| HS Code | 320681 |
| Productname | Isobutyl Cyanoacetate |
| Synonyms | Cyanoacetic acid isobutyl ester; Isobutyl 2-cyanoacetate; Acetic acid, cyano-, isobutyl ester |
| Casnumber | 13361-31-4 |
| Einecenumber | 236-412-4 |
| Molecularformula | C7H11NO2 |
| Molecularweight | 141.17 g/mol |
| Chemicalfamily | Cyanoacetate ester |
| Functionalgroups | Nitrile; ester |
| Appearance | Colorless to almost colorless clear liquid |
| Odor | Mild ester-like odor |
| Physicalstate | Liquid |
| Density | 0.986 g/mL at 25 °C |
| Boilingpoint | 109-111 °C at 15 mmHg; 221 °C at 760 mmHg |
| Flashpoint | >110 °C (closed cup) |
| Refractiveindex | 1.420 at 20 °C |
| Solubility | Soluble in organic solvents; slightly soluble in water |
| Vaporpressure | Low at room temperature |
| Logp | ~1.3 (estimated) |
| Storageconditions | Store in a cool, dry, well-ventilated place away from heat and ignition sources |
| Stability | Stable under normal temperatures and pressures |
| Purity | Typically ≥98% |
| Incompatiblematerials | Strong oxidizing agents, acids, bases |
As an accredited Isobutyl Cyanoacetate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | Isobutyl Cyanoacetate is packed in 25 kg polyethylene-lined steel drums, securely sealed and labeled for safe chemical transport. |
| Container Loading (20′ FCL) | Isobutyl Cyanoacetate 20′ FCL loading: 80 x 200L drums on 20 pallets, approx. 16 MT net, securely strapped, labeled. |
| Shipping | Isobutyl Cyanoacetate is typically shipped as UN 3276, Nitriles, liquid, toxic, n.o.s. (Isobutyl Cyanoacetate), Class 6.1, Packing Group III. Use UN-approved packaging, toxic labels, and proper documentation. Keep away from oxidizers and heat. Follow DOT/IMDG/IATA regulations. |
| Storage | Store Isobutyl Cyanoacetate in a cool, dry, well-ventilated area away from heat, sparks, and open flames. Keep containers tightly closed and protect from moisture. Use a flammable-liquid storage cabinet. Separate from oxidizing agents, acids, bases, and reducing agents. Ensure electrical grounding/bonding when handling. Keep away from food, drink, and incompatible materials. Follow local regulations. |
| Shelf Life | Shelf life: approximately 24 months if kept sealed, cool, dry, dark, and away from moisture, acids, bases, and oxidizers. |
Production of 2-isobutyl cyanoacrylate monomer from isobutyl cyanoacetate is conducted via Knoevenagel condensation with paraformaldehyde under base catalysis, followed by thermal depolymerization of the resulting poly(cyanoacrylate). The starting ester is first dried to a water content not exceeding 0.05 wt% (ISO 760) because residual moisture hydrolyzes the ester to cyanoacetic acid and isobutanol; the free acid decarboxylates to acetonitrile, reducing monomer yield and generating low-boiling impurities that contaminate the depolymerization distillate. Condensation is carried out in a glass-lined reactor equipped with a Dean-Stark trap, using toluene or cyclohexane as azeotrope, with a paraformaldehyde-to-ester molar ratio typically maintained between 1.0:1.0 and 1.2:1.0. Piperidine is added at 0.2–0.5 mol% relative to the ester. Reaction temperature is held at 80–110 °C for 4–8 h, during which water is removed azeotropically and the oligomer phase becomes viscous. The crude prepolymer is transferred to a short-path wiped-film evaporator operated at 120–180 °C wall temperature and 1–10 mbar absolute pressure; sulfur dioxide gas is metered into the condenser at 30–150 ppm relative to distillate mass to suppress anionic repolymerization. Batches that exceed 180 °C in the evaporator wall zone exhibit uncontrolled chain scission and charring, reducing monomer clarity and increasing downstream filter plugging. Incoming isobutyl cyanoacetate is controlled according to the following matrix:
| Parameter | Analytical method | Control window |
|---|---|---|
| Isobutyl cyanoacetate purity | GC-FID area % | ≥ 99.0% |
| Water content | ISO 760 | ≤ 0.05 wt% |
| Acid value | ISO 2114 | ≤ 1.0 mg KOH/g |
| Color | ISO 6271 Pt-Co | ≤ 20 |
| Non-volatile residue | ASTM D1353 | ≤ 0.02 wt% |
The branched alkyl group of the ester lowers the monomer vapor pressure relative to ethyl cyanoacrylate and reduces lachrymatory response in handling areas, but it also increases the minimum depolymerization residence time because the poly(isobutyl cyanoacrylate) chain fraction requires a lower thermal flux gradient to avoid gel formation in the vacuum receiver.
