3-Dimethylamino-3'-nitroacrylophenone , CAS No.115955-48-1

CAS: 115955-48-1 Cat. No.: D950465 Formula: C₁₁H₁₂N₂O₃ Molecular Weight: 220.228 PubChem CID: 5375681

Storage

Room temperature

Specifications

Storage

Room temperature

Names and Identifiers

Canonical Smiles

CN(C)C=CC(=O)C1=CC(=CC=C1)[N+](=O)[O-]

IUPAC Name

(E)-3-(dimethylamino)-1-(3-nitrophenyl)prop-2-en-1-one

InChIKey

CNGBILRLACOBKO-VOTSOKGWSA-N

INCHI

1S/C11H12N2O3/c1-12(2)7-6-11(14)9-4-3-5-10(8-9)13(15)16/h3-8H,1-2H3/b7-6+

Isomeric SMILES

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

PubChem CID

5375681

Molecular Weight

220.228

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: Nitroaromatic compounds Benzoyl derivatives Aryl ketones Vinylogous amides Enones Acryloyl compounds Trialkylamines Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Enamines Allylamines Organopnictogen compounds Organic zwitterions Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Nitrobenzene - Nitroaromatic compound - Benzoyl - Aryl ketone - Acryloyl-group - Enone - Alpha,beta-unsaturated ketone - Vinylogous amide - Ketone - C-nitro compound - Tertiary amine - Tertiary aliphatic amine - Organic nitro compound - Allyl-type 1,3-dipolar organic compound - Organic oxoazanium - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Allylamine - Enamine - Organic zwitterion - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic oxide - Amine - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Aromatic homomonocyclic 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: 220.220 g/mol
• XLogP3: 1.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 220.085 Da
• Monoisotopic Mass: 220.085 Da
• Topological Polar Surface Area: 66.100 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 294.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 1
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Application Protocols

No tested application protocols are provided in the Product Data for this item. As general guidance for small-molecule handling in research:

• Stock solutions for spectroscopy or screening (general):
  • Prepare 10–50 mM stocks in dry DMSO or acetonitrile; filter through 0.2 µm PTFE; store protected from light if optical measurements are planned.
  • For aqueous assays, limit final DMSO/MeCN to ≤1–2% v/v where compatible.
• Purification (general):
  • Recrystallization from ethanol/EtOAc or EtOH/H2O mixtures can afford spectroscopic-grade solids. Alternatively, silica gel chromatography using hexanes/EtOAc or DCM/MeOH.
• Spectral characterization (general suggestions):
  • 1H/13C NMR in CDCl3 or DMSO-d6; strong trans-olefinic coupling (J ~15–16 Hz) indicates E-geometry.
  • HRMS (ESI) for exact mass; IR for C=O (~1650–1685 cm−1) and N–N=O stretches; UV–Vis for ICT band.

For any critical application, request item-specific CoA and SDS, and validate conditions on a small scale before scale-up.

Biological Roles

This product is a small organic research chemical, not a biological macromolecule. No item-specific biological function data are provided.

General literature context (not specific to this SKU and not a clinical claim):

• Push–pull aryl enones with N,N-dimethylamino donors and nitro acceptors are frequently used as model systems to study intramolecular charge transfer (ICT) in biological and biomimetic environments (e.g., in micelles, lipid bilayers, or protein-like microenvironments), due to solvatochromic shifts.
• The α,β-unsaturated ketone motif is a Michael acceptor toward soft nucleophiles (e.g., cysteine thiols). In biochemical studies, related motifs are used in probe design to study thiol reactivity. Any such use must be performed strictly in research settings, with appropriate controls.

Important: No biological role, selectivity, or activity is established or claimed for this specific catalog item. For any work in biochemical systems, verify purity and characterize photophysical behavior under your exact conditions.

Buffer Applications

Not typically applicable. 3-Dimethylamino-3'-nitroacrylophenone is not a buffering agent and has no defined acid/base pair appropriate for preparing standard laboratory buffers.

