| HS Code | 573660 |
| Product Name | Isopropyl Cyanoacetate |
| Synonyms | Isopropyl cyanoacetate; propan-2-yl 2-cyanoacetate; 2-propyl cyanoacetate; cyanoacetic acid isopropyl ester |
| Cas Number | 14447-15-5 |
| Molecular Formula | C6H9NO2 |
| Linear Formula | NCCH2COOCH(CH3)2 |
| Molecular Weight | 127.14 g/mol |
| Iupac Name | Propan-2-yl 2-cyanoacetate |
| Chemical Family | Cyanoacetate ester |
| Physical State | Liquid |
| Appearance | Colorless to almost colorless clear liquid |
| Odor | Characteristic ester-like odor |
| Boiling Point | 207-208 °C |
| Density | 0.977 g/mL at 25 °C |
| Refractive Index | n20/D 1.419 |
| Flash Point | 198 °F (92 °C) |
| Solubility | Soluble in organic solvents; slightly soluble in water |
| Storage Conditions | Store in a cool, dry, well-ventilated place; keep container tightly closed |
| Stability | Stable under normal temperatures and pressures |
| Incompatible Materials | Strong oxidizing agents, strong acids, strong bases |
| Decomposition Products | Carbon monoxide, carbon dioxide, nitrogen oxides |
| Typical Purity | ≥98% |
| Hazard Statements | May cause skin, eye, and respiratory irritation |
| Signal Word | Warning |
As an accredited Isopropyl Cyanoacetate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | Isopropyl Cyanoacetate is packaged in 1 L amber glass bottles with PTFE-lined caps, individually sealed and clearly labeled. |
| Container Loading (20′ FCL) | 20′ FCL container loaded with Isopropyl Cyanoacetate in sealed drums, palletized, evenly distributed, properly secured, and labeled for safe transport. |
| Shipping | Isopropyl cyanoacetate is generally not classified as dangerous goods for transport. Ship in tightly closed, properly labeled containers in a cool, dry, ventilated area away from oxidizers and ignition sources. Consult the current SDS and DOT/IATA/IMDG rules, as requirements may vary. |
| Storage | Store Isopropyl Cyanoacetate in a cool, dry, well-ventilated area, away from heat, sparks, flames, and direct sunlight. Keep containers tightly closed and labeled. Segregate from strong oxidizers, acids, bases, and reducing agents. Do not store near food, feed, or incompatible materials. Ensure adequate ventilation and secondary containment where appropriate, following local regulations. |
| Shelf Life | Stable for about two years if kept tightly sealed, cool, dry, and protected from moisture, heat, light, and oxidizing agents. |
In cyanoacrylate monomer production, isopropyl cyanoacetate is charged into a glass-lined 500–2000 L reactor with 1.05–1.20 mol paraformaldehyde per 1.00 mol ester, 0.02–0.05 mol piperidinium acetate, and 250–400 mL toluene per mole ester. The mixture is heated to 105–112°C under azeotropic reflux. Water is removed through a Dean-Stark trap until water collection rate falls below 0.1 mL/h. The resulting poly(isopropyl 2-cyanoacrylate) is washed with 5 wt% sodium chloride solution and dried at 50–60°C under reduced pressure. Depolymerization is performed in a wiped-film evaporator with heated area 0.04–0.10 m² per kg/h feed, jacket temperature 160–190°C, and absolute pressure 0.5–2.0 kPa. 0.1–0.5 wt% hydroquinone and 0.05–0.2 wt% phosphorus pentoxide are added to the oligomer feed. The monomer vapor is condensed at −5–0°C and stabilized with 30–100 ppm sulfur dioxide or 100–500 ppm methanesulfonic acid. Gas chromatography with flame ionization detection confirms monomer purity above 99.0 area%. Water content is held below 0.05 wt% by ASTM E203. Residual isopropyl cyanoacetate above 0.3 wt% is a batch-to-batch failure mode; the unconverted ester plasticizes the cured bond line and reduces tensile lap-shear strength measured according to ASTM D1002 on grit-blasted 2024-T3 aluminium coupons. Production lines reject such batches rather than redistill because the boiling point difference between the ester and the monomer narrows under high vacuum. The isopropyl monomer has a bulkier side chain than ethyl 2-cyanoacrylate, which modifies cure speed on low-energy plastics. Published comparative adhesion data for this monomer on specific plastic substrates is limited; target-substrate validation must follow ISO 4587 tensile lap-shear testing. Basic contaminants and amine-containing equipment lubricants must be excluded because trace alkalinity initiates anionic repolymerization.
