2-Ethoxyprop-2-enenitrile , CAS No.19479-65-3

CAS: 19479-65-3 Cat. No.: E1012465 Formula: C₅H₇NO Molecular Weight: 97.12 PubChem CID: 12349940

Storage

Room temperature

Specifications

Storage

Room temperature

Names and Identifiers

• Canonical Smiles: CCOC(=C)C#N
• IUPAC Name: 2-ethoxyprop-2-enenitrile
• InChIKey: RVBFWXYFXKDVKG-UHFFFAOYSA-N
• INCHI: 1S/C5H7NO/c1-3-7-5(2)4-6/h2-3H2,1H3
• Isomeric SMILES: CCOC(=C)C#N
• PubChem CID: 12349940
• Molecular Weight: 97.12

Chemical and Physical Properties

• Molecular Weight: 97.120 g/mol
• XLogP3: 1.100
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 97.0528 Da
• Monoisotopic Mass: 97.0528 Da
• Topological Polar Surface Area: 33.000 Ų
• Heavy Atom Count: 7
• Formal Charge: 0
• Complexity: 108.000
• 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

No tested bioassay or immunoassay protocols are provided for this item in the Product Data. As a synthetic reagent, typical “protocols” are reaction procedures; see the Reaction Conditions and Synthetic Utility sections for literature-style guidance.

If incorporating this compound into a custom protocol (e.g., conjugate addition or cycloaddition):

• Establish solvent and base/acid compatibility with small-scale screens.
• Control temperature and inhibitor content to suppress polymerization.
• Validate quench and workup to avoid hydrolysis on silica or in acidic aqueous phases.

For any application, consult the lot-specific CoA/SDS and adapt standard operating procedures to your lab’s EHS requirements.

Biological Roles

Item-specific biological/biochemical data: Not specified for this item; refer to CoA/SDS for any additional notes. Research Use Only (per Product Data).

General context (not a clinical claim):

• 2-Ethoxyprop-2-enenitrile is a small, non-natural organic building block with an enol-ether and nitrile functionality. It does not have an established endogenous biological role.
• Nitriles in general can serve as bioisosteres of amides or carbonyls in medicinal chemistry; however, this compound is primarily used as a synthetic intermediate rather than a biomolecule or probe.
• In biological media, donor–acceptor alkenes may undergo conjugate additions with nucleophilic residues (e.g., cysteine), implying potential reactivity toward proteins under certain conditions. Such reactivity underscores the need for careful handling and quench strategies in biochemical assay development.
• Hydrolytic stability: enol ethers are susceptible to acid-catalyzed hydrolysis; neutral to mildly basic aqueous conditions slow this process but do not eliminate it. In buffered aqueous systems, expect gradual decomposition rather than persistent biological activity.

Conclusion: treat this reagent strictly as a chemical tool/intermediate. If exposure to biological matrices is contemplated (e.g., for derivatization), pre-validate stability and reactivity. No pharmacological or physiological roles are claimed or implied.

Buffer Applications

This compound is not a buffering agent and is not typically employed to prepare biological buffers or maintain pH.

Practical note:

• If reactions are conducted in biphasic or aqueous-organic systems, use an external buffer appropriate to the transformation (e.g., phosphate, acetate, or carbonate) while keeping the reagent predominantly in the organic phase to limit hydrolysis/polymerization. Avoid acidic buffers if preservation of the enol-ether is required.

No item-specific buffer recipes or pKa data are provided for this product.

Green Alternatives

Greenness considerations relate mainly to solvent/process choices rather than replacement of the reagent itself (a specific push–pull alkene). Where feasible, adopt greener media and controls.

Potential greener solvent choices (literature-based):

• 2-MeTHF or CPME in place of THF/MTBE: bio-based origins (2-MeTHF), better phase separation, lower peroxide rates, and improved safety profiles; may alter rates/selectivities—pilot trials advised.
• EtOAc or Me-PEG 200/400 as alternatives to DCM: reduced chlorinated waste; EtOAc offers easy removal and favorable EHS profile.
• Toluene or xylene instead of chlorinated aromatics: lower environmental impact; higher bp aids thermal control for some transformations.

Comparison (general):

• DCM vs EtOAc: DCM provides higher polarity and often faster reactions; EtOAc is greener but can participate in acylation under strong conditions—verify compatibility.
• THF vs 2-MeTHF: similar solvency; 2-MeTHF is less miscible with water and often enables easier workups.

