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.)

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

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

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Acryloylmorpholine Usage And Synthesis

Description

4-Acryloylmorpholine (4-AM) is a water-soluble monomer, an acrylamide derivative containing a heterocyclic tetrahydrooxazine substituent. Homo- and copolymers of 4-АМ have several valuable properties. They are soluble both in water and in many organic solvents such as alcohols, chloroform, tetrahydrofuran, and dioxane, are non-toxic, and are used for solid-phase synthesis of peptides in chromatography, as materials for composite semipermeable membranes, in catalysis, and for biomedical purposes. Various functional groups are introduced into poly-4-AM to expand its application fields. Random copolymers of 4-АМ with carboxylic acids (acrylic, 4-pentenoic, undecenoic, 2-acrylamido-2-methyl-1-propanesulfonic), behaving as anionic polyelectrolytes, and copolymers with N-hydroxysuccinimide ester of acrylic acid, acting as polymeric carriers, have been synthesized[2-3].

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.
[2] T. Nekrasova. “pH- and thermosensitive copolymers of 4-acryloylmorpholine and 2-dialkylaminoethyl methacrylates and silver-containing nanocomposites based on these copolymers.” Materials Today Communications (2019).
[3] Yu. I. Zolotova. “Copolymers of 4-Acryloylmorpholine with 2-Dimethyl- and 2-Diethylaminoethyl Methacrylate and Silver-Containing Nanocomposites Based on Them.” Russian Journal of Applied Chemistry 91 4 (2018): 623–628.

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