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Sigma-Aldrich

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

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

Related Categories

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Urara Hasegawa et al.
Macromolecular bioscience, 15(11), 1512-1522 (2015-06-24)
Prodrug micelles carrying 5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione (ADT-OH), a compound possessing chemopreventive properties, are prepared from amphiphilic block copolymers linking ADT-OH via an ester bond using glycine (PAM-PGlyADT) and isoleucine linkers (PAM-PIleADT). The release of ADT-OH from the PAM-PIleADT micelles is much slower

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