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Sigma-Aldrich

2-Aminoethyl methacrylate hydrochloride

contains ~500 ppm phenothiazine as stabilizer, 90%

Synonym(s):

2-Aminoethyl 2-methylacrylate hydrochloride, 2-Propenoic acid, 2-methyl-, 2-aminoethyl ester, hydrochloride (1:1) (ACI)

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About This Item

Linear Formula:
H2C=C(CH3)CO2CH2CH2NH2 · HCl
CAS Number:
2420-94-2
Molecular Weight:
165.62
EC Number:
219-343-4
MDL number:
MFCD00078260
UNSPSC Code:
12162002
PubChem Substance ID:
24873869
NACRES:
NA.23

Assay

90%

contains

~500 ppm phenothiazine as stabilizer

mp

102-110 °C (lit.)

storage temp.

2-8°C

SMILES string

Cl.CC(=C)C(=O)OCCN

InChI

1S/C6H11NO2.ClH/c1-5(2)6(8)9-4-3-7;/h1,3-4,7H2,2H3;1H

InChI key

XSHISXQEKIKSGC-UHFFFAOYSA-N

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General description

Aminoethyl methacrylate hydrochloride (AMA) is an amine based methacrylic monomer used in the production of polymers and copolymers that are utilized in a wide range of applications, including coatings, adhesives, and medical devices. It is a highly reactive monomer due to the presence of the methacrylate group, which enables it to undergo both free radical polymerization and other polymerization reactions. Due to its biocompatibility and low toxicity, it is widely used in biomedical research and as a crosslinking agent for hydrogels and other biomaterials. It is used in the synthesis of poly (2-aminoethylmethacrylate), a biocompatible cationic polymer widely used in the biomedical field.

Application

2-Aminoethylmethacrylate hydrochloride(AMA) can be used as a precursor to synthesize:
  • Homo and copolymer brushes of AMA, which can be used to tune the electrochemical properties of silicon wafers.
  • Poly(3-hydroxybutyrate) based polyurethane/urea composite scaffolds for tissue engineering applications.
  • Antimicrobial bacterial cellulose/poly (AMA) nanocomposites. Polymer incorporation imparts mechanical properties and antimicrobial activity to bacterial cellulose membranes.
It can also be used for the efficient functionalization of hyaluronic acid via triazine-mediated amidation.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Liao T-Y, et al.
ACS biomaterials science & engineering, 6, 3349-3360 (2020)
Poly (ethylene glycol)-block-poly (2-aminoethyl methacrylate hydrochloride)-Based Polyplexes as Serum-Tolerant Nanosystems for Enhanced Gene Delivery
Santo D, et al.
Molecular Pharmaceutics, 16, 2129-2141 (2019)
Gaëlle Levourch et al.
Polymers, 12(6) (2020-07-01)
In biomedical diagnosis and bionanotechnologies, the extraction and purification of proteins and protein derivatives are of great interest. In fact, to purify recombinant proteins for instance, new methodologies and well appropriate material supports need to be established and also to
Tina Borke et al.
Carbohydrate polymers, 116, 42-50 (2014-12-03)
Triazine-based coupling agents have the potential to replace carbodiimides in the functionalization of hyaluronic acid (HA) giving derivatives with high degrees of substitution (DS) under mild conditions with excellent efficiency. Kinetics of the triazine-mediated amidation of HA in aqueous solution
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