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Merck
CN

245801

N-(Hydroxymethyl)acrylamide solution

48 wt. % in H2O

Synonym(s):

Monomethylolacrylamide, N-(Hydroxymethyl)acrylamide, N-Methanolacrylamide

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About This Item

Linear Formula:
CH2=CHCONHCH2OH
CAS Number:
Molecular Weight:
101.10
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
506646
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form

liquid

Quality Level

contains

30 ppm monomethyl ether hydroquinone as inhibitor

concentration

48 wt. % in H2O

refractive index

n20/D 1.413

density

1.074 g/mL at 25 °C

SMILES string

OCNC(=O)C=C

InChI

1S/C4H7NO2/c1-2-4(7)5-3-6/h2,6H,1,3H2,(H,5,7)

InChI key

CNCOEDDPFOAUMB-UHFFFAOYSA-N

General description

N-(Hydroxymethyl)acrylamide (NHMA) is a bifunctional monomer with both a reactive vinyl group and a hydroxymethyl group, making it significant in polymer chemistry. It is known for forming hydrophilic, cross-linked networks, with applications in biomedical fields such as drug delivery systems, contact lenses, and tissue engineering, as well as in industrial UV-curable resins. NHMA is commonly used in hydrogel formulations for drug delivery and wound dressings. Additionally, it can be applied in creating bioadhesives or sealants for medical purposes, such as sealing wounds or attaching medical devices to tissues.

Application

N-(Hydroxymethyl)acrylamide can be used as:
  • A monomer in the development of polymer gel dosimeters specifically designed for radiation therapy applications. The incorporation of NHMA enhances the sensitivity of the dosimeter to radiation doses.
  • A monomer in the development of thermo-responsive polymeric gates, which exhibits thermo-responsive behavior. The incorporation of NHMA enhances the overall properties of the polymer, allowing for better control over the release mechanisms in response to temperature changes.
  • A key monomer in the synthesis of double-hydrophilic and amphiphilic block glycopolymers, contributing to their self-assembly properties, biocompatibility, and functionalization potential. These characteristics make NHMA-based glycopolymers valuable for various biomedical applications, including drug delivery systems, biosensors, and tissue engineering.


pictograms

Skull and crossbonesHealth hazard

signalword

Danger

target_organs

Peripheral nervous system

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Hazard Classifications

Acute Tox. 3 Oral - Carc. 1B - Muta. 1B - PBT - Repr. 2 - Skin Sens. 1 - STOT RE 1 - STOT RE 2 Oral - vPvB



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Articles

Professor Mitsuhiro Ebara provides insights on several types of smart nanofiber mesh systems that have been explored for different drug delivery purposes.


Birgit Paulsson et al.
Mutation research, 516(1-2), 101-111 (2002-04-12)
The reactive industrial chemicals acrylamide (AA) and N-methylolacrylamide (MAA) are neurotoxic and carcinogenic in animals, MAA showing a lower potency than AA. The causative agent in AA-induced carcinogenesis is assumed to be the epoxy metabolite, glycidamide (GA), which in contrast
J R Bucher et al.
Journal of toxicology and environmental health, 31(3), 161-177 (1990-11-01)
Toxicology and carcinogenicity studies of N-methylolacrylamide were conducted by administering the chemical by gavage in water to both sexes of F344/N rats and B6C3F1 mice 5 times per week for 16 d, 13 wk, or 2 yr. In 16-d studies
Lars Ole Goffeng et al.
Neurotoxicology and teratology, 30(3), 186-194 (2008-03-21)
The study examines possible persisting effects on the peripheral nervous system and visual system in tunnel workers previously exposed to acrylamide and N-methylolacrylamide during grouting work. We compared neurophysiological function in 44 tunnel workers previously exposed during grouting operations (2-10



Global Trade Item Number

SKUGTIN
245801-100G04061825849683
245801-1KG04061825849690