| HS Code | 942189 |
| Product Name | Methoxyethyl Cyanoacetate |
| Iupac Name | 2-Methoxyethyl 2-cyanoacetate |
| Synonyms | 2-Methoxyethyl cyanoacetate; Cyanoacetic acid 2-methoxyethyl ester; Methoxyethyl cyanoacetate |
| Cas Registry Number | 10256-29-8 |
| Ec Number | 233-596-5 |
| Molecular Formula | C6H9NO3 |
| Molecular Weight | 143.14 g/mol |
| Smiles | COCCOC(=O)CC#N |
| Appearance | Clear colorless to pale yellow liquid |
| Odor | Mild ester-like odor |
| Density | 1.083 g/mL at 25 °C |
| Boiling Point | 118-120 °C at 10 mmHg |
| Refractive Index | n20/D 1.437 |
| Flash Point | >110 °C |
| Solubility | Soluble in water and common organic solvents |
| Vapor Pressure | Low at room temperature |
| Stability | Stable under normal conditions |
| Storage Conditions | Store in a cool, dry, well-ventilated area away from heat and ignition sources |
| Incompatible Materials | Strong oxidizing agents, strong acids, strong bases |
| Hazard Classification | Irritant; may be harmful if swallowed |
| Pubchem Cid | 66385 |
| Hs Code | 2926.90 |
As an accredited Methoxyethyl Cyanoacetate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | Methoxyethyl Cyanoacetate is packaged in 25 kg UN-approved steel drums, tightly sealed and clearly labeled for safe handling. |
| Container Loading (20′ FCL) | 20′ FCL container loaded with chemical Methoxyethyl Cyanoacetate in drums, palletized, securely stowed and braced for safe ocean transport. |
| Shipping | Methoxyethyl cyanoacetate is shipped as a liquid in sealed, UN-approved, leakproof containers, typically drums or jugs. Transport per applicable regulations with appropriate hazard labeling (harmful/irritant), SDS, and secondary containment. Store upright, cool, dry, away from oxidizers, heat, and ignition sources. Follow carrier and local rules. |
| Storage | Store Methoxyethyl Cyanoacetate in a cool, dry, well-ventilated area away from heat, sparks, flames, and sunlight. Keep containers tightly closed, preferably under nitrogen, to prevent moisture and hydrolysis. Separate from oxidizers, acids, bases, amines, and other incompatible materials. Use compatible, labeled containers; avoid prolonged storage. Provide spill containment and follow local regulations. |
| Shelf Life | Methoxyethyl cyanoacetate has a shelf life of about 2 years when stored sealed, cool, dry, and away from incompatible materials. |
At production scale, methoxyethyl cyanoacetate (CAS 32804-77-6) is converted to 2-methoxyethyl cyanoacrylate monomer via base-catalysed Knoevenagel condensation with paraformaldehyde followed by thermal depolymerisation. The condensation charge is 1.00 mol methoxyethyl cyanoacetate to 1.02–1.05 mol formaldehyde equivalents, with piperidine catalyst at 0.4–0.6 mol% relative to the cyanoacetate; the charge is stirred in methanol at 55–65°C for 6–8 h in a glass-lined batch reactor equipped with an anchor agitator and hot-oil jacket. Exotherm control is maintained at 65±2°C because the condensation is moderately exothermic and excursions beyond 70°C increase oligomer molecular weight, which subsequently lowers monomer recovery in the depolymerisation step. Reaction water is removed continuously by azeotropic distillation with cyclohexane through a Dean-Stark trap; if the water phase is not separated within 30 min intervals, the equilibrium shifts and the isolated oligomer yield falls below 78%. The oligomeric poly(methoxyethyl cyanoacrylate) is then fed to a wiped-film evaporator operated at 150–190°C and 1–5 mbar absolute pressure, using 0.5–1.0 wt% phosphoric acid as the acid-catalysed cracking agent. Monomer vapour is condensed on a short-path condenser held at 30–40°C and immediately stabilised with 200–500 ppm hydroquinone monomethyl ether and 50–150 ppm methanesulfonic acid to prevent anionic polymerisation. The monomer intended for medical closure devices is tested for cytotoxicity per ISO 10993-5:2009, for irritation and skin sensitisation per ISO 10993-10:2021, and is manufactured under a quality management system aligned with ISO 13485:2016. Residual formaldehyde and oligomer content in the final monomer are controlled by chemical characterisation per ISO 10993-18:2020. Terminal product types include topical skin adhesive ampoules, wound closure devices, veterinary tissue adhesives, and low-odour cyanoacrylate adhesives for applications where volatile monomer exposure must be reduced.