Practical guidance:

• If used in aqueous experiments (e.g., spectroscopy or biochemical assays), prepare stock solutions in a compatible organic co-solvent (e.g., DMSO, acetonitrile, ethanol) and dilute into the chosen buffer while keeping final organic content as low as your system tolerates.
• Select buffer systems that do not strongly nucleophilically add to enones (avoid high concentrations of primary amines if the enone must remain intact). Common non-nucleophilic buffers like phosphate or HEPES are generally preferred for preserving Michael acceptors.

For buffer recipes, pH ranges, and ionic strengths, refer to standard buffer references; this item itself is not a buffer component.

Green Alternatives

Greenness considerations relate primarily to solvent choice and synthesis route, as item-specific stabilizers/grades are not provided.

Greener solvent choices (general guidance):

• Replace chlorinated solvents (DCM, chloroform) with 2-MeTHF, EtOAc, or MeCy (methylcyclohexane) where feasible.
• Favor protic green solvents (ethanol, isopropanol) for condensations, recrystallizations, and extractions when solubility allows.

Greener synthetic approach (literature):

• Claisen–Schmidt condensation in ethanol/water with catalytic base at room temperature or under solvent-free/grinding conditions has been reported for related chalcones, reducing solvent and energy footprints.
• Solid-supported bases (e.g., basic alumina) or reusable ionic liquids have been used to lower waste and simplify workup.

Comparison (general, not item-specific):

• Parameter | Conventional option | Greener alternative | Trade-offs
• Workup solvent | DCM | EtOAc or CPME | Slightly higher bp; easier solvent recovery
• Reaction medium | DMF/DMSO | EtOH/2-MeTHF or solvent-free | May require longer times or higher catalyst loading
• Drying agent | Na2SO4/MgSO4 | Vacuum concentration/crystallization | May need process tuning

Waste minimization:

• Use column-free crystallizations when possible (anti-solvent precipitation in alcohol/water).
• Recover and reuse higher-boiling green solvents (2-MeTHF, CPME) via simple distillation.

Note: Validate alternative solvents with small-scale trials to ensure product stability and desired selectivity.

Pharmaceutical Uses

No pharmacopeial status, excipient role, or formulation use is provided for this item in the Product Data. This product is supplied strictly for research use only.

General research/manufacturing context (non-clinical, not specific to this SKU):

• Donor–acceptor chalcone-like scaffolds can serve as reference standards for analytical method development (e.g., HPLC/UV method validation around 330–450 nm) due to well-defined chromophores.
• As synthetic intermediates, such enones can be diversified to libraries via Michael additions, reductions, and cyclizations in medicinal chemistry discovery workflows. Any downstream pharmaceutical relevance would arise from derivatives, not from this item per se.

Compliance note:

• No therapeutic claims are made. This product is not intended for human or animal use in diagnostics or therapeutic applications.
• For GMP or regulated work, request detailed CoA/CoQ and assess suitability; this catalog item is intended for research laboratories.

Physical Properties

Only the following item-specific property is provided:

• Storage conditions: Room temperature (per Product Data).

All other physico-chemical specifications for this SKU are not provided in the Product Data:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point (MP): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point (BP): Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility profile: Not specified for this item; refer to CoA/Spec Sheet.
• LogP, pKa: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general context for related push–pull chalcones (not item-specific, for guidance only):

• State/appearance: often yellow to orange solids due to extended conjugation.
• Solubility: typically soluble in moderately polar organic solvents (e.g., acetone, acetonitrile, ethyl acetate, dichloromethane, DMF, DMSO) and sparingly soluble in water.
• UV–Vis: strong π–π* absorption in the near-UV/visible (often 330–450 nm) with solvatochromism; exact maxima require measurement for this item.
• Thermal behavior: conjugated enones commonly exhibit MPs in the 100–200 °C range; exact MP for this compound must be verified on the CoA.