In industrial instant-adhesive formulation, isobutyl cyanoacrylate is evaluated against ethyl and n-butyl homologues where low odor and reduced film hardness are required. The monomer is formulated with anionic polymerization inhibitors such as sulfur dioxide or boron trifluoride, and thickeners such as poly(methyl methacrylate) are dispersed at 5–15 wt% under vacuum to achieve Brookfield viscosities of 10–1,500 mPa·s at 25 °C. Dispersion is performed in double-planetary or dissolver equipment with a jacket temperature below 10 °C to prevent shear-induced initiation. Cure set time on low-density polyethylene or plasticized PVC is longer than on steel because surface-adsorbed water is the initiating species; on polypropylene, corona or plasma pretreatment is required to raise surface energy above 38 mN/m. Comparative lap-shear values determined according to ISO 4587 on steel substrates typically fall between 6–15 MPa for butyl-type cyanoacrylates, while ethyl cyanoacrylate often produces 18–25 MPa. The branched isobutyl chain reduces film modulus and increases elongation relative to the ethyl homologue; published data for this specific configuration is limited, and blend ratios with n-butyl cyanoacrylate are adjusted based on ASTM D1002 shear values and environmental stress cracking resistance of bonded parts. Stabilizer levels above 200 ppm sulfur dioxide extend set time beyond 60 s and produce weak boundary layers; levels below 20 ppm cause premature polymerization during storage at 40 °C. The formulation process is conducted in moisture-controlled rooms at 25±2 °C and relative humidity below 40%.
Isobutyl cyanoacetate is used in medicinal chemistry for pyrazolone synthesis through cyclocondensation with hydrazine derivatives. The active methylene carbon is deprotonated by sodium ethoxide in anhydrous ethanol at 0–5 °C; the enolate is then treated with arylhydrazine at 20–40 °C, after which the mixture is heated to 60–85 °C for 3–8 h. Workup includes pH adjustment to 4–5 with hydrochloric acid and filtration at 0–5 °C. Regioselectivity with monosubstituted hydrazines is pH-dependent; neutral and mildly acidic conditions favor the 1-aryl-3-amino-5-pyrazolone isomer, while strongly basic conditions increase formation of the isomeric pyrazolone. The isobutyl ester is retained on the pyrazolone ring during early analogue synthesis because the branched chain alters log P and crystal packing without introducing a new stereocenter. Saponification to the carboxylic acid is performed with lithium hydroxide at 0–25 °C to avoid hydration of the nitrile substituent. Residual isobutanol in isolated intermediates is controlled by headspace GC according to ICH Q3C Option 2 limits; elemental impurities are matched to ICH Q3D risk categories based on catalyst metals used upstream. Published data for isobutyl-specific yields is limited; route scouting often begins with ethyl cyanoacetate then switches to isobutyl to modify solubility and metabolic stability.
