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245801

Sigma-Aldrich

N-(Hydroxymethyl)acrylamide solution

48 wt. % in H2O

Synonyme(s) :

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

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About This Item

Formule linéaire :
CH2=CHCONHCH2OH
Numéro CAS:
924-42-5
Poids moléculaire :
101.10
Beilstein:
506646
Numéro MDL:
MFCD00004597
Code UNSPSC :
12162002
ID de substance PubChem :
24854759
Nomenclature NACRES :
NA.23

Forme

liquid

Contient

30 ppm monomethyl ether hydroquinone as inhibitor

Concentration

48 wt. % in H2O

Indice de réfraction

n20/D 1.413

Densité

1.074 g/mL at 25 °C

Chaîne SMILES 

OCNC(=O)C=C

InChI

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

Clé InChI

CNCOEDDPFOAUMB-UHFFFAOYSA-N

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Description générale

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.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Classification des risques

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

Organes cibles

Peripheral nervous system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Listes réglementaires

Les listes réglementaires sont principalement fournies pour les produits chimiques. Seules des informations limitées peuvent être fournies ici pour les produits non chimiques. L'absence d'indication signifie qu'aucun des composants n'est répertorié. Il incombe à l'utilisateur de s'assurer de l'utilisation sûre et légale du produit.

EU REACH SVHC Candidate List

CAS No.

EU REACH Annex XVII (Restriction List)

CAS No.

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Certificats d'analyse (COA)

Lot/Batch Number
MKCH6850
MKCH4199
MKCB2394V
MKCB2392V
MKBV3486V

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Consulter la Bibliothèque de documents

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
Timothy R Fennell et al.
Toxicological sciences : an official journal of the Society of Toxicology, 71(2), 164-175 (2003-02-04)
Acrylamide (AM) and N-methylolacrylamide (NMA) are used in the formulation of grouting materials. AM undergoes metabolism to a reactive epoxide, glycidamide (GA). Both AM and GA react with hemoglobin to form adducts that can be related to exposure to AM.
Helge Kjuus et al.
Scandinavian journal of work, environment & health, 30(1), 21-29 (2004-03-17)
This study evaluates the possible toxic effects on the peripheral nervous system of tunnel workers exposed to acrylamide and N-methylolacrylamide during grouting work. Symptoms and nerve conduction velocities (NCV) were recorded for 24 tunnel workers 4 and 16 months after
Kristine L Witt et al.
Environmental and molecular mutagenesis, 41(2), 111-120 (2003-02-28)
N-Hydroxymethylacrylamide (NHMA), a mouse carcinogen inactive in the Salmonella assay and mouse micronucleus (MN) assay, was tested for reproductive effects in a mouse continuous breeding study. In that study, increased embryonic deaths were observed after 13 weeks exposure of parental
H Tanii et al.
Toxicology letters, 58(2), 209-213 (1991-10-01)
Acrylamide and 6 derivatives inhibited neurite growth from rat dorsal root ganglion in culture. The half-maximum inhibition concentration (I50) varied among test compounds, ranging from 0.8 mM for acrylamide and N-hydroxymethylacrylamide to 30 mM for methacrylamide. The value correlated well
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