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Merck

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:
924-42-5
Molecular Weight:
101.10
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
24854759
MDL number:
MFCD00004597
Beilstein/REAXYS Number:
506646

Key Documents

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Product Name

N-(Hydroxymethyl)acrylamide solution, 48 wt. % in H2O

InChI

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

SMILES string

OCNC(=O)C=C

InChI key

CNCOEDDPFOAUMB-UHFFFAOYSA-N

form

liquid

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

Quality Level

100

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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.

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.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ9086
MKCV6687
MKCH6850
MKCH4199
MKCB2394V

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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
T Fukushima et al.
Journal of dentistry, 29(3), 227-234 (2001-04-18)
The effect of experimental dentin primers containing N-methylolacrylamide (MEAA) or N-methylolmethacrylamide (MEMA) on bond durability of a resin composite (Photo Clearfil A) with a bonding agent (Clearfil Photo Bond) to bovine dentin was investigated. The etching agents were 10% maleic
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
R E Chapin et al.
Fundamental and applied toxicology : official journal of the Society of Toxicology, 27(1), 9-24 (1995-08-01)
Acrylamide is a known genetic, reproductive, and neural toxicant, although it is not known if one effect is predominant. The toxicities of several structural analogues of acrylamide have been incompletely characterized, and the relative sensitivity of the second generation is
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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