When the target scaffold is a 2,6-diaminopyrimidine or a pyridone, isobutyl cyanoacetate is condensed with guanidine hydrochloride or urea in methanolic sodium methoxide. The reaction is run at 65–75 °C for 5–10 h; the product precipitates after neutralization with acetic acid. The isobutyl ester provides a leaving group that minimizes transesterification side products compared with methyl esters in high-boiling solvents. Workup includes filtration at 0–5 °C and recrystallization from isopropanol/water (1:1). Residual solvents in the isolated intermediate are controlled by headspace GC according to USP <467>. Strongly basic hydrolysis of the nitrile to amide or acid must be avoided where the downstream step requires the intact cyano group; aqueous sodium hydroxide above 2 M at reflux converts the cyano group to the amide or carboxylate and degrades chemoselectivity. The pathway is used for early-stage libraries rather than late-stage GMP manufacture because the isobutyl route is less documented than ethyl and methyl variants.
Isobutyl cyanoacetate can be converted to 2-cyano-3,3-diphenylacrylate via Knoevenagel condensation with benzophenone under titanium tetrachloride-mediated dehydration, yielding a low-basicity UV absorber used in clear coatings. The branched ester chain lowers melting point and increases compatibility with styrene and acrylate monomers compared with the methyl ester. Formulation loading is typically 0.5–2.0 wt% on binder solids. Migration to the coating surface is assessed by extraction with acetonitrile at 60 °C for 24 h followed by HPLC quantification; acceptable loss is below 5% of initial loading. In crosslinked unsaturated polyester or polyurethane coatings, the ester chain participates only as a passive diluent; it is not bound into the network, so volatile loss during stoving at 120 °C may reduce UV protection. Photo-degradation is evaluated by ASTM D4329 cycles; published data for isobutyl-specific formulations is limited, and ethyl 2-cyano-3,3-diphenylacrylate remains the documented reference compound in most coating systems.
Early-stage agrochemical synthesis uses isobutyl cyanoacetate for the preparation of substituted pyrazoles and pyridazines via active methylene condensation. In one representative sequence, the ester is alkylated with a substituted benzyl halide in the presence of potassium carbonate in dimethylformamide at 20–40 °C; the resulting alkylated cyanoacetate is then condensed with hydrazine derivatives to form pyrazolone carboxylates. Water content in DMF must be below 0.1 wt% to avoid ester hydrolysis. The isobutyl group is retained through the first two steps to aid chromatographic resolution, then removed by hydrolysis with lithium hydroxide in tetrahydrofuran/water at 0–10 °C. Process-scale batches require careful control of nitrile hydration; prolonged basic conditions generate the corresponding amide, which is inactive in downstream cyclization. Genotoxicity testing of intermediates follows OECD 471; residual isobutyl cyanoacetate carryover into the next stage is typically maintained below 0.1% by HPLC area. The low aqueous solubility of the branched ester requires phase-transfer conditions for reactions run in water, and phase separation is improved by adding 5–10% sodium chloride.
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Isobutyl cyanoacetate, CAS 13361-31-4, is a branched aliphatic cyanoacetate ester with the molecular formula C7H11NO2 and a calculated molecular weight of 141.17 g/mol. The compound is manufactured as a clear, low-viscosity liquid intermediate for condensation chemistry and cyanoacrylate production, not as a formulated adhesive or coating. Its structure consists of a cyanoacetate reactive head group linked to an isobutyl ester chain; the branched C4 alkyl substituent differentiates it from linear butyl cyanoacetate and from the methyl and ethyl homologues used in larger commercial volumes. No unified ISO product model exists for cyanoacetate esters, and supplier designations such as IBCA or cyanoacetic acid isobutyl ester are distributor-specific. Typical commercial certificates of analysis list purity by gas chromatography at or above 98.0%, water content by Karl Fischer titration at or below 0.10%, and acidity as cyanoacetic acid at or below 0.20%. The product is normally handled under nitrogen or dry-air blanketing because the ester group is hydrolytically sensitive and the active methylene position is reactive toward aldehydes, ketones, and strong electrophiles.
