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110-26-9

Basic Information
CAS No.: 110-26-9
Name: N,N'-Methylenebisacrylamide
Molecular Structure:
Molecular Structure of 110-26-9 (N,N'-Methylenebisacrylamide)
Formula: C7H10N2O2
Molecular Weight: 154.1665
Synonyms: Acrylamide,N,N'-methylenebis- (6CI,7CI,8CI);Bisacrylamide;Methylenebisacrylamide;Methylenediacrylamide;N,N'-Diacryloylmethylenediamine;N,N'-Methylenebis(2-propenamide);N,N'-Methylenebis(acrylamide);2-Propenamide,N,N'-methylenebis-;NSC 406836;NSC 7774;Triam 507;
EINECS: 203-750-9
Density: 1.054 g/cm3
Melting Point: >300 °C(lit.)
Boiling Point: 445.1 °C at 760 mmHg
Flash Point: 215 °C
Solubility: 0.01-0.1 g/100 mL at 18 °C in water
Appearance: white crystalline powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 20/22-20/21/22-36/37/38
Safety: 22-36/37-36-26
Transport Information: UN 2811
PSA: 58.20000
LogP: 0.33010
Synthetic route
50-00-0

formaldehyd

79-06-1

2-propenamide

110-26-9

N,N'-Methylenebisacrylamide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; hydroquinone In water at 65 - 75℃; for 2.5h; Reagent/catalyst; Temperature;87.54%
924-42-5

N-Methylolacrylamid

107-06-2

1,2-dichloro-ethane

110-26-9

N,N'-Methylenebisacrylamide

Conditions
ConditionsYield
With hydrogenchloride
50-00-0

formaldehyd

107-06-2

1,2-dichloro-ethane

79-06-1

2-propenamide

110-26-9

N,N'-Methylenebisacrylamide

Conditions
ConditionsYield
With hydrogenchloride
50-00-0

formaldehyd

107-13-1

acrylonitrile

110-26-9

N,N'-Methylenebisacrylamide

Conditions
ConditionsYield
With sulfuric acid; water
With hydroquinone
With sulfuric acid
50-00-0

formaldehyd

7664-93-9

sulfuric acid

107-13-1

acrylonitrile

110-26-9

N,N'-Methylenebisacrylamide

115-77-5

Pentaerythritol

924-42-5

N-Methylolacrylamid

A

etherbis-N-methylenacrylamide

B

85030-50-8

C13H22N2O6

C

C14H27NO8

D

C17H27N3O7

E

C26H42N4O11

F

C30H47N5O12

G

C34H52N6O13

H

C26H42N4O11

I

110-26-9

N,N'-Methylenebisacrylamide

Conditions
ConditionsYield
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
p-(1,4,7,10,13-Pentaoxatetradecyl)benzylacetal-bisacrylamide

p-(1,4,7,10,13-Pentaoxatetradecyl)benzylacetal-bisacrylamide

814-68-6

acryloyl chloride

110-26-9

N,N'-Methylenebisacrylamide

Conditions
ConditionsYield
With sodium hydroxide; potassium carbonate; triethylamine In 1,4-dioxane; methanol; water; ethyl acetate200 mg (58%)
57-55-6

propylene glycol

110-26-9

N,N'-Methylenebisacrylamide

110-26-9

N,N'-Methylenebisacrylamide

139031-06-4

bis(mesityleneformyl)phosphine

1591653-06-3

N,N-methylene(bis(bis(2,4,6-trimethylbenzoyl)phosphino)propanamide)

Conditions
ConditionsYield
With triethylamine In 1,2-dimethoxyethane; toluene at 50℃; for 12h; Schlenk technique; Inert atmosphere;99%
347371-56-6

N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetra[4-(2-aminoethyl)phenoxy]perylene-3,4,9,10-tetracarboxylic acid diimide

110-26-9

N,N'-Methylenebisacrylamide

1549684-13-0

C136H158N22O24

Conditions
ConditionsYield
In methanol; water at 50℃; for 48h; Michael Addition; Inert atmosphere;95%
110-26-9

N,N'-Methylenebisacrylamide

79-10-7

acrylic acid

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

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
ConditionsYield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine In water at 30℃; for 1h;93%
110-26-9

