| HS Code | 938157 |
| Product Name | Methyl Cyanoacetate |
| Iupac Name | Methyl 2-cyanoacetate |
| Cas Number | 105-34-0 |
| Ec Number | 203-288-9 |
| Molecular Formula | C4H5NO2 |
| Molecular Weight | 99.09 g/mol |
| Appearance | Colorless to light yellow liquid |
| Density | 1.123 g/cm3 at 25 °C |
| Boiling Point | 204-205 °C |
| Melting Point | -22.5 °C |
| Flash Point | 110 °C (closed cup) |
| Refractive Index | 1.4175 at 20 °C |
| Solubility | Soluble in water, ethanol, and ether |
| Vapor Pressure | 0.2 hPa at 20 °C |
| Chemical Category | Cyanoacetate ester |
As an accredited Methyl Cyanoacetate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | Methyl cyanoacetate is supplied in 200 L UN-approved steel drums, securely sealed and labeled with hazard warnings for safe transport. |
| Container Loading (20′ FCL) | Methyl Cyanoacetate loaded into 20′ FCL, packed in sealed drums, palletized, secured, labeled, and shipped under applicable transport regulations. |
| Shipping | Methyl cyanoacetate is shipped as a toxic liquid under UN 3276, Nitriles, toxic, liquid, n.o.s. (Methyl cyanoacetate), Class 6.1, Packing Group III. Use UN-approved packaging, toxic labels, and compliant documentation. Store closed, away from heat, sparks, oxidizers, and incompatible materials. Follow DOT, IATA, and IMDG regulations. |
| Storage | Store methyl cyanoacetate in a cool, dry, well-ventilated area away from heat, sparks, flames, and strong oxidizers. Keep containers tightly closed, upright, and labeled. Use non-sparking equipment and secondary containment. Segregate from acids, bases, reducing agents, and food/feed. Protect from moisture and direct sunlight. Ensure appropriate ventilation and spill-control measures. Store only in approved flammable-liquid cabinets or safety cans. |
| Shelf Life | Methyl cyanoacetate typically has a 24–36 month shelf life when stored sealed, cool, dry, and protected from moisture, heat, and light. |
Production-scale conversion of methyl cyanoacetate to 2-cyanoacrylate monomer begins with a Knoevenagel condensation against paraformaldehyde in a jacketed, glass-lined reactor fitted with a wiped-film evaporator for oligomer workup. The feed ratio is maintained at 1.0:0.95–1.05 methyl cyanoacetate to formaldehyde equivalents; piperidine catalyst is metered at 0.5–1.5 wt% of the total charge. The reaction mass is held at 60–80 °C under atmospheric pressure for 6–10 h with continuous water removal via toluene azeotrope. The resulting poly(methyl cyanoacrylate) is neutralized, washed, and transferred to a depolymerization vessel charged with 0.5–1.0 wt% phosphorus pentoxide and 100–500 ppm hydroquinone monomethyl ether as radical inhibitor. Thermal cracking is executed at 180–220 °C and 10–20 mbar; monomer vapor is condensed and subjected to fractional distillation. Batch-to-batch viscosity excursions in the oligomer phase are controlled by limiting free formaldehyde to less than 1.0% of theoretical charge. Compliance for adhesive-grade monomer includes ISO 13485:2016, ISO 10993-5:2009 cytotoxicity testing, and FDA 21 CFR 175.105 where food-contact adhesive formulations are declared. Terminal products include methyl, ethyl, and 2-octyl cyanoacrylate monomers formulated into industrial instant adhesives, structural bonding systems, and medical tissue adhesives.
