4-Acryloylmorpholine

Synonym(s):1-(Morpholin-4-yl)propenone;1-Morpholinoprop-2-en-1-one;4-(1-Oxo-2-propenyl)morpholine;4-Acryloylmorpholine;Acryloylmorpholine

CAS NO.：5117-12-4
Empirical Formula: C7H11NO2
Molecular Weight: 141.17
MDL number: MFCD00047413
EINECS: 418-140-1
SAFETY DATA SHEET (SDS)
Update Date: 2024-12-18 14:08:52

What is 4-Acryloylmorpholine?

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.

The Uses of 4-Acryloylmorpholine

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].
4-Acryloylmorpholine reaction

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). Synthesis_5117-12-4 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.

Properties of 4-Acryloylmorpholine

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.)
Flash point:	>230 °F
storage temp.	2-8°C
solubility	Soluble in water
form	Liquid
pka	-1.08±0.20(Predicted)
color	Colorless to yellow
Water Solubility	1000g/L at 20℃
Sensitive	Light Sensitive
BRN	119302
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 for 4-Acryloylmorpholine

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07 Health Hazard GHS08
GHS Hazard Statements	H302:Acute toxicity,oral H317:Sensitisation, Skin H318:Serious eye damage/eye irritation H373:Specific target organ toxicity, repeated exposure
Precautionary Statement Codes	P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.