N,N′-Methylenebisacrylamide = Bisacrylamide
CAS number: 110-26-9
EC number: 203-750-9
Hill Formula: C₇H₁₀N₂O₂
Chemical formula: (CH₂CHCONH)₂CH₂
Molar Mass: 154.17 g/mol
HS Code: 2924 19 00
N,N′-Methylenebisacrylamide (MBAm or MBAA) is the organic compound with the formula CH2[NHC(O)CH=CH2]2.
A colorlesss solid, N,N′-Methylenebisacrylamide is a crosslinking agent in polyacrylamides, e.g., as used for SDS-PAGE.
N,N′-Methylenebisacrylamide, also known as N,n'-methylene-bis(acrylamide), belongs to the class of organic compounds known as acrylic acids and derivatives.
These are organic compounds containing acrylic acid CH2=CHCO2H or a derivative thereof.
Based on a literature review a significant number of articles have been published on N,N'-METHYLENEBISACRYLAMIDE.
N,N′-Methylenebisacrylamide has been identified in human blood as reported by (PMID: 31557052 ).
N,n'-methylenebisacrylamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives.
Technically N,N′-Methylenebisacrylamide is part of the human exposome.
The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health.
An individual's exposure begins before birth and includes insults from environmental and occupational sources.
General description of N,N′-Methylenebisacrylamide:
N,N′-Methylenebis(acrylamide) is a cross linking agent that polymerizes with acrylamide and creates cross links within the polyacrylamide gel.
N,N′-Methylenebisacrylamide is capable of creating a network rather than linear chains which helps in maintaining the firmness of gel.
Bisacrylamide, also called N,N'-Methylenebisacrylamide, is a crosslinking agent commonly used for the formation of polymers such as polyacrylamide gels.
Bisacrylamide polymerizes with acrylamide and is capable of creating cross-links between polyacrylamide chains, which creates a network of polyacrylamide instead of unconnected linear chains.
The ratio of bis-acrylamide to acrylamide determines the porosity of the polyacrylamide gel.
Bisacrylamide is essential in the preparation of protein electrophoresis gels, such as those used in SDS-PAGE.
Applications of N,N′-Methylenebisacrylamide:
N,N′-Methylenebis(acrylamide) has been used in gel preparation.
N,N′-Methylenebisacrylamide has also been used as a test compound for studying the biochemical isolation of insoluble Tau in transgenic mouse models of tauopathy by examining the two main isolation methods sarkosyl and formic acid extraction.
N,N′-Methylenebisacrylamide is a cross-linking agent for preparation of polyacrylamides.
The reaction proceeds via N-hydroxymethylacrylamide, which can be detected in alkaline solution and decomposes in acid to give N,N′-methylenebisacrylamide.
Using acrylamide and paraformaldehyde in 1,2-dichloroethane gives a clear solution upon heating, from which MBA crystallizes.
In aqueous media, acrylonitrile also reacts with formaldehyde to give crude N,N′-methylenebisacrylamide, which can be purified by recrystallization with acetone/water.
As a symmetric, unconjugated divinyl monomer, MBA can be used with suitable initiators in cyclopolymerizations to create linear, soluble polymers whose backbones are built from five- and seven-membered rings.
With acrylic and vinylic monomers such as acrylonitrile, acrylamide, and substituted acrylamides, MBA can undergo radical copolymerization to form highly crosslinked gels, using peroxides, UV light, or redox initiators.
The properties of such gels are determined by the crosslink density, and targeted gel formation using MBA crosslinking gives useful technical properties used in various applications, such as in adhesives, paints, and superabsorbents.
In biochemistry, MBA is used for chromatography gels and polyacrylamide gel electrophoresis.
Reactions and uses of N,N′-Methylenebisacrylamide:
Under basic conditions, MBA reacts further with formaldehyde at the amide nitrogen to give N-hydroxymethyl,N,N′-methylenebisacrylamide.
Nucleophiles such as alcohols, amines, or thiols add across the activated vinyl groups, giving mixtures of mono- and disubstituted products.
As a bifunctional electron-poor dienophile, MBA reacts with electron-rich dienes, such as cyclopentadiene, in Diels–Alder reactions, giving the corresponding norbornene adducts.
Bisacrylamide, also called N,N'-Methylenebisacrylamide, is a crosslinking agent commonly used for the formation of polymers such as polyacrylamide gels.