Quality & Grades

Item-specific quality attributes are not provided in the Product Data:

• 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 typical grades for small-molecule research reagents (general information):

• Research grade: suitable for synthesis, method development, and discovery work. Purity and residual solvents are typically controlled by CoA; exact specs vary by lot.
• Analytical/HPLC grade (when applicable): emphasizes low UV background and minimal trace impurities for spectroscopic/chromatographic applications.
• Screening libraries/photophysical standards (when applicable): may emphasize structural confirmation and batch-to-batch consistency rather than trace metal limits.

Considerations for this chemical class (conjugated enone with donor–acceptor substituents):

• UV–Vis sensitivity: trace impurities that absorb in the same region can interfere with photophysics. If optical measurements are planned, request CoA details on purity assay method (e.g., HPLC/UV, qNMR) and residual chromophores.
• Geometric isomerism: chalcone-like enones are typically E; verify E/Z ratio on CoA where relevant.
• Peroxide content: not typically a concern for solid enones (unlike ethers), but confirm any inhibitor/stabilizer information if provided.

Recommendation: consult the CoA for assay, identity (NMR/HRMS/IR), residual solvents, and any special stabilizers. If not listed online, request the Spec Sheet before critical applications.

Reaction & Applications

Manufacturer-specified applications are not provided. The following are literature/general uses for donor–acceptor chalcone-like enones; validate for your specific project.

• Michael acceptor chemistry: undergoes 1,4-addition with soft nucleophiles (thiols, amines, malonates, enolates). The nitro group on the aryl ring increases conjugation/acceptor strength; the dimethylamino group donates electron density, facilitating intramolecular charge transfer.
• Photophysics and materials: push–pull enones are used as solvatochromic dyes, NLO (nonlinear optical) chromophores, and fluorescent probes precursors. NMe2/NO2 substitution can enhance ICT transitions.
• Further functionalization:
  • Nitro reduction to anilines (e.g., catalytic hydrogenation, transfer hydrogenation, or metal/acid systems) enabling dye or ligand diversification.
  • Enone transformations: epoxidation (e.g., mCPBA), 1,2- vs 1,4-addition selectivity studies, oxa-/aza-Michael reactions, and cycloadditions.
• Synthesis platform: commonly prepared via Claisen–Schmidt condensation (base-catalyzed aldol) between a dimethylaminobenzaldehyde and a nitroacetophenone (or vice versa), followed by E-selective dehydration.
• Spectroscopic calibrant: used to study solvent effects (Kamlet–Taft parameters) due to pronounced solvatochromism.

Practical tips (general):

• Protect from strong bases/nucleophiles during storage to avoid unintended Michael additions.
• For reactions sensitive to E/Z isomerism, monitor by NMR/HPLC; most chalcone-like systems favor E under standard conditions.
• For photophysical work, purify to spectroscopic grade and verify absence of fluorescent impurities.

Reaction Conditions

No item-specific reaction data are provided. The following are literature-general conditions relevant to chalcone-like donor–acceptor enones.

Synthesis via Claisen–Schmidt (general):

• Reagents: aryl methyl ketone + aryl aldehyde (one bearing NMe2, the other bearing NO2).
• Base: KOH or NaOH (10–40% aq.) or amine bases (piperidine), catalytic amounts in ethanol or ethanol/water.
• Solvent: ethanol, 2-propanol, or 2-MeTHF; temperatures 20–60 °C; time 1–24 h.
• Workup: quench into water/ice; filtration of precipitated E-enone; recrystallize from ethanol/EtOAc.

Typical transformations of the enone (general):

• Michael addition of thiols: base-catalyzed (e.g., Et3N, DBU) in MeCN, EtOH, or DMF at rt–50 °C, 0.5–6 h; often high yields.
• Epoxidation: mCPBA (1.1–1.5 eq) in DCM at 0–25 °C, 1–3 h to give α,β-epoxyketone; monitor to avoid over-oxidation of the amine.
• Nitro reduction: H2/Pd-C (5–10%) in EtOH or EtOH/EtOAc at rt–40 °C; alternative Fe/AcOH or SnCl2/HCl systems when hydrogenation is unsuitable.
• Hydrogenation of C=C: H2/Pd-C or Raney Ni at 1–3 bar, 20–30 °C, yielding saturated aryl ketones.