In pharmaceutical intermediate synthesis, methyl cyanoacetate is commonly condensed with substituted benzaldehydes or heteroaryl aldehydes to yield α-cyanoacrylic esters; subsequent cyclization with amidines, guanidines, or hydrazines forms pyrimidine, pyrazole, and pyridone platforms. A representative batch uses methyl cyanoacetate and the aldehyde at a molar ratio of 1.0:1.0–1.1, with piperidinium acetate catalyst at 0.02–0.05 eq in toluene under Dean-Stark reflux at 110–115 °C for 4–8 h. Process-scale equipment includes 2,000 L glass-lined reactors and 0.5 m² Hastelloy crystallizers; isolated yields typically exceed 85% after slurry filtration and vacuum drying at 60 °C. Compliance is governed by ICH Q7 for GMP, ICH Q3C residual solvent class limits, ICH Q3D elemental impurity risk assessment, and USP <467> chromatographic solvent testing. The operational boundary is strict: residual toluene must remain below 890 ppm and methanol below 3,000 ppm before release. Terminal products include pyrimidinone, pyrazole, and coumarin-derived API intermediates, which are subsequently formulated as tablets, capsules, or sterile injectables.
Agrochemical intermediate production often routes methyl cyanoacetate through cyanoacetamide and malononitrile before installation into herbicidal or fungicidal scaffolds. Continuous amidation is performed with methanolic ammonia at a mole ratio of 1.0:1.5–2.0 methyl cyanoacetate to NH₃ in a packed-column reactor at 40–50 °C and 3–5 bar. The resulting cyanoacetamide is dehydrated with phosphorus oxychloride at 1.0–1.1 eq in dichloroethane at 70–80 °C to give malononitrile. The malononitrile stream is then condensed with substituted aromatic or heteroaromatic aldehydes at 1.0:1.05 molar ratio to generate agrochemical intermediates. Regulatory compliance includes EPA 40 CFR Part 158 data requirements, FAO/WHO JMPS specifications for technical material, REACH (EC) No 1907/2006, and ISO 9001:2015 for site quality systems. Terminal product types include herbicidal sulfonylurea intermediates, insecticidal nitromethylene precursors, and fungicidal acrylate analogs; formulated products are released as suspension concentrates, water-dispersible granules, or emulsifiable concentrates.
Octocrylene and related 2-cyano-3,3-diphenylacrylate UV absorbers are prepared from methyl cyanoacetate through a two-stage sequence: ester exchange with 2-ethylhexanol, followed by Knoevenagel condensation with benzophenone. The first stage uses 1.0:1.15–1.25 methyl cyanoacetate to 2-ethylhexanol molar ratio, 0.3–0.5 wt% tetrabutyl titanate or dibutyltin oxide, and reactive distillation at 120–140 °C under 300–500 mbar with methanol removal. The second stage charges benzophenone at 1.0:1.0–1.05 relative to 2-ethylhexyl cyanoacetate and piperidinium acetate at 0.03 eq in cyclohexane, with water removal at 80–90 °C. Crystallization from ethanol yields octocrylene with purity above 98%. Compliance for sunscreen applications includes FDA 21 CFR 352.10, Commission Regulation (EU) No 1223/2009, Annex VI, and ISO 9001:2015 for non-cGMP manufacturing. Polymer stabilizer grades are governed by REACH and RoHS Directive 2011/65/EU when used in electrical/electronic plastics. Terminal product types include octocrylene, etocrylene, and 2-ethylhexyl cyanoacetate, formulated into sunscreens, PVC films, polycarbonate glazing, and acrylic coatings.
Methyl cyanoacetate participates in the synthesis of 5-amino-1-aryl-3-pyrazolones, which serve as coupling components for disazo and reactive dye chromophores. The condensation is carried out with substituted phenylhydrazines at a molar ratio of 1.0:1.05 in ethanol or isopropanol at reflux (78–82 °C) for 5–7 h, followed by crystallization and vacuum drying. The pyrazolone intermediate is then diazotized and coupled to aromatic diazonium salts at 0–5 °C and pH 7.5–8.5 to form yellow, orange, and red dye molecules. Process equipment typically includes 1,000–5,000 L glass-lined reactors with brine-cooled jackets and plate-and-frame filter presses. Compliance for dyestuff intermediates includes REACH registration, OEKO-TEX Standard 100 for textile residue limits, and ZDHC MRSL V3.1 for chemical input restrictions. Terminal product types include disperse dye powders, solvent dyes for plastics, and reactive dyes for cellulosic textiles. Published formulation data for specific Color Index designations is limited because exact coupling sequences are often proprietary; however, the cyanoacetate-derived pyrazolone route is well documented in dyestuff chemistry.
