Name: 2-Cyanoethyl 3-oxobutanoate
CAS No. 65193-87-5
EINECS No. 613-755-1
Chemical Formula C₇H₉NO₃
Molecular Weight 155.15 g/mol
InChI InChI=1S/C7H9NO3/c1-6(9)5-7(10)11-4-2-3-8/h2,4-5H2,1H3
Density 1.123 ± 0.06 g/cm³ (20°C, Predicted)
Boiling Point 288.2 ± 20.0°C (760 mmHg, Predicted)；264.32°C (Calculated)
Flash Point 124.2 ± 12.0°C (Predicted)；124.214°C (Calculated)
Water Solubility 3.991×10⁵ mg/L (25°C, Soluble in water; readily soluble in polar organic solvents such as methanol, ethanol, acetone, and ethyl acetate.
Vapor pressure: 0.002 mmHg at 25°C (Predicted)
Refractive index: 1.437 (Calculated)
Storage conditions: Store in a sealed, dry place; freeze below -20°C; protect from light and moisture.
Sensitivity: Sensitive to strong alkalis, high temperatures, and prolonged humidity; chemically stable under neutral and dry conditions.
Appearance: Yellow to brown liquid; or colorless to pale yellow liquid (high purity product).
Specific gravity: 1.123 (20/4°C, Predicted)
Color: Yellow to brown; high purity product is colorless to pale yellow.
MDL number: MFCD24687999
Hazard symbol: GHS07 (exclamation mark); Signal word: Warning
Risk terms: H302 (harmful if swallowed); H312 (harmful if in contact with skin); H315 (causes skin irritation); H319 (causes serious eye irritation); H332 (Harmful if inhaled); H335 (May cause respiratory irritation) Safety Terms P261 (Avoid inhalation of dust/fumes/gases/mist/vapors/sprays); P264 (Wash thoroughly after handling); P280 (Wear protective gloves/clothing/eye protection/face shield); P305+P351+P338 (If in eyes: Rinse carefully with water for several minutes); P304+P340 (Move to fresh air after inhalation); P312 (If feeling unwell, call a poison control center/doctor) Customs Code 2926909090 (Other nitrile compounds; Most Favored Nation Tariff 6.5%; Value Added Tax 13%; Tax Refund 9%) II. Properties Ethyl 2-cyanoacetoacetate (CAS 65193-87-5) is a β-keto ester compound containing three functional groups: cyano (-CN), ketone carbonyl (=O), and ester (-COOR), exhibiting significant chemical reactivity. Its IUPAC name is 2-cyanoethyl 3-oxobutanoate, and its SMILES structural formula is CC(=O)CC(=O)OCCC#N. The α-hydrogen in this compound is located between the ketone and ester groups, making it a strong acid with a pKa value of approximately 10.04 ± 0.46 (Predicted). It readily undergoes various reactions including condensation, cyclization, and substitution.
Physically, this compound is a yellow to brown liquid at room temperature (high-purity products can be colorless to pale yellow), with a density of approximately 1.123 g/cm³, a boiling point of approximately 288.2°C (760 mmHg, Predicted), and a flash point of approximately 124.2°C. It has good water solubility (3.991 × 10⁵ mg/L, 25°C) and is also soluble in polar organic solvents such as methanol, ethanol, acetone, and ethyl acetate.
Regarding chemical stability, this compound is chemically stable under neutral and dry conditions, but is sensitive to strong alkalis, high temperatures, and prolonged moisture, and may undergo hydrolysis or degradation of β-keto esters. It should be stored in a sealed, dry place, and freezing below -20°C is recommended. The cyano group in the molecule can participate in hydrolysis and reduction reactions, while the ketone carbonyl and ester groups can undergo typical carbonyl chemical reactions, making it a crucial multifunctional building block in organic synthesis.
III. Uses
Ethyl 2-cyanoacetoacetate (CAS 65193-87-5) is an important pharmaceutical intermediate and organic synthesis building block, with main applications including:
1. Pharmaceutical Synthesis
Finerenone Synthesis: As a key intermediate in the drug finerenone for treating diabetic nephropathy, it participates in drug construction through Knoevenagel condensation and Hantzsch cyclization. Finerenone is a selective nonsteroidal mineralocorticoid receptor antagonist (MRA) that blocks the renin-angiotensin-aldosterone system (RAAS), slowing the progression of diabetic nephropathy.
Dihydropyridine calcium channel blockers: Used in the synthesis of felodipine and its label Felodipine-d3, among other antihypertensive drugs.
Clevidipine Butyrate: An important intermediate in the synthesis of this antihypertensive drug.
Cephalosporin antibiotics: May participate in the construction of cephalosporin side chains, improving the antibacterial activity and stability of the drug.
Other drugs: Used in the synthesis of cyano-containing heterocyclic compounds (such as thiazole, pyridine, and pyrimidine derivatives), structures widely found in anticancer and antiviral drugs.
2. Pesticides: Important intermediates in the synthesis of highly effective insecticides, fungicides, and herbicides. Derivatives containing thiazole, pyridine, and other functional groups exhibit excellent herbicidal activity against weeds such as rapeseed and amaranth.
3. Dyes and Materials: Used in the synthesis of cyanine dyes, J-aggregate dyes, and electron acceptor dyes.
Applications include electron transport materials in dye-sensitized solar cells (DSSC).
4. Fine Chemicals An important precursor for the synthesis of heterocyclic derivatives such as pyrazole and isoxazole.
A raw material for the synthesis of downstream products such as 2-cyanoethyl (2Z)-2-[(3-nitrophenyl)methylene]-3-oxobutyrate.