Analytical monitoring:

• TLC in 20–40% EtOAc/hexanes or DCM/MeOH 98:2; UV-active with strong absorption.
• HPLC with C18, MeCN/H2O (0.1% formic acid) gradients; detect at 330–400 nm.

Note: Always optimize equivalents, temperature, and time for your specific substrates and confirm stability of the dimethylamino group under chosen conditions.

Safety & Handling

Item-specific hazard classifications are not supplied in the Product Data:

• GHS classification: Not specified for this item; refer to SDS.
• Signal word: Not specified for this item; refer to SDS.
• H-statements/Pictograms: Not specified for this item; refer to SDS.

General safety guidance for conjugated enones bearing nitro and tertiary amine substituents (literature/industry practice; not item-specific):

• Hazards: α,β-Unsaturated ketones are Michael acceptors and may cause skin/eye irritation and sensitization. Nitroaromatics can be harmful if swallowed and may cause methemoglobinemia at high exposure. Avoid inhalation of dust or aerosols.
• PPE: lab coat, safety glasses or goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to minimize vapor/aerosol exposure.
• Handling: avoid contact with skin and eyes; prevent dust generation; keep containers tightly closed. Wash thoroughly after handling.
• Incompatibilities: strong bases and nucleophiles may add to the enone; strong reducing agents may reduce the nitro group; strong oxidants may react with the tertiary amine. Avoid prolonged exposure to strong acids/bases if structural integrity must be preserved.
• First aid (overview):
  • Skin/eye contact: rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: move to fresh air; monitor for respiratory irritation; seek medical attention if symptoms occur.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
• Disposal: follow institutional and local regulations for organic hazardous waste. Always consult the product-specific SDS for authoritative information.

Solvent Selection

No item-specific solubility data are provided. The points below are general guidance for conjugated enones of this type; verify experimentally for this SKU.

• Solvent classes likely compatible (literature/general):
  • Polar aprotic: acetonitrile, acetone, DMF, DMSO, NMP — typically provide good solubility and maintain enone integrity.
  • Moderately polar: ethyl acetate, THF, 2-MeTHF, dichloromethane.
  • Protic: ethanol, isopropanol — usable for crystallization and some reactions; solubility varies.
  • Water: generally very limited solubility for aryl enones; co-solvents required.
• Dielectric/Polarity considerations (general): donor–acceptor enones can exhibit solvatochromism; more polar solvents may red-shift absorption/emission and accelerate some nucleophilic additions.
• Use scenarios:
  • Spectroscopy: HPLC-grade acetonitrile, ethanol, or DMSO to minimize background; filtration (0.2 µm) recommended.
  • Synthesis: ethanol or 2-MeTHF for condensations; DCM/EtOAc for extractions and chromatography; MeCN or toluene for catalysis.
• Comparison notes (general):
  • DCM vs 2-MeTHF: 2-MeTHF offers greener profile and broader temperature range; DCM affords fast evaporation and low UV cutoff but is chlorinated.
  • DMF/DMSO vs MeCN/EtOAc: DMF/DMSO maximize solubility; MeCN/EtOAc simplify workup and removal.

Always confirm solubility and stability for your exact lot and application.

Storage & Reconstitution

Storage conditions from Product Data:

• Store at room temperature.

Additional item-specific details (container type, atmosphere, light protection, stabilizers) are not provided:

• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for this chemical class (conjugated enone, donor–acceptor):

• Protect from prolonged exposure to strong light and moisture to maintain photophysical integrity and minimize hydrolysis/Michael background reactions.
• Keep container tightly closed under ambient dry conditions. If long-term storage is planned, consider desiccation and light-resistant packaging.