| Raw material control parameter | Specification | Test method |
|---|---|---|
| Purity by GC | ≥ 99.0% area | Capillary GC, FID |
| Water content | ≤ 0.05 wt% | ASTM E203 |
| Acidity as cyanoacetic acid | ≤ 0.1 wt% | Alkalimetric titration |
| Boiling range | 194–196°C at 101.3 kPa | ASTM D1078 |
| Color | ≤ 20 APHA | ASTM D1209 |
Pharmaceutical intermediate synthesis with isopropyl cyanoacetate follows active methylene condensation first, not ester hydrolysis. A glass-lined reactor is charged with 1.00 mol isopropyl cyanoacetate, 1.00–1.10 mol substituted benzaldehyde, 0.03–0.08 mol piperidinium acetate, and 300–500 mL cyclohexane per mole ester. The batch is refluxed at 70–80°C for cyclohexane-water azeotrope removal or at 110–115°C when toluene is used. The endpoint is determined by capillary GC when the residual ester peak falls below 0.5 area%. The condensation product, isopropyl 2-cyano-3-arylacrylate, is isolated by crystallization. Cyclization with hydrazine hydrate in ethanol at 75–80°C forms 5-amino-1H-pyrazole-4-carboxylate intermediates. The isopropyl ester is selected over the methyl ester when the subsequent route requires mild ester hydrolysis; isopropyl esters release isopropanol rather than methanol, which simplifies solvent recovery in GMP intermediate production. Water content above 0.1 wt% in the raw ester causes partial hydrolysis to cyanoacetic acid, which decarboxylates at elevated temperature and reduces conversion. Glass-lined equipment is required because trace iron under acidic conditions promotes color formation and can catalyze ester hydrolysis. The isolated intermediate is dried at 45–50°C under vacuum before cyclization. Residual solvent control follows ICH Q3C; toluene is held below 890 ppm and cyclohexane below 3880 ppm in the final isolated intermediate. Published yield data for this specific isopropyl ester route is limited compared with ethyl cyanoacetate; pilot batches should confirm crystallization behavior.
Among azo dye intermediate supply chains, direct use of isopropyl cyanoacetate as a coupling component is not standard industrial practice. The ester is first aminolysed with ammonia or primary amines to form cyanoacetamide derivatives, which are active methylene components for disperse azo dye synthesis. Published data specific to isopropyl cyanoacetate in azo coupler production is limited; methyl and ethyl cyanoacetates dominate documented dye routes because their lower molecular weight and easier crystallization reduce solvent recovery costs.
When a toll manufacturing site operates isopropanol recovery capacity, isopropyl cyanoacetate can serve as a transesterification feedstock for methyl or ethyl cyanoacetate. The ester is reacted with 1.5–3.0 mol methanol per mole ester in a jacketed stainless steel reactor with 0.5–1.0 wt% titanium tetraisopropoxide or dibutyltin oxide. The batch is held at 60–70°C for 4–8 h. Isopropanol is withdrawn through a fractional distillation column with 10–15 theoretical plates to shift equilibrium. After washing with 5 wt% sodium bicarbonate, methyl cyanoacetate is fractionated at 202–204°C at atmospheric pressure. The recovered isopropanol is dried and reused. The main batch failure is retained isopropyl ester above 0.5 wt% in the methyl cyanoacetate cut; this level changes crystallization rates in the subsequent pyrimidine ring closure for agrochemical intermediates. The route is adopted only when site-specific cost analysis shows that transesterification yield loss and energy recovery remain acceptable against direct methyl cyanoacetate purchase.
