• Molecular Weight: 226.230 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 226.074 Da
• Monoisotopic Mass: 226.074 Da
• Topological Polar Surface Area: 58.700 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 278.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Application Protocols

No validated bioassay protocols are provided for this item.

• For materials/analytical use (general guidance)

  • Stock preparation: dissolve at 10–50 mM in anhydrous DMSO or MeCN; vortex and sonicate if needed; filter (0.2 µm PTFE).
  • Spectroscopy: record UV–vis/fluorescence in optically transparent solvents (MeCN, EtOH, CH2Cl2) at 10–50 µM. Use matched quartz cuvettes and protect from strong light to limit E/Z isomerization.
  • Metal complex preparation: mix equimolar ligand and metal salt in MeCN/EtOH under inert atmosphere as required; stir 1–12 h; characterize by NMR, MS, elemental analysis, and, if possible, single-crystal XRD.

• If your application requires specific conditions (e.g., thin-film casting, electrochemistry), contact our technical support with your SKU for tailored recommendations.

Biological Roles

This compound is a synthetic heteroaromatic chromophore and is not a natural metabolite.

• Item-specific biological role claims: Not applicable; for research use only.

• Literature/general context

  • Acts as a neutral ligand in coordination chemistry; complexes of 2‑styrylpyridines have been explored as fluorescent probes and photosensitizers in purely chemical/photophysical studies (no medical claims).
  • The para‑nitro group serves as an electron sink, enabling intramolecular charge transfer; this is relevant to sensing and materials, not to intrinsic biochemistry.
  • No established roles in metabolic pathways or signaling networks are reported for this small molecule itself.

• Practical lab note

  • For any bioassay use, dissolve first in high‑purity DMSO or ethanol, then dilute into buffered media with attention to final cosolvent content; verify solubility and absence of aggregation by UV–vis.

Buffer Applications

Not a buffering reagent. It lacks acid/base pairs with appropriate aqueous solubility to act as a pH buffer.

• If used in aqueous assays, prepare solutions in DMSO or ethanol and dilute into pre-made biological buffers (e.g., PBS, HEPES) at low cosolvent fractions (<1–2%) to avoid precipitation.
• For protonation studies of the pyridine nitrogen, use strong acid buffers to generate the corresponding pyridinium salt for spectroscopic characterization; this is an analytical approach, not a buffering application.

Green Alternatives

• Solvent considerations (literature-based)

  • Prefer greener dipolar aprotics when possible: replace DMF/NMP with acetonitrile, propylene carbonate, or Cyrene where compatible.
  • Replace chlorinated solvents with ethyl acetate, 2‑methyltetrahydrofuran (2‑MeTHF), or toluene for workups and chromatography when resolution allows.

• Greener synthesis/processing angles

  • Nitro reductions: use catalytic transfer hydrogenation (e.g., Pd/C with formate) or Fe/acid aqueous systems rather than stoichiometric tin salts to reduce waste toxicity.
  • Avoid DMF/NMP in couplings; if metal complexation is the goal, ethanol or water–ethanol mixtures under mild acid/base can sometimes substitute.
  • Energy: conduct photophysical measurements and crystallizations at ambient temperature to minimize heating demands; employ LED sources for photoinduced studies.

• Tradeoffs

  • 2‑MeTHF and CPME are safer ethers, but may solubilize conjugated aromatics less effectively than THF/DCM.
  • Acetonitrile has good EHS profile vs DMF/NMP but is more volatile and flammable; ensure ventilation.

• Mini comparison (literature)

  • DMF/NMP: excellent solvency; reproductive toxicity concerns; difficult removal.
  • MeCN: greener among dipolar aprotics; good optical window; easy removal.
  • 2‑MeTHF: biorenewable; peroxide risk (monitor), hydrophobic; good for extractions.
  • Ethyl acetate: low toxicity, biodegradable; mid‑polarity; limited high‑temp range.

Pharmaceutical Uses

No pharmacopeial or excipient roles are established for this compound.

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

• Literature/general context

  • As a conjugated heteroaromatic, it may serve as a research intermediate or ligand in discovery chemistry and materials evaluation.
  • Not used as an approved excipient; not intended for human or veterinary use. For research use only (per Product Data).

• Formulation notes for research

  • Stock solutions can be prepared in DMSO or ethanol; filter through 0.2 µm PTFE before use in analytical or materials testing to remove particulates.
  • For solid-state studies (films/coatings), consider spin-coating from chlorobenzene, toluene, or mixed solvent systems to tailor morphology.

