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234907

Sigma-Aldrich

2-(Dimethylamino)ethyl methacrylate

contains 700-1000 ppm monomethyl ether hydroquinone as inhibitor, 98%

Synonym(s):

Methacrylic acid 2-(dimethylamino)ethyl ester

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About This Item

Linear Formula:
CH2=C(CH3)COOCH2CH2N(CH3)2
CAS Number:
2867-47-2
Molecular Weight:
157.21
Beilstein:
1757048
MDL number:
MFCD00008589
UNSPSC Code:
12162002
PubChem Substance ID:
24854063
NACRES:
NA.23

vapor density

5.4 (vs air)

vapor pressure

<1 mmHg ( 25 °C)

Assay

98%

form

liquid

contains

700-1000 ppm monomethyl ether hydroquinone as inhibitor

refractive index

n20/D 1.439 (lit.)

bp

182-192 °C (lit.)

density

0.933 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C8H15NO2/c1-7(2)8(10)11-6-5-9(3)4/h1,5-6H2,2-4H3

InChI key

JKNCOURZONDCGV-UHFFFAOYSA-N

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General description

2-(Dimethylamino)ethyl methacrylate (DMAEMA) is a methacrylic acid derivative that is used as a monomer in the production of polymers with a wide range of applications. The most common use of DMAEMA is in the production of cationic polymers, which are highly charged and have applications such as flocculants, coagulants, dispersants, and stabilizers. In addition, DMAEMA-based polymers have found uses in drug delivery systems, tissue engineering, and gene therapy, owing to their excellent biocompatibility and biodegradability properties. DMAEMA can also be used as a modifying agent in coatings, adhesives, and textiles to improve properties such as adhesion, hardness, and water resistance.

Application

2-(Dimethylamino)ethyl methacrylate (DMAEMA) can be used as starting material in the synthesis of poly (DMAEMA) and amphiphilic block copolymers. Poly (DMAEMA) is a thermal and pH-sensitive biocompatible polymer widely used in the following applications.

  • Quaternized poly (DMAEMA) can be used to prepare highly efficient antibacterial magnetic particles. The high density of quaternary ammonium groups generated via surface-initiated ATRP are responsible for high antibacterial activity.
  • Ag nanoparticles immobilized into a poly (DMAEMA) brush layer can be used as a sensor platform for the detection of organic molecules by surface-enhanced Raman spectroscopy (SERS).
  • It can also be used to prepare stable polymer-based gene delivery systems.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 + H312,H314,H317

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 1

Flash Point(F)

147.2 °F - closed cup

Flash Point(C)

64 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Joseph M Antonucci et al.
Dental materials : official publication of the Academy of Dental Materials, 28(2), 219-228 (2011-11-01)
The widespread incidence of recurrent caries highlights the need for improved dental restorative materials. The objective of this study was to synthesize low viscosity ionic dimethacrylate monomers (IDMAs) that contain quaternary ammoniums groups (antimicrobial functionalities) and are compatible with existing
Anu M Alhoranta et al.
Biomacromolecules, 12(9), 3213-3222 (2011-07-19)
A series of amphiphilic star and linear block copolymers were synthesized using ATRP. The core consisted of either polystyrene (PS) or poly(n-butyl acrylate) (PBuA), having different glass-transition (T(g)) values. These polymers were used as macroinitiators in the polymerization of the
Saadyah E Averick et al.
Biomacromolecules, 13(11), 3445-3449 (2012-09-13)
Cationic nanogels with site-selected functionality were designed for the delivery of nucleic acid payloads targeting numerous therapeutic applications. Functional cationic nanogels containing quaternized 2-(dimethylamino)ethyl methacrylate and a cross-linker with reducible disulfide moieties (qNG) were prepared by activators generated by electron
Synthesis of well-defined amphiphilic block copolymers with 2-(dimethylamino) ethyl methacrylate by controlled radical polymerization
Zhang Y and Matyjaszewski K
Macromolecules, 32(6), 1763-1766 (1999)
Ying Wang et al.
Biomacromolecules, 13(8), 2585-2593 (2012-07-05)
Photo- and pH-responsive amphiphilic hyperbranched star copolymers, poly(6-O-methacryloyl-1,2;3,4-di-O-isopropylidene-d-galactopyranose)[poly(2-(N,N-dimethylaminoethyl) methacrylate)-co-poly(1'-(2-methacryloxyethyl)-3',3'-dimethyl-6-nitro-spiro(2H-1-benzo-pyran-2,2'-indoline))](n)s [HPMAlpGP(PDMAEMA-co-PSPMA)(n)], were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization of the DMAEMA and the SPMA using hyperbranched PMAlpGP as a macro RAFT agent. In aqueous solution, the copolymers self-assembled to
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