Process-integrated improvements:

• Minimize peroxide risk by selecting ethers with lower peroxide formation tendencies (CPME > 2-MeTHF > THF) and by adding validated inhibitors/scavengers.
• Employ continuous flow for exothermic additions/polymerization-prone steps, reducing solvent volumes and improving safety.
• Design for recovery: choose solvents that can be distilled/recycled without promoting hydrolysis or polymerization of the enol ether.

Note: No item-specific “green grade” or solvent requirement is specified for this product.

Pharmaceutical Uses

Item-specific pharmacopeial status or excipient role: Not specified for this item; refer to CoA/Spec Sheet. Research Use Only.

General, non-clinical context:

• Role in discovery chemistry: 2-ethoxyprop-2-enenitrile can be used as a versatile electrophilic building block to install nitrile-containing, carbonyl-precursor motifs via conjugate addition or controlled hydrolysis, supporting structure–activity relationship (SAR) exploration.
• Process considerations: when used in route scouting, attention to inhibitor content, residual acidity, and peroxide levels is important for reproducibility and impurity control.
• Regulatory note: nitrile-bearing intermediates require appropriate purge strategies and analytical controls in GMP settings due to potential for reactive impurities and polymeric byproducts. This product is not offered as an API, excipient, or for therapeutic use.

Any application in pharmaceutical manufacturing must be supported by internal qualification of quality attributes from the lot-specific CoA and by a full SDS risk assessment.

Physical Properties

Item-specific specifications (as supplied):

• 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.

Literature/computed (non-spec) properties for 2-ethoxyprop-2-enenitrile (reference only):

• Approximate molecular formula/MW (computed from representative structure): C5H7NO, ~97.1 g/mol.
• Physical state: typically a low–to–moderate boiling liquid for this class of enol-ether nitriles.
• Volatility: expected to be moderately volatile; handle in a fume hood to minimize inhalation.
• Solubility: miscible with common organic solvents (ethers, esters, aromatics, chlorinated solvents); low aqueous solubility expected for small alkenyl nitriles.
• Polarity: polar-aprotic functionality due to nitrile; weakly hydrogen-bond accepting via nitrile and ether oxygen; no H-bond donation.
• Refractive index/density, bp/mp, UV cutoff: Not specified for this item; consult literature and verify against CoA for lot-specific values.

Practical notes:

• As a donor–acceptor substituted alkene, it may absorb in the UV; verify UV background before chromatographic or spectrophotometric uses.
• Enol ethers can form peroxides upon air/light exposure; check peroxide content as appropriate (spec limit Not specified for this item).

Quality & Grades

Item-specific quality 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.

General guidance (for context):

• Research grade: suitable for general laboratory synthesis and method development. For moisture-/air-sensitive enol ethers, lot-to-lot control of acidity, peroxide level, and UV background can be important depending on the application.
• Chromatography/UV-sensitive work: when reactions or analyses are UV-detected, low-UV or HPLC-grade solvents/reagents are preferred. If using this reagent in photochemical or spectroscopic contexts, confirm background absorbance on the provided CoA.
• Polymerization control: donor–acceptor alkenes may self-polymerize. Suppliers sometimes include trace inhibitors (e.g., BHT, MEHQ) to enhance storage stability. If an inhibitor-sensitive application is planned (e.g., radical polymerizations), confirm presence/absence and type on the CoA/SDS and, if needed, pre-treat (e.g., inhibitor removal) immediately before use.
• Trace impurities: water content, acidity, and peroxides can impact reactivity/selectivity. Where critical, request these as certificate parameters. For this catalog item, specific impurity limits are Not specified for this item.

Recommendation: Verify required quality attributes (purity assay, stabilizer content, water/peroxide levels, UV absorbance) on the lot-specific CoA prior to use in sensitive transformations.

Reaction & Applications

Manufacturer Applications: Not specified in Product Data.

Literature/general applications for 2-ethoxyprop-2-enenitrile (push–pull alkene; enol-ether nitrile):

• Michael-type reactivity: as a donor–acceptor alkene, it can undergo conjugate additions with soft nucleophiles (e.g., thiols, malonates, stabilized enolates) at the terminal carbon, furnishing β-ethoxy nitriles that can be further elaborated (e.g., hydrolysis to carbonyls, reductive transformations).
• Cycloadditions: serves as an activated/donor-substituted alkene (dienophile) in [4+2] (hetero-Diels–Alder) and [2+2] photocycloadditions. The nitrile enhances LUMO lowering; alkoxy donation can modulate regioselectivity.
• Electrophilic trapping and rearrangements: protonation at the enol ether site followed by nucleophilic capture; acid-catalyzed hydrolysis to oxo–nitrile motifs.
• Polymerization propensity: radical or cationic conditions can induce polymerization; leverage for specialty polymer synthesis or rigorously suppress during fine chemical synthesis (inhibitors, low-temperature handling).
• Building-block strategy: a masked 1,3-heteroatom–functionalized nitrile. Hydrolysis/solvolysis yields carbonyl–nitrile frameworks valuable in medicinal and agrochemical discovery.

