Ethyl 3-(3-nitrophenyl)prop-2-ynoate - ≥95% , CAS No.35283-09-1

CAS: 35283-09-1 Cat. No.: E1007993 Formula: C₁₁H₉NO₄ Peso molecolare: 219.190 Numero EC: 869-961-9

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: CCOC(=O)C#CC1=CC(=CC=C1)[N+](=O)[O-]
• IUPAC Name: ethyl 3-(3-nitrophenyl)prop-2-ynoate
• InChIKey: BDBUSSJVLJJIDV-UHFFFAOYSA-N
• INCHI: 1S/C11H9NO4/c1-2-16-11(13)7-6-9-4-3-5-10(8-9)12(14)15/h3-5,8H,2H2,1H3
• Peso molecolare: 219.190

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 Fatty acid esters Ynoate esters Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Monocarboxylic acids and derivatives Organonitrogen compounds Organic salts Organic oxides Hydrocarbon derivatives Carbonyl compounds Organic cations
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Nitrobenzene - Nitroaromatic compound - Fatty acid ester - Fatty acyl - Ynoate ester - Alpha,beta-unsaturated carboxylic ester - Organic nitro compound - Carboxylic acid ester - C-nitro compound - Carboxylic acid derivative - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Monocarboxylic acid or derivatives - Organic oxoazanium - Hydrocarbon derivative - Organic oxide - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organic salt - 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: 219.190 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 219.053 Da
• Monoisotopic Mass: 219.053 Da
• Topological Polar Surface Area: 72.100 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 333.000
• 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 standardized biological assay protocols (WB, IHC, IF, FC) are associated with this small‑molecule reagent.

For synthetic applications, see Reaction Conditions and Synthetic Utility for general procedural guidance. Item-specific protocols: Not specified for this item; refer to CoA/Spec Sheet.

Biological Roles

This product is intended for research and synthetic chemistry. No inherent biological role is assigned.

General considerations (literature/general):

• Nitroaromatic esters are not endogenous metabolites and typically act as hydrophobic electrophilic building blocks in chemical biology probe synthesis, not as biologically functional molecules themselves.
• The electron‑poor alkyne can be used to construct heterocycles and scaffolds that may later be evaluated in biochemical assays; however, any such uses are downstream of synthesis and outside the scope of this product listing.

Research Use Note (from Product Data): For research use only.

Buffer Applications

Not typically applicable. This is a nonionic organic reagent rather than a buffering salt. It is not used to prepare biological buffers or to control pH.

For practical work, choose an appropriate organic solvent system as outlined under Solvent Selection; aqueous buffer systems are generally irrelevant unless performing biphasic or emulsion catalysis.

Green Alternatives

Greener practice considerations relate primarily to solvent and energy use; the reagent itself is a specialty building block.

• Prefer greener solvents where compatible (literature/general):
  • Replace DCM/CHCl3 with EtOAc, MeCN, 2‑MeTHF, or CPME when solubility and selectivity permit.
  • Use ethanol/isopropanol for reductions or catalytic hydrogenations when feasible.
• Reaction engineering:
  • Flow chemistry can improve heat/mass transfer for exothermic additions and reduce solvent volumes.
  • Photoredox catalysis under visible light can operate at ambient temperature, reducing energy input.

Illustrative solvent comparison (general; not item-specific):

• DCM vs 2‑MeTHF: similar solvating power for many transformations; 2‑MeTHF is bio‑based, higher boiling, and allows water separation—useful for workups.
• Toluene vs CPME: CPME offers azeotrope‑free drying and enhanced safety profile with comparable apolarity.

Waste minimization:

• Choose catalysts enabling high atom economy (e.g., hydrofunctionalizations over stoichiometric reagents).
• Employ telescoped sequences (e.g., conjugate addition → reduction) to avoid intermediate isolations.

Pharmaceutical Uses

Not typically applicable as a direct excipient or formulation aid. This compound is a synthetic intermediate/building block.

