| HS Code | 298023 |
| Productname | 2-Octyl Cyanoacetate |
| Casno | 52688-23-4 |
| Iupacname | octan-2-yl 2-cyanoacetate |
| Molecularformula | C11H19NO2 |
| Molecularweight | 197.27 g/mol |
| Exactmass | 197.1416 Da |
| Smiles | CCCCCCC(C)OC(=O)CC#N |
| Inchi | InChI=1S/C11H19NO2/c1-3-4-5-6-7-8(2)14-11(13)9-10-12/h8H,3-7H2,9H2,1-2H3 |
| Synonyms | Cyanoacetic acid 2-octyl ester; 2-octyl 2-cyanoacetate; octan-2-yl cyanoacetate |
| Chemicalclass | Ester; nitrile |
| Appearance | Colorless to pale yellow liquid |
| Solubility | Slightly soluble in water; soluble in common organic solvents |
| Density | 0.95 g/cm3 at 25 degC (estimated) |
| Boilingpoint | 305 degC at 760 mmHg (estimated) |
| Flashpoint | 138 degC (estimated) |
| Refractiveindex | n20/D 1.440 (estimated) |
| Hydrogenbonddonorcount | 0 |
| Hydrogenbondacceptorcount | 3 |
| Topologicalpolarsurfacearea | 50.1 A^2 |
| Storage | Store in a cool, dry, well-ventilated area away from ignition sources |
As an accredited 2-Octyl Cyanoacetate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 2-Octyl Cyanoacetate is packed in 25 kg chemical-resistant polyethylene drums, securely sealed for industrial shipping and storage. |
| Container Loading (20′ FCL) | 20′ FCL container loaded with 2-Octyl Cyanoacetate in sealed drums, palletized, secured, labeled, and documented for ocean freight. |
| Shipping | 2-Octyl Cyanoacetate is generally not classified as a dangerous good for transport under DOT, IATA, IMDG, or ADR. Ship in clean, sealed, compatible containers with standard chemical labeling. Store away from oxidizers, heat, and moisture. Always verify current regulations and the supplier’s SDS before shipment. |
| Storage | Store 2-Octyl Cyanoacetate in a cool, dry, well-ventilated area away from heat, sparks, and open flames. Keep containers tightly closed, labeled, and upright. Protect from moisture, direct sunlight, and ignition sources. Separate from strong acids, bases, oxidizers, and reducing agents. Use secondary containment and grounding where required. Follow local regulations and the safety data sheet. |
| Shelf Life | Typically 2 years when stored sealed, cool, dry, protected from light and moisture; avoid acids, bases, and oxidizing agents. |
For medical-grade monomer production from 2-octyl cyanoacetate, the condensation feedstock is set to a molar ratio of 2-octyl cyanoacetate to formaldehyde of 1.0:1.05–1.10, using 37 wt% formalin or paraformaldehyde as the formaldehyde source and piperidine at 0.5–1.0 mol% relative to the ester. The reaction is run in a 1,500 L glass-lined reactor fitted with a reflux splitter and Dean-Stark trap under a nitrogen blanket at 70–90 °C for 4–8 h. Water is removed by azeotropic distillation to drive the Knoevenagel condensation; residual water above 0.2 wt% in the oligomer feed causes hydrolysis of the ester and lowers depolymerization yield. The process is controlled under ISO 13485:2016, and the resulting monomer is later evaluated against ISO 10993-1:2018 when it enters a medical device supply chain. Temperature overshoot above 75 °C during the first 30 minutes of reflux triggers aldol side-product formation, which appears in subsequent batches as a 3–7 °C shift in depolymerization temperature. The oligomer layer is washed with deionized water until the aqueous phase reaches pH 6.0–7.0 and is then dried over anhydrous sodium sulfate.
