This compound belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).
External Descriptors
Not available
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Punto di infiammabilità (°F)
Not applicable
Punto di infiammabilità (°C)
Not applicable
Punto di fusione (°C)
69-71℃ (lit.)
Peso molecolare
138.120 g/mol
XLogP3
0.100
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
2
Exact Mass
138.043 Da
Monoisotopic Mass
138.043 Da
Topological Polar Surface Area
73.900 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
223.000
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
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
No validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent.
Synthetic usage notes (general):
For deprotonation/alkylation, ensure rigorously dry glassware and anhydrous solvents; add base at 0 °C and allow controlled warming while monitoring by TLC/LC-MS.
For transesterification, titrate catalyst loading to minimize over-reaction; employ an internal standard for GC/LC quantification.
For scale-up, perform calorimetric assessment if strong bases are used; manage off-gassing and heat release.
Refer to the Reaction Conditions section for detailed parameter ranges. For any biological testing, develop and validate protocols de novo.
Biological Roles
This product is intended for research and synthetic chemistry applications. No biological function or role is assigned for laboratory use.
General information (biochemistry context):
Nitrile-containing small molecules are relatively rare in primary metabolism of higher organisms; when present, nitriles can be metabolized by specialized enzymes (nitrilases/nitrile hydratases) in microorganisms, converting nitriles to amides or acids (literature).
The gem-dinitrile motif is strongly electron-withdrawing and typically reduces basicity and nucleophilicity of adjacent atoms, resulting in low intrinsic biological reactivity under neutral conditions.
Esters are susceptible to enzymatic hydrolysis (esterases) in biological systems; however, the presence of two nitriles adjacent to the alkoxy carbon may alter enzyme recognition relative to simple aliphatic esters.
Applicability to this item:
No specific biological roles, targets, or pathways are claimed or implied for α,α-dicyanoethyl acetate. It should not be used for diagnostic, therapeutic, or clinical purposes.
Any biological testing should be performed under institutional approvals, and interpretation must consider potential hydrolysis to 1,1-dicyanoethanol or other derivatives.
Refer to the SDS for toxicological information and handle strictly as a research chemical.
Buffer Applications
Not typically applicable. α,α-Dicyanoethyl acetate is a neutral organic ester with limited aqueous solubility and is not used as a buffering agent or pH control component.
Practical note:
If reactions involve aqueous phases (e.g., hydrolysis or biphasic extractions), choose buffer systems that do not promote ester cleavage unless intended (e.g., avoid strong basic carbonate buffers when preserving the ester).
For kinetic or enzymatic studies in mixed solvents, maintain organic co-solvent content to keep the compound in solution and validate that buffer salts do not catalyze unwanted transesterification.
For synthetic applications, refer to the Solvent Selection and Reaction Conditions sections rather than buffer guidance.
Green Alternatives
Greener practice with α,α-dicyanoethyl acetate emphasizes solvent and base choices, since the substrate itself contains two nitriles and an ester (functionalities not readily “greenable”).
Greener solvent swaps (general guidance):
Replace DMF/DMAc/NMP with Cyrene, propylene carbonate, 2-MeTHF, or EtOAc where compatible.
Prefer acetonitrile or EtOAc over chlorinated solvents for routine processing and crystallization when feasible.
Greener base/catalyst choices:
Use organic superbases (DBU, TBD) catalytically where stoichiometric alkoxides/hydrides would otherwise be used, reducing inorganic waste.
Employ solid-supported bases (e.g., PS–DBU) to simplify workup.
Example comparison (general; selection depends on reaction):
Greener choice vs conventional choice
2-MeTHF vs THF: similar polarity and utility, lower peroxidation risk and renewable origin.
EtOAc vs DCM: biodegradable, lower toxicity and environmental impact.
Acetonitrile vs DMF: higher volatility for easier recovery; lower chronic toxicity profile.
Process considerations:
Minimize aqueous basic hydrolysis during workup to reduce nitrile- and acetate-derived waste.
Solvent recycling (e.g., MeCN or EtOAc) can significantly reduce environmental footprint.
Note: Always confirm reaction performance after solvent/base changes; kinetics and selectivity can shift for dicyanomethyl chemistry.
Pharmaceutical Uses
No pharmaceutical or clinical uses are claimed for this product. It is supplied strictly for research and laboratory synthesis.