General context (literature/general):

• Alkynyl esters are sometimes employed in medicinal chemistry routes to assemble aromatic scaffolds or heterocycles. Any presence in a pharmaceutical context would be as a process intermediate, not as an API or excipient.
• No pharmacopeial monograph is expected for this specialized reagent.

Physical Properties

Item-specific physical specifications (bp, mp, density, refractive index, UV cutoff, residuals, metals): Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed general properties for compounds of this structure (for planning only):

• Physical state: typically a pale yellow to amber liquid or low-melting solid for nitro‑aryl ynoate esters (literature, qualitative).
• Solubility: expected to be poorly soluble in water and freely soluble in common organic solvents (EtOAc, DCM, THF, toluene, MeCN, alcohols) due to aromatic and ester character (literature, qualitative).
• Polarity: moderately polar aprotic; contains a strongly electron‑deficient C≡C adjacent to an ester carbonyl (general chemical knowledge).
• Estimated molecular weight: ~219.20 g/mol (from C11H9NO4; computed/literature).
• Vapor pressure: expected low at ambient temperature for an aryl ynoate (literature, qualitative).

Practical implications:

• Handles readily under standard dry organic conditions; consider gentle warming to reduce viscosity if needed.
• Light sensitivity is not typically severe, but storing away from strong light is prudent for conjugated esters.
• Avoid prolonged exposure to strong bases or nucleophiles if neat, as Michael-type additions can occur at the activated alkyne.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.

General guidance on quality for this compound class (literature/general):

• For use as a Michael acceptor or cycloaddition partner, low levels of hydrolytic impurities (acids/alcohols) and minimal polymerization/byproducts are desirable. Verify by 1H/13C NMR (alkynyl and ester resonances), IR (C≡C ~2100–2200 cm−1, C=O ~1715–1740 cm−1), and LC/MS.
• If HPLC or photochemical applications are intended, low UV background and minimal colored impurities are beneficial. Nitroaromatics absorb strongly in the near‑UV; baseline selection for chromatographic detection should account for this.
• Suggested acceptance tests (typical for research grade, not item-specific): GC/LC purity, water content by KF, and residual solvent analysis. Refer to the item’s CoA for actual specifications.

Reaction and Applications

Ethyl 3-(3-nitrophenyl)prop-2-ynoate is an electron-poor ynoate (conjugated C≡C–C(=O)OR) further deactivated by a meta‑nitro aryl group. This combination makes it a versatile electrophile and dipolarophile.

Key application families (literature/general):

• Conjugate additions to alkynes (formal Michael additions): Thiols, malonates, 1,3‑dicarbonyls, and amines can add across the C≡C to give functionalized enoates, often under base or Lewis acid catalysis. Organocatalysts (e.g., tertiary amines) and phase-transfer conditions are common.
• 1,3‑Dipolar cycloadditions: Reactive toward nitrile oxides and nitrones to furnish isoxazoles/isoxazolines and isoxazolidines, exploiting the activated alkyne; the ester assists regiocontrol.
• Annulation chemistry: Participates in gold-, silver-, or copper-catalyzed hydrofunctionalizations (hydroarylation, hydroamination, hydrothiolation) to provide substituted enoates with high Markovnikov/anti‑Markovnikov selectivity depending on the catalyst system.
• Hydrogenation/semi-hydrogenation: Selective reduction of the C≡C to E- or Z‑alkenes under Lindlar or poisoned catalysts; further hydrogenation to saturated esters is possible. Nitro group remains a competing reducible site; catalyst choice controls chemoselectivity.
• Radical additions/photoredox: Visible-light photoredox systems (e.g., Ir/Ru or organic dyes) enable radical Giese‑type additions to the activated alkyne/enoate manifold.
• Arylnitro handle: While meta‑nitro is less directing, it can be leveraged for subsequent transformations (e.g., reduction to anilide followed by cross‑coupling) after the alkyne chemistry.

Practical tips:

• Exclude strong bases when not intended—uncontrolled polymerization or transesterification can occur.
• Dry, oxygen‑free conditions improve reproducibility for nucleophilic and radical additions. Monitor by TLC/LC–MS; the alkyne → alkene shift is easily tracked by IR (loss of C≡C band).