After concentration at 40–60 °C and 5–10 kPa, the poly(2-octyl cyanoacrylate) oligomer is injected into a wiped-film evaporator with an internal condenser maintained at 190–210 °C and 0.1–0.5 kPa. Sulfur dioxide at 50–200 ppm and phosphorus pentoxide at 0.1–0.3 wt% relative to oligomer are dosed into the feed to suppress radical and anionic side reactions during thermal cracking. The depolymerization residence time is kept between 10 s and 30 s; prolonged exposure at wall temperatures above 210 °C raises colour body formation, while shorter residence time leaves low-molecular-weight oligomer in the distillate. Crude monomer is fractionally distilled in a short-path evaporator at 95–110 °C and 0.05–0.15 kPa. The terminal product is high-purity 2-octyl cyanoacrylate monomer. Downstream terminal products manufactured from this monomer include human topical skin adhesives, veterinary wound closure adhesives, and low-odour industrial cyanoacrylate adhesives.
Finished human wound closure adhesives formulated from 2-octyl cyanoacrylate monomer are constrained by residual formaldehyde and residual 2-octyl cyanoacetate levels rather than by solvent loading. The formulation addition ratio in a low-tension topical skin adhesive is 98.0–99.8 wt% 2-octyl cyanoacrylate monomer, 0–1.5 wt% thickener, 50–300 ppm hydroquinone, and 10–80 ppm methanesulfonic acid. The monomer content is held above 98 wt% because lower purity reduces the 24 h lap-shear strength measured according to ASTM F2255-05. Compounding is performed under dry nitrogen in a stainless steel planetary mixer with the jacket at 15–20 °C; the mixer is purged until the outlet dew point is below −40 °C. Residual monomer, residual formaldehyde, and residual 2-octyl cyanoacetate are controlled under ISO 10993-1:2018, ISO 14971:2019, and FDA 21 CFR 878.4010 for topical wound closure devices.
| Parameter | Limit | Method |
|---|---|---|
| 2-Octyl cyanoacrylate monomer content | 98.0–99.8 wt% | GC-FID internal standard |
| Residual 2-octyl cyanoacetate | <0.1 wt% | GC-FID internal standard |
| Residual formaldehyde | ≤0.1 wt% | HPLC after dinitrophenylhydrazine derivatization |
| Water content | ≤50 ppm | ISO 760:1978 Karl Fischer coulometric method |
| Hydroquinone | 50–300 ppm | HPLC-UV at 290 nm |
The compounded adhesive is filtered through a 0.2 μm PTFE membrane under nitrogen pressure below 70 kPa to remove particulate nuclei that could initiate polymerization. Filling takes place in an ISO Class 100 cleanroom into aluminium tubes or high-density polyethylene dropper bottles. The terminal product types are topical skin closure adhesives, suture-replacement adhesives, and wound closure strips for low-tension lacerations. The critical operational boundary is water: residual moisture above 50 ppm accelerates thickening in the filling valve and causes valve blockage within 2–4 h of continuous operation. Amine-bearing processing aids, gaskets, and packaging components are excluded because amines at ppm levels trigger rapid anionic polymerization.
In veterinary wound closure systems, the formulation derived from 2-octyl cyanoacrylate monomer is adjusted for movable skin and fur-bearing surgical fields. The compliance package includes ISO 10993-1:2018 for systemic toxicity endpoints, ISO 10993-10:2021 for skin sensitization, and OECD 409 for repeated-dose dermal toxicity in the target animal species. The formulation addition ratio is 95–99 wt% 2-octyl cyanoacrylate monomer, 1–4 wt% poly(methyl methacrylate) thickener, and 50–200 ppm hydroquinone. The thickener raises viscosity to 200–600 mPa·s at 25 °C, which prevents run-off on vertical hoof or claw surfaces. Compounding is performed in a low-moisture planetary mixer under nitrogen at 10–30 rpm; the powder thickener is added in three equal portions to prevent agglomeration. The mixture is then vacuum-transferred at 5–10 kPa into a piston filler. Terminal products include canine and feline surgical wound glue, equine hoof repair adhesive, and livestock horn repair adhesive. The narrow mixing window is the main processing constraint: high-shear mixing beyond 30 minutes raises the batch temperature above 30 °C and initiates polymerization, while inadequate dispersion leaves tip-clogging agglomerates at the 0.5–1.0 μm level.
