| HS Code | 757575 |
| Product Name | 2-Ethoxyethyl Cyanoacetate |
| Synonyms | 2-Ethoxyethyl cyanoacetate; 2-Ethoxyethyl 2-cyanoacetate; Cyanoacetic acid 2-ethoxyethyl ester |
| Cas Number | 13289-18-4 |
| Iupac Name | 2-Ethoxyethyl 2-cyanoacetate |
| Molecular Formula | C7H11NO3 |
| Molecular Weight | 157.17 g/mol |
| Exact Mass | 157.0739 g/mol |
| Physical State | Liquid |
| Appearance | Clear, colorless to pale yellow liquid |
| Density | 1.054 g/mL at 25 °C |
| Boiling Point | 115-118 °C at 5 mmHg |
| Flash Point | >110 °C |
| Refractive Index | n20/D 1.432 |
| Solubility | Soluble in common organic solvents |
| Topological Polar Surface Area | 59.3 Ų |
| Logp | 0.8 (predicted) |
| Storage Conditions | Store in a cool, dry, well-ventilated place away from moisture, heat, and ignition sources |
| Smiles | CCOCCOC(=O)CC#N |
| Inchi | InChI=1S/C7H11NO3/c1-2-10-4-5-11-7(9)3-6-8/h2-5H2,1H3 |
As an accredited 2-Ethoxyethyl Cyanoacetate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 2-Ethoxyethyl Cyanoacetate is supplied in 25 kg polyethylene-lined steel drums, securely sealed with GHS-compliant hazard labels and lot identification. |
| Container Loading (20′ FCL) | 2-Ethoxyethyl Cyanoacetate is loaded in a 20′ FCL container, securely packaged, palletized, braced, and sealed for ocean shipment. |
| Shipping | 2-Ethoxyethyl Cyanoacetate is generally not regulated as dangerous goods for transport. Ship in sealed, compatible containers under ambient conditions, protected from heat, moisture, and ignition sources. No UN number, hazard class, or packing group is assigned. Always confirm against the current SDS and applicable DOT/IATA/IMDG regulations. |
| Storage | Store 2-Ethoxyethyl Cyanoacetate in a cool, dry, well-ventilated area away from heat, sparks, open flames, and strong oxidizers, acids, and bases. Keep containers tightly closed under inert gas if possible to prevent moisture degradation. Use chemically compatible, clearly labeled containers. Avoid direct sunlight and temperatures above 25–30°C. Follow local regulations and maintain spill containment. |
| Shelf Life | Shelf life: typically 24 months when stored cool, dry, tightly sealed, away from light and moisture; stable under recommended conditions. |
Within Class IIa topical wound closure device production, 2-ethoxyethyl cyanoacetate (CAS 32804-77-6, molecular weight 157.17 g/mol) is consumed as the immediate precursor to 2-ethoxyethyl cyanoacrylate, which undergoes anionic polymerization on skin moisture to form a flexible poly(alkyl cyanoacrylate) film. The condensation stage charges 2-ethoxyethyl cyanoacetate with paraformaldehyde at a molar ratio of 1.00:1.02 to 1.00:1.05 in the presence of 0.5–1.0 wt% piperidine base, with cyclohexane used for azeotropic water removal. The resulting oligomer is thermally depolymerized in a thin-film wiped evaporator at 1–10 mbar and a jacket temperature not exceeding 120°C; exceeding this threshold initiates uncontrolled repolymerization that fouls the internal condenser and reduces monomer yield below 60%. Crude 2-ethoxyethyl cyanoacrylate is stabilized with 20–50 ppm hydroquinone and 30–80 ppm methanesulfonic acid before fractional distillation. Finished tissue adhesive formulations maintain monomer content at ≥98.0 wt%, with ≤2.0 wt% polymeric thickener and 50–200 ppm free-radical and anionic stabilizers. Compliance for this downstream sector includes ISO 10993-1:2018 biological evaluation, ISO 10993-5:2009 cytotoxicity, ISO 10993-10:2010 skin sensitization, USP Class VI extraction testing, ISO 13485:2016 quality management, and FDA 21 CFR 878.4010 tissue adhesive classification. Terminal finished product types are single-use topical skin adhesive applicators for emergency wound closure and surgical incision closure in Class IIa medical device kits. The operational boundary is that the monomer is not indicated for internal tissue approximation or infected wound beds; moisture-rich exudate accelerates polymerization, shortening repositioning time to 3–8 s on exposed dermis.
