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ChemicalBook >> CAS DataBase List >>4-Acryloylmorpholine

4-Acryloylmorpholine

CAS No.
5117-12-4
Chemical Name:
4-Acryloylmorpholine
Synonyms
ACRYLOYL MORPHOLINE;1-Morpholinoprop-2-en-1-one;N-ACRYLOYLMORPHOLINE;N-Acrylylmorpholine;4-AcryL;yyyy-m-d;Acrylmorpholide;Acryloylmorpholin;4-Acrylmorpholine;ACRYOYL MORPHOLINE
CBNumber:
CB3229639
Molecular Formula:
C7H11NO2
Molecular Weight:
141.17
MDL Number:
MFCD00047413
MOL File:
5117-12-4.mol
MSDS File:
SDS
Last updated:2024-12-18 14:08:52

4-Acryloylmorpholine 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
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)
EWG's Food Scores 1-3
FDA UNII K0Y58P61JA
NIST Chemistry Reference N-acryloylmorpholine(5117-12-4)
EPA Substance Registry System Morpholine, 4-(1-oxo-2-propenyl)- (5117-12-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07,GHS08
Signal word  Danger
Hazard statements  H302-H317-H318-H373
Precautionary statements  P280-P305+P351+P338
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
NFPA 704
1
2 0

4-Acryloylmorpholine price More Price(15)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 448273 4-Acryloylmorpholine 97%, contains 1,000 ppm monomethyl ether hydroquinone as inhibitor 5117-12-4 50ml $82.3 2024-03-01 Buy
Sigma-Aldrich 448273 4-Acryloylmorpholine 97%, contains 1,000 ppm monomethyl ether hydroquinone as inhibitor 5117-12-4 250ml $288 2024-03-01 Buy
TCI Chemical A0841 4-Acryloylmorpholine (stabilized with MEHQ) >98.0%(GC) 5117-12-4 25mL $28 2024-03-01 Buy
TCI Chemical A0841 4-Acryloylmorpholine (stabilized with MEHQ) >98.0%(GC) 5117-12-4 100mL $77 2024-03-01 Buy
Alfa Aesar L12947 4-Acryloylmorpholine, 98+%, stab. with 4-methoxyphenol 5117-12-4 5g $36.65 2024-03-01 Buy
Product number Packaging Price Buy
448273 50ml $82.3 Buy
448273 250ml $288 Buy
A0841 25mL $28 Buy
A0841 100mL $77 Buy
L12947 5g $36.65 Buy

4-Acryloylmorpholine Chemical Properties,Uses,Production

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].
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_5117-12-4Fig. 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.

860248-52-8
5117-12-4
Synthesis of 4-Acryloylmorpholine from 1-Propanone, 3-methoxy-1-(4-morpholinyl)-

4-Acryloylmorpholine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 4-Acryloylmorpholine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
4-Acryloylmorpholine pictures 2024-12-20 4-Acryloylmorpholine
5117-12-4
 US $78.00-35.00 / kg 1kg 99% 20ton Hebei Zhuanglai Chemical Trading Co.,Ltd
4-Acryloylmorpholine pictures 2024-11-11 4-Acryloylmorpholine
5117-12-4
 US $7.60-3.10 / kg 1kg 99% 10 tons Shandong Deshang Chemical Co., Ltd.
4-Acryloylmorpholine pictures 2024-11-05 4-Acryloylmorpholine
5117-12-4
 US $1.00 / kg 1kg 99% 10mt Hebei Weibang Biotechnology Co., Ltd
4-ACRYLOYLMORPHOLINE 4-(1-oxo-2-propenyl)-Morpholine N-Acrolylmorpholine ACRYOYL MORPHOLINE 4-Acryloylmorpholine (stabilized with MEHQ) Morpholine, 4-(1-oxo-2-propenyl)- Acryloylmorpholin 4-ACRYLOYLMORPHOLINE, 98+%, STAB. WITH 4-METHOXYPHENOL 4-Acryloylmorpholine,98+% 2-Propen-1-one,1-(4-Morpholinyl)- 4-AcryloylMorpholine 97%, contains 1,000 ppM MonoMethyl ether hydroquinone as inhibitor 1-Morpholino-2-propen-1-one 4-Acrylylmorpholine 4-Propenoylmorpholine Acrylmorpholide 4-Acryloylmorpholine, Stab. With 4-Methoxyphenol 4-Acryloylmorpholine, stabilized with 4-methoxyphenol 4-Acryloylmorpholine (contains 1,000 ppm monomethyl ether hydroquinone as inhibitor)≥ 99% (Assay) 4-Acryloylmorpholine(ACMO) 2-Propen-1-one,1-(4-morpholinyl)- /ACMO 4-AcryL 4-Acryloylmorpholine(stabilizedwithMEHQ)> AMCO、4-Acryloylmorpholine Metformin Impurity 42 ACRYLOYL MORPHOLINE N-ACRYLOYLMORPHOLINE N-Acrylylmorpholine 1-Morpholinoprop-2-en-1-one 4-Acrylmorpholine Photoinitiator 4-Acrylmorpholine Sinomer? ACMO Monomer / 4-acryloylmorpholine yyyy-m-d 5117-12-4 C7H11O2N AMINE Acrylate Acrylic Monomers Monomers