In pharmaceutical intermediate manufacture, methoxyethyl cyanoacetate functions as the active methylene component in a Knoevenagel condensation with substituted benzaldehydes prior to cyclisation into pyrimidinone or pyrazole scaffolds. The addition ratio is 1.00 mol methoxyethyl cyanoacetate to 1.03–1.10 mol substituted benzaldehyde, with piperidine at 0.03–0.05 mol per mol aldehyde as base catalyst and toluene as the azeotropic carrier. The reaction mass is held at 78–83°C for 8–12 h in a glass-lined or stainless-steel batch reactor fitted with a Dean-Stark separator. Water removal is the rate-limiting parameter: if the condensed water is not drawn off at least once per 30 min, the conversion of the aldehyde to the 2-cyano-3-arylacrylate intermediate stalls and the isolated yield falls below 80%; this is attributed to the reversal of the Knoevenagel equilibrium in the presence of accumulated water. After the condensation step, toluene is distilled under reduced pressure at 60–70°C and 80–120 mbar, and the intermediate is redissolved in isopropanol for cyclisation with guanidine hydrochloride or a substituted amidine at 50–60°C for 4–6 h. The crude pyrimidinone intermediate is cooled to 0–5°C, filtered on a pressure nutsche, washed with chilled isopropanol, and dried at 50–60°C under 20–40 mbar for 8–10 h. Compliance for pharmaceutical intermediate supply includes ICH Q7 Good Manufacturing Practice for active pharmaceutical ingredients, residual solvent control per ICH Q3C, elemental impurity control per ICH Q3D with analytical testing aligned to USP <232> and USP <233>, and registration obligations under REACH Annex VIII when the isolated intermediate is placed on the European market under strictly controlled conditions. Terminal product types are pyrimidinone and pyrazole carboxylate building blocks intended for downstream API synthesis; published data for specific drug candidates using this exact methoxyethyl ester intermediate is limited, so batch-specific impurity profiling by HPLC-MS is required before the material is released for pharmaceutical use.
Following the agrochemical route, methoxyethyl cyanoacetate is condensed with substituted hydrazine hydrate to construct pyrazole carboxylate intermediates that are subsequently hydrolysed to the corresponding carboxylic acids. The addition ratio is 1.00 mol methoxyethyl cyanoacetate to 1.00–1.05 mol substituted hydrazine hydrate, in the presence of 1.05–1.10 mol sodium methoxide dissolved in methanol. The methoxyethyl cyanoacetate is added dropwise at 0–5°C over 2–3 h to a jacketed glass-lined reactor; maintaining the low addition temperature prevents localized exotherm and suppresses the formation of the corresponding cyanoacetamide byproduct, which can remain as a contaminant through the downstream crystallisation. After the addition is complete, the batch is heated to 64–66°C and held for 4–6 h to close the pyrazole ring. Methanol is then partially distilled under reduced pressure at 40–50°C and 100–150 mbar, and the crude ester is saponified with 30 wt% aqueous sodium hydroxide at 80–85°C for 3–4 h. Acidification to pH 2.0–2.5 with dilute hydrochloric acid precipitates the pyrazole carboxylic acid, which is filtered on a centrifuge, washed with deionised water until the filtrate conductivity is below 50 µS/cm, and dried in a rotary vacuum dryer at 60–70°C and 20–50 mbar for 8–10 h. Compliance for non-isolated agrochemical intermediates placed on the market in Europe follows REACH Annex VIII for tonnage bands of 10–100 t/a; ready biodegradability is screened according to OECD TG 301B, and process effluent controls are typically embedded in a site environmental management system certified to ISO 14001. Terminal product types are pyrazole carboxylic acid intermediates used in subsequent herbicide and fungicide synthesis; published data for this exact methoxyethyl ester route is limited, and regional active-ingredient registrations require dossier-level impurity and residue data rather than generic intermediate specifications.