Batch-to-batch variation in depolymerization is governed by acid stabilizer carry-over; if the condensation batch retains ≥500 ppm piperidine, the subsequent depolymerization temperature must be reduced by 5–10°C to avoid high molecular weight oligomer formation. Wiped-film evaporators with 0.5–1.0 m² heater surface and rotor speed 300–500 rpm are used; monomer vapour is condensed at −5°C to 0°C to prevent repolymerization in the condenser. The final applicator filling line maintains room humidity below 30% RH and uses nitrogen-purged positive displacement pumps.
In high-density circuit assembly, the primary process conflict is the need for rapid fixture while avoiding white bloom on adjacent soldermask surfaces. 2-Ethoxyethyl cyanoacetate is converted to the corresponding monomer and blended with ethyl cyanoacrylate at 15–35 wt% 2-ethoxyethyl cyanoacrylate; this range reduces volatile monomer deposition while retaining fixture times below 20 s on FR-4 substrates. Higher fractions above 35 wt% increase open time beyond 60 s and may require a calixarene-based accelerator at 0.1–0.5 wt% to restore cure speed. The production process includes vacuum degassing at ≤10 mbar for 15–20 min to prevent air entrapment in Luer-lock dispensing tips, followed by filling into HDPE cartridges. Table 1 lists the compliance matrix for this application.
| Standard / mandate | Scope | Test method / clause |
|---|---|---|
| ASTM D5363-16 | Anaerobic and cyanoacrylate adhesive classification | Thread locking / bond strength |
| IPC J-STD-004B | Flux classification / ionic contamination | Surface insulation resistance |
| IEC 61249-2-21 | Halogen-free PCB laminate | Halogen content limits |
| RoHS 2011/65/EU | Restricted substances in electronics | Pb, Hg, Cd, Cr6+, PBB, PBDE |
| REACH (EC) No 1907/2006 | Substance registration and SVHC screening | Article 57 SVHC review |
The process limitation on mixed-line dispensing is the interaction between acidic anionic stabilizers and amine-containing flux residues; when flux residues exceed 1.5 μg/cm² chloride equivalent per IPC J-STD-004B, cationic cure fronts can become erratic. Terminal products include low-bloom cyanoacrylate adhesives for optical module tacking, wire tacking on flexible printed circuits, and camera module positioning in smartphone assembly. Published data for specific lens substrate adhesion is limited; qualification requires shear testing on each coated glass type.
Because low-bloom behaviour on dark leather grain is a process-critical requirement, leather and footwear repair lines substitute 2-ethoxyethyl cyanoacrylate for ethyl cyanoacrylate in gap-filling formulations. The adhesive component is compounded with 70–90 wt% 2-ethoxyethyl cyanoacrylate, 5–15 wt% poly(methyl methacrylate) thickener, 2–6 wt% fumed silica, and 100–300 ppm boron trifluoride etherate stabilizer. High-shear rotor-stator mixing at 500–1,000 rpm under dry nitrogen is followed by vacuum degassing at 5–15 mbar. The production process applies the adhesive through a 1–2 mm nozzle onto sanded leather edges; the anionic polymerization initiates from residual moisture on the leather surface and from carboxylate sites on chrome-tanned leather. Terminal finished product types include leather edge repair adhesives, shoe sole sidewall bonding adhesives, and furniture upholstery leather lamination adhesives. Compliance for this sector is governed by REACH (EC) No 1907/2006 registration and SVHC screening, California Proposition 65 volatile organic compound reporting, and ISO 9001:2015 batch records. The operational boundary is that aniline-dyed leather can act as an amine-like cure accelerator and reduce open time below 5 s; pre-wiping with solvent is required to avoid unpredictable fixture speed.
Substituted 2-aminothiophene scaffolds are produced by Gewald condensation from a ketone, elemental sulfur, and an active methylene cyanoacetate. 2-Ethoxyethyl cyanoacetate is charged with the ketone at a molar ratio of 1.00:1.00 to 1.10:1.00; elemental sulfur is added at 1.1–1.3 mol per mole ketone, and morpholine is used as base at 0.5–1.0 mol. The reaction is run in a glass-lined batch reactor under nitrogen at 35–50°C for 4–8 h, with controlled ketone dosing over 60–90 min to manage the condensation exotherm. The ester side chain contributes to intermediate solubility in ethanol and ethyl acetate, enabling crystallization without chromatographic purification. Downstream production processes include aqueous quenching, vacuum filtration, and recrystallization from ethanol/water mixtures. Terminal finished product types are 2-aminothiophene carboxylate intermediates, cyanoacetamide derivatives, and heterocyclic ester building blocks for pharmaceutical intermediate synthesis. Compliance includes ICH Q7 GMP for active pharmaceutical ingredient intermediates, ICH Q3D elemental impurity risk assessment, and REACH (EC) No 1907/2006. The operational boundary is to avoid strong aqueous alkali above 40°C; saponification of the ester and subsequent nitrile hydrolysis generates cyanoacetate salt and may release trace hydrogen cyanide under acidification.