Cyanoacetamide is obtained from isopropyl cyanoacetate by controlled aminolysis under aqueous ammonia. A stainless steel pressure reactor is charged with 1.00 mol ester and 1.5–2.5 mol ammonia as 25 wt% ammonium hydroxide. The reaction is held at 40–50°C until capillary GC shows residual ester below 0.5 area%. Isopropanol and residual water are stripped under vacuum at 60–70°C. The crude cyanoacetamide is recrystallized from ethanol or water to ≥ 99.0% purity by HPLC. Cyanoacetamide is a precursor for malononitrile via dehydration with phosphorus oxychloride or via cyano group exchange. The isopropyl route is selected when low-chloride cyanoacetamide is required because the ester can be distilled to chloride levels below 10 ppm. Ammonium hydroxide addition must be controlled to keep the batch below 50°C because the aminolysis is exothermic. Equipment construction must be stainless steel or glass-lined because the released isopropanol forms a flammable vapour space. Published data for continuous aminolysis of isopropyl cyanoacetate in microreactors is limited.
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Isopropyl cyanoacetate (CAS 13361-30-3) is the branched propan-2-yl ester of cyanoacetic acid, C6H9NO2, molar mass 127.14 g/mol. Commercial material is supplied as a clear, colorless to pale-yellow liquid with a density of 1.012–1.013 g/cm³ at 20 °C when measured by ASTM D4052. A representative boiling point at 101.3 kPa is 206 °C, and refractive index at 20 °C falls near 1.4160. The ester is miscible with toluene, ethyl acetate, acetone, and dichloromethane, while water solubility remains low but increases as hydrolysis proceeds. Two general supply grades dominate: technical-grade material with assay ≥98.0% by GC and fine-chemical-grade with assay ≥99.0%. Moisture is controlled to ≤0.10% by ASTM E203 Karl Fischer titration for standard material and ≤0.05% for cyanoacrylate monomer feedstock. Acidity is controlled to ≤0.10% as cyanoacetic acid, and APHA color is typically ≤20 by ASTM D1209. Packaging in 200 kg HDPE drums or 1000 kg IBCs under nitrogen headspace is standard. Proprietary model identifiers vary by distributor; a purchase specification should therefore reference assay, moisture, acidity, and color rather than trade names alone.
The isopropoxy substituent introduces steric bulk adjacent to the carbonyl carbon, and this geometry modifies base-catalyzed condensation behavior relative to methyl cyanoacetate and ethyl cyanoacetate. In Knoevenagel condensations with aromatic aldehydes, the isopropyl ester typically displays slower conversion than the methyl ester under identical molar charge, yet it produces less dark self-condensation residue when reactions are run at 60–90 °C in toluene with ammonium acetate and acetic acid as catalyst. A 1.0 mol charge of isopropyl cyanoacetate corresponds to 127.14 g and approximately 125.6 mL, whereas 1.0 mol of methyl cyanoacetate occupies 88.2 mL. This volumetric difference affects reactor fill calculations, especially in multi-purpose plants where vessel freeboard must accommodate reflux and water removal. The branched ester also reduces premature hydrolysis during mildly acidic workup because the isopropoxy group shields the ester carbonyl from nucleophilic water attack more effectively than the unbranched methoxy or ethoxy groups.
| Cyanoacetate ester | CAS registry number | Molar mass (g/mol) | Boiling point at 101.3 kPa (°C) | Density at 20 °C (g/cm³) |
|---|---|---|---|---|
| Methyl cyanoacetate | 105-34-0 | 99.09 | 204–205 | 1.123 |
| Ethyl cyanoacetate | 105-56-6 | 113.11 | 208–210 | 1.063 |
| Isopropyl cyanoacetate | 13361-30-3 | 127.14 | 206 | 1.012 |
| n-Butyl cyanoacetate | 5459-58-5 | 141.17 | 228–230 | 0.993 |
In a 1000 L glass-lined reactor equipped with a 3 m² jacket cooling surface and a Dean-Stark trap, a substituted benzaldehyde condensation using isopropyl cyanoacetate in toluene at reflux requires a 5–10 °C jacket differential to control the exotherm. If addition is permitted to outrun heat removal, batch temperature can rise above 90 °C and increase dark polymeric impurities that persist through filtration and reduce isolated yield. The isopropyl ester’s steric profile reduces aldol-type self-condensation compared with methyl cyanoacetate during long feed additions in shared production vessels. This property is valuable when the same reactor must handle varied cyanoacetate feedstocks and cleaning between campaigns cannot fully eliminate trace alkaline residues. Published data for exact yield ranges in this specific isopropyl ester configuration is limited; process capability is generally established by calorimetry and batch pilot trials rather than literature values.
