N-Methylolacrylamide Chemical Properties

Melting point:

74-75°C

Boiling point:

277°C(lit.)

Density 

1.082 g/mL at 20 °C

vapor pressure 

31 hPa (25 °C)

refractive index 

n20/D 1.413

Flash point:

100°C

storage temp. 

Store at <= 20°C.

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

13.25±0.10(Predicted)

form 

Solid

Specific Gravity

1.074

color 

White to Off-White

PH

6.0-7.0 (H2O, 20°C)

Water Solubility 

<0.1 g/100 mL at 20.5 ºC

BRN 

506646

Stability:

Light Sensitive, Moisture Sensitive

InChI

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

InChIKey

CNCOEDDPFOAUMB-UHFFFAOYSA-N

SMILES

OCNC(=O)C=C

LogP

-1.81 at 20℃ and pH7

CAS DataBase Reference

924-42-5(CAS DataBase Reference)

NIST Chemistry Reference

2-Propenamide, n-(hydroxymethyl)-(924-42-5)

IARC

3 (Vol. 60) 1994

EPA Substance Registry System

N-Methylolacrylamide (924-42-5)

Safety Information

Hazard Codes 

Xn,T

Risk Statements 

22-36/37/38-62-48/20/21/22-43-46-45

Safety Statements 

26-45-36/37-53

RIDADR 

2810

WGK Germany 

3

RTECS 

AS3600000

TSCA 

TSCA listed

HazardClass 

4.1

PackingGroup 

III

HS Code 

29241990

Storage Class

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

Hazard Classifications

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

Hazardous Substances Data

924-42-5(Hazardous Substances Data)

MSDS

• Language:English Provider:N-(Hydroxymethyl)acrylamide
• Language:English Provider:SigmaAldrich

N-Methylolacrylamide Usage And Synthesis

Chemical Properties

White solid

Uses

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.

Definition

ChEBI: N-Methylolacrylamide is a secondary carboxamide.

General Description

A colorless or yellow aqueous solution.

Air & Water Reactions

Soluble in water.

Reactivity Profile

N-Methylolacrylamide may be sensitive to prolonged exposure to light. Polymerization and generation of heat and flames may occur on exposure to to heat or contaminants. Incompatible with strong oxidizers.

Fire Hazard

Literature sources indicate that N-Methylolacrylamide is nonflammable.

Synthesis

(1), the acrylamide is added to the reaction kettle containing solvent acetone, the polymerization blocking agent is added, and the temperature is raised to 42??45??;

(2), adding catalyst sodium methanol, adjusting the pH value in the reaction solution to 8.88;

(3), adding formaldehyde, adjusting the pH of the reaction solution to 8.5, and reacting at constant temperature for 1 hour;

(4), add phthalic acid, adjust its reaction solution pH to 7.2;

(5), cooling, crystallization, filtration to get the finished product N-hydroxymethacrylamide.

N-Methylolacrylamide (924-42-5)Related Product Information

• N,N'-Methylenebisacrylamide
• Tris(hydroxymethyl)nitromethane
• N-Isopropylacrylamide
• Acrylamide
• Methacrylamide
• POLY(N-ISOPROPYL ACRYLAMIDE)
• N,N-Dimethylacrylamide
• 1,4-Dimethyl-3-cyano-6-hydroxypyrid-2-one
• N,N'-(1,2-DIHYDROXYETHYLENE)BISACRYLAMIDE
• N-(ISOBUTOXYMETHYL)ACRYLAMIDE
• N-(ISOBUTOXYMETHYL)ACRYLAMIDE
• POLYMETHACRYLAMIDE
• N-(METHOXYMETHYL)METHACRYLAMIDE
• N-(ISO-BUTOXY METHYL)METHACRYLAMIDE
• ACRYLAMIDO BUFFER
• N-METHYLOL METHACRYLAMIDE
• N-Hydroxymethyl-3,4,5,6-tetrahydrophthalimide
• Tetramethrin