N-Methylol acrylamide
Product Information
Molecular Formula
C4H7NO2
Molecular Weight
101.1
Description
N-methylolacrylamide appears as a colorless or yellow aqueous solution.
Synonyms
2-Propenamide,N-(hydroxymethyl)-; Acrylamide, N-(hydroxymethyl)-; Monomethylolacrylamide; n-(hydroxymethyl)-2-propenamid; n-(hydroxymethyl)-acrylamid; NCI-C60333; NM-AMD; N-Methanolacrylamide
IUPAC Name
N-(hydroxymethyl)prop-2-enamide
SMILES
C=CC(=O)NCO
InChI
InChI=1S/C4H7NO2/c1-2-4(7)5-3-6/h2,6H,1,3H2,(H,5,7)
InChI Key
CNCOEDDPFOAUMB-UHFFFAOYSA-N
Boiling Point
318.1°C at 760mmHg
Melting Point
74-75°C
Purity
95%
Density
1.074
Solubility
less than 1 mg/mL at 68.9 °F
Appearance
A colorless or yellow aqueous solution.
Application
Used in adhesives, binders, surface coatings, and resins; Used as a starch modifier.
Storage
Refrigerator
Stability
May undergo spontaneous combustion in storage.
LogP
-1.81 (calculated)
Vapor Pressure
0.000205 [mmHg]
Decomposition
When heated to decomposition it emits toxic fumes of /nitrogen oxides.
Safety Information
Hazards
H301:
Toxic if swallowed.
H317:
May cause an allergic skin reaction.
H319:
Causes serious eye irritation.
H340:
May cause genetic defects.
H360:
May damage fertility or the unborn child.
H371:
May cause damage to organs.
H372:
Causes damage to organs through prolonged or repeated exposure.
Toxic if swallowed.
H317:
May cause an allergic skin reaction.
H319:
Causes serious eye irritation.
H340:
May cause genetic defects.
H360:
May damage fertility or the unborn child.
H371:
May cause damage to organs.
H372:
Causes damage to organs through prolonged or repeated exposure.
Precautionary Statement
P201:
Obtain special instructions before use.
P260:
Do not breathe dust, fumes, gas, mist, vapours, spray.
P264:
Wash thoroughly after handling.
P280:
Wear protective gloves/protective clothing/eye protection/face protection.
P301+P310+P330:
IF SWALLOWED:
Immediately call a POISON CENTER or doctor/physician.
Rinse mouth.
P308+P311:
If exposed or concerned:
Call a POISON CENTER or doctor/physician.
Obtain special instructions before use.
P260:
Do not breathe dust, fumes, gas, mist, vapours, spray.
P264:
Wash thoroughly after handling.
P280:
Wear protective gloves/protective clothing/eye protection/face protection.
P301+P310+P330:
IF SWALLOWED:
Immediately call a POISON CENTER or doctor/physician.
Rinse mouth.
P308+P311:
If exposed or concerned:
Call a POISON CENTER or doctor/physician.
Computed Properties
XLogP3
-0.5
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
101.047678466 g/mol
Monoisotopic Mass
101.047678466 g/mol
Topological Polar Surface Area
49.3Ų
Heavy Atom Count
7
Formal Charge
0
Complexity
79.8
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| US-2015382473-A1 | Photosensitive dry film and process for producing printed wiring board using the same | 2014-06-30 |
| EP-2960713-A1 | Backlight unit and display device having the same | 2014-06-27 |
| US-2015378216-A1 | Backlight unit and display device having the same | 2014-06-27 |
| WO-2015199985-A1 | Phosphorous-acid monomer containing emulsion polymer modified urea-formaldehyde resin compositions for making fiberglass products | 2014-06-27 |
| WO-2015192175-A1 | Polymer hydrogel | 2014-06-18 |
| WO-2015195211-A1 | Peelable composition | 2014-06-18 |
| US-2015361418-A1 | Systems and Methods for Substrate Enrichment | 2014-06-11 |
| WO-2015185430-A1 | Agrochemical suspoemulsion comprising polymer particles made of methyl (meth)acrylate and c2-c12 alkyl (meth)acrylate | 2014-06-03 |
| WO-2015183719-A1 | Water-based uv inkjet ink | 2014-05-29 |
| WO-2015181733-A1 | Cosmetic composition for make up and for taking care of keratin materials | 2014-05-28 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 30203046 | 2019-01-01 | Chemical Activation of the Constitutive Androstane Receptor Leads to Activation of Oxidant-Induced Nrf2 | Toxicological sciences : an official journal of the Society of Toxicology |
| 30114225 | 2018-01-01 | Activation of Nrf2 in the liver is associated with stress resistance mediated by suppression of the growth hormone-regulated STAT5b transcription factor | PloS one |
| 26558449 | 2015-12-01 | Gene expression analysis in the lung of the rasH2 transgenic mouse at week 4 prior to induction of malignant tumor formation by urethane and N-methylolacrylamide | The Journal of toxicological sciences |
| 22730900 | 2012-07-18 | Utilization of wheat straw for the preparation of coated controlled-release fertilizer with the function of water retention | Journal of agricultural and food chemistry |
| 21919207 | 2011-12-08 | Self-driven gel conveyer: effect of interactions between loaded cargo and self-oscillating gel surface | Macromolecular bioscience |
| 21992656 | 2011-11-24 | Influence of denaturants on native-state structural fluctuations in azurin probed by molecular size-dependent quenching of Trp phosphorescence | The journal of physical chemistry. B |
| 20740266 | 2011-03-01 | Self-reported symptoms and neuropsychological function among tunnel workers previously exposed to acrylamide and N-methylolacrylamide | Scandinavian journal of work, environment & health |
| 21218776 | 2011-02-15 | Amplitude spectrum of structural fluctuations in proteins from the internal diffusion of solutes of increasing molecular size: a Trp phosphorescence quenching study | Biochemistry |
| 20626931 | 2011-01-01 | Thermo-responsive Mn-Zn ferrite/poly(N,N'-isopropyl acrylamide-co-N-hydroxymethylacrylamide) core/shell nanocomposites for drug-delivery systems | Journal of biomaterials science. Polymer edition |
| 20725771 | 2010-12-01 | Polymeric micelles in anticancer therapy: targeting, imaging and triggered release | Pharmaceutical research |
