110-26-9

Basic information

• Product Name: N,N'-Methylenebisacrylamide
• Synonyms: ADENINE SULFATE HIGH PURITY GRADE;SALINE PEPTONE WATER 10X90ML;URIDINE ULTRA PURE GRADE;N,N'-Methylenebis-Acrylamide, 2%;MBA/BIS/NAPP;N,N'-METHYLENEBISACRYLAMIDE, POWDER;Methylenediacrylamide;n,n’-methylenebis-2-propenamid
• CAS NO: 110-26-9
• Molecular Formula: C₇H₁₀N₂O₂
• Molecular Weight: 154.17
• EINECS: 203-750-9
• Product Categories: Triazines;Biochemistry;Reagents for Electrophoresis;Acrylamide;Molecular Biology;Nucleic Acid Electrophoresis;fine chemical;fine chemicals
• Mol File: 110-26-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 277.52°C (rough estimate)
• Flash Point: 215 °C
• Appearance: White/powder
• Density: 1.235
• Vapor Density: 5.31 (vs air)
• Vapor Pressure: 0-0.073Pa at 20-84.85℃
• Refractive Index: 1.4880 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: 20 mg/mL at 20 °C, clear, colorless
• PKA: 13.07±0.46(Predicted)
• Water Solubility: 0.01-0.1 g/100 mL at 18 ºC
• Sensitive: Air & Light Sensitive
• BRN: 1706297
• CAS DataBase Reference: N,N'-Methylenebisacrylamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Methylenebisacrylamide(110-26-9)
• EPA Substance Registry System: N,N'-Methylenebisacrylamide(110-26-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/22-20/21/22-36/37/38
• Safety Statements: 22-36/37-36-26
• RIDADR: UN 2811
• WGK Germany: 2
• RTECS: AS3678000
• F: 8
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 110-26-9(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 110-26-9 differently. You can refer to the following data:
1. Organic intermediate, cross-linking agent.
2. 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.
3. N,N'-Methylenebisacrylamide is used in the preparation of polyacrylamide gels for electrophoretic separation of nucleic acids and proteins. It 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

White crystalline powder with a neutral odor.

Air & Water Reactions

Very slightly water soluble.

Reactivity Profile

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

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. [Beilstein 2 IV 1472.] VERY TOXIC (neurotoxic).

Synthetic route

formaldehyd (50-00-0) + 2-propenamide (79-06-1) → N,N'-Methylenebisacrylamide (110-26-9)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; hydroquinone In water at 65 - 75℃; for 2.5h; Reagent/catalyst; Temperature;	87.54%

N-Methylolacrylamid (924-42-5) + 1,2-dichloro-ethane (107-06-2) → N,N'-Methylenebisacrylamide (110-26-9)

Conditions	Yield
With hydrogenchloride

formaldehyd (50-00-0) + 1,2-dichloro-ethane (107-06-2) + 2-propenamide (79-06-1) → N,N'-Methylenebisacrylamide (110-26-9)

Conditions	Yield
With hydrogenchloride

formaldehyd (50-00-0) + acrylonitrile (107-13-1) → N,N'-Methylenebisacrylamide (110-26-9)

Conditions	Yield
With sulfuric acid; water
With hydroquinone
With sulfuric acid

formaldehyd (50-00-0) + sulfuric acid (7664-93-9) + acrylonitrile (107-13-1) → N,N'-Methylenebisacrylamide (110-26-9)

Pentaerythritol (115-77-5) + N-Methylolacrylamid (924-42-5) → etherbis-N-methylenacrylamide + C13H22N2O6 (85030-50-8) + C14H27NO8 + C17H27N3O7 + C26H42N4O11 + C30H47N5O12 + C34H52N6O13 + C26H42N4O11 + N,N'-Methylenebisacrylamide (110-26-9)

Conditions	Yield
Stage #1: Pentaerythritol; N-Methylolacrylamid With tempol; toluene-4-sulfonic acid In methanol at 86℃; for 1.5h; Stage #2: With ammonia In methanol; propyleneglycol monomethylether; water