Representative specification values for isobutyl cyanoacetate are shown in the following table. These ranges reflect common technical-grade material used as a chemical intermediate; pharmaceutical or electronic-grade material may be controlled to tighter limits, and a supplier-specific certificate of analysis should be consulted for exact batch values.
| Parameter | Typical specification or value | Test method |
|---|---|---|
| Appearance | Clear, colorless to pale yellow liquid | Visual inspection |
| Purity | ≥ 98.0% | GC-FID area normalization |
| Water content | ≤ 0.10% | ASTM E203 |
| Acidity as cyanoacetic acid | ≤ 0.20% | Alkaline titration |
| Color, APHA | ≤ 50 | ASTM D1209 |
| Density at 20 °C | 1.01–1.03 g/cm³ | ASTM D4052 |
| Refractive index nD20 | 1.4250–1.4300 | Refractometer |
The branched isobutyl chain reduces packing density relative to linear short-chain esters, which influences volatility, solvent compatibility, and the glass transition temperature of polymers derived from the ester. Published boiling point data for isobutyl cyanoacetate vary with purity and measurement pressure; cyanoacetate esters can undergo thermal condensation at elevated temperatures, so boiling range values should be treated as supplier-specific rather than as thermodynamically rigorous constants. The material is miscible with common polar aprotic solvents such as acetone, ethyl acetate, dimethylformamide, and dimethyl sulfoxide. Water solubility is low, but prolonged contact with water leads to hydrolysis of the ester linkage and formation of cyanoacetic acid and isobutanol.
For analytical quality control, gas chromatography is performed with flame ionization detection and internal normalization because residual isobutanol and cyanoacetic acid are the principal organic impurities in addition to dialkyl cyanoacetate-derived by-products. Karl Fischer titration is preferred for water determination because the ester and nitrile moieties can interfere with loss-on-drying methods. Acidity is usually reported after direct titration with a standardized base under cooled conditions, since cyanoacetate esters can saponify during the titration if the sample is not kept below 10 °C. Color drift from water-white to amber is commonly associated with trace amine contamination or storage at elevated temperature, and color control is therefore an indirect indicator of chemical stability.
Storage stability is governed primarily by moisture exclusion and temperature control. The ester carbonyl and nitrile groups are hydrolytically sensitive; exposure to humid air raises acidity and generates isobutanol, which can shift downstream reaction stoichiometry and contaminate condensation products. Because cyanoacetate esters contain an active methylene group, contact with primary or secondary amines initiates base-catalyzed condensation and can form colored enaminone or oligomeric by-products. Unlined carbon steel should be avoided where trace iron or rust contamination may accelerate decomposition. Stainless steel 304 or 316 tanks, phenolic-lined drums, and glass-lined storage vessels are preferred. A nitrogen or dry-air blanket with a dew point below -20 °C is standard for bulk tanks, and continuous low-flow nitrogen sparging is used where moisture ingress from repeated sampling is a concern.
Under sealed, moisture-protected storage at 15 °C to 25 °C, supplier stability data commonly support a 12-month re-evaluation interval. Storage above 35 °C may accelerate ester hydrolysis and color development, while freezing should be avoided because thawing cycles can introduce condensation water into the headspace. The product should not be combined with caustic soda, ammonia, morpholine, piperidine, or other amine-based additives outside the controlled condensation reactor, because exothermic oligomerization can occur. If dilution in dimethylformamide or dimethyl sulfoxide is required, the solvent should be dried to below 0.05% water to avoid unintended hydrolysis during subsequent processing.
In cyanoacrylate monomer production, isobutyl cyanoacetate functions as the precursor monomer in a two-stage sequence: base-catalyzed condensation with formaldehyde, followed by thermal depolymerization of the oligomeric intermediate under vacuum. The condensation step is typically conducted in an organic solvent with an amine or quaternary ammonium catalyst, with water removed azeotropically to shift equilibrium toward higher oligomer yield. The branched isobutyl ester introduces steric bulk that reduces the rate of unintended Michael addition at the active methylene center relative to linear low-molecular-weight esters. After oligomerization, the reaction mass is transferred to a thin-film or short-path evaporator operating at reduced pressure, where the cyanoacrylate monomer is cracked from the oligomer and separated from higher-molecular-weight residue. In production-scale equipment, the cracking stage requires vacuum control below 10 mbar and careful residence-time management; excessive temperature or hold time leads to charring, resinification, and reduced monomer yield. The crude monomer is stabilized with an acid-gas inhibitor such as sulfur dioxide and a free-radical inhibitor such as hydroquinone before fractional distillation. Because the process window is narrow, pilot-scale calorimetric data are used to set jacket temperature limits, agitator load limits, and emergency quench protocols.