General industry context (non-clinical):
Nitrile-bearing esters can serve as synthetic intermediates in medicinal chemistry campaigns, enabling rapid access to dicyanomethyl-derived scaffolds that can be further diversified (e.g., conversion of nitriles to amides/acids or reduction to amines).
As a process intermediate, attention is required to potential hydrolysis and to removal of residual solvents and related impurities to meet quality targets in later-stage development.
Compliance and standards:
No pharmacopeial monograph is indicated for α,α-dicyanoethyl acetate. Any use in regulated settings would require establishing in-house specifications for identity, purity, residual solvents, and elemental impurities per ICH guidelines.
All references here concern formulation/manufacturing context only and do not imply therapeutic activity.
Physical Properties
Item-specific specifications (from 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 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 properties (for general guidance; not product specifications):
Molecular formula (literature): C5H4N2O2
Molecular weight (literature): ~124.09 g/mol
2D descriptor: acetate ester bearing a gem-dinitrile methine
Expected polarity: Moderately polar aprotic due to ester and nitriles; non-protic, H-bond acceptor only.
Solubility (qualitative, literature/general):
Likely miscible or highly soluble in polar aprotic solvents (e.g., acetonitrile, acetone, DMSO, DMF).
Limited solubility expected in water (gem-dinitrile reduces hydrophilicity despite ester carbonyl).
Soluble in common organic solvents such as ethyl acetate, dichloromethane, and THF.
Acid–base behavior (general): The methine α to two nitriles is relatively acidic compared with simple ethers/esters (cf. malononitrile pKa ~11, literature), enabling base-mediated deprotonation.
Not available in supplied data (do not construe as item specs): boiling point, melting point, density, refractive index, logP, UV cutoff. For these, refer to the CoA/Spec Sheet or SDS for the supplied lot.
Quality and Grades
Item-specific details from 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 quality considerations for this compound class (general):
For use in base-mediated C–C bond formation or anion chemistry, low water content and low basic/acidic impurities are important to prevent premature hydrolysis or side reactions. Karl Fischer moisture and acid value are typical control parameters; consult CoA for lot-specific values.
If LC or GC monitoring is planned, an HPLC or GC assay with reporting of related substances is recommended. For photochemically sensitive nitriles/esters, amber packaging helps reduce degradation; check packaging in the CoA.
Metal content is generally less critical unless used in metal-catalyzed cross-coupling or enolate chemistry where trace metals may poison catalysts; when relevant, request trace metal analysis.
UV cut-off and baseline suitability matter if the solvent matrix (e.g., using the compound as an additive in chromatography) is critical; not typically applicable here but CoA may report UV spectral purity.
Documentation: Always verify lot-specific assay, residual solvents, and impurity profile on the CoA/Spec Sheet before use in sensitive synthetic sequences.
Reaction and Applications
α,α-Dicyanoethyl acetate combines an electrophile-sensitive ester with a gem-dinitrile-stabilized methine. This motif supports several synthetic maneuvers.
General reaction families (literature/general):
Base-mediated deprotonation at the dicyanomethyl center to generate a resonance-stabilized carbanion that can undergo C–C bond formation with alkyl halides, activated alkenes, or carbonyl compounds.
Transesterification/solvolysis of the acetate to access 1,1-dicyanoethanol derivatives, which can be further elaborated (e.g., dehydration to 1,1-dicyanoalkenes under acidic conditions).
Condensation chemistry leveraging a dicyanomethyl donor (cf. Knoevenagel-type couplings when suitably activated), forming push–pull olefins with strong electron-withdrawing character.
Subsequent functional group interconversions of nitriles (partial/complete hydrolysis to amides/carboxylic acids, reduction to amines), enabling divergent synthesis from a common intermediate.
Practical notes (general):
Use dry, oxygen- and moisture-excluded conditions when forming the anion; typical bases include DBU, potassium tert-butoxide, sodium hydride, or LDA (choice depends on substrate sensitivity).
Monitor for competing ester cleavage in strongly basic media; milder non-nucleophilic bases are often preferred.
Workups should quench bases cautiously and minimize prolonged aqueous exposure to limit hydrolysis.
The gem-dinitrile can strongly influence spectroscopic signatures: characteristic nitrile stretches ~2250 cm−1 (IR, literature) and downfield 13C shifts for nitrile carbons (110–120 ppm region, literature).
