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{{Short description|Chemical compound, polyacrylamide crosslinker}} |
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{{DISPLAYTITLE:''N'',''N'''-Methylenebisacrylamide}} |
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{{redirect|MBAm|the computer software|Malwarebytes' Anti-Malware|the museum|Montreal Museum of Fine Arts}} |
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{{DISPLAYTITLE:''N'',''N''<nowiki/>'-Methylenebisacrylamide}} |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 409945633 |
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| Name=''N'',''N'''-Methylenebisacrylamide |
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| Name=''N'',''N''′-Methylenebisacrylamide |
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| ImageFile = methylenebisacrylamide.png |
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| ImageFile = methylenebisacrylamide.png |
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| ImageSize = 200px |
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| ImageSize = 200px |
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| ImageAlt = Skeletal formula of methylenebisacrylamide |
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| IUPACName = ''N''-prop-2-enamide |
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| ImageFile1 = Methylenebisacrylamide 3D ball.png |
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| OtherNames = |
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| ImageSize1 = 240 |
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| Section1 = {{Chembox Identifiers |
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| ImageAlt1 = Ball-and-stick model of the methylenebisacrylamide model |
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| PIN = ''N'',''N''′-Methylenedi(prop-2-enamide) |
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| OtherNames = ''bis'' |
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|Section1={{Chembox Identifiers |
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| CASNo = 110-26-9 |
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| CASNo = 110-26-9 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = EDK4RIE19C |
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| PubChem = 8041 |
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| PubChem = 8041 |
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| SMILES = C=CC(=O)NCNC(=O)C=C |
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| SMILES = C=CC(=O)NCNC(=O)C=C |
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| EINECS = 203-750-9 |
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| ChemSpiderID = 7750 |
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| InChI = 1/C7H10N2O2/c1-3-6(10)8-5-9-7(11)4-2/h3-4H,1-2,5H2,(H,8,10)(H,9,11) |
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| InChIKey = ZIUHHBKFKCYYJD-UHFFFAOYAA |
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| StdInChI = 1S/C7H10N2O2/c1-3-6(10)8-5-9-7(11)4-2/h3-4H,1-2,5H2,(H,8,10)(H,9,11) |
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| StdInChIKey = ZIUHHBKFKCYYJD-UHFFFAOYSA-N |
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| RTECS = |
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| MeSHName = C021221 |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=7 | H=10 | N=2 | O=2 |
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| C=7 | H=10 | N=2 | O=2 |
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| Appearance = |
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| Appearance = white solid |
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| Density = |
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| Density = |
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| MeltingPtC = 181-182 |
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| Solubility = }} |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = }} |
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}} |
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{{redirect|MBAM|the computer software|Malwarebytes' Anti-Malware}} |
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'''''N'',''N''′-Methylenebisacrylamide''' (MBAm or MBAA, colloquially "''bis''") is the ] with the formula CH<sub>2</sub><sub>2</sub>. A colorless solid, this compound is a ] in ]s, e.g., as used for ].<ref>{{cite journal|journal=ACS Macro Letters|date=2014|volume=3|issue=5|pages=496–500|doi=10.1021/mz500221j|author=Yuan-na Sun|title=Super Tough, Ultrastretchable, and Thermoresponsive Hydrogels with Functionalized Triblock Copolymer Micelles as Macro-Cross-Linkers|pmid=35590790 |display-authors=etal}}</ref><ref>{{cite book |doi=10.1007/978-1-4939-7741-3_8|chapter=Biofunctionalization of Poly(acrylamide) Gels|title=Biomaterials for Tissue Engineering|series=Methods in Molecular Biology|year=2018|last1=Paez|first1=Julieta I.|last2=Farrukh|first2=Aleeza|last3=Ustahüseyin|first3=Oya|last4=Del Campo|first4=Aránzazu|volume=1758|pages=101–114|pmid=29679325|isbn=978-1-4939-7739-0}}</ref> |