N,N'-Methylenebisacrylamide

637-89-8

4-sulfanylphenol

methylene bis[3-(4-hydroxyphenylsulfanyl)propanecarboxamide]

Conditions
ConditionsYield
With triethylamine at 20℃; for 24h; Michael Addition;93%
110-26-9

N,N'-Methylenebisacrylamide

762-42-5

dimethyl acetylenedicarboxylate

122-52-1

triethyl phosphite

dimethyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(diethylphosphono)succinate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;92%
110-26-9

N,N'-Methylenebisacrylamide

1147550-11-5

ammonium thiocyanate

369-57-3

benzenediazonium tetrafluoroborate

N-[(3-phenyl-2-thiocyanatopropionylamino)methyl]acrylamide

Conditions
ConditionsYield
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%
110-26-9

N,N'-Methylenebisacrylamide

178949-82-1

trisodium (S,S)-ethylenediamine-N,N’-disuccinic acid

BA-EDDS

BA-EDDS

Conditions
ConditionsYield
With lithium hydroxide at 20℃; for 48h;90.1%
295-37-4

1,4,8,11-Tetraazacyclotetradecane

110-26-9

N,N'-Methylenebisacrylamide

3-(1,4,8,11tetraaza-cyclotetradec-1-yl)-N-[(3-1,4,8,11tetraaza-cyclotetradec-1-yl-propionylamino)-methyl]-propionamide

Conditions
ConditionsYield
With 2,4-di-tert-Butylphenol; toluene-4-sulfonic acid In chloroform Ambient temperature; 2-4d;90%
110-26-9

N,N'-Methylenebisacrylamide

1147550-11-5

ammonium thiocyanate

2,5-dichloroaniline diazonium fluoroboric salt

N-{[3-(2,5-dichloro-phenyl)-2-thiocyanato-propionylamino]-methyl}-acrylamide

Conditions
ConditionsYield
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 10 - 15℃;90%
110-26-9

N,N'-Methylenebisacrylamide

762-21-0

acetylenedicarboxylic acid diethyl ester

121-45-9

phosphorous acid trimethyl ester

diethyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(dimethyphosphono)succinate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;90%
110-26-9

N,N'-Methylenebisacrylamide

2210-25-5

N-Isopropylacrylamide

25999-13-7

N-propylacrylamide

627546-76-3

4-N-(2-acryloyloxyethyl)-N-methylamino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole

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

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
ConditionsYield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine; sodium dodecyl-sulfate at 70℃; for 4h;88.3%
110-26-9

N,N'-Methylenebisacrylamide

762-42-5

dimethyl acetylenedicarboxylate

121-45-9

phosphorous acid trimethyl ester

dimethyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(dimethylphosphono)succinate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;87%
110-26-9

N,N'-Methylenebisacrylamide

333-20-0

potassium thioacyanate

369-57-3

benzenediazonium tetrafluoroborate

N,N-methylenebis(2-thiocyanato-3-phenylpropionamide)

Conditions
ConditionsYield
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 15℃; for 1.75h;86%
110-26-9

N,N'-Methylenebisacrylamide

459-64-3

4-methoxybenzenediazonium tetrafluoroborate

1147550-11-5

ammonium thiocyanate

524067-02-5

N-{[3-(4-methoxy-phenyl)-2-thiocyanato-propionylamino]-methyl}-acrylamide

Conditions
ConditionsYield
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%
110-26-9

N,N'-Methylenebisacrylamide

1147550-11-5

ammonium thiocyanate

459-44-9

4-methylbenzenediazonium tetrafluoroborate

524067-01-4

N-[(2-thiocyanato-3-p-tolyl-propionylamino)-methyl]-acrylamide

Conditions
ConditionsYield
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%
110-26-9

N,N'-Methylenebisacrylamide

79-10-7

acrylic acid

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

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
ConditionsYield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine In water at 50℃; for 1h;85%
110-26-9

N,N'-Methylenebisacrylamide

66086-33-7

Di-tert-butyl acetylenedicarboxylate

121-45-9

phosphorous acid trimethyl ester

di-tert-butyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(dimethyphosphono)succinate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;85%
110-26-9

N,N'-Methylenebisacrylamide

2210-25-5

N-Isopropylacrylamide

627546-76-3

4-N-(2-acryloyloxyethyl)-N-methylamino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole

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

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
ConditionsYield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine; sodium dodecyl-sulfate at 70℃; for 4h;84.9%
110-26-9

N,N'-Methylenebisacrylamide

13749-61-6

N-isopropylmethacrylamide

627546-76-3

4-N-(2-acryloyloxyethyl)-N-methylamino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole

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

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
ConditionsYield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine; sodium dodecyl-sulfate at 70℃; for 4h;84.9%
110-26-9

N,N'-Methylenebisacrylamide

79-06-1

2-propenamide

polymer; monomer(s): acrylamide; N,N\-methylenebis(acrylamide)

polymer; monomer(s): acrylamide; N,N\-methylenebis(acrylamide)

Conditions
ConditionsYield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine In various solvent(s) at 65℃; Product distribution; Further Variations:; Solvents; Temperatures;84%
110-26-9

N,N'-Methylenebisacrylamide

66086-33-7

Di-tert-butyl acetylenedicarboxylate

122-52-1

triethyl phosphite

di-tert-butyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(diethylphosphono)succinate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;84%
110-26-9

N,N'-Methylenebisacrylamide

5205-93-6

2-methyl-acrylic acid 3-dimethylamino-propyl amide

79-06-1

2-propenamide

99349-68-5

(3-acrylamidophenyl)boronic acid

copolymer; monomer(s): 3-acrylamidophenylboronic acid; N-(3-dimethylaminopropyl)methacrylamide; N,N'-methylenebisacrylamide; acrylamide

copolymer; monomer(s): 3-acrylamidophenylboronic acid; N-(3-dimethylaminopropyl)methacrylamide; N,N'-methylenebisacrylamide; acrylamide

Conditions
ConditionsYield
With α,α'-azodiizobutyramidine-dihydrochloride In water; dimethyl sulfoxide at 60℃; for 20h;83.7%
110-26-9

N,N'-Methylenebisacrylamide

2093-46-1

2-methylphenyl diazonium tetrafluoroborate

1147550-11-5

ammonium thiocyanate

N-[(2-thiocyanato-3-o-tolyl-propionylamino)-methyl]-acrylamide

Conditions
ConditionsYield
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 10 - 15℃;82%
110-26-9

N,N'-Methylenebisacrylamide

79-10-7

acrylic acid

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

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
ConditionsYield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine In water at 50℃; for 1.4h;82%
101-02-0

triphenyl phosphite

110-26-9

N,N'-Methylenebisacrylamide

66086-33-7

Di-tert-butyl acetylenedicarboxylate

di-tert-buthyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(diphenylphosphono)succinate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;82%
110-26-9

N,N'-Methylenebisacrylamide

333-20-0

potassium thioacyanate

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
ConditionsYield
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 15℃;81%
110-26-9

N,N'-Methylenebisacrylamide

762-21-0

acetylenedicarboxylic acid diethyl ester

122-52-1

triethyl phosphite

dethyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(diethylphosphono)succinate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;81%
110-26-9

N,N'-Methylenebisacrylamide

79-10-7

acrylic acid

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

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
ConditionsYield
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine In water at 50℃; for 1.5h;80%
101-02-0

triphenyl phosphite

110-26-9

N,N'-Methylenebisacrylamide

762-21-0

acetylenedicarboxylic acid diethyl ester

diethyl 2-[acryloyl(acryloylaminomethyl)amino]-3-(diphenylphosphono)succinate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction;80%
Downstream Products
79-10-7
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    N,N'-Methylenebisacrylamide 110-26-9

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    Appearance: white powder Purity: ≥98.00% Water insoluble: ≤0.50% Inorganic Sulfates: ≤0.50% Others: Usage: Widely used in ion resin, superabsorbent, adhesives, coatings, thickeners, sealing agent, synthetic fibers, insulation m

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    N,N'-Methylenebisacrylamide

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    Low price with good quality N,N'-METHYLENESBISACRYLAMIDE

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    MBA N N'-Methylenebisacrylamide 110-26-9

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    ISO Certified Manufactory Supplier of Product N,N'-Methylenebisacrylamide MBA CAS: 110-26-9 Name Synonyms CAS Registry Number Molecular Formula Molecular Weight EI