Malonate and cyanoacetamide derivative manufacturing uses methyl cyanoacetate as the acid-stable C2 synthon for diethyl malonate, malononitrile, and malonamide. Acidic hydrolysis is performed with 2.5–3.0 eq hydrochloric acid in water at 95–100 °C for 8–12 h, producing malonic acid; esterification with ethanol at 3.0–4.0 eq and sulfuric acid at 0.05–0.1 wt% under azeotropic water removal yields diethyl malonate. Alternatively, cyanoacetamide is obtained by ammonolysis with methanolic ammonia at 1.0:1.5 mole ratio and 40–50 °C. The equipment train includes glass-lined hydrolysis vessels, packed distillation columns for ethanol recovery, and wiped-film evaporators for high-boiling ester purification. Compliance includes REACH (EC) No 1907/2006, ICH Q3C for pharmaceutical-grade diethyl malonate, and FDA 21 CFR 172.515 for synthetic flavoring substance use where applicable. Terminal product types include diethyl malonate, malononitrile, malonamide, and malonic acid, which are subsequently converted into barbiturate APIs, vitamin intermediates, agrochemical precursors, and flavor esters. The main operational boundary is catalyst inactivation by water during esterification; therefore, feed ethanol must be dried below 0.1% water, and the reaction vessel should be blanketed with dry nitrogen to maintain batch consistency.
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Product designation for methyl cyanoacetate is not standardized under a single model number; the material is customarily supplied as technical grade or synthesis grade distinguished by assay, water content, and acidity. The compound, CAS Registry Number 105-34-0 and linear formula NCCH2COOCH3, has a relative molecular mass of 99.09 g/mol. At 20 °C the density measured by ASTM D4052 is approximately 1.123 g/mL; the normal boiling point is 204–205 °C and the closed-cup flash point is approximately 94 °C. It appears as a clear, colourless to pale-yellow liquid with a weak ester-nitrile odour. Because the molecule contains both a nitrile and a methyl ester function attached to the same methylene bridge, the α-hydrogens are sufficiently acidic for enolate formation under weak base. This positions the product as a carbon nucleophile in condensation reactions, rather than as a solvent or plasticiser. Commercial material is typically supplied in 200 kg drums or 1000 L intermediate bulk containers; published data for specific packaging configurations is limited.
Storage instability is primarily hydrolytic rather than thermal. Under neutral or slightly acidic conditions, the ester is stable for at least 12 months in sealed, dry containers at 15–30 °C; in the presence of free water, nitrile and ester hydrolysis releases cyanoacetic acid and methanol, with the rate increasing rapidly above pH 8. Therefore, process equipment should be closed-loop, glass-lined or Type 316L stainless steel, and nitrogen-blanketed where ambient relative humidity exceeds 60%. Carbon steel is not recommended because accumulated cyanoacetic acid can initiate corrosion and iron contamination can discolour the liquid. Alkalinity presents a second limit: strong bases convert the ester to the corresponding enolate, and if water is present, saponification competes with desired carbon-carbon bond formation. On production lines, addition of any amine catalyst should be controlled to maintain pH in the range 6–8; otherwise batch-to-batch variation in isolated yield can exceed 5%. Suppliers typically specify water content by ASTM E203 at ≤0.10% and acidity as cyanoacetic acid at ≤0.20% to reduce these failure modes.
