| Identification | More | [Name]
4-Acryloylmorpholine | [CAS]
5117-12-4 | [Synonyms]
4-ACRYLOYLMORPHOLINE
ACRYLOYL MORPHOLINE
N-ACRYLOYLMORPHOLINE
4-(1-oxo-2-propenyl)-Morpholine
N-Acrolylmorpholine
N-Acrylylmorpholine
4-Acryloylmorpholine,98+%
Morpholine, 4-(1-oxo-2-propenyl)-
Acryloylmorpholin
4-ACRYLOYLMORPHOLINE, 98+%, STAB. WITH 4-METHOXYPHENOL
ACRYOYL MORPHOLINE
4-Acryloylmorpholine (stabilized with MEHQ)
1-Morpholino-2-propen-1-one
4-Acrylylmorpholine
4-Propenoylmorpholine
Acrylmorpholide | [EINECS(EC#)]
418-141-0 | [Molecular Formula]
C7H11NO2 | [MDL Number]
MFCD00047413 | [Molecular Weight]
141.17 | [MOL File]
5117-12-4.mol |
| Chemical Properties | Back Directory | [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 | [Cosmetics Ingredients Functions]
PLASTICISER | [InChI]
1S/C7H11NO2/c1-2-7(9)8-3-5-10-6-4-8/h2H,1,3-6H2 | [InChIKey]
XLPJNCYCZORXHG-UHFFFAOYSA-N | [SMILES]
C=CC(=O)N1CCOCC1 | [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]
5117-12-4(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
  
GHS05,GHS07,GHS08 | [Signal word ]
Danger | [Hazard statements ]
H302-H317-H318-H373 | [Precautionary statements ]
P280-P305+P351+P338 | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R41:Risk of serious damage to eyes.
R43:May cause sensitization by skin contact.
R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
2
| [TSCA ]
Yes | [REACH Registrations]
Active | [HS Code ]
29349990 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1
Skin Sens. 1
STOT RE 2 Oral |
| Hazard Information | Back Directory | [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 is Clear liquid
| [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]
Nonflammable | [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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Alfa Aesar
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Energy Chemical
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China Langchem Inc.
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