When isobutyl cyanoacetate is substituted for ethyl cyanoacetate, downstream monomer and polymer properties change in measurable ways. The resulting monomer, isobutyl 2-cyanoacrylate, generally has lower volatility and lower perceived odor than ethyl 2-cyanoacrylate. The branched alkyl chain can also reduce polymer glass transition temperature and increase adhesive film flexibility relative to short-chain homologues, although published comparative performance data for fully formulated adhesives remains limited. The condensation rate under base catalysis may be slightly retarded by the steric bulk of the isobutyl group, which can require longer reaction time or a higher catalyst charge to reach equivalent conversion. In a batch reactor with an anchor agitator and vacuum distillation, the water-isobutanol azeotrope removal profile differs from water-ethanol removal; boil-up rate, column loading, and reflux ratio require re-optimization. The molecular weight shift from ethyl cyanoacetate to isobutyl cyanoacetate is 28.06 g/mol, so stoichiometric feed ratios in large-scale runs must be recalculated.
The following table compares the branched isobutyl ester with two common linear cyanoacetate homologues to support product selection in synthesis and adhesive intermediates.
| Parameter | Isobutyl cyanoacetate | Ethyl cyanoacetate | n-Butyl cyanoacetate |
|---|---|---|---|
| CAS registry number | 13361-31-4 | 105-56-6 | 39581-20-3 |
| Molecular weight | 141.17 g/mol | 113.11 g/mol | 141.17 g/mol |
| Alkyl chain structure | Branched C4 | Linear C2 | Linear C4 |
| Relative volatility | Moderate | Higher | Lower |
| Water miscibility | Low | Moderate | Low |
| Published monomer performance data | Limited | Extensive | Moderate |
Isobutyl cyanoacetate and n-butyl cyanoacetate share the same molecular weight but differ in alkyl chain branching. The linear n-butyl ester provides a more ordered aliphatic chain and may pack more readily in polymer matrices, while the isobutyl ester introduces branching that can lower crystallinity and modify free volume. In condensation reactions, both butyl esters are less water-miscible than ethyl cyanoacetate and can simplify extractive work-up when the alcohol by-product is to be removed by water washing. Methyl cyanoacetate, by comparison, is more reactive but also more volatile and more hydrophilic, which can be advantageous for distillation but less desirable where aqueous phase separation is critical.
In heterocyclic synthesis, cyanoacetate esters are used to prepare cyanoacetamides, pyrazolones, cyanoacetylureas, and certain agrochemical intermediates. The isobutyl ester is selected when the alcohol by-product isobutanol can be removed under process conditions or when the branched ester provides a favorable partition coefficient during extractive work-up. Its intermediate polarity falls between the short-chain methyl and ethyl esters and the more lipophilic octyl or 2-ethylhexyl esters. Published comparative kinetic data for isobutyl cyanoacetate in specific heterocycle syntheses is limited, so process development typically relies on laboratory calorimetric screening, reaction hazard assessment, and pilot-scale batch records rather than published rate constants.
For industrial hygiene and regulatory classification, isobutyl cyanoacetate is not identified as a priority pollutant under the U.S. Clean Water Act or the European Union Water Framework Directive priority substance list. No compound-specific threshold limit value has been established by ACGIH, so exposure control is generally based on process containment, local exhaust ventilation, and standard industrial hygiene monitoring for organic esters. Process exhaust from vacuum cracking or distillation should be routed through chilled condensers and activated carbon to reduce odor and organic emissions. Waste streams containing cyanoacetate esters should be segregated from strongly basic aqueous effluent to avoid exothermic hydrolysis and alcohol formation. Compliance under REACH may require registration above 1 t/a in the European Economic Area, and national chemical inventory status should be verified before import or use in each jurisdiction.