Reaction Conditions

General, literature-based guidance for this class (adjust to your substrate/scope):

• Michael-type additions to the activated alkyne:
  • Typical solvents: MeCN, THF, DCM, toluene; dry conditions beneficial.
  • Bases/catalysts: tertiary amines (Et3N, DBU), inorganic bases (K2CO3, Cs2CO3), or Lewis acids (Zn, Cu salts) depending on nucleophile.
  • Temperature: 0–60 °C; often rt to 40 °C suffices.
  • Atmosphere: inert gas recommended for moisture/oxygen‑sensitive partners.
• 1,3‑Dipolar cycloadditions (e.g., nitrile oxides, nitrones):
  • Solvents: toluene, DCM, MeCN.
  • Conditions: thermal (rt–80 °C) or base-generated dipoles in situ; catalytic Cu/Ag salts may accelerate.
• Hydrofunctionalizations (Au/Cu catalysis):
  • Catalysts: Ph3PAuCl/AgSbF6 (1–5 mol%) or Cu salts (5–10 mol%).
  • Solvents: DCM, DCE, toluene; 0–60 °C.
  • Notes: control Markovnikov/anti‑Markovnikov by catalyst/ligand choice.
• Hydrogenation/semi-hydrogenation:
  • Catalyst: Pd/C (5–10 wt%), Lindlar for partial reduction.
  • Solvent: EtOH/EtOAc/MeOH; 1–3 bar H2 at rt–40 °C.
  • Caution: Nitro group reduction competes; lower H2 pressure and poisoned catalysts favor C≡C selectivity.

Workup/analysis:

• Monitor by IR (loss of C≡C), TLC/LC–MS; quench bases carefully to avoid saponification.

All conditions are literature/general guidance; optimize for your specific transformation.

Safety and Handling

GHS classification, signal word, pictograms, and H‑statements: Not specified for this item; refer to the product SDS for authoritative safety information.

General laboratory safety guidance for nitro‑aryl alkynyl esters (literature/general):

• Hazards: May cause skin/eye irritation; harmful if swallowed or inhaled. Nitroaromatic compounds can have increased toxicity relative to unsubstituted arenes. Avoid inhalation of vapors or aerosols.
• Peroxide formation: Not a typical peroxide former (unlike ethers), but avoid strong oxidizers and reducing agents.
• Incompatibilities: Strong bases and nucleophiles (can add to the activated alkyne), strong acids (hydrolysis), strong oxidizers/reductants (may affect the nitro group), and reactive metals.
• PPE: Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control vapors/aerosols.
• First aid (summary; defer to SDS):
  • Skin contact: Wash with soap and water; remove contaminated clothing.
  • Eye contact: Rinse cautiously with water for several minutes; 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.
• Fire safety: Treat as a combustible organic liquid/solid. Use CO2, dry chemical, or foam. Thermal decomposition may produce NOx and CO/CO2.
• Spill response: Absorb with inert material, collect for disposal. Prevent entry to drains.
• Waste: Dispose of according to local regulations; treat as halogen‑free organic waste unless otherwise specified by SDS.

Storage note from Product Data: Store at room temperature.

Solvent Selection

This substance is a moderately polar, aprotic organic reagent with an activated alkyne and an ester. It dissolves readily in many organic solvents.

• Polarity/miscibility (literature/general):
  • Highly soluble: DCM, CHCl3, EtOAc, THF, toluene, MeCN, acetone, ethyl acetate, alcohols.
  • Poorly soluble: Water and highly nonpolar alkanes at room temperature (qualitative expectation for aryl esters).
• Dielectric context: Reactions involving nucleophilic additions to the alkyne often benefit from polar aprotic media (e.g., MeCN, DMF, DMSO) to enhance rates; pericyclic/cycloaddition chemistry can proceed well in toluene, DCM, or neat conditions (literature/general).
• When to choose alternatives:
  • If base-sensitive conditions are expected, avoid strongly basic alcoholic media (risk of transesterification/addition). Opt for non-nucleophilic solvents like DCM or toluene.
  • For photoredox additions, MeCN and MeOH mixtures are commonly used; oxygen exclusion is often beneficial.

