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4-Acryloylmorpholine

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CAS:5117-12-4
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4-Acryloylmorpholine Basic information
Product Name:4-Acryloylmorpholine
Synonyms: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
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
4-Acryloylmorpholine Structure
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
form Liquid
pka-1.08±0.20(Predicted)
color Colorless to yellow
Water Solubility 1000g/L at 20℃
Sensitive Light Sensitive
BRN 119302
InChIKeyXLPJNCYCZORXHG-UHFFFAOYSA-N
LogP-0.46 at 20.5-21℃
CAS DataBase Reference5117-12-4(CAS DataBase Reference)
NIST Chemistry ReferenceN-acryloylmorpholine(5117-12-4)
EPA Substance Registry SystemMorpholine, 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
ProviderLanguage
SigmaAldrich English
ALFA English
4-Acryloylmorpholine Usage And Synthesis
Chemical Properties4-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.
Uses4-Acryloylmorpholine is used in adhesives, UV curable resins, industrial coatings, UV printing ink, oil recovery polymer, medicinal and commodity chemicals.
ReactionsUsing 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 ExplosibilityNon flammable
SynthesisA 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.
4-Acryloylmorpholine Preparation Products And Raw materials
Raw materialsMorpholine
Tag:4-Acryloylmorpholine(5117-12-4) Related Product Information
Dodecyl acrylate DIHYDRODICYCLOPENTADIENYL ACRYLATE Sodium allylsulfonate Allylboronic acid pinacol ester Isobornyl acrylate 1-Benzylimidazole Dimethomorph Flumorph N-METHACRYLOYLMORPHOLINE 4-Acryloylmorpholine poly(acryloylmorpholine) 3-CHLORO-1-(4-CHLOROBENZYL)-5-(MORPHOLINOCARBONYL)-2(1H)-PYRIDINONE 1-(3-CHLOROBENZYL)-3-(MORPHOLINOCARBONYL)-2(1H)-PYRIDINONE 4-[(2E)-3-(4-METHOXYPHENYL)PROP-2-ENOYL]MORPHOLINE 3-(MORPHOLINOCARBONYL)-1-[4-(TRIFLUOROMETHYL)BENZYL]-2(1H)-PYRIDINONE AURORA 1080 SALOR-INT L202282-1EA 1-(3,4-DICHLOROBENZYL)-5-(MORPHOLINOCARBONYL)-2(1H)-PYRIDINONE