Practical tips:

• Moisture/acid control: trace acids trigger hydrolysis/polymerization. Use base-washed glassware, neutral alumina for chromatography, and buffered aqueous workups.
• Temperature: perform additions at 0–25 °C initially; exotherms possible during nucleophile addition or acid quench.
• Monitoring: TLC with UV visualization often effective; GC/GC–MS suitable given volatility. Quench samples with base/neutral media to avoid on-plate hydrolysis.

All examples above are general literature guidance; optimize for your specific substrate set.

Reaction Conditions

The following are general, literature-based conditions that have been applied to donor–acceptor enol-ether nitriles; they are not item-specific specifications.

• Conjugate additions (Michael-type):

  • Solvents: toluene, EtOAc, MeCN, THF/2-MeTHF.
  • Bases/catalysts: tertiary amines (e.g., DIPEA), DBU, or Lewis acids (e.g., Zn(II), Mg(II)) depending on nucleophile.
  • Temperature: 0–25 °C initially; warm to rt after controlled addition. Typical times 0.5–6 h. Monitor for onset of polymerization; include inhibitor if necessary.

• Hetero-Diels–Alder / cycloadditions:

  • Solvents: toluene, DCM, CPME.
  • Catalysis: optional Lewis acids (BF3·OEt2, TiCl4) at −78 to 0 °C for enhanced regio-/stereocontrol; or thermal conditions at rt–60 °C without catalyst. Reaction times 1–24 h.

• Acid-catalyzed hydrolysis (to carbonyl–nitrile derivatives):

  • Reagents: dilute mineral acids (HCl, H2SO4) or organic acids (TFA) in aqueous–organic mixtures.
  • Conditions: 0–25 °C start; avoid strong/prolonged acidity if over-hydrolysis is undesired. Work up promptly to isolate oxo–nitrile products.

• Reductions of the nitrile (downstream):

  • Reagents: Raney Ni/H2, Pd/C/H2, or borane reagents; protect or first convert the enol ether to a carbonyl to avoid side reactions.

General cautions:

• Polymerization risk increases with heat, light, acids, and radicals—use inhibitors, exclude oxygen, and maintain low temperatures as appropriate.
• Scale-up: dose-controlled addition and calorimetry recommended to manage exotherms.

Safety & Handling

Item-specific hazard information (from Product Data):

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

General safety guidance for enol-ether nitriles (literature/experience-based; not a substitute for SDS):

• Likely hazards: flammable liquid and vapor; irritation to skin/eyes/respiratory tract possible. Avoid inhalation and contact. Use in a certified fume hood.
• Peroxide formation: enol ethers may autoxidize to peroxides on storage, especially with air/light. Periodically test and avoid distilling to dryness. Use inhibitor strategies as appropriate for process scale.
• Incompatibilities: strong acids (can hydrolyze the enol ether), strong bases (can induce polymerization or addition), strong oxidizers, and radical initiators (may promote unwanted polymerization/addition).
• PPE: lab coat, safety glasses or splash goggles, chemically resistant gloves (e.g., nitrile). For scale-up or splash risk, add face shield and apron.
• First aid (overview): move to fresh air if inhaled; rinse skin/eyes with water for ≥15 minutes upon contact; seek medical attention if irritation persists. If ingested, do not induce vomiting—seek medical attention immediately.
• Fire response: use dry chemical, CO2, or alcohol-resistant foam. Water spray can cool containers but may be ineffective on the fire itself.

Always defer to the Aladdin SDS for authoritative hazard statements, exposure limits, and spill/fire response instructions.

Solvent Selection

This product is a reactive liquid reagent rather than a working solvent. Selection of process solvent should balance solubility, stability (against hydrolysis/polymerization), and downstream handling.

General, literature-based guidance:

• Polarity profile: polar-aprotic functionality (nitrile + ether) with limited hydrogen-bond basicity. Typically soluble in ethers (THF, MTBE), esters (EtOAc), aromatics (toluene), and chlorinated solvents (DCM). Poorly soluble in water.
• Stability considerations: avoid protic/strongly acidic media if the enol ether motif must be preserved; acid catalysis can hydrolyze to a carbonyl–nitrile derivative.
• Typical choices:
  • Neutral/aprotic: toluene, EtOAc, MeCN, DCM/CH2Cl2, CPME, 2-MeTHF—good balance of solubility and moderated reactivity.
  • For polar transformations: MeCN or DMF/DMSO can be used if compatible with base/acids present; monitor for conjugate additions/polymerization.
• Drying: use molecular sieves (3Å/4Å) for water control when hydrolysis is a concern. Avoid acid-activated clays/silica unless quenching is intended.