Industrial low-bloom instant adhesive formulations built from methoxyethyl cyanoacrylate monomer derived from methoxyethyl cyanoacetate typically use 10–30 wt% methoxyethyl cyanoacrylate as a low-volatility comonomer with ethyl or methyl cyanoacrylate. Stabiliser loading is 0.1–0.3 wt% hydroquinone and 0.05–0.2 wt% methanesulfonic acid; thickened grades incorporate 5–10 wt% polymethyl methacrylate with weight-average molecular weight between 120,000 g/mol and 350,000 g/mol. Mixing is carried out in a planetary mixer with vacuum degassing at 50–100 mbar and jacket temperature 20–25°C for 60–120 min at 20–40 rpm blade speed. The target Brookfield viscosity at 25°C is 800–2,500 mPa·s depending on the dispense method; needle-dispensed grades are held near the lower end of that range, while gel grades approach the upper limit. Bond performance is measured on abrasive-blasted mild steel lap shear specimens per ISO 4587:2003; after 24 h cure at 23±2°C and 50±5% RH, tensile shear strength typically falls between 14 MPa and 18 MPa for low-bloom grades. Fixture time on abraded steel is 10–25 s and on cured natural rubber is 5–15 s. Low-bloom behaviour is evaluated on black ABS coupons exposed to 40°C and 90% RH for 24 h; formulations containing 20 wt% methoxyethyl cyanoacrylate generally reduce visible white deposit relative to ethyl-only controls, but the reduction is substrate-dependent and must be confirmed by an internal test method because no harmonised international standard defines bloom acceptance limits. Compliance for the formulated adhesive includes ISO 4587:2003 for lap shear, ASTM D638-14 for cured film tensile properties, and REACH registration for the methoxyethyl cyanoacrylate monomer imported into the European Economic Area. Operational boundaries include a reduction in open time when ambient relative humidity exceeds 70%, a viscosity drift above 25°C during prolonged storage, and incompatibility with amine-containing substrates or accelerators that can initiate uncontrolled anionic cure. Terminal product types are electronics wire tacking adhesives, speaker assembly adhesives, low-fogging automotive interior trim adhesives, and general plastic bonding grades.
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2-Methoxyethyl cyanoacetate is the 2-methoxyethyl ester of cyanoacetic acid, NCCH2COOCH2CH2OCH3, with a molecular weight of 143.14 g/mol and CAS registry number 10258-54-5. The product is supplied primarily as a technical-grade liquid for condensation chemistry and as an intermediate in alkoxyethyl cyanoacrylate adhesive production. Commercial designations commonly use a suffix such as “-99T” to indicate a 99.0% minimum assay by gas chromatography. The molecule contains a single active methylene group between the nitrile and carbonyl functions, which is the reactive site for Knoevenagel, Gewald, and Michael addition chemistry. The terminal β-methoxy substituent is the principal structural difference from methyl cyanoacetate and ethyl cyanoacetate, because it introduces an additional ether oxygen without adding a second reactive center.
Because the side chain is more polar than a simple alkyl chain, the product shows greater water tolerance and different solvent affinity. These properties affect downstream processing: the ester is more readily partitioned into polar oxygenated solvents, and the resulting cyanoacrylate monomer exhibits different polymer-chain mobility and hydrolytic stability than ethyl cyanoacrylate. The following sections define the comparative position, analytical release controls, and operational limits of the product.