KEYWORDS:
110-26-9, 203-750-9, Bisacrylamide, NN'-Methylenediacrylamide, 2-Propenamide NN'-methylenebis-, N-[(prop-2-enoylamino)methyl]prop-2-enamide, UNII-EDK4RIE19C, NSC 406836, MBAA, EDK4RIE19C
CAS Number: 110-26-9
ChemSpider: 7750
ECHA InfoCard: 100.003.411
EC Number: 203-750-9
MeSH: C021221
PubChem CID: 8041
UNII: EDK4RIE19C
CompTox Dashboard (EPA): DTXSID8025595
N,N’-Methylenebisacrylamide can be analyzed by this reverse phase (RP) HPLC method with simple conditions.
The mobile phase contains an acetonitrile (MeCN), water, and phosphoric acid.
For Mass-Spec (MS) compatible applications the phosphoric acid needs to be replaced with formic acid. Smaller 3 µm particles columns available for fast UPLC applications.
This liquid chromatography method is scalable and can be used for isolation impurities in preparative separation.
N,N′-Methylenebisacrylamide also suitable for pharmacokinetics.
Chemical Properties of N,N′-Methylenebisacrylamide:
white crystalline powder
Uses of N,N′-Methylenebisacrylamide:
Organic intermediate, cross-linking agent.
Uses of N,N′-Methylenebisacrylamide:
N,N-Methylene-bis-acrylamide is an organic intermediate; cross-linking agent for preparation of polyacrylamides; in preparing poly-acrylamide gel for e1ectrophoresis, chemical grouting and other purposes; in NAPP and Nyloprint UV-cured printing plates.
Uses of N,N′-Methylenebisacrylamide:
N,N'-Methylenebisacrylamide is used in the preparation of polyacrylamide gels for electrophoretic separation of nucleic acids and proteins.
N,N′-Methylenebisacrylamide has also been used as a test compound for studying the biochemical isolation of insoluble Tau in transgenic mouse models of tauopathy by examining the two main isolation methods sarkosyl and formic acid extraction.
General Description of N,N′-Methylenebisacrylamide:
N,N′-Methylenebisacrylamide is a white crystalline powder with a neutral odor.
Air & Water Reactions of N,N′-Methylenebisacrylamide:
Very slightly water soluble.
Reactivity Profile of N,N′-Methylenebisacrylamide:
N,N'-Methylenebisacrylamide is incompatible with strong oxidizers, strong acids and strong bases.
Hazard:
Toxic by ingestion.
Fire Hazard:
Flash point data for N,N'-Methylenebisacrylamide are not available; however, N,N'-Methylenebisacrylamide is probably combustible.
Safety Profile:
-Poison by ingestion.
-Experimental reproductive effects.
-Mutation data reported.
-When heated to decomposition it emits toxic fumes of NOx.
Purification Methods of N,N′-Methylenebisacrylamide:
Recrystallise the amide from MeOH (100g dissolved in 500mL boiling MeOH) and filter without suction in a warmed funnel.
Allow to stand at room temperature and then at -15oC overnight.
The crystals are collected with suction in a cooled funnel and washed with cold MeOH.
The crystals are air-dried in a warm oven.
Appearance: White Crystalline Powder
CAS Number: 110-26-9
Density: 1.054 g/cm3
EINECS Number: 203-750-9
HS Code: 29241900
IUPAC Name: N-[(Prop-2-Enoylamino)Methyl]Prop-2-Enamide
InChI: 1S/C7H10N2O2/c1-3-6(10)8-5-9-7(11)4-2/h3-4H,1-2,5H2,(H,8,10)(H,9,11)
InChIKey: ZIUHHBKFKCYYJD-UHFFFAOYSA-N
Melting Point: >300 °C
Molar Mass: 154.17 g/mol
Molecular Formula: C7H10N2O2
RTECS Number: AS3678000
Solubility: Insoluble
Synonyms: MBAm;Acrylamide,N,N'-methylenebis-;Methylenebisacrylamide;N,N'-Methylenebis(2-Propenamide)
Chemical formula: C7H10N2O2
Molar mass: 154.169 g·mol−1
Appearance: white solid
Melting point: 181–182 °C (358–360 °F; 454–455 K)
Synthesis of N,N′-Methylenebisacrylamide:
Acrylamide reacts with an aqueous solution of formaldehyde in the presence of copper(I) chloride as a polymerization inhibitor and sulfuric acid as catalyst to form N,N′-methylenebisacrylamide with yields of 60 to 80%.
