FEMA No. 2375
Ethyl malonate
CAS: 105-53-3;145601-68-9
Molecular Formula: C7H12O4
FEMA No. 2375 - Names and Identifiers
FEMA No. 2375 - Physico-chemical Properties
| Molecular Formula | C7H12O4 |
| Molar Mass | 160.17 |
| Density | 1.055 g/mL at 25 °C (lit.) |
| Melting Point | -51--50 °C (lit.) |
| Boling Point | 199 °C (lit.) |
| Flash Point | 212°F |
| JECFA Number | 614 |
| Water Solubility | Miscible with ethyl alcohol, ether, chloroform and benzene. Slightly miscible with water. |
| Solubility | 20.8g/l (External MSDS) |
| Vapor Presure | 1 mm Hg ( 40 °C) |
| Vapor Density | 5.52 (vs air) |
| Appearance | Colorless liquid |
| Color | colourless liquid |
| Odor | Sweet ester odor |
| Merck | 14,3823 |
| BRN | 774687 |
| pKa | 13.5(at 25℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, |
| Sensitive | Sensitive to humidity |
| Explosive Limit | 0.8-12.8%(V) |
| Refractive Index | n20/D 1.413(lit.) |
| MDL | MFCD00009195 |
| Physical and Chemical Properties | Character colorless liquid, with a sweet ether odor. melting point -50 ℃ boiling point 199.3 ℃ relative density 1.0551 refractive index 1.4135 flash point 100 ℃ solubility miscible with alcohols and ethers, soluble in chloroform, benzene and other organic solvents. Slightly soluble in water. The solubility in water is 2.08g/100ml at 20 °c. |
| Use | It is used as an intermediate of sulfanilamide and barbiturate in medicine, and is also an intermediate of perfume and dye. |
FEMA No. 2375 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R36 - Irritating to the eyes |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 1 |
| RTECS | OO0700000 |
| TSCA | Yes |
| HS Code | 29171910 |
| Hazard Note | Irritant |
| Toxicity | LD50 orally in Rabbit: 15720 mg/kg LD50 dermal Rabbit > 16000 mg/kg |
FEMA No. 2375 - Upstream Downstream Industry
FEMA No. 2375 - Nature
Open Data Verified Data
a colorless liquid with a sweet ether odor. The relative density was 1. 0551. Melting Point -50 °c. Boiling point 199.3 °c. Refractive index 4135. Flash point 100 ° C and alcohol, ether miscible, soluble in chloroform, benzene and other organic solvents. Slightly soluble in water, 20 ° C water solubility of 2. 08g/lOOmL.
Last Update：2025-06-10 22:55:16
FEMA No. 2375 - Preparation Method
Open Data Verified Data
- sodium chloroacetate method sodium chloroacetic acid is neutralized with sodium carbonate at 30 ° C. To form sodium chloroacetate, cyanated with sodium cyanide at 92-95 ° C., and then hydrolyzed with alkali to form sodium malonate. After drying, sodium malonate is esterified with ethanol at 70-72 °c in the presence of sulfuric acid. The esterification product was washed and distilled to obtain the final diethyl malonate.
- The sodium cyanoacetate method is derived from the direct esterification of cyanoacetic acid with ethanol.
Last Update：2022-01-01 10:33:40
FEMA No. 2375 - Introduction
Slightly aromatic. Soluble in alcohol, ether, benzene and chloroform, insoluble in water.
Last Update：2022-10-16 17:11:43
FEMA No. 2375 - Application
Open Data Verified Data
mainly used in organic synthesis, is the intermediate of dyes, spices, but also the synthesis of chloroquine, phenylbutazone, barbiturate and other pharmaceutical raw materials.
Last Update：2025-08-19 16:24:40
FEMA No. 2375 - Safety
Open Data Verified Data
- This product is of low toxicity, rat oral LD50 >1600mg/kg, but in the body will be hydrolyzed into acid, to avoid contact. Wash after contact. Operators should wear rubber gloves.