The table compares structural identifiers and qualitative volatility differences among the three most common cyanoacetate esters used in Knoevenagel chemistry. Quantitative vapor-pressure data must be taken from the supplier safety data sheet for the specific lot, because trace solvent and inhibitor content can shift the measured values.
| Parameter | Methyl cyanoacetate | Ethyl cyanoacetate | 2-Methoxyethyl cyanoacetate |
|---|---|---|---|
| CAS registry number | 105-34-0 | 105-56-6 | 10258-54-5 |
| Molecular formula | C4H5NO2 | C5H7NO2 | C6H9NO3 |
| Molecular weight | 99.09 g/mol | 113.11 g/mol | 143.14 g/mol |
| Side-chain terminal group | Methyl | Ethyl | 2-Methoxyethyl |
| Relative volatility at processing temperature | Higher | Moderate | Lower |
| Typical downstream monomer | Methyl cyanoacrylate | Ethyl cyanoacrylate | 2-Methoxyethyl cyanoacrylate |
Relative to methyl cyanoacetate and ethyl cyanoacetate, the 2-methoxyethyl ester is less volatile and more polar. This does not automatically make it a slower condensation partner; reaction rates in Knoevenagel condensations are solvent- and catalyst-dependent, and the ether oxygen can coordinate weakly with Lewis acid catalysts or polar intermediates. In adhesive monomer production, the ester is converted to 2-methoxyethyl cyanoacrylate, which provides a more flexible side chain than ethyl cyanoacrylate and is evaluated where lower volatile bloom or increased bond-line flexibility is required. Published side-by-side adhesion data for all homologs under identical surface preparation and cure conditions are limited.
Because residual water and acidity affect condensation stoichiometry and product color, commercial material is controlled by capillary gas chromatography, Karl Fischer titration, and acidity titration. The release matrix below is representative of a condensation-grade specification; it is not a universal pharmacopoeial monograph.
| Property | Typical specification | Test method |
|---|---|---|
| Assay | ≥ 99.0% by GC-FID | In-house capillary GC calibrated with reference standard |
| Water | ≤ 0.10% | ASTM E203-16 |
| Acidity | ≤ 0.50 mg KOH/g | ASTM D1613-17 |
| Density at 20 °C | 1.12–1.14 g/cm³ | ASTM D4052 |
| Refractive index at 20 °C | 1.428–1.434 | ASTM D1218 |
| Inhibitor content | Trace radical inhibitor, product-specific | Supplier certificate |
Purity by GC-FID is typically run on a low-bleed methyl polysiloxane capillary column using split injection and flame ionization detection. Residual cyanoacetic acid and 2-methoxyethanol are quantitated by external calibration against reference materials. No single ASTM or ISO consensus method covers the trace assay of methoxyethyl cyanoacetate, so supplier in-house methods are normalized to certified reference standards. For pharmaceutical intermediate use, impurity and residual solvent limits should be reviewed under ICH Q3A and ICH Q3C rather than relying solely on area-percent purity.
In cyanoacrylate monomer production, methoxyethyl cyanoacetate is condensed with paraformaldehyde or formalin in the presence of a secondary amine catalyst, forming a cyanoacrylate oligomer. The condensation is usually controlled at 60–80 °C, and the oligomer is then dehydrated and depolymerized under high vacuum. Production-scale depolymerization generally uses a wiped-film evaporator, short-path evaporator, or agitated thin-film dryer with the heating medium held below 200 °C and system pressure below 10 mbar. At wall temperatures above 210 °C, residue tar formation and ester decomposition increase sharply; below 160 °C, monomer takeoff becomes too slow for continuous operation. Acidic depolymerization catalysts such as p-toluenesulfonic acid or phosphorus pentoxide are common, and a free-radical inhibitor such as hydroquinone or 4-methoxyphenol is added to the receiver to prevent premature polymerization. The methoxyethyl side chain produces a monomer with lower vapor pressure and greater side-chain mobility than ethyl cyanoacrylate, but the same structural feature narrows the thermal cracking window. Batch-to-batch variation in moisture above 0.15% is particularly destructive because water hydrolyzes the ester, releases cyanoacetic acid, and shifts oligomer molecular-weight distribution. Reactor systems are therefore dried before charging and blanketed with nitrogen to maintain a low dew point. Published data for this specific configuration is limited.