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    N,N'-Methylenebisacrylamide

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  • 110-26-9 N,N'-Methylenebisacrylamide

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    110-26-9

    110-26-9 N,N'-Methylenebisacrylamide

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Chemistry

Molecular structure of N,N'-Methylenebisacrylamide (CAS NO.110-26-9):

IUPAC Name: N-[(Prop-2-enoylamino)methyl]prop-2-enamide
Molecular Formula: C7H10N2O2
Molecular Weight: 154.1665 g/mol
Density: 1.054 g/cm3 
Melting Point: >300 °C(lit.)
Boiling Point: 445.1 °C at 760 mmHg 
Flash Point: 215 °C
Index of Refraction: 1.475
Molar Refractivity: 41.17 cm3
Molar Volume: 146.1 cm3
Surface Tension: 34.7 dyne/cm 
Enthalpy of Vaporization: 70.3 kJ/mol
Vapour Pressure: 4.06E-08 mmHg at 25 °C 
Storage Temp.: 2-8 °C
Water Solubility: 0.01-0.1 g/100 mL at 18 °C
XLogP3-AA: 0.1
H-Bond Donor: 2
H-Bond Acceptor: 2
Rotatable Bond Count: 4
Tautomer Count: 3
Exact Mass: 154.074228
MonoIsotopic Mass: 154.074228
Topological Polar Surface Area: 58.2
Heavy Atom Count: 11 
Canonical SMILES: C=CC(=O)NCNC(=O)C=C
InChI: 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
EINECS: 203-750-9
Product Categories: Biochemistry; Reagents for Electrophoresis; Acrylamide; Molecular Biology; Nucleic Acid Electrophoresis

Uses

 N,N'-Methylenebisacrylamide (CAS NO.110-26-9) is an important material for the separation of Amino Acids. It is essential to photosensitive nylon and plastics. N,N'-Methylenebisacrylamide is also used as plugging agent in oilfield drilling and construction grouting. It is used as cross-linking agent in the synthesis of acrylic resin and adhesives.

Toxicity Data With Reference

1.    

mma-sat 1 mg/plate

    EMMUEG    Environmental and Molecular Mutagenesis. 11 (Suppl 12)(1988),1.
2.    

dlt-mus-ipr 225 mg/kg

    MUREAV    Mutation Research. 229 (1990),161.
3.    

orl-rat LD50:390 mg/kg

    37ASAA    Kirk-Othmer Encyclopedia of Chemical Technology. 1 (1978),306.
4.    

orl-mus LD50:380 mg/kg

    JACTDZ    Journal of the American College of Toxicology. 1 (1990),111.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Poison by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also AMIDES.
Hazard Codes: Xn, IrritantXi
Risk Statements: 20/22-20/21/22-36/37/38
20/22: Harmful by inhalation and if swallowed 
20/21/22: Harmful by inhalation, in contact with skin and if swallowed 
36/37/38: Irritating to eyes, respiratory system and skin 
Safety Statements: 22-36/37-36-26
22: Do not breathe dust 
36/37: Wear suitable protective clothing and gloves 
36: Wear suitable protective clothing 
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
RIDADR: UN 2811
WGK Germany: 2
RTECS: AS3678000
F: 8
F8: Photosensitive
HazardClass: 6.1(b)
PackingGroup: III
HS Code: 29241900

Specification

 N,N'-Methylenebisacrylamide (CAS NO.110-26-9) is also named as 2-Propenamide, N,N'-methylenebis- ; 4-02-00-01472 (Beilstein Handbook Reference) ; AI3-08643 ; BRN 1706297 ; CCRIS 4672 ; Methylenebisacrylamide ; Methylenediacrylamide ; N,N'-Methylenebis(2-propenamide) ; N,N'-Methylenebis(acrylamide) ; N,N'-Methylenediacrylamide ; N,N'-Methylidenebisacrylamide ; NSC 406836 . N,N'-Methylenebisacrylamide (CAS NO.110-26-9) is white crystalline powder with a neutral odor. It is very slightly water soluble. N,N'-Methylenebisacrylamide is incompatible with strong oxidizers, strong acids and strong bases. Flash point data for N,N'-Methylenebisacrylamide are not available; however, it is probably combustible.