Product Introduction
Dimethyl malonate Basic information |
| Product Name: | Dimethyl malonate |
| Synonyms: | dimthyl malonate;DiMethyl Malonate, 97% 250ML;Malonic Acid Dimethyl Ester Methyl Malonate;DIMETHYL MALONATE FOR SYNTHESIS;Propanedioicacid, 1,3-diMethyl ester;Malonic acid d;Dimethyl malonate Vetec(TM) reagent grade, 98%;PROPANEDIOIC ACID DIMETHYL ESTER |
| CAS: | 108-59-8 |
| MF: | C5H8O4 |
| MW: | 132.11 |
| EINECS: | 203-597-8 |
| Product Categories: | Thiazoles;Building Blocks;C2 to C5;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;C2 to C5;Carbonyl Compounds;Esters;bc0001;108-59-8 |
| Mol File: | 108-59-8.mol |
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| Dimethyl malonate Chemical Properties |
| Melting point | -62 °C (lit.) |
| Boiling point | 180-181 °C (lit.) |
| density | 1.156 g/mL at 25 °C (lit.) |
| vapor density | >1 (vs air) |
| vapor pressure | 0.15 hPa (20 °C) |
| refractive index | n20/D 1.413(lit.) |
| Fp | 194 °F |
| storage temp. | Store below +30°C. |
| solubility | alcohol: miscible |
| pka | 11.80±0.46(Predicted) |
| form | Liquid |
| color | Clear colorless |
| Odor | fruity |
| explosive limit | 1.3-17.4%(V) |
| Water Solubility | negligible |
| Merck | 14,6096 |
| BRN | 774261 |
| Dielectric constant | 10.4(20℃) |
| Stability: | Stable. Incompatible with strong oxidizing agents. Flammable. |
| InChIKey | BEPAFCGSDWSTEL-UHFFFAOYSA-N |
| LogP | -0.05 at 20-25℃ and pH6.4 |
| CAS DataBase Reference | 108-59-8(CAS DataBase Reference) |
| NIST Chemistry Reference | Propanedioic acid, dimethyl ester(108-59-8) |
| EPA Substance Registry System | Dimethyl malonate (108-59-8) |
| Safety Information |
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 1 |
| RTECS | OO0950000 |
| Autoignition Temperature | 440 °C |
| Hazard Note | Irritant |
| TSCA | Yes |
| HS Code | 29171910 |
| Toxicity | LD50 orally in Rabbit: 5331 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| MSDS Information |
| Provider | Language |
|---|---|
| Methyl malonate | English |
| SigmaAldrich | English |
| ACROS | English |
| ALFA | English |
| Dimethyl malonate Usage And Synthesis |
| Description | Dimethyl malonate is a diester derivative of malonic acid. It is a common reagent for organic synthesis used, for example, as a precursor for barbituric acid. It is also used in the malonic ester synthesis. It can be synthesized from dimethoxymethane and carbon monoxide. |
| Chemical Properties | liquid |
| Chemical Properties | Dimethyl malonate is soluble in alcohol and ether and very slightly soluble in water. It may slowly decompose. |
| Uses | It is used in fragrances and some artificial flavorings . |
| Uses | Dimethyl malonate is a reagent used in organic synthesis. It acts as a precursor for the synthesis of mono-substituted and di-substituted acetic acid, barbiturates, vitamin B1 and vitamin B6. It is used in the pharmaceutical industry to prepare pharmaceuticals like chloroquine and butazolidin. It is involved in the synthesis of diastereomeric pure thienylpyridines by reacting with 1,3-diphenylprop-2-enyl acetate. |
| Application | Dimethyl malonate undergoes enantioselective palladium-catalyzed allylic substitution reaction with 1,3-diphenylprop-2-enyl acetate to yield diastereomeric pure thienylpyridines. Dimethyl malonate was used in gold catalyzed oxidative esterification of glycerol, 1,2-propanediol and 1,3-propanediol. |
| Production Methods | Dimethyl malonate is produced via direct esterification of methanol with malonic acid under azeotropic conditions. |
| General Description | Dimethyl malonate undergoes enantioselective palladium-catalyzed allylic substitution reaction with 1,3-diphenylprop-2-enyl acetate to yield diastereomeric pure thienylpyridines. |
| Dimethyl malonate Preparation Products And Raw materials |
| Raw materials | Hydrochloric acid-->Methanol-->Sulfuric acid-->Sodium carbonate-->Sodium cyanide-->Chloroacetic acid-->Sodium chloroacetate-->Cyanoacetic acid-->MALONIC ACID DISODIUM SALT |
| Preparation Products | 1-AMINO-CYCLOPROPANEMETHANOL-->DIMETHYL METHOXYMALONATE-->Chlorimuron-ethyl-->3-(4-FLUOROPHENYL)PROPIONIC ACID-->ADS-->TERT-BUTYL METHYL MALONATE-->2-Methylpyrimidine-->Methyl 3-cyclopentenecarboxylate-->Sethoxydim-->Primisulfuron-methyl-->8-METHOXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID AMIDE-->7-HYDROXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID AMIDE-->3-CARBETHOXY-4-HYDROXYCOUMARIN-->5-(2-ETHYLTHIO PROPYL)-1,3-CYCLOHEXANEDIONE-->6-Chlorooxindole-->Pipemidic acid-->5-Fluoro-2-oxindole-->DIMETHYL BROMOMALONATE-->7-HYDROXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID METHYL ESTER-->7-HYDROXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID METHYL ESTER-->1,1-Cyclopropanedicarboxylic acid dimethyl ester-->6-CHLORO-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID-->MALONIC ACID DI-N-BUTYL ESTER-->Dimethyl ethylmalonate-->Dimethyl chloromalonate-->5-MESITYL-1,3-CYCLOHEXANEDIONE-->5-(TETRAHYDRO-2H-THIOPYRAN-3-YL)-1,3-CYCLOHEXANEDIONE |
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