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Merck
CN

448273

4-Acryloylmorpholine

97%, contains 1,000 ppm monomethyl ether hydroquinone as inhibitor

Synonym(s):

1-(Morpholin-4-yl)propenone, 1-Morpholinoprop-2-en-1-one, 4-(1-Oxo-2-propenyl)morpholine, 4-Acryloylmorpholine, Acryloylmorpholine

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About This Item

Empirical Formula (Hill Notation):
C7H11NO2
CAS Number:
5117-12-4
Molecular Weight:
141.17
EC Number:
418-140-1
MDL number:
MFCD00047413
UNSPSC Code:
12162002
PubChem Substance ID:
24868398
NACRES:
NA.23

Key Documents

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Quality Level

100

Assay

97%

contains

1,000 ppm monomethyl ether hydroquinone as inhibitor

refractive index

n20/D 1.512 (lit.)

mp

−35 °C (lit.)

density

1.122 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C=CC(=O)N1CCOCC1

InChI

1S/C7H11NO2/c1-2-7(9)8-3-5-10-6-4-8/h2H,1,3-6H2

InChI key

XLPJNCYCZORXHG-UHFFFAOYSA-N

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General description

4-Acryloylmorpholine(ACMO) is an acrylate monomer widely used as a crosslinking agent in the polymer industry. It is used to form three-dimensional polymer networks to enhance the mechanical strength, stability, and durability of materials. The morpholine moiety in acryloylmorpholine imparts hydrophilicity to the molecule facilitating its applications in the field of adhesives, biocompatible coatings, and drug delivery systems. It is also used as a reactive monomer to synthesize hydrogels for drug delivery, photocurable materials for 3D bioprinting and display devices.

Application

4-Acryloylmorpholine can be used as a monomer:
  • To synthesize multiblock copolymers via RAFT polymerization. These functional block copolymers find application in the fields of medicine, energy, and nanotechnology.
  • To prepare organogel electrode frame via photopolymerization and cross-linking. This can be used to fabricate triboelectric nanogenerators with excellent transparency, stretchability, and interface adhesion.
  • For printing thermoplastic 3D tissue scaffolds. ACMO′s water solubility,and remarkably low viscosity, combined with surface oxygen inhibition, promoteswift liquid flow during high-speed open-air printing.

Signal Word

Danger

Hazard Statements

H302,H317,H318,H373

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1 - STOT RE 2 Oral

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

259.7 °F - closed cup

Flash Point(C)

126.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ9364
MKCZ1241
MKCZ2066
MKCX4699
MKCW4883

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Rapid open-air digital light 3D printing of thermoplastic polymer
Shihong Deng, et al.
Advanced Materials, 31, 1903970-1903970 (2019)
Organ gel electrode enables highly transparent and stretchable triboelectric nanogenerators of high power density for robust and reliable energy harvesting
Titao Jing, et al.
Nano Energy, 78, 105373-105373 (2020)
Ultrafast RAFT polymerization: multiblock copolymers within minutes
Guillaume Gody, et al.
Polymer Chemistry: Introduction to an Indispensable Science, 6, 1502-1511 (2015)
Kalyan Ramesh et al.
Materials (Basel, Switzerland), 13(17) (2020-08-28)
Owing to their unique topology and physical properties, micelles based on miktoarm amphiphilic star block copolymers play an important role in the biomedical field for drug delivery. Herein, we developed a series of AB2-type poly(D,L-lactide-co-glycolide)-b-poly(N-acryloyl morpholine) (PLGA-b-PNAM2) miktoarm star block
Hafiz Awais Nawaz et al.
Journal of materials chemistry. B, 9(9), 2295-2307 (2021-02-23)
Injectable gelatine-based hydrogels are valuable tools for drug and cell delivery due to their extracellular matrix-like properties that can be adjusted by the degree of cross-linking. We have established anhydride-containing oligomers for the cross-linking of gelatine via anhydride-amine-conjugation. So far
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