...Expand

p-(1,4,7,10,13-Pentaoxatetradecyl)benzylacetal-bisacrylamide + acryloyl chloride (814-68-6) → N,N'-Methylenebisacrylamide (110-26-9)

Conditions	Yield
With sodium hydroxide; potassium carbonate; triethylamine In 1,4-dioxane; methanol; water; ethyl acetate	200 mg (58%)

propylene glycol (57-55-6) + TOP (4731-53-7) → N,N'-Methylenebisacrylamide (110-26-9)

N,N'-Methylenebisacrylamide (110-26-9) + bis(mesityleneformyl)phosphine (139031-06-4) → N,N-methylene(bis(bis(2,4,6-trimethylbenzoyl)phosphino)propanamide) (1591653-06-3)

Conditions	Yield
With triethylamine In 1,2-dimethoxyethane; toluene at 50℃; for 12h; Schlenk technique; Inert atmosphere;	99%

N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetra[4-(2-aminoethyl)phenoxy]perylene-3,4,9,10-tetracarboxylic acid diimide (347371-56-6) + N,N'-Methylenebisacrylamide (110-26-9) → C136H158N22O24 (1549684-13-0)

Conditions	Yield
In methanol; water at 50℃; for 48h; Michael Addition; Inert atmosphere;	95%

N,N'-Methylenebisacrylamide (110-26-9) + acrylic acid (79-10-7) → poly(acrylic acid), cross-linked by 0.15 wt % of N,N'-methylenebisacrylamide, neutralized with degree of neutralization 0.3; monomer(s): acrylic acid; N,N'-methylenebisacrylamide

Conditions	Yield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine In water at 30℃; for 1h;	93%

N,N'-Methylenebisacrylamide (110-26-9) + 4-sulfanylphenol (637-89-8) → methylene bis[3-(4-hydroxyphenylsulfanyl)propanecarboxamide]

Conditions	Yield
With triethylamine at 20℃; for 24h; Michael Addition;	93%

N,N'-Methylenebisacrylamide (110-26-9) + dimethyl acetylenedicarboxylate (762-42-5) + triethyl phosphite (122-52-1) → dimethyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(diethylphosphono)succinate

Conditions	Yield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;	92%

N,N'-Methylenebisacrylamide (110-26-9) + ammonium thiocyanate (1147550-11-5) + benzenediazonium tetrafluoroborate (369-57-3) → N-[(3-phenyl-2-thiocyanatopropionylamino)methyl]acrylamide

Conditions	Yield
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 10 - 15℃; for 1.25h;	91%
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 10 - 15℃; for 0.75h;	91%

N,N'-Methylenebisacrylamide (110-26-9) + trisodium (S,S)-ethylenediamine-N,N’-disuccinic acid (178949-82-1) → BA-EDDS

Conditions	Yield
With lithium hydroxide at 20℃; for 48h;	90.1%

1,4,8,11-Tetraazacyclotetradecane (295-37-4) + N,N'-Methylenebisacrylamide (110-26-9) → 3-(1,4,8,11tetraaza-cyclotetradec-1-yl)-N-[(3-1,4,8,11tetraaza-cyclotetradec-1-yl-propionylamino)-methyl]-propionamide

Conditions	Yield
With 2,4-di-tert-Butylphenol; toluene-4-sulfonic acid In chloroform Ambient temperature; 2-4d;	90%

N,N'-Methylenebisacrylamide (110-26-9) + ammonium thiocyanate (1147550-11-5) + 2,5-dichloroaniline diazonium fluoroboric salt → N-{[3-(2,5-dichloro-phenyl)-2-thiocyanato-propionylamino]-methyl}-acrylamide

Conditions	Yield
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 10 - 15℃;	90%

N,N'-Methylenebisacrylamide (110-26-9) + acetylenedicarboxylic acid diethyl ester (762-21-0) + phosphorous acid trimethyl ester (121-45-9) → diethyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(dimethyphosphono)succinate

