
Product Introduction
| 4-Acryloylmorpholine Basic information |
| Product Name: | 4-Acryloylmorpholine |
| Synonyms: | ACRYLOYL MORPHOLINE;4-ACRYLOYLMORPHOLINE;N-ACRYLOYLMORPHOLINE;4-(1-oxo-2-propenyl)-Morpholine;N-Acrolylmorpholine;N-Acrylylmorpholine;ACRYOYL MORPHOLINE;4-Acryloylmorpholine (stabilized with MEHQ) |
| CAS: | 5117-12-4 |
| MF: | C7H11NO2 |
| MW: | 141.17 |
| EINECS: | 418-140-1 |
| Product Categories: | Acrylate;Acrylic Monomers;Monomers |
| Mol File: | 5117-12-4.mol |
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| 4-Acryloylmorpholine Chemical Properties |
| Melting point | −35 °C(lit.) |
| Boiling point | 158°C 50mm |
| density | 1.122 g/mL at 25 °C(lit.) |
| vapor pressure | 1.03-1.64Pa at 25-29.9℃ |
| refractive index | n20/D 1.512(lit.) |
| Fp | >230 °F |
| storage temp. | 2-8°C |
| solubility | Soluble in water |
| pka | -1.08±0.20(Predicted) |
| form | Liquid |
| color | Colorless to yellow |
| Water Solubility | 1000g/L at 20℃ |
| Sensitive | Light Sensitive |
| BRN | 119302 |
| InChIKey | XLPJNCYCZORXHG-UHFFFAOYSA-N |
| LogP | -0.46 at 20.5-21℃ |
| CAS DataBase Reference | 5117-12-4(CAS DataBase Reference) |
| NIST Chemistry Reference | N-acryloylmorpholine(5117-12-4) |
| EPA Substance Registry System | Morpholine, 4-(1-oxo-2-propenyl)- (5117-12-4) |
| Safety Information |
| Hazard Codes | Xn |
| Risk Statements | 22-41-43-48/22 |
| Safety Statements | 23-26-36/37/39 |
| WGK Germany | 2 |
| TSCA | Yes |
| HS Code | 29349990 |
| MSDS Information |
| Provider | Language |
|---|---|
| SigmaAldrich | English |
| ALFA | English |
| 4-Acryloylmorpholine Usage And Synthesis |
| Chemical Properties | 4-Acryloylmorpholine has a melting point of ?35 °C and is clear liquid at room temperature. At 25 °C, it has a density of 1.122 g/mL. It needs to be stored at 2-8°C. |
| Uses | 4-Acryloylmorpholine is used in adhesives, UV curable resins, industrial coatings, UV printing ink, oil recovery polymer, medicinal and commodity chemicals. |
| Reactions | Using cobalt catalysis, diethylzinc promotes the conjugate reduction of 4-acryloylmorpholine to produce the corresponding ethylzinc enolate, which reacts with N-tosyl aldimines to afford β-aminoamides[1].![]() |
| Flammability and Explosibility | Non flammable |
| Synthesis | A solution of 0.04 mol of the corresponding amine in 20 ml of anhydrous methylene chloride was slowly added at 0-5??C to 0.02 mol of acryloyl chloride in 20 ml of anhydrous methylene chloride. The mixture was stirred for 3 h at room temperature in an inert atmosphere, and the precipitate was filtered off and washed with methylene chloride (2 ?á 10 ml). The organic layer was washed in succession with 5 ml of water and 5 ml of a saturated solution of NaHCO3 and dried over Na2SO4, the solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel using hexane-ethyl acetate (5 : 1 to 1 : 1) as eluent. 4-Acryloylmorpholine, Yield 1.78 g (63%). IR spectrum, |í, cm-1: 2857, 1647, 1612, 1439, 1263, 1238, 1115, 1038, 953. 1H NMR spectrum, |?, ppm: 3.51-3.73 m (8H, NCH2CH2O), 5.72 d.d (1H, 3-Hcis, 3J = 10.6, 2J = 1.9 Hz), 6.29 d.d (1H, 3-Htrans, 3J = 16.7, 2J = 1.9 Hz), 6.57 d.d (1H, 2-H, J = 16.7, 10.6 Hz). 13C NMR spectrum, |?C, ppm: 41.74 and 45.66 (CH2N), 66.22 (CH2O), 126.64 (C2), 127.69 (C3), 164.92 (C1). Mass spectrum, m/z (Irel, %): 141 (36) [M]+, 140 (12), 126 (58), 112 (22), 111 (15), 110 (15), 109 (12), 98 (10), 96 (26), 86 (72), 83 (13), 70 (14), 68 (14), 57 (17), 56 (86), 55 (100), 42 (23). Fig. The synthetic method 2 of 4-Acryloylmorpholine |
| References | [1] PRIETO O, LAM H W. Cobalt-catalyzed reductive Mannich reactions of 4-acryloylmorpholine with N-tosyl aldimines??[J]. Organic & Biomolecular Chemistry, 2007. DOI:10.1039/B715839D. |
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Fig. The synthetic method 2 of 4-Acryloylmorpholine




