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274135

Sigma-Aldrich

N,N-Dimethylacrylamide

99%, contains 500 ppm monomethyl ether hydroquinone as inhibitor

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Synonym(s):
2-Propenamide
Linear Formula:
CH2=CHCON(CH3)2
CAS Number:
2680-03-7
Molecular Weight:
99.13
Beilstein:
1742219
EC Number:
220-237-5
MDL number:
MFCD00008626
PubChem Substance ID:
24856566
NACRES:
NA.23

Quality Level

200

Assay

99%

form

liquid

contains

500 ppm monomethyl ether hydroquinone as inhibitor

refractive index

n20/D 1.473 (lit.)

bp

80-81 °C/20 mmHg (lit.)

density

0.962 g/mL at 25 °C (lit.)

SMILES string

CN(C)C(=O)C=C

InChI

1S/C5H9NO/c1-4-5(7)6(2)3/h4H,1H2,2-3H3

InChI key

YLGYACDQVQQZSW-UHFFFAOYSA-N

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This Item
109606D137510773212
N,N-Dimethylacrylamide 99%, contains 500 ppm monomethyl ether hydroquinone as inhibitor

Sigma-Aldrich

274135

N,N-Dimethylacrylamide

Methacrylamide 98%

Sigma-Aldrich

109606

Methacrylamide

N,N-Dimethylacetamide ReagentPlus®, 99%

Sigma-Aldrich

D137510

N,N-Dimethylacetamide

N,N-Diethylacrylamide contains <200 ppm MEHQ as inhibitor, 99%

Sigma-Aldrich

773212

N,N-Diethylacrylamide

form

liquid

form

solid

form

liquid

form

liquid

contains

500 ppm monomethyl ether hydroquinone as inhibitor

contains

-

contains

-

contains

<200 ppm MEHQ as inhibitor

refractive index

n20/D 1.473 (lit.)

refractive index

-

refractive index

n20/D 1.437 (lit.)

refractive index

n20/D 1.468

bp

80-81 °C/20 mmHg (lit.)

bp

-

bp

164.5-166 °C (lit.)

bp

-

density

0.962 g/mL at 25 °C (lit.)

density

-

density

0.937 g/mL at 25 °C (lit.)

density

0.924 at 25 °C

General description

N,N-Dimethylacrylamide (DMAA) is a non-ionic monomer with high reactivity and low initiation temperature. It is commonly used as a monomer in the production of polymers and copolymers for various applications such as hydrogels, polymeric flocculants, biomedical and drug delivery applications, polymer coatings, smart coatings, adhesives, sensors, self-healing materials, and water treatment agents. The unique structure of DMMA can form a three-dimensional network with other hydrogels and enhance their water retention capacity. It is also used as a crosslinking agent in polymerization reactions.

Application

N, N-Dimethylacrylamide(DMAA) can be used in the following applications:
  • Synthesis of poly(N,N-dimethylacrylamide) (PDMAA) nanoparticles which are used in biomedical and drug delivery applications.
  • Use as a co-monomer in the synthesis of thermoresponsive polymers used in smart coatings, adhesives, and sensors.
  • As a reactive diluent in the manufacture of UV-cured coatings and inks.
  • Use as a co-monomer with polyethylene glycol dimethacrylate (PEGDMA) and a chitosan derivative to develop an injectable hydrogel that can be used as a bone tissue engineering matrix.
  • A series of DMMA-based hydrogels for the removal of heavy metals and organic dyes from polluted water. These hydrogels are highly efficient in removing cationic dyes due to electrostatic interaction and hydrogen bonding in the DMMA backbone.
  • Non-toxic luminescent carbon dot/poly(DMMA) nanocomposite via surface-initiated reversible addition-fragmentation chain transfer polymerization.
  • Polymer coating for quartz crystal microbalance(QCM) sensor. The poly(DMMA) gel acts as a sensing material to adsorb Au(III) ions from HCl aqueous solution and it is inactive to most other metal ions and organic compounds.

Features and Benefits

  • It is an appropriate precursor for copolymerization due to its low initiation temperature and high reactivity.
  • Its unique structure forms a 3D network and improves the water retention capacity of hydrogels.
  • It is highly soluble in water.
  • It can easily bind to colloidal particles to enhance the bridging effect which plays a key role in flocculation.

Pictograms

CorrosionSkull and crossbones
GHS05,GHS06

Signal Word

Danger

Hazard Statements

H301 + H311 - H318

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Eye Dam. 1

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

158.0 °F

Flash Point(C)

70 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Syed Ragib Safi et al.
Scientific reports, 9(1), 11909-11909 (2019-08-17)
Arsenic contamination of groundwater is a serious concern worldwide. The research gaps in removing arsenic are selectivity, regeneration and effective removal rate at neutral pH levels. In this study, we discussed the reasons of the high arsenic adsorption from groundwater
Graft copolymerization of N, N-Dimethylacrylamide to cellulose in homogeneous media using atom transfer radical polymerization for hemocompatibility
Yan L and Wei T
Journal of Biomedical Science and Engineering, 10(1), 37-37 (2008)
Yuriko Matsumura et al.
Polymers, 11(7) (2019-07-20)
In order to clarify the local environment during interpolymer complex formation between poly(carboxylic acids) and poly(acrylamide derivatives) with different N-substitutions, a fluorescence label technique was used. 3-(2-propenyl)-9-(4-N,N-dimethylaminophenyl) phenanthrene (VDP) was used as an intramolecular fluorescence probe. All polymers were synthesized
Koki Sano et al.
Nature communications, 7, 12559-12559 (2016-08-31)
Fluids that contain ordered nanostructures with periodic distances in the visible-wavelength range, anomalously exhibit structural colours that can be rapidly modulated by external stimuli. Indeed, some fish can dynamically change colour by modulating the periodic distance of crystalline guanine sheets
S Q Liu et al.
Molecular bioSystems, 1(2), 158-165 (2006-08-02)
Thermally sensitive micelles self-assembled from poly(N-isopropylacrylamide-co- N,N-dimethylacrylamide)-b-poly(d,l-lactide-co-glycolide)[P(NIPAAm-co-DMAAm)-b-PLGA] are fabricated and used as a carrier for the controlled delivery of paclitaxel. Paclitaxel is efficiently loaded into the micelles by a membrane dialysis method. The lower critical solution temperature (LCST) of the
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