Conditions	Yield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;	90%

N,N'-Methylenebisacrylamide (110-26-9) + N-Isopropylacrylamide (2210-25-5) + N-propylacrylamide (25999-13-7) + 4-N-(2-acryloyloxyethyl)-N-methylamino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole (627546-76-3) → polymer, emulsion polymerization; Monomer(s): N-isopropylacrylamide, 75 mM; N-n-propylacrylamide, 25 mM; N,N\-methylenebisacrylamide, 1 mM; 4-N-(2-acryloyloxyethyl)-N-methylamino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole, 0.1 mM

Conditions	Yield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine; sodium dodecyl-sulfate at 70℃; for 4h;	88.3%

N,N'-Methylenebisacrylamide (110-26-9) + dimethyl acetylenedicarboxylate (762-42-5) + phosphorous acid trimethyl ester (121-45-9) → dimethyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(dimethylphosphono)succinate

Conditions	Yield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;	87%

N,N'-Methylenebisacrylamide (110-26-9) + potassium thioacyanate (333-20-0) + benzenediazonium tetrafluoroborate (369-57-3) → N,N-methylenebis(2-thiocyanato-3-phenylpropionamide)

Conditions	Yield
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 15℃; for 1.75h;	86%

N,N'-Methylenebisacrylamide (110-26-9) + 4-methoxybenzenediazonium tetrafluoroborate (459-64-3) + ammonium thiocyanate (1147550-11-5) → N-{[3-(4-methoxy-phenyl)-2-thiocyanato-propionylamino]-methyl}-acrylamide (524067-02-5)

Conditions	Yield
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 10 - 15℃;	85%
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 10 - 15℃;	85%

N,N'-Methylenebisacrylamide (110-26-9) + ammonium thiocyanate (1147550-11-5) + 4-methylbenzenediazonium tetrafluoroborate (459-44-9) → N-[(2-thiocyanato-3-p-tolyl-propionylamino)-methyl]-acrylamide (524067-01-4)

Conditions	Yield
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 10 - 15℃;	85%
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 10 - 15℃;	85%

N,N'-Methylenebisacrylamide (110-26-9) + acrylic acid (79-10-7) → poly(acrylic acid), cross-linked by 0.2 wt % of N,N'-methylenebisacrylamide, neutralized with degree of neutralization 0.4; monomer(s): acrylic acid; N,N'-methylenebisacrylamide

Conditions	Yield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine In water at 50℃; for 1h;	85%

N,N'-Methylenebisacrylamide (110-26-9) + Di-tert-butyl acetylenedicarboxylate (66086-33-7) + phosphorous acid trimethyl ester (121-45-9) → di-tert-butyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(dimethyphosphono)succinate

Conditions	Yield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;	85%

N,N'-Methylenebisacrylamide (110-26-9) + N-Isopropylacrylamide (2210-25-5) + 4-N-(2-acryloyloxyethyl)-N-methylamino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole (627546-76-3) → polymer, emulsion polymerization; Monomer(s): N-isopropylacrylamide, 100 mM; N,N\-methylenebisacrylamide, 1 mM; 4-N-(2-acryloyloxyethyl)-N-methylamino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole, 0.1 mM

Conditions	Yield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine; sodium dodecyl-sulfate at 70℃; for 4h;	84.9%

N,N'-Methylenebisacrylamide (110-26-9) + N-isopropylmethacrylamide (13749-61-6) + 4-N-(2-acryloyloxyethyl)-N-methylamino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole (627546-76-3) → polymer, emulsion polymerization; Monomer(s): N-isopropylmethacrylamide, 100 mM; N,N\-methylenebisacrylamide, 1 mM; 4-N-(2-acryloyloxyethyl)-N-methylamino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole, 0.1 mM

Conditions	Yield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine; sodium dodecyl-sulfate at 70℃; for 4h;	84.9%

N,N'-Methylenebisacrylamide (110-26-9) + 2-propenamide (79-06-1) → polymer; monomer(s): acrylamide; N,N\-methylenebis(acrylamide)

Conditions	Yield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine In various solvent(s) at 65℃; Product distribution; Further Variations:; Solvents; Temperatures;	84%