Physical Properties

• Item-specific (from Product Data)

  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed (general guidance; not product specifications)

  • Physical state: typically a yellow to orange crystalline solid for nitrostyryl aromatics (literature, class behavior).
  • Molecular properties (from literature structure C13H10N2O2): MW ~226.23 g/mol; heavy atom count 17.
  • Solubility: sparingly soluble in water; soluble in polar aprotic and aromatic organic solvents such as DMSO, DMF, NMP, acetonitrile, dichloromethane, chloroform, THF, toluene, and moderately in ethanol/isopropanol (literature trends for nitrostyryl pyridines).
  • Acid–base: pyridine nitrogen pKaH (conjugate acid) typically ~5.0–5.5 (literature, pyridines); neutral at basic/neutral pH, protonated in strong acids.
  • Lipophilicity: logP for similar nitrostilbenes typically in the 2.0–3.0 range (literature class estimate).
  • UV–vis: extended π‑conjugation gives strong absorption in near‑UV/visible (approx. 320–420 nm), with solvatochromism depending on solvent polarity (literature for donor–acceptor stilbenes).
  • Melting point / boiling point / density / refractive index: Not established here; consult primary literature or the CoA for item-specific values.

Quality & Grades

• Item-specific

  • 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 for this compound class

  • Typical offerings for heteroaromatic building blocks include: research grade (assay reported by HPLC/GC/NMR), and sometimes spectroscopy grade (controlled UV background). In absence of a stated grade, treat as research grade suitable for general synthetic and materials R&D.
  • Purity reporting: For conjugated stilbene-like compounds, HPLC area% and 1H NMR integration are common. Residual solvents and water (KF) may be reported on the CoA; check also for E/Z ratio if relevant to your application.
  • Isomeric integrity: This product specifies the E (trans) configuration by name; vendors often control and report E/Z ratio. If your application is photophysical or ligand-related, request the CoA for E-content and any photoisomerization precautions.
  • Trace metal/UV cutoff specs: Not specified for this item; refer to CoA/Spec Sheet.
  • Practical note: If chromatographic purity is critical (e.g., for photophysics), pre-use recrystallization or flash purification under subdued light may improve baseline.

Reaction & Applications

• Typical applications (literature; not item-specific claims)

  • Conjugated D–π–A chromophore: the electron-donating pyridine (donor when deprotonated/metal-bound) and electron-withdrawing p‑nitrophenyl (acceptor) confer strong intramolecular charge transfer, used in photophysical studies, nonlinear optics, and as reporter ligands in coordination complexes.
  • Metal coordination: the 2‑pyridyl nitrogen binds transition metals (e.g., Zn(II), Ru(II), Ir(III)), enabling emissive complexes and supramolecular assemblies.
  • Reactive handle chemistry:
    • Nitro reduction to para‑amino derivatives (via catalytic hydrogenation or transfer hydrogenation) enabling further coupling, diazotization, or ring closure.
    • Hydrogenation of the C=C to the ethyl linker, modulating conjugation and optical properties.
    • Electrophilic/nucleophilic aromatic substitution on the nitro-activated phenyl (though para position is occupied).
    • Quaternization of the pyridine nitrogen to pyridinium salts, useful in ionic materials and as phase-transfer motifs.
  • Material science: component in charge-transfer polymers and surface-bound sensors; the E‑isomer offers extended conjugation for thin-film studies.

• Practical tips

  • Maintain subdued light during extended manipulations to minimize E↔Z photoisomerization common to stilbene analogs.
  • For metalation, dry and degas solvents (MeCN, EtOH, CH2Cl2) and consider base (NEt3) to prevent adventitious protonation.
  • For reductions, choose chemoselectivity: Fe/AcOH, SnCl2, or Pd/C–H2 can target the nitro and/or C=C depending on conditions.
  • Purification often benefits from silica deactivation (1–2% triethylamine) to reduce tailing of basic heteroaromatics.

Reaction Conditions

General, literature-based guidance for this scaffold (not product specifications):

• Dissolution and handling

  • Prepare 10–100 mM stock in anhydrous DMSO, DMF, or acetonitrile. Filter through PTFE (0.2 µm) for photophysical or analytical experiments.

