Product Name

  • Name

    N,N'-Methylenebisacrylamide

  • EINECS 203-750-9
  • CAS No. 110-26-9
  • Density 1.054 g/cm3
  • Solubility 0.01-0.1 g/100 mL at 18 °C in water
  • Melting Point >300 °C(lit.)
  • Formula C7H10N2O2
  • Boiling Point 445.1 °C at 760 mmHg
  • Molecular Weight 154.169
  • Flash Point 215 °C
  • Transport Information UN 2811
  • Appearance white crystalline powder
  • Safety 22-36/37-36-26
  • Risk Codes 20/22-20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 110-26-9 (N,N'-Methylenebisacrylamide)
  • Hazard Symbols HarmfulXn,IrritantXi
  • 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;
  • PSA 58.20000
  • LogP 0.33010

Synthetic route

formaldehyd
50-00-0

formaldehyd

2-propenamide
79-06-1

2-propenamide

N,N'-Methylenebisacrylamide
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%
N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

Conditions
ConditionsYield
With hydrogenchloride
formaldehyd
50-00-0

formaldehyd

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

2-propenamide
79-06-1

2-propenamide

N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

Conditions
ConditionsYield
With hydrogenchloride
formaldehyd
50-00-0

formaldehyd

acrylonitrile
107-13-1

acrylonitrile

N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

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

formaldehyd

sulfuric acid
7664-93-9

sulfuric acid

acrylonitrile
107-13-1

acrylonitrile

N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

Pentaerythritol
115-77-5

Pentaerythritol

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

A

etherbis-N-methylenacrylamide

etherbis-N-methylenacrylamide

B

C13H22N2O6
85030-50-8

C13H22N2O6

C

C14H27NO8

C14H27NO8

D

C17H27N3O7

C17H27N3O7

E

C26H42N4O11

C26H42N4O11

F

C30H47N5O12

C30H47N5O12

G

C34H52N6O13

C34H52N6O13

H

C26H42N4O11

C26H42N4O11

I

N,N'-Methylenebisacrylamide
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

acryloyl chloride
814-68-6

acryloyl chloride

N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

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

propylene glycol

N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

bis(mesityleneformyl)phosphine
139031-06-4

bis(mesityleneformyl)phosphine

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

N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

C136H158N22O24
1549684-13-0

C136H158N22O24

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

N,N'-Methylenebisacrylamide

acrylic acid
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%
N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

4-sulfanylphenol
637-89-8

4-sulfanylphenol

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

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

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

N,N'-Methylenebisacrylamide

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

triethyl phosphite
122-52-1

triethyl phosphite

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

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

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

N,N'-Methylenebisacrylamide

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

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

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

N,N'-Methylenebisacrylamide

trisodium (S,S)-ethylenediamine-N,N’-disuccinic acid
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%
1,4,8,11-Tetraazacyclotetradecane
295-37-4

1,4,8,11-Tetraazacyclotetradecane

N,N'-Methylenebisacrylamide
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

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

N,N'-Methylenebisacrylamide

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

2,5-dichloroaniline diazonium fluoroboric salt

2,5-dichloroaniline diazonium fluoroboric salt

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

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

N,N'-Methylenebisacrylamide

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

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

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

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

N,N'-Methylenebisacrylamide

N-Isopropylacrylamide
2210-25-5

N-Isopropylacrylamide

N-propylacrylamide
25999-13-7

N-propylacrylamide

4-N-(2-acryloyloxyethyl)-N-methylamino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole
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%
N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

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

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

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

N,N'-Methylenebisacrylamide

potassium thioacyanate
333-20-0

potassium thioacyanate

benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

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

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

N,N'-Methylenebisacrylamide

4-methoxybenzenediazonium tetrafluoroborate
459-64-3

4-methoxybenzenediazonium tetrafluoroborate

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

N-{[3-(4-methoxy-phenyl)-2-thiocyanato-propionylamino]-methyl}-acrylamide
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%
N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

4-methylbenzenediazonium tetrafluoroborate
459-44-9

4-methylbenzenediazonium tetrafluoroborate

N-[(2-thiocyanato-3-p-tolyl-propionylamino)-methyl]-acrylamide
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%
N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

acrylic acid
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%
N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

Di-tert-butyl acetylenedicarboxylate
66086-33-7

Di-tert-butyl acetylenedicarboxylate

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

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

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

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

N,N'-Methylenebisacrylamide

N-Isopropylacrylamide
2210-25-5

N-Isopropylacrylamide

4-N-(2-acryloyloxyethyl)-N-methylamino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole
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%
N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

N-isopropylmethacrylamide
13749-61-6

N-isopropylmethacrylamide

4-N-(2-acryloyloxyethyl)-N-methylamino-7-N,N-dimethylaminosulfonyl-2,1,3-benzoxadiazole
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%
N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

2-propenamide
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%
N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

Di-tert-butyl acetylenedicarboxylate
66086-33-7

Di-tert-butyl acetylenedicarboxylate

triethyl phosphite
122-52-1

triethyl phosphite

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

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

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

N,N'-Methylenebisacrylamide

2-methyl-acrylic acid 3-dimethylamino-propyl amide
5205-93-6

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

2-propenamide
79-06-1

2-propenamide

(3-acrylamidophenyl)boronic acid
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%
N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

2-methylphenyl diazonium tetrafluoroborate
2093-46-1

2-methylphenyl diazonium tetrafluoroborate

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

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

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

N,N'-Methylenebisacrylamide

acrylic acid
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%
triphenyl phosphite
101-02-0

triphenyl phosphite

N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

Di-tert-butyl acetylenedicarboxylate
66086-33-7

Di-tert-butyl acetylenedicarboxylate

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

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

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

N,N'-Methylenebisacrylamide

potassium thioacyanate
333-20-0

potassium thioacyanate

2,5-dichloroaniline diazonium fluoroboric salt

2,5-dichloroaniline diazonium fluoroboric salt

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

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

N,N'-Methylenebisacrylamide

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

triethyl phosphite
122-52-1

triethyl phosphite

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

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

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

N,N'-Methylenebisacrylamide

acrylic acid
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%
triphenyl phosphite
101-02-0

triphenyl phosphite

N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

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

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

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

N,N'-Methylenebisacrylamide Chemical Properties

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

N,N'-Methylenebisacrylamide 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.

N,N'-Methylenebisacrylamide 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.

N,N'-Methylenebisacrylamide Consensus Reports

Reported in EPA TSCA Inventory.

N,N'-Methylenebisacrylamide 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

N,N'-Methylenebisacrylamide 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.

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