Dimethyl malonate
Dimethyl malonate
CAS: 108-59-8
Molecular Formula: C5H8O4
Dimethyl malonate - Names and Identifiers
| Name | Dimethyl malonate |
| Synonyms | Malonic acid d Methyl malonate dimthyl malonate Dimethyl malonate dimethylpropanedioate dimethyl propanedioate DIMETHYL MALONATE FOR SYNTHESIS PROPANEDIOIC ACID DIMETHYL ESTER Propanedioicacid, 1,3-diMethyl ester Malonic Acid Dimethyl EsterMethyl Malonate |
| CAS | 108-59-8 |
| EINECS | 203-597-8 |
| InChI | InChI=1/C5H8O4/c1-5(2,3(6)7)4(8)9/h1-2H3,(H,6,7)(H,8,9)/p-2 |
| InChIKey | BEPAFCGSDWSTEL-UHFFFAOYSA-N |
Dimethyl malonate - Physico-chemical Properties
| Molecular Formula | C5H8O4 |
| Molar Mass | 132.11 |
| Density | 1.156 g/mL at 25 °C (lit.) |
| Melting Point | -62 °C (lit.) |
| Boling Point | 180-181 °C (lit.) |
| Flash Point | 194°F |
| Water Solubility | negligible |
| Solubility | Soluble in organic solvents such as alcohol and ether, slightly soluble in water. |
| Vapor Presure | 0.15 hPa (20 °C) |
| Vapor Density | >1 (vs air) |
| Appearance | Transparent liquid |
| Color | Clear colorless |
| Merck | 14,6096 |
| BRN | 774261 |
| pKa | 11.80±0.46(Predicted) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Incompatible with strong oxidizing agents. Flammable. |
| Sensitive | Easily absorbing moisture |
| Explosive Limit | 1.3-17.4%(V) |
| Refractive Index | n20/D 1.413(lit.) |
| MDL | MFCD00008460 |
| Physical and Chemical Properties | Characteristics of colorless liquid, can be miscible with ether, alcohol and oil, with aromatic odor. soluble in alcohol, ether and other organic solvents, slightly soluble in water. |
| Use | For pharmaceutical and organic synthesis; Organic synthesis. Commonly used in pharmaceutical pipemidic acid intermediates and perfume intermediates, pesticide intermediates |
Dimethyl malonate - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 1 |
| RTECS | OO0950000 |
| TSCA | Yes |
| HS Code | 29171910 |
| Hazard Note | Irritant |
| Toxicity | LD50 orally in Rabbit: 5331 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
Dimethyl malonate - Upstream Downstream Industry
Dimethyl malonate - Nature
Open Data Verified Data
colorless liquid. The relative density was 1. 156. Melting Point -62 °c. Boiling point 181.4 °c. Refractive index 4135. Soluble in alcohol, ether and other organic solvents, slightly soluble in water.
Last Update：2025-06-10 22:55:16
Dimethyl malonate - Preparation Method
Open Data Verified Data
sodium chloroacetate was formed by the interaction of chloroacetic acid and sodium carbonate, and then sodium cyanoacetate was obtained by cyanidation with sodium cyanide. Sodium cyanoacetate is hydrolyzed into sodium malonate, and then esterified with methanol in the presence of sulfuric acid to obtain crude dimethyl malonate, which is washed and distilled to obtain a finished product.
Last Update：2022-01-01 10:33:38
Dimethyl malonate - Application
Open Data Verified Data
pharmaceutical intermediates.
Last Update：2025-08-19 16:24:40
Dimethyl malonate - Safety
Open Data Verified Data
- This product is slightly more toxic than diethyl malonate. Rat oral LD50 53 31mg/kg. Malonic acid dimethyl ester in the body will be hydrolyzed to produce malonic acid, should try to avoid inhalation or skin contact, contact should be timely washed.
- This product is packed in an iron drum, 200kg per barrel. There is no special requirement for storage. According to the general provisions of the storage and transportation of chemicals.
Last Update：2022-01-01 10:33:39
Dimethyl malonate - Reference Information
| LogP | -0.05 at 20-25℃ and pH6.4 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| use | used in pharmaceutical and organic synthesis dimethyl malonate is an important raw material for the production of pharmaceutical pipemidic acid. Foreign dimethyl malonate is mainly used as a raw material for the production of pipemidic acid by non-ethoxymethylene process, and it reacts with orthoformate and urea to produce pipemidic acid. At present, most of the dimethyl malonate produced by related enterprises in China is used to produce pipemidic acid except for export. gas chromatography analysis standard. Organic synthesis. gas chromatography comparison sample, organic synthesis. |
| production method | cyanide esterification method is mostly used. Chloroacetic acid and sodium carbonate are neutralized to form sodium chloroacetate, and then sodium cyanide is used for cyanidation to obtain sodium cyanoacetate. Sodium cyanoacetate is hydrolyzed into sodium malonate, and then esterified with methanol in the presence of sulfuric acid to obtain dimethyl malonate, which is washed and distilled to obtain the finished product. Industrial products contain more than 98% esters. Raw material consumption quota: chloroacetic acid 1120kg/t, sodium cyanide 551kg/t, methanol 955kg/t. The new process developed abroad is mainly based on catalytic carbonylation, that is, using chloroacetate, carbon monoxide, and methanol as raw materials, in the presence of a catalyst, one-step reaction synthesis of dimethyl malonate. In contrast, the catalytic carbonylation process is advanced in technology, but the process is complex, the reaction conditions are harsh, and it is difficult to realize industrialization. |
| spontaneous combustion temperature | 440°C |
Last Update：2024-04-09 02:00:05
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Raw Materials for Dimethyl malonate
Downstream Products for Dimethyl malonate