2-Isocyanatoethyl Acrylate
- CAS NO.:13641-96-8
- Empirical Formula: C6H7NO3
- Molecular Weight: 141.12
- MDL number: MFCD11112219
- EINECS: 482-140-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-07-22 19:45:42
What is 2-Isocyanatoethyl Acrylate?
The Uses of 2-Isocyanatoethyl Acrylate
2-Isocyanatoethyl Acrylate is an important compound intermediate commonly used in chemical research and development as an API for organic synthesis.
Synthesis
2-Isocyanatoethyl Acrylate is prepared by the reaction of phosgene, ethanolamine and 2-chloropropionyl chloride. The steps are as follows:
In a 500 mL four-necked flask equipped with a stirrer, condenser, thermometer and inner tube, 250 mL of toluene and 25 g (0.41 mol) of 2-aminoethanol were added, heated to 90° C. and supplied with about 20 g of hydrogen chloride gas. Then 56 g (0.44 mol) of 3-chloropropionic acid chloride was added dropwise over 90 minutes and heated at 90° C. for 1 hour. Thereafter, 80 g (0.81 mol) of phosgene was supplied. Dissolved phosgene was then removed by nitrogen gas bubbling. Subsequently, 0.4 g of phenothiazine and 0.4 g of 2,6-bis-t-butylhydroxytoluene were added, and 50 g of triethylamine (0.49 mol) was supplied, and the mixture was heated and stirred at 50° C. for 6 hours. Thereafter, the mixture was cooled to room temperature, the formed hydrochloride salt was filtered, and toluene was distilled off. By the above process, Mixture 2 containing the main product of 2-acryloyloxyethyl isocyanate (AOI) 55 g (0.35 mol) (87% yield) and the by-product of 2-acryloyloxyethyl acrylate (2547 ppm by mass) was obtained.
Properties of 2-Isocyanatoethyl Acrylate
Melting point: | -25 °C |
Boiling point: | 80-95 °C(Press: 15 Torr) |
Density | 1.05 |
vapor pressure | 21.4Pa at 20℃ |
refractive index | 1.4470 to 1.4510 |
Flash point: | 97°C(lit.) |
storage temp. | Keep in dark place,Inert atmosphere,2-8C |
form | clear liquid |
color | Colorless to Almost colorless |
Specific Gravity | 1.10 |
EPA Substance Registry System | 2-Propenoic acid, 2-isocyanatoethyl ester (13641-96-8) |
Safety information for 2-Isocyanatoethyl Acrylate
Computed Descriptors for 2-Isocyanatoethyl Acrylate
Related products of tetrahydrofuran
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