When 2-octyl cyanoacetate is used as a lipophilic active methylene building block in medicinal chemistry, the primary reaction is a Knoevenagel condensation with substituted aromatic aldehydes. The stoichiometric addition ratio is aldehyde to 2-octyl cyanoacetate at 1.0:1.05–1.20, with piperidine or L-proline at 0.05–0.20 equivalents in ethanol or toluene at 60–80 °C. Water removal by azeotropic distillation or molecular sieves drives conversion above 85%. The process is managed under ICH Q7:2016 when intermediates are advanced beyond screening scale, and elemental impurity controls follow ICH Q3D(R2). The condensation product is isolated by vacuum distillation at 90–110 °C and 0.1–0.3 kPa or by silica gel chromatography. The terminal product types are substituted 2-amino-4H-pyran-3-carbonitrile derivatives and pyrazolone precursors used as lipophilic analogs in anti-inflammatory and kinase inhibitor programmes. Published data for the specific octyl ester in commercial API synthesis is limited; most literature uses methyl or ethyl cyanoacetate, but the octyl ester is selected when increased logP is required for cell permeability. Hydrolysis of the octyl ester during cyclization is an operational boundary: pH above 8.0 or aqueous heating above 70 °C saponifies the ester and reduces isolated yield by 10–20%.
Industrial low-odour cyanoacrylate adhesives based on 2-octyl cyanoacrylate monomer are used where flexible bonds and low bloom are required on clear plastics, rubber gaskets, and wire-tacking lines. The compliance framework includes ISO 4587:2003 for tensile lap-shear strength, ISO 19212:2006 for cyanoacrylate classification, and REACH (EC) No 1907/2006 for substance registration. The formulation addition ratio is 92–99 wt% 2-octyl cyanoacrylate monomer, 0–5 wt% ethylene/vinyl acetate copolymer flexibilizer, 0–3 wt% poly(methyl methacrylate) thickener, and 50–150 ppm hydroquinone. Compounding uses a planetary mixer under dry air with a dew point below −30 °C; moisture above 200 ppm causes gelation in the transfer line. Production filling is performed with a stainless steel piston filler having PTFE seals to limit metal-ion-initiated polymerization. Terminal product types include low-bloom adhesives for clear plastic display assembly, flexible adhesives for rubber-to-metal bonding, and primerless adhesives for low-surface-energy substrates. Set time on low-density polyethylene is 20–60 s, while on polypropylene it can exceed 90 s without a polyolefin primer; production lines therefore apply a primer or use surface activation before adhesive placement.
Under continuous purification of 2-octyl cyanoacrylate monomer produced from 2-octyl cyanoacetate, the critical processing variable is condenser pressure drop rather than feedstock stoichiometry. The stabilizer addition ratio in the oligomer feed is 100–300 ppm sulfur dioxide and 0.1–0.3 wt% phosphorus pentoxide; the feed itself is poly(2-octyl cyanoacrylate) with a number-average molecular weight of 1,000–3,000 g/mol. The compliance framework for medical-grade monomer batches is ISO 13485:2016 for traceability and ISO 10993-1:2018 for biocompatibility when the monomer is used in device manufacturing. Depolymerization is carried out in a wiped-film evaporator at 190–210 °C and 0.1–0.5 kPa; the pressure drop across the internal condenser must remain below 0.05 kPa. Higher pressure drop increases the effective boiling point of the monomer, extends residence time beyond 30 s, and produces yellow degradation products that raise APHA colour above 20. Fractionation follows in a short-path evaporator at 95–110 °C and 0.05–0.15 kPa, with final filtration through a 0.2 μm PTFE membrane under nitrogen. Terminal products are colour-stable 2-octyl cyanoacrylate monomer batches for high-clarity medical adhesives and optical bonding applications. Pre-drying of the oligomer feed with molecular sieves or azeotropic distillation is required at relative humidity above 60% because residual water above 0.3 wt% raises condenser pressure drop by 0.02–0.05 kPa within the first hour of operation.
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2-Octyl cyanoacetate is the 2-octyl ester of cyanoacetic acid and is supplied as a clear, low-volatility liquid intermediate for alkyl cyanoacrylate monomer synthesis. The substance is identified by CAS registry number 52688-08-1, molecular formula C11H19NO2, and molecular weight 197.27 g/mol. Commercial model differentiation is supplier-specific; a representative high-purity monomer precursor designation is 2-OCA-HP, while a technical intermediate designation is 2-OCA-T. The high-purity grade is controlled to assay ≥98.0%, water content ≤0.10%, acid number ≤0.5 mg KOH/g, and APHA color ≤50, using ASTM E203, ASTM D1613, and ASTM D1209. Technical grade material permits wider moisture and color limits but is not usable in medical monomer synthesis without repurification. The branched 2-octyl structure lowers vapour pressure relative to methyl and ethyl cyanoacetate and produces a precursor that is less volatile and less lachrymatory during bulk handling.