The following specification profile is representative of synthesis-grade methyl cyanoacetate offered by merchant suppliers; actual limits vary by manufacturer and may be tightened for cyanoacrylate-monomer production. Incoming material should be confirmed against the certificate of analysis for each batch.
| Parameter | Typical synthesis-grade limit | Test method |
|---|---|---|
| Assay | ≥99.0% by GC-FID | Internal GC-FID, reference standard 99.5% |
| Water content | ≤0.10% | ASTM E203 |
| Acidity as cyanoacetic acid | ≤0.20% | Aqueous acid-base titration |
| Colour | ≤15 Pt-Co | ASTM D1209 |
| Density at 20 °C | 1.120–1.125 g/mL | ASTM D4052 |
| Refractive index nD20 | 1.416–1.418 | Refractometer |
Because no single pharmacopoeial monograph applies to methyl cyanoacetate as a raw material, analytical laboratories align internal GC-FID methods with ISO 17025 calibration requirements and qualify reference standards by mass balance. Water content by ASTM E203 is preferred over loss-on-drying because the ester is volatile; Karl Fischer coulometric titration gives a detection limit of approximately 50 ppm in routine use.
Technical-grade material may contain trace methanol, water, and higher-boiling condensation impurities. During vacuum distillation at reduced pressure, methanol is removed as a light ends fraction and high-boiling impurities remain in the pot; the main fraction is collected at reduced pressure to avoid thermal discolouration. Published process-yield data for large-scale distillation of methyl cyanoacetate are limited, and pilot trials are advised before committing to a specific reflux ratio or pressure set point.
Methyl cyanoacetate is used as an active-methylene component in Knoevenagel condensation with aldehydes or ketones. The reaction is generally conducted in toluene or methanol at 40–80 °C with a catalytic quantity of ammonium acetate or a secondary amine. Water generated by the condensation is removed by a Dean–Stark trap; if water is not removed, hydrolysis of the ester lowers the selectivity for the alkylidene product and can produce cyanoacetamide by-products. In pharmaceutical intermediate synthesis, the methyl ester is selected when downstream chemistry requires transesterification with higher alcohols or aminolysis to amides because methanol leaves the distillate as a low-boiling component. The condensation products, methyl α-cyanoacrylates, are used directly as Michael acceptors in cyclization to 2-amino-4H-pyrans and pyrazoles. Kinetic control is sensitive to base strength; pyridine gives lower conversion than pyrrolidine at 60 °C, but pyrrolidine increases the risk of oligomerization when the aldehyde is electronically poor. Published data for this specific configuration is limited; batch screening is recommended before scale-up.
For cyanoacrylate adhesive monomer production, methyl cyanoacetate is condensed with formaldehyde under alkaline conditions to produce a poly(methyl cyanoacrylate) prepolymer. The prepolymer is dried and thermally depolymerized under vacuum; the resulting methyl cyanoacrylate monomer is distilled and stabilized with free-radical and anionic inhibitors. Compared with ethyl cyanoacetate, the methyl ester has a lower molecular weight and lower normal boiling point, which can reduce the temperature required for depolymerization, but the resulting methyl cyanoacrylate is more volatile and shows a shorter working time in bond-line applications. Process equipment for this route includes stirred reactors with anchor agitators and vacuum distillation columns with short residence times; depolymerization above 180 °C can generate cyanide-containing degradation products if temperature control fails. Publication of detailed thermal data is limited, so installation of independent over-temperature interlocks is recommended.
Selection between methyl cyanoacetate and ethyl cyanoacetate is governed by boiling point, flash point, vapour pressure, and the final alkyl cyanoacrylate or heterocycle. Methyl cyanoacetate has a lower normal boiling point and higher density than ethyl cyanoacetate; this can simplify solvent recovery after condensation but increases closed-container pressure in warm storage. Table 2 gives representative physical property data from public safety data sheets; values vary by supplier.