- This product is packaged in iron drum or galvanized iron drum with a specification of 200kg. According to the provisions of combustible chemicals storage and transportation.
Last Update：2022-01-01 10:33:41
FEMA No. 2375 - Reference Information
| FEMA | 2375 | DIETHYL MALONATE |
| LogP | 0.96 at 20℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | malonic acid and its derivatives are widely used in pharmaceutical, perfume, food additive, polyester and other industries, and are important fine chemical raw materials and intermediates. Especially in pharmaceutical intermediates, diethyl malonate is widely used in the synthesis of barbian acid, amino acids, vitamins B1, B2 and B6, sleeping pills and phenylbutazone and other drugs. |
| properties | diethyl malonate is an important fine chemical raw material, because the methylene hydrogen in its molecule is easily replaced by a variety of groups, And then generate a variety of important derivatives, which are widely used in various chemical production fields, including food, medicine, pesticides, industrial dyes, liquid crystal materials and other industries. |
| Use | Diethyl malonate is an important intermediate for the preparation of 2-amino -4, 6-dimethoxypyrimidine, and can be used to prepare sulfonylurea Herbicides, such as bensulfuron-methyl, pyrisulfuron-methyl, nicosulfuron-methyl, etc., are also intermediates for sulfa drugs and barbiturates in medicine. It can also be used in gas chromatography stationary liquid (the maximum use temperature is 40 ℃, the solvent is benzene, chloroform, ethanol) to verify ammonia and potassium. In addition, diethyl malonate is also a edible spice permitted by GB 2760-96. It is mainly used to prepare fruit flavors such as pears, apples, grapes, cherries, etc. |
| production method | chloroacetic acid is used as raw material, dissolved in water, sodium carbonate aqueous solution is added to pH = 7 at <30 ℃, sodium cyanide is added to the sodium chloroacetate solution after being dissolved in water, cyanidation reaction at 92~95 ℃ for 1h, alkali solution is added, heating reaction at 100~105 ℃ for 1h, hydrolysis is carried out, and then heating to remove water, ethanol and toluene are added, a little sulfuric acid is added dropwise, and the reaction is carried out at 68~70 ℃ for 3h, esterification is carried out, and then the ester layer is taken for vacuum distillation to obtain the finished product. ClCH2COOH + Na2CO3 → ClCH2COONaClCH2COONa + NaCH → NCCH2COONa + NaClNCCH2COONa + NaOH[H2O]→ NaOOC-CH2-COONa + NH3 The production methods of diethyl malonate are mainly cyanide esterification and catalytic carbonylation. At present, the traditional cyanide esterification method is still widely used in industry. It is obtained by neutralization, cyanidation, hydrolysis and esterification of chloroacetic acid. Chloroacetic acid is neutralized with sodium carbonate at 30°C to generate sodium chloroacetate, cyanated with sodium cyanide at 92-95°C, and then hydrolyzed with alkali to generate sodium malonate. After drying, sodium malonate is esterified with ethanol in the presence of sulfuric acid at 70-72°C. The esterification product is washed and distilled to obtain the finished diethyl malonate. Raw material consumption quota: chloroacetic acid (95%)650 kg/t, sodium cyanide (95%)340 kg/t, ethanol (95%)910 kg/t. The new process developed abroad is mainly based on catalytic carbonylation, that is, using chloroacetate, carbon monoxide, and ethanol as raw materials to synthesize diethyl malonate in the next step of the catalyst. In contrast, the catalytic carbonylation process is also the sodium cyanoacetate process, which is obtained by direct esterification of cyanoacetic acid and ethanol. It is obtained by co-boiling, distillation, and esterification of malonic acid and ethanol in benzene medium. It is obtained by esterification of sodium malonate and ethanol under sulfuric acid catalysis and then distillation. |
| spontaneous combustion temperature | 435°C DIN 51794 |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:05
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Raw Materials for FEMA No. 2375
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