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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
Pricing and availability is not currently available.

vapor density

5.4 (vs air)

Quality Level

200

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM5542
BCCL9959
BCCM4038
BCCL7298
BCCJ9139

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Sang Beom Lee et al.
Biomacromolecules, 4(5), 1386-1393 (2003-09-10)
Amphiphilic random, gradient, and block copolymers of 2-(dimethylamino)ethyl methacrylate (DMAEMA) and n-butyl methacrylate (BMA) were synthesized by atom transfer radical polymerization (ATRP) in water/2-propanol mixtures using a methoxy-poly(ethylene glycol) (MPEG) (M(n) = 2000) macroinitiator. Kinetic studies indicate that the copolymerization
Freeze-drying of poly((2-dimethylamino)ethyl methacrylate)-based gene delivery systems.
J Y Cherng et al.
Pharmaceutical research, 14(12), 1838-1841 (1998-02-07)
Jingwei He et al.
Dental materials : official publication of the Academy of Dental Materials, 28(8), e110-e117 (2012-05-12)
The purpose of this study was to prepare antibacterial and radiopaque dental resin through adding one polymerizable quaternary ammonium compound with iodine as counter anion into Bis-GMA/TEGDMA (50/50, wt/wt) dental resin system, and evaluate the degree of monomer conversion, mechanical
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
Hong Y Cho et al.
Biomacromolecules, 12(10), 3478-3486 (2011-09-08)
Star polymers with poly(ethylene glycol) (PEG) arms and a degradable cationic core were synthesized by the atom transfer radical copolymerization (ATRP) of poly(ethylene glycol) methyl ether methacrylate macromonomer (PEGMA), 2-(dimethylamino)ethyl methacrylate (DMAEMA), and a disulfide dimethacrylate (cross-linker, SS) via an
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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