IV. Preparation Methods The industrial production of ethyl 2-cyanoacetoacetate (CAS 65193-87-5) mainly employs the following synthetic routes:
1. Diketene Method (Mainstream Process) 3-Hydroxypropionitrile (also known as ethylene cyanohydrin ECN, CAS 109-78-4) is thoroughly mixed with a base (such as triethylamine, imidazole, DMAP, sodium methoxide, sodium tert-butoxide, etc.), and then diketene is added dropwise at a certain temperature to initiate the reaction. After the addition is complete, the reaction is carried out at room temperature for more than 18 hours. The crude product is then dissolved, extracted, and purified to obtain a high-purity product. This process uses readily available and inexpensive raw materials and operates under mild reaction conditions, making it the most commonly used industrial preparation method, achieving a product purity of over 99%.
Reaction Equation: NC-CH₂-CH₂-OH + Diketene → 2-Cyanoethyl 3-oxobutanoate
2. Acyl Chloride Method: 3-O-butyric acid (acetoacetic acid) is first converted to 3-oxobutyryl chloride (using thionyl chloride SOCl₂ or oxaloyl chloride (COCl)₂), then reacted with 2-cyanoethanol (3-hydroxypropionitrile) to generate the target product. This method is rapid and tends to be complete, but requires treatment of acidic byproducts.
3. Transesterification Method: Using methyl acetoacetate or ethyl acetoacetate as raw materials, a transesterification reaction is carried out with 2-cyanoethanol in the presence of acid, base, or enzyme catalysts. This method uses inexpensive and readily available raw materials, but the reaction is reversible and requires distillation to remove the byproduct alcohol to drive the reaction toward the product.
4. Continuous Flow Chemistry and Biocatalysis (Emerging Green Processes)
Continuous Flow Chemistry: Reactions are carried out continuously in microreactors, enabling more precise temperature and pressure control, improving safety and yield.
Biocatalysis: Utilizing enzyme catalysts such as lipases for transesterification, the reaction conditions are mild, with high selectivity, conforming to green chemistry principles.
V. Safety Information
Hazard Overview: Ethyl 2-cyanoacetoacetate is a hazardous chemical. According to GHS classification, its hazard categories include: acute toxicity (oral, dermal, inhalation), skin corrosion/irritation, serious eye damage/eye irritation, and specific target organ toxicity (single exposure, respiratory irritation). The warning word is “Warning,” and the pictogram is GHS07 (exclamation mark).
Main Hazards:
H302: Harmful if swallowed
H312: Harmful if skin contact
H315: Causes skin irritation
H319: Causes severe eye irritation
H332: Harmful if inhaled
H335: May cause respiratory irritation
Protective Measures:
Handling should be carried out in a well-ventilated area. Avoid inhalation of dust/fumes/gases/mist/vapors/sprays.
Wear protective gloves, protective clothing, goggles, and a face shield.
Wash hands thoroughly after handling.
Store in a cool, dry, well-ventilated warehouse, away from fire and heat sources.
Store in a sealed, dry place. Freezing at -20°C or below is recommended.
Store separately from oxidizers and strong alkalis.
Emergency Treatment:
Skin Contact: Immediately remove contaminated clothing and wash hands with… Wash thoroughly with soap and water, seek medical attention.
Eye contact: Lift eyelids and rinse with running water or saline solution for at least 15 minutes, seek medical attention.
Inhalation: Immediately move to fresh air and keep the airway open. If you feel unwell, call a poison center/doctor.
Ingestion: Rinse mouth, do not induce vomiting. If you feel unwell, call a poison center/doctor.
Spill handling: Wear protective equipment, absorb with inert material, and collect in a sealed container for disposal.
Transportation information:
Transportation temperature: Ambient temperature or cold chain transportation (according to supplier requirements).
Packaging type: Select appropriate packaging according to quantity and purity requirements.
Storage temperature: Sealed and dry, frozen storage below -20°C (for long-term storage).
VI. Our company’s production advantages and capacity
1. Leading technology and superior quality
Our company adopts an independently developed improved diketene process, combined with continuous production technology, to achieve a stable product purity of over 98%, with single impurities controlled below 0.1%, meeting the needs of high-end pharmaceutical customers (standards for intermediates of innovative drugs such as phenelzine). 1. We possess a comprehensive quality control system, equipped with advanced analytical instruments such as HPLC, GC-MS, and NMR, ensuring traceability of each batch of products. We can provide complete COA, MSDS, and analytical method validation documents.
2. We have standardized GMP workshops and dedicated warehousing facilities. We can provide industrial-grade (≥98%) packaging in 1kg, 5kg, 25kg, and 200kg drums according to customer needs. Sufficient inventory ensures rapid delivery.
3. Cost optimization and reasonable pricing: Through process optimization and large-scale production, we achieve industry-leading raw material conversion rates, effectively reducing production costs. We have established long-term strategic partnerships with upstream core raw material suppliers (3-hydroxypropionitrile, diketene, etc.) to ensure stable raw material supply and price advantages, providing customers with competitive product prices.
4. Compliant production, safe and environmentally friendly: We hold complete hazardous chemical production licenses and safety production standardization certifications, strictly adhering to GMP standards and the ISO quality management system. Equipped with professional environmental treatment facilities, we achieve compliant wastewater and exhaust gas emissions, committed to green and sustainable production. All products comply with REACH regulations, and relevant registration supporting documents are available. 5. Professional Service and Rapid Response
We have a professional technical and sales service team, providing comprehensive technical support including product technical consultation, customized synthesis, and process optimization. Free sample trials are available, with short delivery cycles (3-5 days to major domestic areas) and export business covering Europe, America, Japan, South Korea, Southeast Asia, and other countries and regions. For innovative drug projects such as fenelazol, we offer full technical support from laboratory to industrial scale-up.
For further product details or to request samples, please feel free to contact our sales department.
Post time: Jul-02-2026