Small comparison (literature/general):

• DCM: excellent solubility, easy handling; chlorinated waste burden.
• THF/2-MeTHF: good balance of polarity and greener profile (for 2‑MeTHF); ensure dryness for base-catalyzed additions.
• Toluene: good for thermal cycloadditions; higher bp allows elevated temperatures.

Storage and Reconstitution

• Storage Conditions (from Product Data): Room temperature.
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
• Form: Not specified for this item; refer to CoA/Spec Sheet.

General handling (literature/general):

• Keep container tightly closed in a dry, well‑ventilated place away from strong acids/bases, oxidizers/reductants, and direct sunlight.
• For long-term integrity, storing under inert gas and desiccation can minimize hydrolysis or adventitious addition to the alkyne.
• If solidifies or is viscous, warm gently to ambient temperature to homogenize before use.
• No reconstitution is typically required; if supplied as a neat liquid/solid, dissolve directly in a suitable anhydrous organic solvent (e.g., DCM, THF, MeCN, EtOAc) immediately before use.

Always consult the SDS and the item’s CoA/Spec Sheet for definitive storage and handling guidance.

Structure and Identity

Ethyl 3-(3-nitrophenyl)prop-2-ynoate is an electron‑deficient alkynyl ester bearing a meta-nitro substituent on the arene and an ethyl carboxylate at the acetylenic carbonyl terminus.

• SKU: E1007993
• CAS: 35283-09-1
• PubChem CID: 13281361 (literature identifier)
• InChIKey: 21683 (as provided; atypical length for an InChIKey)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: C11H9NO4 (computed/literature for the named structure)
• Molecular weight: ~219.20 g/mol (computed from C11H9NO4; literature)

Structural features (descriptive):

• Aromatic ring (benzene) substituted at meta position with a nitro group (–NO2) and at another position with a conjugated alkynyl ester side chain (–C≡C–C(=O)OEt).
• Functional groups: nitro (strongly electron‑withdrawing), internal alkyne conjugated to an ester carbonyl (ynone ester/ynoate), ethyl ester.
• The 2D structure can be visualized as m‑NO2‑C6H4–C≡C–C(=O)–O–CH2–CH3 with the nitro group meta to the alkynyl substituent on the ring.

Notes:

• Item-specific identifiers not listed above are Not specified for this item; refer to CoA/Spec Sheet.

Synthetic Utility

Functional group leverage (literature/general):

• Activated alkyne (ynoate): strong Michael acceptor character enables C–C and C–heteroatom bond formation. Ester adjacency controls regioselectivity and stabilizes vinylic anions formed post‑addition.
• Nitro‑aryl ring: provides a handle for late‑stage modification (reduction → aniline; nucleophilic aromatic substitutions are less favorable at meta, but nitro reduction can unlock Sandmeyer-type diversifications after diazotization of derived anilines).

Named/representative transformations:

• Conjugate addition of 1,3‑dicarbonyls (Knoevenagel‑Michael cascades) to forge substituted cinnamate analogs from alkynes.
• Nitrile oxide cycloaddition → isoxazoles; subsequent N–O bond reduction opens β‑ketoamide/β‑hydroxyketone chemistry.
• Hydrothiolation/hydroamination under Au(I)/Au(III), Cu, or photoredox catalysis to access β‑heteroatom‑substituted enoates.
• Selective semi‑hydrogenation (Lindlar) to E/Z‑alkenyl esters; careful catalyst choice avoids nitro reduction.
• Transesterification to other alkyl esters or conversion to acids/amides for library diversification.

Retrosynthetic value:

• Serves as an electrophilic lynchpin where nucleophile identity dictates downstream functionality; nitro group offers orthogonal reactivity allowing two‑directional diversification on aryl and side chain.

Target Specificity

Not applicable. This product is a small-molecule synthetic reagent and does not possess biological target specificity (no antigen/epitope/clone/isotype information). Item-specific bioaffinity data: Not specified for this item; refer to CoA/Spec Sheet if applicable.