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731099

Sigma-Aldrich

N-(3-Aminopropyl)methacrylamide hydrochloride

contains ≤1,000 ppm MEHQ as stabilizer, 98% (HPLC)

Synonym(s):

APMA

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About This Item

Empirical Formula (Hill Notation):
C7H14N2O · HCl
CAS Number:
72607-53-5
Molecular Weight:
178.66
MDL number:
MFCD00078257
UNSPSC Code:
12162002
PubChem Substance ID:
329764619
NACRES:
NA.23

Assay

98% (HPLC)

form

powder

contains

≤1,000 ppm MEHQ as stabilizer

mp

123-128 °C

storage temp.

2-8°C

SMILES string

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

InChI

1S/C7H14N2O.ClH/c1-6(2)7(10)9-5-3-4-8;/h1,3-5,8H2,2H3,(H,9,10);1H

InChI key

XHIRWEVPYCTARV-UHFFFAOYSA-N

General description

N-(3-Aminopropyl)methacrylamide hydrochloride (APMA) is an aminoalkyl methacrylamide which can be synthesized by adding 1,3-diaminopropane to 1,3-diaminopropane dihydrogen chloride solution and further mixing the solution with methacrylic anhydride and hydroquinone. It has a primary amine that provides attractive features such as pH-responsiveness, affinity for anionic drugs and conjugation for variety of chemical structures.

Application

APMA can be used in the preparation of copolymers and cross-linked miscellas for gene delivery, drug delivery and diagnostics applications.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC5123V
BGBC5122V
BGBC5121V
BGBC5120V
BGBC3369V

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Efficient RAFT polymerization of N-(3-aminopropyl) methacrylamide hydrochloride using unprotected ?clickable? chain transfer agents
Mendoncca PV, et al.
Reactive and Functional Polymers, 81(2), 1-7 (2014)
Facile synthesis of controlled-structure primary amine-based methacrylamide polymers via the reversible addition-fragmentation chain transfer process
Deng Z, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 46(15), 4984-4996 (2008)
Gaurasundar M Conley et al.
Nature communications, 10(1), 2436-2436 (2019-06-06)
Thermosensitive microgels are widely studied hybrid systems combining properties of polymers and colloidal particles in a unique way. Due to their complex morphology, their interactions and packing, and consequentially the viscoelasticity of suspensions made from microgels, are still not fully
Polymer mediated peptide immobilization onto amino-containing N-isopropylacrylamide-styrene core-shell particles
Rossi S, et al.
Colloid and Polymer Science, 282(3), 215-222 (2004)
Michika Onoda et al.
Nature communications, 8, 15862-15862 (2017-07-14)
In the field of polymer science, many kinds of polymeric material systems that show a sol-gel transition have been created. However, most systems are unidirectional stimuli-responsive systems that require physical signals such as a change in temperature. Here, we report
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