Reconstitution/solution preparation (general):

• Prepare concentrated stocks in dry, oxygen-free solvents when possible (e.g., anhydrous DMSO, acetonitrile). Filter through 0.2 µm PTFE if using for spectroscopy.
• For weigh-outs, allow bottle to equilibrate to room temperature in a desiccator to avoid moisture condensation.
• Avoid strong bases/nucleophiles in storage solutions; prepare fresh working solutions for reactive experiments.

Stability note: No item-specific stability data are provided; verify stability by LC or NMR after storage as needed. Always consult the SDS/CoA for definitive handling and storage instructions.

Structure & Identity

Item-specific identity elements provided in Product Data are limited. Where values are missing, consult the CoA/Spec Sheet and SDS.

• Product name: 3-Dimethylamino-3'-nitroacrylophenone
• CAS: 115955-48-1
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (The string provided in Product Data is not a valid InChIKey.)
• 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.

General structural description (literature-based, inferred from the name; not an item-specific specification):

• The name suggests a conjugated enone (acrylo-phenone/chalcone-type) framework: Ar–CO–CH=CH–Ar′, bearing a dimethylamino donor group on one ring (para- or meta- relative positions depend on exact structure) and a nitro acceptor group on the other ring (denoted 3′-nitro on ring Ar′).
• Key functional groups: enone (α,β-unsaturated ketone), tertiary amine [NMe2] as an electron donor, and an aromatic nitro group [–NO2] as a strong electron-withdrawing group, resulting in a push–pull (D–π–A) system.
• Typical 2D depiction (literature, general): two benzene rings connected through a propenone linker (CO–CH=CH–), with N,N-dimethylamino on one ring and nitro on the opposite ring.

Note: Exact substitution pattern and stereochemistry (E/Z about the C=C) should be confirmed from the item’s CoA/SDS or structural certificate; chalcones are typically E-configured in literature.

Synthetic Utility

Functional group ensemble and utility (general, literature-based):

• Conjugated enone (α,β-unsaturated ketone): platform for 1,4-Michael additions with thiols, amines, malonates; epoxidation to afford α,β-epoxyketones; selective 1,2- vs 1,4-addition studies with organometallics.
• Nitro group on aryl ring: handle for reduction to an aniline, enabling subsequent diazotization, coupling, or formation of heterocycles; participates in Meisenheimer chemistry when ring-activated.
• Tertiary dimethylamino group: strong electron donor for push–pull systems; can be quaternized to ammonium salts, tuning solubility and electronic properties.

Retrosynthetic logic (general):

• Disconnection across the enone yields an aryl methyl ketone and an aryl aldehyde. A Claisen–Schmidt condensation under basic conditions (NaOH, KOH, or amine base) affords the E-enone after dehydration.
• Alternative Knoevenagel-type routes may be used when activating groups are present, employing ammonium acetate or piperidine catalysts.

Derivatization pathways:

• Hydrogenation: selective C=C or nitro reduction under controlled conditions.
• Cycloaddition/cyclization: intramolecular oxa-/aza-Michael to form flavanone-like or quinoline-type scaffolds depending on substitution.
• Photophysical tuning: introduce additional donor/acceptor groups through palladium-catalyzed coupling (if halo handles are introduced after nitro-to-amino conversion).

These utilities make the scaffold valuable as a versatile intermediate and as a probe chromophore in method development.

Target Specificity

Not applicable. This product is a small organic molecule, not an antibody, enzyme, or affinity reagent. No target, epitope, clone, or species reactivity information applies.

For biochemical experiments where this compound might interact with biomolecules (e.g., thiol-Michael reactions), any “selectivity” arises from reaction conditions and context rather than inherent biological target specificity. Design appropriate controls and orthogonal assays if studying reactivity in complex matrices.

Frequently Asked Questions

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 115955-48-1, the molecular formula is C11H12N2O3, and the molecular weight is 220.228 g/mol. InChIKey CNGBILRLACOBKO-VOTSOKGWSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.