In short-cycle furniture assembly, the two-part process separates adhesive monomer from amine accelerator until the moment of dowel insertion. The adhesive component contains ≥95.0 wt% 2-ethoxyethyl cyanoacrylate, 1–3 wt% poly(methyl methacrylate) thickener, and 50–200 ppm methanesulfonic acid stabilizer; the activator component contains 0.1–0.3 wt% N,N-dimethyl-p-toluidine in acetone. The production process applies activator to the dowel surface by brush or spray and adhesive to the drill hole; after insertion, anionic cure completes within 10–20 s, reaching handling strength at 60–90 s. Terminal finished product types include edge banding adhesives, dowel joint reinforcement adhesives, and veneer splicing adhesives for furniture assembly. Compliance for this sector is anchored to REACH (EC) No 1907/2006 and ISO 9001:2015; formaldehyde emission standards such as CARB ATCM 93120 apply to the wood substrate, not to the cyanoacrylate adhesive. The operational boundary is that high-moisture wood above 12–15% moisture content produces foam-like cure and reduced lap shear strength; drying or kiln conditioning is required before adhesive application.
Veterinary topical tissue adhesive use differs from human wound closure in the need for low-odour monomer and rapid positioning on mobile animals. 2-Ethoxyethyl cyanoacrylate monomer, synthesized from 2-ethoxyethyl cyanoacetate, is formulated at ≥95.0 wt% monomer with 5–50 ppm hydroquinone and 20–60 ppm methanesulfonic acid stabilizer. The production process includes sterile filtration through 0.2 μm PTFE membrane into single-use applicators; terminal sterilization is typically avoided because radiation can initiate anionic polymer chain formation, so aseptic filling is used. Terminal finished product types include veterinary topical skin adhesive applicators for equine lower-leg lacerations, canine surgical incision closure, and companion animal superficial wound closure. Compliance for this sector includes ISO 10993-1:2018, ISO 10993-5:2009, USP Class VI, and the VICH GL9 good manufacturing practice guidance for veterinary products. The operational boundary is that the adhesive should not be applied to infected or macerated tissue; on large wounds exceeding 10 cm², localized polymerization exotherm may raise tissue temperature to 40–42°C, requiring re-evaluation of closure method.
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2-Ethoxyethyl cyanoacetate, registered under CAS 32804-77-6 and EINECS 251-229-5, is the 2-ethoxyethyl ester of cyanoacetic acid. The condensed formula is C7H11NO3, corresponding to a relative molecular mass of 157.17 g mol⁻¹ and a monoisotopic mass of 157.0739 g mol⁻¹. The SMILES notation CCOCCOC(=O)CC#N describes a linear ethoxyethyl chain attached through the ester oxygen. At ambient temperature the commercial product is a clear, colourless to pale yellow liquid. It is supplied as a reactive intermediate rather than a finished adhesive or formulated product. The methylene unit between the nitrile and the ester carbonyl is activated for condensation, addition, and cyclization chemistries; this active methylene is the primary reaction centre.
The 2-ethoxyethyl substituent changes the transport and solubility behaviour of the ester relative to methyl and ethyl cyanoacetate without changing the fundamental active methylene reactivity. The β-ether oxygen introduces a hydrogen-bond-accepting site and increases polarity. This polarity reduces the equilibrium vapour pressure of the ester and of the derived 2-ethoxyethyl 2-cyanoacrylate monomer. The structural effect is therefore a volatility and solubility control, not an electronic activation change. The product is selected when a less volatile Knoevenagel substrate or a lower-odour, lower-blooming cyanoacrylate monomer precursor is required.
The principal structural difference is the replacement of one terminal hydrogen in the alkyl chain of ethyl cyanoacetate with a 2-ethoxyethyl group. Methyl cyanoacetate has a relative molecular mass of 99.09 g mol⁻¹; ethyl cyanoacetate has a relative molecular mass of 113.11 g mol⁻¹; 2-ethoxyethyl cyanoacetate has a relative molecular mass of 157.17 g mol⁻¹. This increase in molecular mass and the presence of the ether oxygen lower the vapour pressure of the ester and the corresponding 2-ethoxyethyl 2-cyanoacrylate monomer. Published data for the exact vapour pressure of 2-ethoxyethyl cyanoacetate is limited; however, the direction and magnitude of the change are consistent with molecular-weight and polar-group effects observed across homologous cyanoacetate ester series.