N,N'-Methylenebisacrylamide (110-26-9) + Di-tert-butyl acetylenedicarboxylate (66086-33-7) + triethyl phosphite (122-52-1) → di-tert-butyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(diethylphosphono)succinate

Conditions	Yield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;	84%

N,N'-Methylenebisacrylamide (110-26-9) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) + 2-propenamide (79-06-1) + (3-acrylamidophenyl)boronic acid (99349-68-5) → copolymer; monomer(s): 3-acrylamidophenylboronic acid; N-(3-dimethylaminopropyl)methacrylamide; N,N'-methylenebisacrylamide; acrylamide

Conditions	Yield
With α,α'-azodiizobutyramidine-dihydrochloride In water; dimethyl sulfoxide at 60℃; for 20h;	83.7%

N,N'-Methylenebisacrylamide (110-26-9) + 2-methylphenyl diazonium tetrafluoroborate (2093-46-1) + ammonium thiocyanate (1147550-11-5) → N-[(2-thiocyanato-3-o-tolyl-propionylamino)-methyl]-acrylamide

Conditions	Yield
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 10 - 15℃;	82%

N,N'-Methylenebisacrylamide (110-26-9) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) + acrylic acid (79-10-7) → poly(acrylic acid), cross-linked by 0.15 wt % of N,N'-methylenebisacrylamide, modified by 0.1 wt % of [60]fullerene, neutralized with degree of neutralization 0.4; monomer(s): acrylic acid; N,N'-methylenebisacrylamide; [60]fullerene

Conditions	Yield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine In water at 50℃; for 1.4h;	82%

triphenyl phosphite (101-02-0) + N,N'-Methylenebisacrylamide (110-26-9) + Di-tert-butyl acetylenedicarboxylate (66086-33-7) → di-tert-buthyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(diphenylphosphono)succinate

Conditions	Yield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;	82%

N,N'-Methylenebisacrylamide (110-26-9) + potassium thioacyanate (333-20-0) + 2,5-dichloroaniline diazonium fluoroboric salt → 3-(2,5-dichloro-phenyl)-N-{[3-(2,5-dichloro-phenyl)-2-thiocyanato-propionylamino]-methyl}-2-thiocyanato-propionamide

Conditions	Yield
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 15℃;	81%

N,N'-Methylenebisacrylamide (110-26-9) + acetylenedicarboxylic acid diethyl ester (762-21-0) + triethyl phosphite (122-52-1) → dethyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(diethylphosphono)succinate

Conditions	Yield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;	81%

N,N'-Methylenebisacrylamide (110-26-9) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) + acrylic acid (79-10-7) → poly(acrylic acid), cross-linked by 0.1 wt % of N,N'-methylenebisacrylamide, modified by 0.1 wt % of [60]fullerene, neutralized with degree of neutralization 0.4; monomer(s): acrylic acid; N,N'-methylenebisacrylamide; [60]fullerene

Conditions	Yield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine In water at 50℃; for 1.5h;	80%

triphenyl phosphite (101-02-0) + N,N'-Methylenebisacrylamide (110-26-9) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(diphenylphosphono)succinate

Conditions	Yield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;	80%

Upstream product

• 924-42-5 N-Methylolacrylamid 
• 107-06-2 1,2-dichloro-ethane 
• 50-00-0 formaldehyd 
• 7664-93-9 sulfuric acid 
• 107-13-1 acrylonitrile 
• 79-06-1 2-propenamide 
• 57-55-6 propylene glycol 
• 4731-53-7 TOP 
• 115-77-5 Pentaerythritol 
• 814-68-6 acryloyl chloride 

Downstream Products

• 524067-02-5 N-{[3-(4-methoxy-phenyl)-2-thiocyanato-propionylamino]-methyl}-acrylamide 
• 524067-01-4 N-[(2-thiocyanato-3-p-tolyl-propionylamino)-methyl]-acrylamide 
• 1549684-13-0 C₁₃₆H₁₅₈N₂₂O₂₄ 

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