Water in 2-octyl cyanoacetate alters the stoichiometry of the paraformaldehyde–ester condensation and promotes premature hydrolysis of the cyano group. In monomer production, the ester is condensed with paraformaldehyde in the presence of a weakly basic catalyst such as piperidine acetate. The reaction generates water and oligomeric poly(2-octyl cyanoacrylate). Excess incoming water shifts the equilibrium toward hydrolysis products and reduces the yield of depolymerizable oligomer. Industrial handling practice requires that feed water be held below 0.15% by Karl Fischer titration before charging to the condensation reactor. The ester is dried before use by vacuum stripping at 60–80°C and 5–20 mbar using a receiver protected by a cold trap. Published data for this specific configuration are limited; the stated range reflects common low-moisture ester handling practice rather than a universal thermodynamic limit.
| Parameter | Method | High-purity monomer precursor | Technical intermediate |
|---|---|---|---|
| Assay by GC-FID | Supplier internal method | ≥98.0% | ≥95.0% |
| Water content | ASTM E203 | ≤0.10% | ≤0.30% |
| Acid number | ASTM D1613 | ≤0.5 mg KOH/g | ≤1.0 mg KOH/g |
| Color, APHA | ASTM D1209 | ≤50 | ≤150 |
| Density at 20°C | ASTM D4052 | 0.950–0.960 g/cm³ | 0.945–0.965 g/cm³ |
| Refractive index at 20°C | ASTM D1218 | 1.440–1.445 | 1.438–1.448 |
These values are representative contract specifications; actual limits vary by manufacturer and should be verified against the supplier certificate of analysis. Residual acidity consumes the basic condensation catalyst and shifts the formaldehyde–ester condensation toward unreacted ester. Trace iron and copper are controlled because these metals catalyze discoloration and can interfere with the downstream thermal depolymerization of the oligomer.
During monomer synthesis, 2-octyl cyanoacetate is condensed with paraformaldehyde in a jacketed glass-lined reactor equipped with a reflux splitter and azeotropic water removal using toluene or cyclohexane. The resulting oligomer is dried and then thermally depolymerized under high vacuum. A short-path wiped-film evaporator with an internal condenser is the typical production unit for monomer generation; the wiper spreads the oligomer into a thin film and removes monomer vapour rapidly enough to limit re-polymerization. The processing window is narrow: pot temperatures above 110°C accelerate char formation, while vacuum above 1 mbar reduces monomer recovery. The 2-octyl chain imposes a higher boiling range than lower alkyl homologues, requiring deeper vacuum and longer residence time than ethyl cyanoacetate operations. Published data for this specific configuration are limited; batch-to-batch variation in oligomer viscosity remains a primary source of monomer yield fluctuation.
At the storage interface, 2-octyl cyanoacetate is sensitive to moisture and alkaline contaminants. Bulk storage tanks are blanketed with dry nitrogen and fitted with desiccant breathers; transfer lines are constructed from stainless steel 316L or high-density polyethylene. Carbon steel is excluded because trace iron promotes discoloration and side reactions. The material should not be combined with primary or secondary amine additives; amines accelerate amidation and darkening. Storage below 30°C with exclusion of light is typical for high-purity grades. Under ISO 9001 batch records, re-analysis of water content and acidity is required after any tank opening or moisture event exceeding 0.10%. When ambient humidity exceeds 60% RH, transfer is conducted under nitrogen padding to avoid shelf-life loss.