• Nitro reduction

  • Catalytic hydrogenation: 5–10 wt% Pd/C (5–10 mol% cat. relative to substrate), H2 1–3 atm, EtOH or EtOAc, 20–40 °C, 1–6 h; monitor by TLC/LC–MS. Selective for –NO2 at mild pressure/temperature.
  • Transfer hydrogenation: Pd/C (5–10 wt%), ammonium formate or cyclohexene as H‑donor, MeOH/EtOH, 25–50 °C.
  • Iron/acid: Fe powder (3–6 equiv), AcOH/H2O (or NH4Cl/H2O/EtOH), 60–100 °C, 2–6 h; tolerant of C=C.

• C=C transformations

  • Hydrogenation to saturated ethyl linker: H2 5–20 atm, Pd/C or Raney Ni, MeOH/EtOH, 25–50 °C, 2–12 h.
  • Epoxidation: m‑CPBA (1.1–1.5 equiv), CH2Cl2, 0 °C→rt, 1–3 h; subsequent ring opening diversifies the linker.

• Coordination chemistry

  • Complexation with Zn(II), Ru(II), etc.: dissolve ligand and metal salt (e.g., Zn(ClO4)2·6H2O) in MeCN/EtOH, add base (NEt3) if needed, stir at rt–reflux for 1–12 h; isolate complexes by precipitation or chromatography.

• Photophysics

  • UV–vis in MeCN or DCM: expect π–π* bands in near‑UV/visible; record spectra promptly to minimize photoisomerization; use amber glassware where possible.

Reported yields and exact constants vary by substrate and setup; consult primary literature and adjust based on scale and equipment.

Safety & Handling

• Item-specific (from Product Data)

  • Storage Conditions: Room temperature
  • Shipped In: Normal
  • GHS Classification, Signal Word, H-statements, Pictograms: Not specified for this item; refer to SDS.

• General safety information (literature/class-based; defer to SDS for definitive guidance)

  • Likely hazards: Aromatic nitro/styryl compounds are commonly classified as irritants to skin, eyes, and respiratory tract; avoid dust formation and inhalation. Handle as potentially harmful if swallowed.
  • PPE: laboratory coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to prevent inhalation of dust or solvent vapors during handling and dissolution.
  • Incompatibilities: Strong reducing agents (may reduce nitro group), strong oxidizers, strong acids/bases that may lead to degradation or salt formation (protonation of pyridine). Avoid prolonged exposure to light and elevated temperatures to minimize E/Z isomerization or photodegradation typical of stilbene-like systems.
  • First aid (overview): in case of skin contact, wash with soap and water; eye contact, rinse cautiously with water for several minutes and seek medical attention; inhalation, move to fresh air; ingestion, rinse mouth and seek medical advice. Provide SDS to medical personnel.
  • Fire safety: treat as combustible organic solid. Use CO2, dry chemical, or foam. Thermal decomposition may produce nitrogen oxides and other irritant fumes.
  • Waste: collect organic solids/solutions in halogenated or non‑halogenated waste streams per your institutional protocol; do not discharge to drains.
  • Always consult the product’s SDS for authoritative hazard classification and response measures.

Solvent Selection

• Polarity and miscibility (literature expectations)

  • Class: moderately lipophilic, conjugated aromatic nitro compound with a basic pyridine nitrogen.
  • Water: expected very low solubility.
  • Good solvents: DMSO, DMF, NMP, acetonitrile, dichloromethane, chloroform, THF, toluene, ethyl acetate. Alcohols (MeOH/EtOH) offer moderate solubility.
  • Protonation: in strong acids, the pyridine can be protonated to give a pyridinium salt, improving solubility in polar protic media, but altering electronic properties.

• Choosing among common options

  • DMSO/DMF: best for concentrated stock solutions (e.g., 10–100 mM) used in screenings or for metal–ligand complexation studies.
  • Acetonitrile and THF: suitable for photophysics and reactions where low viscosity and good optical transparency are needed.
  • Aromatic solvents (toluene): useful for high‑temperature reactions and to suppress ionization; good for radical or pericyclic chemistry.
  • Halogenated solvents (DCM/CHCl3): efficient dissolution for chromatography and spectroscopy; consider safety and chlorinated waste.

• Small comparison (literature-based)

  • DMSO: maximum solvency, high boiling; harder to remove.
  • MeCN: good balance of polarity/volatility; lower solvency than DMSO.
  • THF: good solvency, ethers can form peroxides—monitor accordingly.
  • Toluene: non-polar environment for mechanistic probes; higher bp for thermal steps.