Applications of N,N′-Methylenebisacrylamide:
N,N'-Methylenebisacrylamide for electrophoresis, special grade for molecular biology.
CAS 110-26-9, EC Number 203-750-9, chemical formula (CH₂CHCONH)₂CH₂.
Physicochemical Information of N,N′-Methylenebisacrylamide:
Density: 1.216 g/cm3 (20 °C)
Melting Point: 173.7 - 185.9 °C (decomposition)
pH value: >=5.0 (25 g/l, H₂O, 20 °C)
Vapor pressure: <1 Pa
Bulk density: 200 kg/m3
Alternative Parents of N,N′-Methylenebisacrylamide:
Secondary carboxylic acid amides
Organopnictogen compounds
Organonitrogen compounds
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
Application Notes about N,N′-Methylenebisacrylamide:
N,N'-Methylene-bis-acrylamide is a cross-linker reagent used for precise, critical PAGE gels.
N,N′-Methylenebisacrylamide may be used in UV scanning gels.
N,N′-Methylenebisacrylamide should mixed with acrylamide for making polyacrylamide gels for use in protein and nucleic acid electrophoresis.
N,N′-Methylenebisacrylamide has also been used as a test compound for studying the biochemical isolation of insoluble Tau in transgenic mouse models of tauopathy by examining the two main isolation methods sarkosyl and formic acid extraction.
Applications of N,N′-Methylenebisacrylamide:
To be mixed with acrylamide for making polyacrylamide gels for use in protein and nucleic acid electrophoresis.
N,N'-Methylenebisacrylamide has been used:• as a crosslinker in the monomer solution to prepare N,N-dimethyl acrylamide (DMAAm)-based cryogel and acrylamide (AAm)-based cryogel matrix• as a crosslinker to prepare tough hydrogel network• in the preparation of acrylamide-bisacrylamide stock solution for the preparation of polyacrylamide gel
General description of N,N′-Methylenebisacrylamide:
N,N'-Methylenebisacrylamide is commonly called as bis.
N,N′-Methylenebisacrylamide is used as a cross-linking agent in the preparation of polyacrylamide gels consisting of chains of acrylamide monomers.
The concentration of N,N'-methylenebisacrylamide and acrylamide determines the pore size of the gel.
The higher concentration of bis forms rigid gels with smaller pores due to more cross-linking leading to polymerization and vice versa.
Synonym : methylene bisacrylamide
Related categories : Specialty Chemicals
TSCA : Yes
Melting point : 365 °F (with decomposition) (NTP, 1992)
Solubility : 0.1 to 1 mg/mL at 64° F (NTP, 1992)
Substituents of N,N′-Methylenebisacrylamide:
Acrylic acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound
Quality Level: 100
vapor density: 5.31 (vs air)
assay: 99%
form: powder
mp: >300 °C (lit.)
solubility: water: soluble 20 g/L at 20 °C
storage temp.: 2-8°C
SMILES string: C=CC(=O)NCNC(=O)C=C
InChI: 1S/C7H10N2O2/c1-3-6(10)8-5-9-7(11)4-2/h3-4H,1-2,5H2,(H,8,10)(H,9,11)
InChI key: ZIUHHBKFKCYYJD-UHFFFAOYSA-N
N,N'-Methylenebisacrylamide (MBA) has an industrial application as a crosslinking agent to increase the quality of naturally occurring fibres1 by graft copolymerization.
Butler and Ingley2 however found that divinyl monomer can occasionally yield soluble, gel free polymers and they suggested a new type of alternating intra-inter molecular propagation for such cases: A variety of N-substituted diacrylamide and dimethacrylamides were cyclopolymerized through free radical initiators. 3 - 7 Otsu and Ohya8 homopolymerized a large number of N-substituted dimethacylamide derivatives and found that the cyclization process occurred through repeated intermolecular tail-tail (t-t) propagation with intramolecular head-head (h-h) cyclization.
Recently the polymerization of this divinyl monomer has been reported by other workers.
Such studies have prompted us to study the kinetics of polymerization of this monomer with redox system of peroxodiphosphate (PDP)-thioacetamide (RSH).
EXPERIMENTAL:
Potassium peroxodiphosphate was generously provided by FMC Corporation and used as obtained.
