2956-58-3

Basic information

• Product Name: N,N'-ETHYLENEBISACRYLAMIDE
• Synonyms: N,N'-DIACRYLOYLETHYLENEDIAMINE;N,N'-ETHYLENEBISACRYLAMIDE, TECH.;N-(2-ACRYLOYLAMINO-ETHYL)-ACRYLAMIDE;TECH. 90-95%;N,N’-Bis(acryloyl)-1,2-diaminoethane, (N,N’-Ethylenebis(acrylamide);N,Nμ-Dimethylenebis(acrylamide), N,Nμ-Bisacryloyl-1,2-diaminoethane;N-(2-acrylamidoethyl)acrylamide;N-[2-(prop-2-enoylamino)ethyl]prop-2-enamide
• CAS NO: 2956-58-3
• Molecular Formula: C₈H₁₂N₂O₂
• Molecular Weight: 168.19
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds
• Mol File: 2956-58-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 138-140 °C(lit.)
• Boiling Point: 456.3 °C at 760 mmHg
• Flash Point: 213 °C
• Appearance: /
• Density: 1.034
• Storage Temp.: 2-8°C
• PKA: 14.07±0.46(Predicted)
• Water Solubility: Soluble in water and methanol.
• Sensitive: Hygroscopic
• BRN: 1771570
• CAS DataBase Reference: N,N'-ETHYLENEBISACRYLAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-ETHYLENEBISACRYLAMIDE(2956-58-3)
• EPA Substance Registry System: N,N'-ETHYLENEBISACRYLAMIDE(2956-58-3)

Safety Data

• Hazard Codes: Xi,Xn,F
• Statements: 36/37/38-40-11
• Safety Statements: 26-36/37/39-20
• RIDADR: 1325
• WGK Germany: 3
• F: 10
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 2956-58-3(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white to light red solid

Uses

N,N'-Ethylenebisacrylamide is used in the preparation of N,N'-dicinnamoyl-ethylendiamine using poly(N-octadecylacrylamide) as a catalyst. It is also used as an intermediate in pharmaceutical industries.

Synthetic route

ethylenediamine (107-15-3) + acryloyl chloride (814-68-6) → N,N'-ethylenebisacrylamide (2956-58-3) + 1,2-diaminoethane dihydrochloride (333-18-6)

Conditions	Yield
In acetonitrile for 2h; Ambient temperature;	A 85% B n/a

ethylenediamine (107-15-3) + acryloyl chloride (814-68-6) → N,N'-ethylenebisacrylamide (2956-58-3)

Conditions	Yield
With sodium acetate; hydroquinone In chloroform for 1h; Heating;	80%
With 4-methoxy-phenol In dichloromethane at 0 - 5℃; for 6h;	56%
With sodium hydroxide In water; acetonitrile at 20℃; for 6h; Cooling with ice;	40%
With sodium acetate In chloroform at 0 - 60℃; for 2.33h;	36%
With triethylamine In chloroform

ethylenediamine (107-15-3) + acrylic acid (79-10-7) + acetylene (74-86-2) → N,N'-ethylenebisacrylamide (2956-58-3)

Conditions	Yield
With carbon monoxide; tetracarbonyl nickel; acetone

N.N'-bis-<3-chloro-propionyl>-ethylenediamine → N,N'-ethylenebisacrylamide (2956-58-3)

Conditions	Yield
With potassium hydroxide at 85 - 90℃;

N,N-Dimethylacrylamide (2680-03-7) + N,N'-ethylenebisacrylamide (2956-58-3) + 2-methoxy-6-[(4-vinyl)benzyloxy]benzylamine hydrochloride → polymer, reverse-phase suspension copolymerization, NH2 content 305 μmol/g; monomer(s): 2-methoxy-6-[(4-vinyl)benzyloxy]benzylamine hydrochloride; N,N-dimethylacrylamide; N,N-ethylenebisacrylamide

Conditions	Yield
With sorbitol tri-oleate; N,N,N,N,-tetramethylethylenediamine; adenosine 5'-phosphosulfate; N,N-dimethyl-formamide In tetrachloromethane; hexane; water at 35℃; for 120h;	99%

iodobenzene (591-50-4) + N,N'-ethylenebisacrylamide (2956-58-3) → N,N'-Dicinnamoyl-ethylendiamin (37946-57-9)

Conditions	Yield
With PNODAM-5 catalyst In n-heptane; N,N-dimethyl acetamide at 100℃; Heck reaction;	96%

N,N-Dimethylacrylamide (2680-03-7) + N,N'-ethylenebisacrylamide (2956-58-3) + 4-(2-aminoethyl)styrene hydrochloride → polymer, reverse-phase suspension copolymerization, NH2 content 932 μmol/g; monomer(s): 4-(2-aminoethyl)styrene hydrochloride; N,N-dimethylacrylamide; N,N-ethylenebisacrylamide

