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731099

Sigma-Aldrich

N-(3-Aminopropyl)methacrylamide hydrochloride

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

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Synonym(s):
APMA
Empirical Formula (Hill Notation):
C7H14N2O · HCl
CAS Number:
72607-53-5
Molecular Weight:
178.66
MDL number:
MFCD00078257
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

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This Item
516155274135697931
N-(3-Aminopropyl)methacrylamide hydrochloride contains ≤1,000 ppm MEHQ as stabilizer, 98% (HPLC)

Sigma-Aldrich

731099

N-(3-Aminopropyl)methacrylamide hydrochloride

2-Aminoethyl methacrylate hydrochloride contains ~500 ppm phenothiazine as stabilizer, 90%

Sigma-Aldrich

516155

2-Aminoethyl methacrylate hydrochloride

N,N-Dimethylacrylamide 99%, contains 500 ppm monomethyl ether hydroquinone as inhibitor

Sigma-Aldrich

274135

N,N-Dimethylacrylamide

N-Hydroxyethyl acrylamide contains 1,000 ppm monomethyl ether hydroquinone as stabilizer, 97%

Sigma-Aldrich

697931

N-Hydroxyethyl acrylamide

form

powder

form

-

form

liquid

form

liquid

contains

≤1,000 ppm MEHQ as stabilizer

contains

~500 ppm phenothiazine as stabilizer

contains

500 ppm monomethyl ether hydroquinone as inhibitor

contains

1,000 ppm monomethyl ether hydroquinone as stabilizer

mp

123-128 °C

mp

102-110 °C (lit.)

mp

-

mp

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

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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Preparation and characterization of narrow compositional distribution polyampholytes as potential biomaterials: Copolymers of N-(3-aminopropyl) methacrylamide hydrochloride (APM) and methacrylic acid (MAA)
Dubey A, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 53(2), 353-365 (2015)
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)
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)
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)
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
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