All other chemicals used were either E. Merck or Analar Grade. B.D.H. (British Drug House) products. N,N'-methylenebisacrylamide was recrystallized from acetone at 40°C and dried in vacuo over silica gel.
The kinetics of the polymerization was followed as reported in our earlier communication.
The per cent conversion was calculated by the modified equation of Wallace and Young.
Most of the reactions were carried out at pH = 2.09 and no induction period was observed for polymerization.
The research investigated the effects of acrylic acid (monomer) and N,N,-methylenebisacrylamide, MBA (crosslinker) toward the percentage of gel content, swelling ratio and ionic strength of a starch-based hydrogel.
Starch grafted on poly (sodium acrylate), St-g-PAANa hydrogel was prepared by incorporating starch extracted from Dioscorea hispida in NaOH/aqueous solution using different composition of acrylic acid (AA) and N,N-methylenebisacrylamide (MBA) in the presence of potassium persulfate (KPS) as chemical initiator.
The highest gel content was observed at 1:30 ratio of starch to AA and 0.10 M of MBA.
Results showed the highest swelling ratio was observed at 1:15 ratio of starch to acrylic acid and 0.02 M of MBA solution.
The same results also gave the highest swelling ratio for the ionic strength study.
The FTIR analysis was also conducted in order to confirm the grafting of AA onto starch backbone.
Specifications of N,N′-Methylenebisacrylamide:
Appearance (Colour): White
Appearance (Form): Crystalline powder
Solubility (Turbidity) 2.5% aq. solution: Clear
Solubility (Colour) 2.5% aq. solution : Colourless
Assay (ex N): min. 99.5%
pH (2.5% aq. solution): min. 5.0
Loss on drying: max. 0.5%
Specific conductance (2% aq. solution): max. 10 μmho/cm
Acrylic acid (C3H4O2): max. 0.02%
Molecular Weight: 154.17
XLogP3-AA: 0.1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 4
Exact Mass: 154.074227566
Monoisotopic Mass: 154.074227566
Topological Polar Surface Area: 58.2 Ų
Heavy Atom Count: 11
Formal Charge: 0
Complexity: 167
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
About N,N′-Methylenebisacrylamide Helpful information:
N,N′-Methylenebisacrylamide is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.
N,N′-Methylenebisacrylamide is used by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses of N,N′-Methylenebisacrylamide:
ECHA has no public registered data indicating whether or in which chemical products N,N′-Methylenebisacrylamide might be used.
ECHA has no public registered data on the routes by which N,N′-Methylenebisacrylamide is most likely to be released to the environment.
Article service life of N,N′-Methylenebisacrylamide:
ECHA has no public registered data on the routes by which N,N′-Methylenebisacrylamide is most likely to be released to the environment.
ECHA has no public registered data indicating whether or into which articles N,N′-Methylenebisacrylamide might have been processed.
Widespread uses of N,N′-Methylenebisacrylamide by professional workers:
N,N′-Methylenebisacrylamide is used in the following products: polymers.
N,N′-Methylenebisacrylamide is used in the following areas: scientific research and development.
Other release to the environment of N,N′-Methylenebisacrylamide is likely to occur from: indoor use as reactive substance.
Formulation or re-packing of N,N′-Methylenebisacrylamide:
ECHA has no public registered data indicating whether or in which chemical products N,N′-Methylenebisacrylamide might be used.
Release to the environment of N,N′-Methylenebisacrylamide can occur from industrial use: formulation of mixtures.
Uses at industrial sites of N,N′-Methylenebisacrylamide:
N,N′-Methylenebisacrylamide is used in the following products: laboratory chemicals and polymers.
N,N′-Methylenebisacrylamide is used in the following areas: scientific research and development.
N,N′-Methylenebisacrylamide is used for the manufacture of: chemicals and plastic products.
Release to the environment of N,N′-Methylenebisacrylamide can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates), for thermoplastic manufacture and as processing aid.
Manufacture of N,N′-Methylenebisacrylamide:
Release to the environment of N,N′-Methylenebisacrylamide can occur from industrial use: manufacturing of the substance.