Use cases (illustrative): preparation of dicyano-substituted building blocks, precursors to electron-poor alkenes for dye/materials chemistry, and handles for subsequent nitrile transformations.
Reaction Conditions
General, literature-style guidance for common transformations involving α,α-dicyanoethyl acetate. These are not product specifications; verify on small scale.
Deprotonation/Alkylation at the dicyanomethyl center:
Base: DBU (0.1–1.5 equiv), t-BuOK (0.5–1.2 equiv), NaH (0.5–1.2 equiv), or LDA (1.1–1.5 equiv) depending on electrophile.
Solvent: dry THF, DMF, DMSO, or MeCN.
Temperature: 0 °C to rt; for sluggish electrophiles, 40–60 °C (sealed tube) may be applied.
Time: 0.5–12 h; monitor by TLC/LC-MS.
Workup: quench with NH4Cl, extract with EtOAc/DCM, minimize basic aqueous exposure to limit ester hydrolysis.
Transesterification/solvolysis of the acetate:
Conditions: catalytic acid (H2SO4, p-TsOH) or base (NaOMe, KOtBu) in corresponding alcohol (MeOH, EtOH, i-PrOH).
Temperature: 25–60 °C; remove generated acetic acid/acetate where beneficial (Dean–Stark in nonpolar co-solvent or apply vacuum purge in polar systems).
Formation of electron-poor alkenes (from related dicyanoethanol derivatives):
Dehydrative protocols: POCl3/pyridine or SOCl2/base; 0–25 °C then warm to 50–80 °C, affording 1,1-dicyanoalkenes (literature precedent with analogous substrates).
Hydrolysis: aq. H2SO4 or NaOH, 60–100 °C, to amide/acid (stepwise control required).
Reduction: LiAlH4 or catalytic hydrogenation (Raney Ni/Pd) to primary amines (conditions substrate-dependent).
Tailor base/solvent to substrate compatibility; pilot experiments are recommended.
Safety and Handling
Item-specific hazard information (from Product Data):
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety considerations for gem-dinitrile esters (literature/general guidance; defer to SDS):
Hazards: Organic nitriles and esters can cause irritation to skin, eyes, and respiratory tract. Some nitriles can release toxic products upon thermal decomposition. Avoid inhalation of vapors/aerosols and contact with skin/eyes.
PPE: Use appropriate lab coat, safety glasses or goggles, and nitrile gloves. Employ local exhaust ventilation or fume hood when handling open quantities.
Incompatibilities: Avoid strong bases and acids that promote rapid hydrolysis/transesterification; strong nucleophiles may attack the ester. Avoid strong oxidizers and reductants. Moisture may accelerate hydrolysis.
Stability: Esters may hydrolyze; gem-dinitrile methine is base-sensitive (deprotonation). Store tightly closed to minimize moisture ingress and adventitious base exposure.
First aid (overview; follow institutional protocols):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/Eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical advice.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Firefighting: Use dry chemical, CO2, or foam. Combustion may produce CO/CO2 and nitrogen-containing gases.
Always consult the product SDS for authoritative hazard classification and response measures.
Solvent Selection
This is a moderately polar, aprotic organic ester bearing two nitriles. Solvent choice should balance solubility with reaction objectives (e.g., deprotonation, nucleophilic substitution, or condensations).
Miscibility and polarity (general expectations):
Good solubility in polar aprotic media: acetonitrile, DMF, DMSO, DMAc, NMP; also soluble in acetone, THF, dichloromethane, and ethyl acetate.
Limited solubility in water; hydrolysis risk increases in aqueous systems, especially under acidic or basic conditions.
Typical selections by application (general guidance):
Base-mediated deprotonation/alkylation of the dicyanomethyl center: Dry, polar aprotic solvents (DMF, DMSO, THF) facilitate anion formation and electrophile capture. Use rigorously anhydrous conditions.
Transesterification or solvolysis: Alcoholic solvents (MeOH, EtOH, i-PrOH) with acid/base catalysts enable exchange at the ester; monitor to avoid overreaction.
Electrophilic trapping/Knoevenagel-type condensations (using related donors): Mixed solvent systems (e.g., toluene/DMF or MeCN) balance solubility and volatility for workup.
Comparison (general):
THF: facilitates organobase solubility; easy removal; peroxide formation risk is not applicable to this substrate but is a property of THF.