In formulated cyanoacrylate adhesives, 2-methoxyethyl cyanoacrylate is sometimes combined with ethyl cyanoacrylate to modify viscosity and cure behavior without the use of non-reactive plasticizers. The ether side chain disrupts crystal packing in the polymer, which tends to lower modulus and increase elongation at break. Adhesive specimens should be tested according to ASTM D1002 or ISO 4587 for single-lap shear, and ASTM D638 or ISO 527 for free-film tensile properties. Because the monomer is less volatile than ethyl cyanoacrylate, visible bloom on surrounding surfaces is reduced, but cure speed can also be retarded by the same molecular-weight effect. Surface-insensitive cyanoacrylate formulations may require crown ether or calixarene accelerators to achieve fixture times comparable to ethyl cyanoacrylate on acidic substrates. Formulation data for this specific product are not publicly standardized across all substrate classes.
For hydrolytic stability screening, accelerated conditioning at 40 °C and 75% RH for 72 h is a common comparative condition, but the results are not a substitute for application-specific environmental testing. Poly(2-methoxyethyl cyanoacrylate) generally absorbs more water than poly(ethyl cyanoacrylate) because of the ether oxygen, and this can reduce lap-shear retention on hydrolytically sensitive substrates. The product is therefore selected when the flexible side chain is functionally necessary, not as a direct drop-in replacement for ethyl cyanoacrylate.
Methoxyethyl cyanoacetate should be stored in sealed stainless steel or glass-lined equipment at 15–25 °C under nitrogen padding. If free water enters a storage vessel, hydrolysis releases cyanoacetic acid and 2-methoxyethanol, increasing acidity and reducing assay. The effect is accelerated by residual alkaline contaminants; strongly basic ion-exchange resins, primary amines, and alkali metal alkoxides should not be used for drying or neutralization because they promote amidation, Michael addition, and darkening. Carbon steel is not recommended for prolonged contact when water is present, because released cyanoacetic acid can corrode plain steel and contaminate the product with iron. For drums and intermediate bulk containers, moisture ingress is controlled by desiccant breathers or nitrogen padding at 0.1–0.3 bar gauge. Re-evaluation after 12 months is common, but the assigned retest period must follow the supplier certificate of analysis and the specific container closure system.
Solvent drying with molecular sieves is generally unsuitable for cyanoacetate esters because sieves can leach alkaline metal ions that catalyze side reactions. If water or acidity exceeds the approved specification, the preferred correction is controlled vacuum distillation under inhibited conditions rather than chemical neutralization. The distillation cut is monitored for color and acidity; fractions outside the release limits are rejected or used only after rework.
In pharmaceutical and agrochemical intermediate synthesis, methoxyethyl cyanoacetate is used as an active methylene building block for 2-aminothiophenes, pyridones, coumarins, and related heterocycles. The ester group often remains in the final product for subsequent hydrolysis or transesterification. Because the β-methoxy substituent is more polar than an ethyl or butyl chain, intermediates may show increased partitioning into polar solvents and easier removal of nonpolar byproducts. The ether oxygen can also coordinate weakly with Lewis acid catalysts or acidic silica gel, which may alter reaction rate or chromatographic retention time. When scaling a route from methyl or ethyl cyanoacetate to the methoxyethyl ester, the solvent ratio and catalyst loading may require adjustment; the change in ester alkyl group is not merely a stoichiometric substitution.
Compared with ethyl cyanoacetate, methoxyethyl cyanoacetate has higher molecular weight, lower volatility, and higher water tolerance. Compared with benzyl cyanoacetate, it avoids introducing an aromatic chromophore that can complicate UV monitoring and aromatic impurity profiles. Compared with direct acrylate or methacrylate monomers, it is not a final adhesive monomer and should not be handled as an acrylate; its toxicological and sensitization profile must be assessed from the supplier safety data sheet because the cyanoacetate ester and its downstream cyanoacrylate monomer are distinct substances under chemical-control frameworks such as REACH and TSCA.