N,N'-METHYLENEBISACRYLAMIDE
110-26-9
N,N'-Methylenediacrylamide
N,N'-Methylene-bis-acrylamide
Methylenebisacrylamide
Methylenediacrylamide
n,n-methylenebisacrylamide
2-Propenamide, N,N'-methylenebis-
N,N'-Methylenebis(acrylamide)
Bisacrylamide
Bis-acrylamide
N-[(prop-2-enoylamino)methyl]prop-2-enamide
N,N'-Methylidenebisacrylamide
Acrylamide, N,N'-methylenebis-
UNII-EDK4RIE19C
N,N'-Methylenebis(2-propenamide)
NSC 406836
MBAA
EDK4RIE19C
MLS001055454
MFCD00008625
Bisacrylamide; MBA;Methylenebisacrylamide
NCGC00090721-03
SMR001227199
2-Propenamide, N,N'-methylenebis-, homopolymer
Acrylamide,N'-methylenebis-
N,N'-Methylenebis[acrylamide]
2-Propenamide,N'-methylenebis-
26949-19-9
CCRIS 4672
EINECS 203-750-9
BRN 1706297
AI3-08643
NAPP
N-(prop-2-enamidomethyl)prop-2-enamide
Methylenebis[acrylamide]
DSSTox_CID_5595
cid_8041
DSSTox_RID_77846
n,n'-methylenebis acrylamide
DSSTox_GSID_25595
N,N'-methylene bisacrylamide
SCHEMBL20000
N,N\'-Methylenebisacrylamide
N-(acrylamidomethyl)acrylamide
N,N' methylene bis acrylamide
N,N`-Methylene-bis-acrylamide
N,N'-Diacryloylmethylenediamine
CHEMBL1401480
DTXSID8025595
N,N'-Methylidenebis[acrylamide]
BDBM74235
NSC7774
N,N'-methanediylbisprop-2-enamide
N-[(Acryloylamino)methyl]acrylamide
NSC-7774
ZINC1688365
Tox21_400038
NSC406836
STL186175
STL257389
AKOS005206740
AKOS025264600
ANGC-110-26-9
N,N'-Methylenebis(acrylamide), 99%
N-[(Acryloylamino)methyl]acrylamide #
MCULE-5665969570
NSC-406836
NCGC00090721-01
NCGC00090721-02
NCGC00090721-04
CAS-110-26-9
N,N'-Methylenebisacrylamide, 2% solution
NCI60_041713
N,N'-Methylenebisacrylamide, p.a., 98%
N-[(prop-2-enamido)methyl]prop-2-enamide
N,N'-Methylenebis(acrylamide), >=99.0%
BB 0295285
CS-0014818
CS-0202692
FT-0629399
M0506
M2877
A905227
N-[(1-oxoprop-2-enylamino)methyl]-2-propenamide
(1Z,1'Z)-N,N'-methanediylbisprop-2-enimidic acid
Q3869308
W-108692
N,N'-Methylenebis(acrylamide), Vetec(TM) reagent grade
Bis-acrylamide, Molecular biology and electrophoresis grade
N,N'-Methylenebisacrylamide, for molecular biology, >=98%
N,N'-Methylenebisacrylamide solution, for electrophoresis, 2% in H2O
N,N'-Methylenebisacrylamide, powder, for molecular biology, for electrophoresis, >=99.5%
N,N'-Methylenebisacrylamide,for electrophoresis, inverted exclamation markY99.0%(T)
N,N'-Methylenebisacrylamide, suitable for electrophoresis (after filtration or allowing insolubles to settle)
Regulatory process names:
N,N'-methylenediacrylamide
N,N'-methylenediacrylamide
IUPAC names:
Bis(acrylamido)methane
Bisacrylamide
Methylene-bis-acrylamide
N,N'-Methylendiacrylamid
N,N'-METHYLENEBIS(ACRYLAMIDE)
N,N'-methylenebis-2-propenamide
N,N'-Methylenebisacrylamide
N,N'-methylenebisacrylamide
N,N'-Methylenebisacrylamide [for Electrophoresis]
N,N'-Methylenediacrylamide
N,N'-methylenediacrylamide
N,N'-methylenediacrylamide
N,N-Methylenbisacrylamide
N,N`-Methylene-bisacrylamide
N-[(prop-2-enamido)methyl]prop-2-enamide
N-[(prop-2-enoylamino)methyl]prop-2-e
N-[(Prop-2-enoylamino)methyl]prop-2-enamide
N-[(prop-2-enoylamino)methyl]prop-2-enamide
N-[(Prop-2-enoylamino)methyl]prop-2-enamide.
Wasmer MBA
Other identifiers:
110-26-9