Acetonitrile: high polarity, low proticity, and chemical compatibility with nitriles/esters; convenient for homogeneous conditions.
DCM/EtOAc: useful for extractions and non-nucleophilic media; lower boiling points aid concentration.
Choose solvent based on base/acid compatibility, moisture control, and downstream isolation strategy.
Storage and Reconstitution
Item-specific storage (from Product Data):
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance (compatible with the above unless superseded by label/SDS):
Keep container tightly closed in a dry, well-ventilated place. Protect from moisture and strong acids/bases to minimize hydrolysis or transesterification.
Store away from oxidizers and strong nucleophiles. Use amber glass if long-term storage under lighted conditions is expected.
After opening, consider storing under inert atmosphere (argon/nitrogen) if frequent base-mediated reactions are planned, to maintain low moisture content.
Reconstitution/handling:
Typically supplied neat. If preparing stock solutions, use dry, aprotic solvents (e.g., acetonitrile, DMSO, THF) and store aliquots tightly sealed. Validate solution stability by LC over time; avoid prolonged storage in alcoholic solvents if ester integrity is critical.
Bring cold materials to room temperature before opening to prevent condensation.
Always follow the label and SDS for definitive storage and handling instructions. For lot-specific stability, consult the CoA/Spec Sheet.
Structure and Identity
Brief overview: α,α-Dicyanoethyl acetate is an organic ester bearing a highly electron-withdrawing 1,1-dicyano-substituted methine bound to an acetate through oxygen. The nitrile pair renders the methine acidic and the fragment synthetically versatile.
Item-specific (from Product Data):
Product Name: α,α-Dicyanoethyl acetate
CAS: 7790-01-4
SKU: D472633
Storage Conditions: Room temperature (per product listing)
Research Use: For research use only
InChIKey: 266259 (as provided in Product Data)
Literature/computed identity (general reference values; verify against CoA/SDS for procurement lots):
Proposed 2D structure (in words): An acetate carbonyl (CH3–C(=O)–O–) attached to a tertiary carbon that also bears two nitrile groups (–C≡N) and one hydrogen: CH3–CO–O–CH(CN)2.
Structural features and consequences (general chemistry):
The gem-dicyano group markedly increases the acidity of the methine proton and stabilizes the corresponding carbanion by resonance into two nitriles.
The ester linkage is susceptible to hydrolysis and transesterification under aqueous basic or acidic conditions.
The motif can serve as a masked dicyanomethyl synthon for C–C bond construction.
Synthetic Utility
Functional group set: an acetate ester tethered to a gem-dinitrile-stabilized methine. This combination enables both nucleophile generation at the methine and electrophile manipulation at the ester.
As a dicyanomethyl synthon (literature/general):
Deprotonation at the methine (between two nitriles) forms a resonance-stabilized anion that adds to electrophiles (alkyl halides, Michael acceptors, carbonyls) to forge C–C bonds. Subsequent nitrile elaboration (hydrolysis, reduction) expands chemical space.
Under acidic dehydrating conditions, precursors derived from 1,1-dicyanoethanol can yield 1,1-dicyanoalkenes (strong acceptor olefins) useful in push–pull chromophores and conjugated materials.
At the ester handle:
Transesterification provides access to diverse 1,1-dicyanoalkyl ethers and esters. Acid- or base-catalyzed exchange allows incorporation of isotopically labeled or functionalized acyl groups.
Selective cleavage to regenerate 1,1-dicyanoethanol offers a branching point to halides (via Appel-type or Mitsunobu variants) or to carbonates/urethanes that retain the gem-dinitrile feature.
Strategy in synthesis:
Use as a masked dicyanomethyl donor where the acetate increases stability and handling compared with free alcohols or halides.
Orthogonal reactivity of the ester vs. the gem-dinitrile enables stepwise diversification, with the option to unmask/convert nitriles at late stage.
Spectroscopic handles:
IR ν(C≡N) ~2230–2260 cm−1; strong. 1H NMR: deshielded methine (adjacent to two –CN and –OR). 13C NMR: nitrile carbons ~110–120 ppm; ester carbonyl ~165–175 ppm (literature ranges).
Target Specificity
Not applicable. This product is a small-molecule organic reagent, not a biological affinity reagent. No antigen, epitope, species reactivity, clone, or isotype information applies.
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