The higher molecular mass also changes distillation behaviour. The ester cannot be recovered from reaction mixtures by simple atmospheric distillation at temperatures below 200 °C; vacuum distillation is required. In reactions conducted in dimethylformamide at 100–120 °C, the higher boiling point reduces ester loss during solvent stripping. Conversely, the increased chain length and ether oxygen raise bulk viscosity and slow phase separation in water wash steps. Production equipment therefore uses gravity settling followed by a coalescer or a polymeric membrane separator rather than a single rapid wash.
| Substance | CAS registry number | Relative molecular mass (g mol⁻¹) | Primary process consequence |
|---|---|---|---|
| Methyl cyanoacetate | 105-34-0 | 99.09 | High headspace concentration; methyl 2-cyanoacrylate monomer exhibits strong odour and visible blooming. |
| Ethyl cyanoacetate | 105-56-6 | 113.11 | Standard industrial precursor; ethyl 2-cyanoacrylate is characterized by rapid fixture and high tensile-shear adhesion. |
| 2-Ethoxyethyl cyanoacetate | 32804-77-6 | 157.17 | Lower ester volatility; precursor to 2-ethoxyethyl 2-cyanoacrylate for low-odour and low-bloom adhesive grades. |
Release specifications for merchant-grade material are not harmonized across all producers. A representative certificate of analysis includes the parameters in the following table; limits vary by application and supplier. Pharmaceutical intermediate users frequently tighten residual 2-ethoxyethanol and moisture limits beyond the values shown. The table is a screening baseline, not a universal standard.
| Property | Acceptance criterion | Test method designation |
|---|---|---|
| Appearance | Clear liquid, free of suspended matter | Visual inspection |
| Assay by gas chromatography–flame ionization detection | ≥ 98.0 area% | GC-FID, internal calibration |
| Moisture by Karl Fischer titration | ≤ 0.10 mass% | ASTM E203-16 |
| Acidity as cyanoacetic acid | ≤ 0.10 mass% | Acid–base titration |
| Colour, platinum–cobalt scale | ≤ 50 APHA | ASTM D1209-05(2019) |
| Density at 20 °C | 1.07–1.08 g cm⁻³ | ASTM D4052-18a |
| Residual 2-ethoxyethanol | ≤ 0.20 mass% | GC-FID |
During bulk esterification, cyanoacetic acid and 2-ethoxyethanol are condensed in a glass-lined reactor using an acid catalyst. Water is removed azeotropically or under reduced pressure. The crude ester is neutralized with aqueous sodium carbonate, washed, and distilled through a short-path or packed-column distillation unit. The final cut controls residual alcohol, colour bodies, and high-boiling diester impurities. Batch-to-batch variance in APHA colour is commonly reduced by a nitrogen sparge and by filtration through 1 µm polypropylene cartridges downstream of the distillation receiver. On production-scale lines, the largest processing bottleneck is slow phase separation after neutralization; residual bicarbonate or carbonate particulate can increase haze and acidity if not removed.
Identity confirmation is performed by Fourier-transform infrared spectroscopy. The nitrile stretch appears near 2250 cm⁻¹; the ester carbonyl stretch appears near 1740 cm⁻¹. Gas chromatography coupled with mass spectrometry is used to monitor residual 2-ethoxyethanol and to detect transesterification side products. For pharmaceutical intermediate supply, batch traceability is maintained under ISO 9001:2015, clause 8.5.2. Method transfer includes GC-FID assay, Karl Fischer moisture, and headspace GC-MS residual solvent analysis.
The principal industrial use of 2-ethoxyethyl cyanoacetate is as a Knoevenagel substrate in the synthesis of 2-ethoxyethyl 2-cyanoacrylate. The ester is condensed with formaldehyde or paraformaldehyde in the presence of a secondary amine catalyst, such as piperidine or pyridine, to form poly(2-ethoxyethyl 2-cyanoacrylate) oligomer. Thermal depolymerization then releases the monomer under reduced pressure. The 2-ethoxyethyl substituent raises the molecular mass of the monomer and reduces its vapour pressure relative to ethyl 2-cyanoacrylate; this is exploited in adhesives for applications requiring lower visible blooming and lower odour. Published data for this specific configuration is limited, so pilot-scale vapour-pressure and cure-speed mapping is required before transferring a formula from ethyl 2-cyanoacrylate.