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'''''N'',''N'''-Methylenebisacrylamide''' (MBAm) is a ] used during the formation of ]s such as ]. Its molecular formula is C<sub>7</sub>H<sub>10</sub>N<sub>2</sub>O<sub>2</sub>. |
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== Synthesis == |
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] reacts with an aqueous solution of ] in the presence of ] as a polymerization inhibitor and ] as catalyst to form ''N'',''N''′-methylenebisacrylamide with yields of 60 to 80%.<ref>{{Cite patent|country=US|number=2475846A|title=Alkylidene-bis-acrylamides|gdate=1946-10-31|url=https://patents.google.com/patent/US2475846A/en}}</ref><ref>{{Cite book|last=H.|first=Petersen|title=Methods of Organic Chemistry, Vol. E20|isbn=978-3-13-219004-7|pages=1855}}</ref> |
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] |
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{{DEFAULTSORT:Methylene bisacrylamide, N,N'-}} |
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{{organic-compound-stub}} |
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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 ] in 1,2-dichloroethane gives a clear solution upon heating, from which MBA crystallizes. |
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] |
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In aqueous media, ] also reacts with formaldehyde to give crude ''N'',''N''′-methylenebisacrylamide, which can be purified by recrystallization with acetone/water.<ref>{{Cite journal|last1=Magat|first1=Eugene E.|last2=Faris|first2=Burt F.|last3=Reith|first3=John E.|last4=Salisbury|first4=L. Frank|date=March 1951|title=Acid-catalyzed Reactions of Nitriles. I. The Reaction of Nitriles with Formaldehyde 1|url=https://pubs.acs.org/doi/abs/10.1021/ja01147a042|journal=Journal of the American Chemical Society|language=en|volume=73|issue=3|pages=1028–1031|doi=10.1021/ja01147a042|issn=0002-7863}}</ref> |
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== Reactions and uses == |
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Under basic conditions, MBA reacts further with formaldehyde at the amide nitrogen to give ''N''-hydroxymethyl,''N'',''N''′-methylenebisacrylamide. Nucleophiles such as ]s, ]s, or ]s add across the activated vinyl groups, giving mixtures of mono- and disubstituted products. |
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:] |
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As a bifunctional electron-poor ], MBA reacts with electron-rich dienes, such as ], in ]s, giving the corresponding ] adducts. |
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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.<ref>{{Cite journal|last1=Okada|first1=Yukinori|last2=Tanaka|first2=Fumihiko|date=May 2005|title=Cooperative Hydration, Chain Collapse, and Flat LCST Behavior in Aqueous Poly( N -isopropylacrylamide) Solutions|url=https://pubs.acs.org/doi/10.1021/ma0502497|journal=Macromolecules|language=en|volume=38|issue=10|pages=4465–4471|doi=10.1021/ma0502497|bibcode=2005MaMol..38.4465O|issn=0024-9297}}</ref><ref>{{Cite journal|last1=Behari|first1=Kunj|last2=Agrawal|first2=Uma|last3=Das|first3=Rima|date=October 1993|title=Gel Free Polymerization of N,N′-Methylenebisacrylamide Initiated by a Peroxodiphosphate-Thioacetamide Redox System. A Kinetic Study|journal=Polymer Journal|volume=25|issue=10|pages=1007–1013|doi=10.1295/polymj.25.1007|s2cid=95392705|issn=0032-3896|doi-access=free}}</ref> With acrylic and vinylic monomers such as acrylonitrile, acrylamide, and substituted acrylamides, MBA can undergo radical ] to form highly crosslinked gels, using peroxides, UV light, or redox initiators. |
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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 ], paints, and ]. In biochemistry, MBA is used for ] and ]. |
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==See also== |
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* ] |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Methylene bisacrylamide, N, N'-}} |
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] |
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] |
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] |
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] |
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{{alkene-stub}} |