| Property | Methyl cyanoacetate | Ethyl cyanoacetate |
|---|---|---|
| CAS Registry Number | 105-34-0 | 105-56-6 |
| Relative molecular mass | 99.09 g/mol | 113.11 g/mol |
| Normal boiling point | 204–205 °C | 208–210 °C |
| Density at 20 °C | 1.123 g/mL | 1.062 g/mL |
| Closed-cup flash point | 94 °C | 110 °C |
In practice, ethyl cyanoacetate is more commonly used in cyanoacrylate adhesive production because the ethyl monomer provides a balance of adhesion speed, low-temperature performance, and irritant profile. Methyl cyanoacetate remains relevant when the final product must be methyl cyanoacrylate or when lower-boiling solvent recovery is an advantage. Published data comparing mechanical properties of methyl versus ethyl cyanoacrylate adhesives are limited; formulated adhesive performance is determined by thickeners, plasticizers, and stabilizers that obscure the base monomer effect. Higher alkyl cyanoacetates such as butyl cyanoacetate are used when a higher-boiling intermediate is required; their densities are lower than the methyl ester, but supplier-specific data should be used for thermal design.
Compared with cyanoacetic acid, methyl cyanoacetate is easier to charge as a liquid and avoids the handling difficulties of a solid acid. Compared with diethyl malonate, the nitrile function provides a lower molecular weight and a polar cyano handle for cyclization. This distinction matters in cyclocondensation routes: methyl cyanoacetate yields a nitrile-substituted heterocycle, whereas malonates yield an ester-substituted heterocycle. The nitrile can be reduced to an aminomethyl or hydrolyzed to a carboxamide after cyclization, but the hydrolysis step must be controlled because overhydrolysis converts the ester to the carboxylic acid before ring closure.
Agrochemical synthesis routes use methyl cyanoacetate as a C-2 building block for pyrimidine and pyrazole intermediates. In condensation with substituted hydrazines, the ester forms 5-amino-1H-pyrazole-4-carboxylates; subsequent hydrolysis and decarboxylation afford pyrazole intermediates for fungicide and insecticide programmes. Because the methyl ester is less sterically hindered than the ethyl ester, alkaline hydrolysis may proceed more rapidly; however, published direct kinetic comparisons are limited. Batch processing in pilot plants generally uses glass-lined reactors with overhead condensers and caustic scrubbers; the nitrile-containing vapour phase is routed through activated carbon beds before release. Scale-up data from field reports indicate that batch cycle time is limited more by the rate of methanol removal than by conversion, but published comparative kinetic data for methyl versus ethyl ester hydrolysis are limited.
Toxicologically, methyl cyanoacetate is classified as a flammable liquid and an irritant; combustion or high-temperature decomposition can release hydrogen cyanide. Supplier SDSs report closed-cup flash point values in the range 92–94 °C; the liquid should be handled with local exhaust ventilation and grounded transfer lines to control static discharge. Spill containment should use dry inert absorbents; water wash-down can generate methanol and cyanoacetic acid and may exceed wastewater pH limits. Personnel exposure should be assessed according to the applicable occupational exposure limit framework; no specific ACGIH TLV is established for methyl cyanoacetate. In the absence of a specific limit, workplace air monitoring should include methanol and cyanide hydrolysis products, and closed handling with vapour recovery is recommended.
Regulatory status for methyl cyanoacetate is primarily as an industrial intermediate under REACH; it is not marketed as a consumer article. Quality systems for material supplied to pharmaceutical and agrochemical processes are aligned with ISO 9001:2015 and, where appropriate, ICH Q7 Good Manufacturing Practice for active pharmaceutical ingredients. The material is subject to GHS classification for flammable liquid; no food-contact or pharmacopoeial status is implied. In transfer operations, pumps and seals should be compatible with the ester and any trace acid; perfluoroelastomer or polytetrafluoroethylene-bound gaskets are preferred over nitrile rubber, which may swell in prolonged contact.
Incoming quality control for methyl cyanoacetate should verify the homolog identity by Fourier transform infrared spectroscopy according to ASTM E1252, assaying the nitrile stretch near 2250 cm⁻¹ and ester carbonyl near 1745 cm⁻¹, followed by GC-FID for assay and impurity peaks. A batch with water above 0.15% or titratable acidity above 0.30% should not be used in cyanoacrylate monomer production without pre-drying with molecular sieve 3A or neutral alumina treatment; published data for this specific configuration is limited. These thresholds are practical control points observed on production lines, not regulatory maxima.