Comparison notes:

• Toluene vs DCM: toluene offers higher boiling point and lower chlorinated waste; DCM provides greater polarity and faster heat removal but higher environmental burden.
• 2-MeTHF/CPME vs THF/MTBE: greener ethers with reduced peroxide formation and improved process safety; assess rate/selectivity impacts case-by-case.

Always validate solvent compatibility with your specific reaction conditions.

Storage & Reconstitution

Item-specific storage/shipping from Product Data:

• Storage conditions: Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance at receipt: Not specified for this item; refer to CoA/Spec Sheet.
• Research use note: For research use only.

General handling and stability guidance (literature-based):

• Container: store tightly closed in an amber glass bottle to limit light exposure; headspace under inert gas (N2/Ar) helps minimize peroxide formation and hydrolysis.
• Segregation: keep away from acids, bases, oxidizers, and radical initiators. Avoid contact with moisture.
• In-use practices: dispense using dry syringes or pipettes; recap promptly. If long-term storage is planned, periodic testing for peroxides is prudent for enol ethers.
• Do not freeze aqueous mixtures; the neat material is usually stored at ambient as specified. If a stabilizer is present or required, consult the CoA/SDS before removal or addition.

Reconstitution: Not applicable—typically supplied neat. If dilution is required, use dry, inhibitor-compatible organic solvents (e.g., toluene, EtOAc, 2-MeTHF) and prepare fresh before use.

Always follow the Aladdin SDS for definitive storage and compatibility information for the specific lot supplied.

Structure & Identity

Item-specific identifiers from Product Data:

• CAS: 19479-65-3
• SKU: E1012465
• 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.

Literature/computed description (for reference only):

• Preferred name: 2-Ethoxyprop-2-enenitrile (an enol ether conjugated to a nitrile; a “push–pull” substituted alkene).
• Representative SMILES (literature): CCOC(=C)C#N
• Structural features: contains a terminal vinyl group (=CH2) conjugated to a β-ethoxy substituent and a nitrile (–C≡N) on the vinylic quaternary carbon; no stereocenters; planar sp2 motif around the C=C; strong –I/–M effect from nitrile and +M donation from the alkoxy group.
• 2D verbal structure: CH2=C(–O–CH2–CH3)–C≡N; the internal alkene carbon bears both the ethoxy substituent and the nitrile carbon.

Notes:

• The above “literature” identifiers are provided as general reference to the named structure and are not item-specific specifications. Always confirm with the CoA/SDS for the exact identifiers of the supplied lot.

Synthetic Utility

Functional group ensemble and reactivity (literature-based):

• Push–pull alkene: the juxtaposition of an electron-donating ethoxy group and an electron-withdrawing nitrile activates the C=C toward polar cycloadditions and controlled conjugate additions, with tunable regio-/chemoselectivity.
• Enol-ether handle: subject to protonation and hydrolysis, enabling conversion into carbonyl–nitrile frameworks; useful entry to β-alkoxy/β-oxo nitriles and subsequent homologations or reductions.
• Nitrile versatility: downstream transformations include hydrolysis to amides/acids, reduction to primary amines (via imine or amidine intermediates), and participation in metal-catalyzed cross-couplings after appropriate activation (e.g., imidate formation).

Strategic uses:

• Michael acceptor partner with soft C-, N-, S-nucleophiles to introduce functionality adjacent to the nitrile; subsequent unmasking of the enol ether furnishes ketone/aldehyde equivalents.
• Dienophile in hetero-Diels–Alder to assemble oxygenated/cyano-substituted carbocycles and heterocycles.
• Monomer/functional comonomer in radical or cationic polymerizations yielding nitrile-functional materials (when polymerization is desired and controlled).

Practical guidance:

• Control acidity and moisture rigorously to maintain the enol ether; quench/neutralize silica before chromatography or use neutral alumina.
• For reductive or nucleophilic steps, begin at low temperature (0–5 °C) to mitigate polymerization and exotherms; add nucleophile slowly.
• Analytical tracking via GC/GC–MS or LC–MS; derivatize if needed to stabilize samples prior to analysis.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent and is not an antibody, enzyme, or affinity reagent. No target/epitope/isotype information is provided in the Product Data.