In medical adhesive raw material production, the 2-octyl cyanoacetate is converted to 2-octyl cyanoacrylate monomer, which is then formulated with stabilizers such as sulfur dioxide, methanesulfonic acid, or free-radical inhibitors. The final polymer is used in tissue adhesives and topical wound closure devices. For the monomer precursor, absence of residual formaldehyde and reactive base is critical. The final cured polymer is evaluated under ISO 10993-5 for cytotoxicity and ISO 10993-10 for sensitization when the intended use is a medical device. Topical skin closure devices using 2-octyl cyanoacrylate are regulated under FDA 21 CFR 878.4010. These requirements apply to the finished monomer and device, but they drive the purity limits placed on the ester intermediate. The 2-octyl ester is selected over methyl or ethyl esters in medical adhesive applications because the final poly(2-octyl cyanoacrylate) film is more flexible and degrades more slowly, reducing brittleness and exothermic sensation upon application. Comparative tensile data under ASTM D638 show longer-chain alkyl cyanoacrylates generally exhibit lower tensile strength and higher elongation than methyl or ethyl cyanoacrylates.
Substitution of methyl cyanoacetate or ethyl cyanoacetate with 2-octyl cyanoacetate changes the vapour-liquid equilibrium, condensation kinetics, and final polymer morphology. The longer 2-octyl chain reduces the vapour pressure of the ester and of the resulting cyanoacrylate monomer; therefore the depolymerization vacuum must be deeper and the overhead line temperature must be held higher to prevent condensation. In batch distillation, a cold trap temperature below −20°C is used to retain lower alkyl monomers, while 2-octyl monomer requires trap temperatures below −40°C. The branched secondary ester is more sterically hindered than n-octyl cyanoacetate, which slows certain transesterification side reactions but does not eliminate them. Operators should not assume that conditions optimized for ethyl cyanoacetate transfer directly to the 2-octyl system; the higher boiling residual fraction increases the risk of thermal decomposition if heating mantles are not reduced after monomer depletion. Published data for this specific configuration are limited; batch-to-batch variance is observed in depolymerization yield when the oligomer molecular weight distribution is not controlled by constant feed ratio.
| Compound | CAS registry number | Molecular weight | Ester structure | Vapour pressure at bulk handling temperature | Final alkyl cyanoacrylate film character |
|---|---|---|---|---|---|
| Methyl cyanoacetate | 105-34-0 | 99.09 g/mol | Linear C1 | Highest | Hard, brittle, fast polymerization |
| Ethyl cyanoacetate | 105-56-6 | 113.11 g/mol | Linear C2 | High | Hard, lower elongation |
| n-Octyl cyanoacetate | 15650-09-4 | 197.27 g/mol | Linear primary C8 | Low | Flexible, lower crystallinity |
| 2-Octyl cyanoacetate | 52688-08-1 | 197.27 g/mol | Branched secondary C8 | Low | Flexible, more amorphous film |
The comparative table is qualitative; exact vapour pressure values are not published for all esters under identical conditions, and final film character depends on monomer purity, stabilizer package, and cure humidity. The 2-octyl ester differs from n-octyl cyanoacetate in the position of the octyl linkage. In 2-octyl cyanoacetate, the ester oxygen is attached to the secondary carbon of the octyl chain; in n-octyl cyanoacetate the linkage is primary. This structural difference changes the hydrolytic stability and the glass transition of the final poly(2-octyl cyanoacrylate) relative to poly(n-octyl cyanoacrylate). The secondary alkyl chain lowers crystallinity and yields a more amorphous adhesive film. For non-medical adhesive grades, this reduces flaking on flexing substrates. The material is not directly interchangeable with n-octyl cyanoacetate in formulations requiring a specific depolymerization rate or viscosity profile. Reformulation should include a distillation curve comparison under ASTM D1160 and a small-scale oligomerization trial before scale-up.
Regulatory documentation for 2-octyl cyanoacetate should include CAS number 52688-08-1, REACH registration status for the relevant tonnage band, and safety data sheet sections for transport, storage, and accidental release. The substance is not itself a tissue adhesive; regulatory status attaches to the finished 2-octyl cyanoacrylate monomer and device. The ester intermediate is handled under strict moisture exclusion, segregated from amines and strong bases, and re-qualified after any bulk transfer where dew point exceeds −20°C. Published data for long-term stability of the 2-octyl ester under tropical storage conditions are limited; therefore high-purity material is not assigned a shelf life beyond the supplier-certified retest window without experimental confirmation.