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

Storage & Reconstitution

• Item-specific (from Product Data)

  • Storage Conditions: Room temperature
  • Shipped In: Normal

• General guidance for this compound class

  • Container: store in a tightly sealed amber glass bottle to minimize light exposure and prevent E/Z photoisomerization of the styryl unit.
  • Atmosphere: keep dry; include a desiccant in secondary packaging to limit moisture uptake and potential protonation of the pyridine nitrogen in acidic environments.
  • Shelf life: under dry, dark, room-temperature conditions, conjugated aromatics are typically stable for ≥12 months; verify by 1H NMR/HPLC prior to critical experiments.

• Reconstitution/solution preparation

  • Prepare concentrated stocks in anhydrous DMSO, DMF, or acetonitrile (e.g., 10–100 mM). For less polar uses, dissolve in CH2Cl2 or toluene.
  • Filter solutions through 0.2 µm PTFE before spectroscopic or device applications.
  • Avoid repeated freeze–thaw of DMSO stocks; aliquot if long-term storage is needed. Store solutions at 2–8 °C, protected from light, and equilibrate to room temperature before use.

• Specifications such as water content, stabilizers, or inhibitor levels: Not specified for this item; refer to CoA/Spec Sheet.

Structure & Identity

Briefly: 2-[(E)-2-(4-nitrophenyl)vinyl]pyridine is an E-stilbene-type, donor–acceptor heteroaromatic composed of a 2-pyridyl ring conjugated through a trans-ethenyl linker to a para‑nitrophenyl ring.

• Item-specific (from Product Data)

  • Product Name: 2-[(E)-2-(4-nitrophenyl)vinyl]pyridine
  • CAS: 24470-06-2
  • CID: 5376482
  • InChIKey: 312342
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/derived identifiers and features (general information, not item-specific specs)

  • Common synonyms: 2-(4-nitrostyryl)pyridine; trans-2-(4-nitrostyryl)pyridine
  • Structural features: one pyridine ring (N-heteroaromatic), one para‑nitro-substituted phenyl ring, connected by a trans‑CH=CH (E‑vinylene) bridge.
  • Functional groups: aromatic nitro (–NO2), pyridine ring nitrogen (basic heteroatom), conjugated C=C (styryl) linker.
  • 2D description in words: starting from the pyridine nitrogen and moving clockwise, the 2‑position of the ring bears a trans‑ethenyl substituent whose distal carbon is bonded to a 4‑nitrophenyl ring (nitro group para to the vinyl linkage).
  • Stereochemistry: defined E (trans) geometry at the C=C bond.
  • Empirical formula and exact mass (literature): commonly reported formula C13H10N2O2; exact mass ~226.07 Da; average molecular weight ~226.23 g/mol (literature).

Synthetic Utility

• Functional handles and reactivity (literature)

  • Nitro group: reducible to an aniline, enabling diazotization, Sandmeyer-type diversification, or formation of push–pull dyes via further coupling.
  • Styryl C=C: subject to hydrogenation, hydroboration–oxidation, epoxidation (e.g., m‑CPBA), or photocycloadditions; E‑isomer offers defined geometry for stereocontrol.
  • Pyridine nitrogen: quaternization (alkylation) to pyridinium salts for phase-transfer or ionic materials; N‑oxide formation for directing-group chemistry; metal‑ligand coordination.

• Retrosynthetic/planning value

  • The scaffold situates donor (pyridyl) and acceptor (p‑nitro) ends across a π‑bridge, making it a modular node in designing charge-transfer chromophores; tuning either ring or bridge modulates optical/electronic properties.
  • Downstream transformations allow orthogonal edits: reduce nitro without saturating the C=C by choosing chemoselective conditions; or saturate C=C while preserving nitro with controlled hydrogenation pressures/catalysts.

• Representative transformations (reported generally)

  • Pd/C, H2 (1–3 atm, EtOH/EtOAc): selective nitro reduction to p‑amino derivative at rt–40 °C.
  • Fe/AcOH/H2O (reflux): nitro to amine with minimal over-reduction of C=C.
  • H2 (≥5 atm), Pd/C or Raney Ni: full hydrogenation to the ethyl-linked aniline/pyridine product.
  • Alkyl iodides/MeOTf in MeCN: quaternization to pyridinium salts at 0–25 °C.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological macromolecule or affinity reagent.

• No antigen/epitope/clone/isotype information applies.
• For metal-binding specificity in coordination chemistry, selectivity depends on metal salt, counterion, and solvent; see Reaction Conditions for general complexation guidance.