2-Propenoic acid, 2-(bromomethyl)-, ethyl ester
Ethyl 2-(bromomethyl)acrylate
CAS: 17435-72-2
Molecular Formula: C6H9BrO2
2-Propenoic acid, 2-(bromomethyl)-, ethyl ester - Names and Identifiers
2-Propenoic acid, 2-(bromomethyl)-, ethyl ester - Physico-chemical Properties
| Molecular Formula | C6H9BrO2 |
| Molar Mass | 193.04 |
| Density | 1.398 g/mL at 25 °C (lit.) |
| Melting Point | 134-136℃ |
| Boling Point | 38 °C/0.8 mmHg (lit.) |
| Flash Point | 178°F |
| Solubility | Soluble in Dichloromethane and Methanol |
| Appearance | Colorless oily |
| Color | Colorless to pale yellow |
| BRN | 970108 |
| Storage Condition | -20°C |
| Refractive Index | n20/D 1.479(lit.) |
| MDL | MFCD00031518 |
| Physical and Chemical Properties | Storage Conditions: 2-8 ℃ WGK Germany:3 |
| Use | An intermediate in the synthesis of aza inhibitors. |
2-Propenoic acid, 2-(bromomethyl)-, ethyl ester - 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. |
| UN IDs | UN 2810 6.1 / PGII |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10-19-23 |
| HS Code | 29161900 |
2-Propenoic acid, 2-(bromomethyl)-, ethyl ester - Reference Information
| Production method | 1.β, β-dibromoisobutyl ester or acid debromination [1], bromination of α-hydroxymethyl acrylate or α-hydroxymethyl acrylate under the action of phosphorus (III) bromide, etc. [2]. 2.? Preparation method: In a reaction bottle equipped with a stirrer, a thermometer, a dropping funnel, and a reflux condenser (with a calcium chloride drying tube on top), add 33.84g(0.26mol) of a-hydroxymethacrylate (2), 250mL of anhydrous ether, stir and cool to -10 ℃, add 34g(11.5mL,0.12mol) of phosphorus tribromide dropwise, and add it for about 15min. After adding, remove the cold bath and stir at 20 ℃ for 3 hours. Then cool to -10 ℃, slowly add 150mL of cold water. Hexane was extracted 4 times, 50mL each time. The organic layers were combined, saturated salt water was washed twice, anhydrous magnesium sulfate was dried, concentrated by rotation, the residue was distilled under reduced pressure, and the fraction of 85~87 ℃/2.66kPa was collected to obtain 43.8g of a-bromoethyl methacrylate (1) with a yield of 87%. [10] 3. Preparation method: A- bromomethacrylic acid (3): 55g(0.25mol) of diethyl dihydroxymethylmalonate (2) and 142mL of 48% hydrobromic acid are added to a reaction bottle equipped with a magnetic stirrer and a fractionation device, and the reaction is carried out at 85~90 ℃ under magnetic stirring. At the same time, the generated bromoethane and water are steamed into the reaction bottle, which takes about 1.5~2 hours. After the reaction, 100mL of water was evaporated by rotating concentration, and the residue was placed overnight in the refrigerator, filtered and dried to obtain 17.9g of a-bromomethacrylic acid (3), mp71 ~ 73 ℃, and the yield was 43%. Petroleum ether recrystallization, mp73 ~ 75 ℃. A- Bromoethyl Methacrylate (1): In a reaction bottle equipped with a stirrer and a water separator, 42g(0.25mol) of the above compound (3),300mL benzene are added, nitrogen is added, and reflux azeotropic dehydration is added. About 50mL of benzene was distilled, 100mL of absolute ethanol and 1mL of concentrated sulfuric acid were added after cooling, and reflux reaction was performed under nitrogen protection for 36h. 100g3A molecular sieve is added to the water separator to remove the generated water. Remove the water separator, evaporate 125mL of liquid (benzene and ethanol) under reduced pressure, add 100mL of benzene, and then evaporate 125mL of liquid. The residue is poured into 200mL of water and neutralized with solid sodium bicarbonate until no carbon dioxide gas is generated. Ether extraction 3 times, combined with ether layer, anhydrous sodium sulfate drying. After diethyl ether is recovered and distilled under reduced pressure, the fraction of 39~40 ℃/120Pa is collected to obtain 33~34g of a-bromoethyl methacrylate (1) with a yield of 71%. [11] |
Last Update：2024-04-09 20:49:11
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