The condensation is exothermic. In a glass-lined stirred reactor, the catalyst is charged as a dilute solution, and the formaldehyde source is fed in a controlled manner. The reaction mass is held below 70 °C during condensation. The reflux condenser is supplied with coolant at or below 10 °C to retain volatile cyanoacetate and formaldehyde. If the exotherm exceeds the set point, an emergency quench with dilute acetic acid is typically designed to stop the base-catalysed condensation without introducing water into the distillation section. The oligomer is then transferred to a short-path molecular distillation unit. Depolymerization of poly(2-ethoxyethyl 2-cyanoacrylate) typically requires internal temperatures above 180 °C and absolute pressures below 1 kPa. The monomer is collected into a chilled receiver charged with an acidic inhibitor, commonly methanesulfonic acid or phosphoric acid, at 5–50 ppm relative to monomer. Hot metal surfaces accelerate monomer polymerization; the distillation path is therefore constructed from glass-lined or fluoropolymer-coated contact surfaces where possible.
The monomer is not the subject of this product specification, but the precursor quality directly affects conversion. Residual moisture above 0.10 mass% in the ester reduces condensation efficiency and increases the apparent catalyst demand. Residual acidity above 0.10 mass% neutralizes the amine catalyst and can shift the condensation endpoint. Residual 2-ethoxyethanol above 0.20 mass% acts as a chain-transfer impurity and can lower oligomer molecular weight, increasing the fraction of low-boiling decomposition products during depolymerization.
Increasing side-chain length and ether content generally reduces cured polymer glass transition temperature and increases flexibility, while also reducing monomer volatility. Formulations based on 2-ethoxyethyl 2-cyanoacrylate are therefore preferred where lower odour and reduced blooming are valued, but adhesion to high-energy metal substrates may require surface primers or blends with ethyl cyanoacrylate. No single ester precursor is universally superior; selection is based on the required balance of fixture speed, bond flexibility, environmental exposure, and residual monomer behaviour.
In pharmaceutical and agrochemical intermediate synthesis, the active methylene of 2-ethoxyethyl cyanoacetate participates in Knoevenagel condensations with substituted benzaldehydes and ketones. Aromatic aldehydes are typically reacted in refluxing toluene or ethanol with a secondary amine catalyst; water is removed azeotropically to drive conversion. The resulting arylidene cyanoacetate is isolated by filtration and converted by cyclocondensation with hydrazine, guanidine, urea, or thiourea into pyrazoles, pyrimidines, and pyridones. The 2-ethoxyethyl ester is retained in some products as a solubilizing ester group, while in other routes it is hydrolyzed to cyanoacetic acid or decarboxylated after cyclization. Compared with the ethyl ester, the ethoxyethyl functionality can reduce the crystallinity of intermediates and alter partition coefficients; published data for all substitution patterns is limited, and process solubility must be verified on a per-product basis.
Solubility behaviour influences workup. The compound is miscible with polar aprotic solvents such as dimethylformamide, dimethyl sulfoxide, and acetonitrile. It partitions into the polar phase in heptane–DMF extraction systems. This behaviour reduces product loss into aliphatic hydrocarbons and changes the choice of extraction solvent relative to ethyl cyanoacetate. In continuous flow synthesis, the higher viscosity of the ester at ambient temperature requires feed-line heating or dilution with a low-viscosity co-solvent. Mass-flow controllers should be calibrated against the density value supplied on the batch certificate; a value near 1.07 g cm⁻³ is used for initial calibration.
Bulk storage should be under dry nitrogen or argon with a dew point below −40 °C for long-term stability. The ester undergoes hydrolysis to 2-ethoxyethanol and cyanoacetic acid when moisture is present; the released acid accelerates further hydrolysis. Release specifications therefore limit moisture to ≤ 0.10 mass% and acidity to ≤ 0.10 mass%. At ambient relative humidity above 60%, bulk transfers should be conducted under a nitrogen pad or the receiving vessel should be pre-dried. Prolonged exposure to humid air results in measurable moisture uptake in the ester layer.
Stainless steel and high-density polyethylene are acceptable contact materials for ambient storage. Carbon steel should be avoided because free iron can increase APHA colour and promote impurity formation. Primary, secondary, and tertiary amines should be excluded from storage and transfer lines; amine bases catalyse condensation with any free aldehyde and can generate colour, heat, and high-molecular-weight by-products. If a shared transfer system has been used for formaldehyde or glyoxal-containing intermediates, the line must be flushed with an inert solvent before and after the ester transfer. The substance is not a finished cyanoacrylate monomer and does not cure by ambient anionic polymerization; however, the downstream monomer is subject to that hazard, so segregation from alkaline aerosols is recommended in manufacturing buildings.