Process design should avoid holding isopropyl cyanoacetate in aqueous caustic solution. At pH above 8.0 and temperature above 40 °C, base-catalyzed hydrolysis to cyanoacetic acid and isopropanol becomes significant enough to alter stoichiometry and generate acid impurities that interfere with base-sensitive downstream catalysts. Aqueous quench operations are therefore usually directed to pH 5.0–6.0 using dilute mineral acid rather than sodium hydroxide. Isopropyl cyanoacetate is also incompatible with primary or secondary amines under prolonged contact; 1.0 equivalent of n-butylamine can displace isopropanol and form the corresponding N-butyl cyanoacetamide. This reaction must be considered in any workup or storage area where amine-containing reagents or corrosion inhibitors are present. Closed nitrogen-blanketed storage in HDPE or epoxy-lined steel is standard, and transfer lines should avoid copper alloys because copper ions can catalyze oxidative discoloration in cyanoacetate esters.
Production of isopropyl 2-cyanoacrylate from isopropyl cyanoacetate follows the classical route: base-catalyzed condensation with formaldehyde yields a poly(alkyl cyanoacrylate) oligomer, followed by acidic stabilization and thermal depolymerization at 180–220 °C under vacuum with an inhibitor such as sulfur dioxide or phosphorus pentoxide. Isopropyl cyanoacetate feedstock for this route is specified with moisture ≤0.05% and acidity ≤0.10% because water consumes catalyst and hydrolysis products reduce distillate purity. The resulting isopropyl cyanoacrylate monomer has a faster set time than butyl cyanoacrylate but exhibits higher brittleness and a lower acceptance profile for medical use than 2-octyl cyanoacrylate. Where tissue contact is intended, biocompatibility evaluation follows ISO 10993-1, and cytotoxicity screening is performed according to ISO 10993-5. For industrial bonding applications, the isopropyl monomer may be selected when a low-viscosity, fast-wetting adhesive is required and structural flexibility is not the primary performance criterion.
Because isopropyl cyanoacetate serves multiple downstream chemistries, certificate-of-analysis parameters are harmonized around moisture, acidity, assay, and color rather than application-specific functional tests. The following parameters represent a typical fine-chemical-grade release profile. ASTM E203 is used for Karl Fischer moisture, ASTM D4052 for density, ASTM D1209 for APHA color, and gas chromatography with a flame ionization detector for assay. Refractive index is measured with an Abbemat 300 refractometer calibrated against certified reference fluids. These methods allow a single release document to support both early-phase clinical intermediate production and larger-scale agrochemical campaigns without repeating method transfer.
| Parameter | Typical value | Reference method or instrument |
|---|---|---|
| Assay by GC-FID | ≥99.0% | In-house GC-FID |
| Moisture | ≤0.10% | ASTM E203 |
| Acidity as cyanoacetic acid | ≤0.10% | Titration |
| Density at 20 °C | 1.012–1.013 g/cm³ | ASTM D4052 |
| Refractive index at 20 °C | 1.4150–1.4170 | Abbemat 300 |
| APHA color | ≤20 | ASTM D1209 |
Recovery of unreacted isopropyl cyanoacetate from a toluene mother liquor in a wiped-film evaporator is constrained by the ester’s thermal sensitivity in the presence of alkaline residues. A 0.5 m² wiped-film unit operating at 80–110 °C and 10–50 mbar can separate the ester from high-boiling condensation byproducts, but the feed must be neutralized to pH 5.0–6.5 before distillation. If residual ammonium acetate remains, flash evaporation can generate acetamide and acidic decomposition products that plate the evaporator surface and reduce heat-transfer efficiency. Batch-to-batch variance in recovered material is typically controlled by limiting pot temperature to ≤110 °C and maintaining a nitrogen sweep to strip isopropanol formed by slow hydrolysis.