Conditions	Yield
With sorbitol tri-oleate; N,N,N,N,-tetramethylethylenediamine; adenosine 5'-phosphosulfate In tetrachloromethane; hexane; water at 35℃; for 1.75h;	92%

N,N-Dimethylacrylamide (2680-03-7) + N,N'-ethylenebisacrylamide (2956-58-3) + 4-aminomethylstyrene hydrochloride → polymer, reverse-phase suspension copolymerization, NH2 content 696 μmol/g; monomer(s): 4-aminomethylstyrene hydrochloride; N,N-dimethylacrylamide; N,N-ethylenebisacrylamide

Conditions	Yield
With sorbitol tri-oleate; N,N,N,N,-tetramethylethylenediamine; adenosine 5'-phosphosulfate In tetrachloromethane; hexane; water at 35℃; for 1.5h;	92%

N,N-Dimethylacrylamide (2680-03-7) + N,N'-ethylenebisacrylamide (2956-58-3) + 4-(4-aminobutyl)styrene hydrochloride → polymer, reverse-phase suspension copolymerization, NH2 content 894 μmol/g; monomer(s): 4-(4-aminobutyl)styrene hydrochloride; N,N-dimethylacrylamide; N,N-ethylenebisacrylamide

Conditions	Yield
With sorbitol tri-oleate; N,N,N,N,-tetramethylethylenediamine; adenosine 5'-phosphosulfate In tetrachloromethane; hexane; water at 35℃; for 1.5h;	92%

1,4,8,11-Tetraazacyclotetradecane (295-37-4) + N,N'-ethylenebisacrylamide (2956-58-3) → 3-(1,4,8,11tetraaza-cyclotetradec-1-yl)-N-[2-(3-1,4,8,11tetraaza-cyclotetradec-1-yl-propionylamino)-ethyl]-propionamide

Conditions	Yield
With 2,4-di-tert-Butylphenol; toluene-4-sulfonic acid In chloroform Ambient temperature; 2-4d;	82%

N,N'-ethylenebisacrylamide (2956-58-3) + Cyclopentanone oxime (1192-28-5) + PVS (5535-48-8) → 2-(2'-phenylsulphonylethyl)-3,3-spirotetramethylene-5-phenylsulphonylisoxazolidine (113410-75-6) + C34H46N4O8S2

Conditions	Yield
In toluene at 110℃; for 24h;	A 15% B 64%

N,N-Dimethylacrylamide (2680-03-7) + N,N'-ethylenebisacrylamide (2956-58-3) + 4-(6-aminohexyl)styrene hydrochloride → polymer, reverse-phase suspension copolymerization, monomer(s): 4-(6-aminohexyl)styrene hydrochloride; N,N-dimethylacrylamide; N,N\-ethylenebisacrylamide

Conditions	Yield
With sorbitol tri-oleate; N,N,N,N,-tetramethylethylenediamine; adenosine 5'-phosphosulfate In tetrachloromethane; hexane; water at 35℃;	51%

N-acryloylpyrrolidine (42104-70-1) + N,N'-ethylenebisacrylamide (2956-58-3) + methyl ester of N-acryloy-β-alanine (86710-95-4) → acetylglycyl-alanyl-lysyl-arginyl-histidyl-arginyl-lysyl-valylmethyl ester (104343-67-1)

Conditions	Yield
Yield given. Multistep reaction;

N-acryloylpyrrolidine (42104-70-1) + N,N'-ethylenebisacrylamide (2956-58-3) + methyl ester of N-acryloy-β-alanine (86710-95-4) → acetylglycyl-alanyl-lysyl-leucyl-arginyl-histidyl-arginyl-lysyl-valylmethyl ester (104343-68-2)

Conditions	Yield
Yield given. Multistep reaction;

N,N'-ethylenebisacrylamide (2956-58-3) + 2-propenamide (79-06-1) + Acrylic acid 6-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexyl ester (255375-05-4) → polyacrylamide

Conditions	Yield
Stage #1: N,N'-ethylenebisacrylamide; 2-propenamide; Acrylic acid 6-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexyl ester With 2,2'-azobis(isobutyronitrile); acetonitrile Polymerization; Stage #2: With N,N`-dimethylethylenediamine at 20℃; aminolysis;

N,N'-ethylenebisacrylamide (2956-58-3) + N,N-diisopropylacrylamide (44975-46-4) + Acrylic acid 6-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexyl ester (255375-05-4) → poly(N,N-diisopropylacrylamide)

Conditions	Yield
Stage #1: N,N'-ethylenebisacrylamide; N,N-diisopropylacrylamide; Acrylic acid 6-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexyl ester With 2,2'-azobis(isobutyronitrile); acetonitrile Polymerization; Stage #2: With N,N`-dimethylethylenediamine for 24h; aminolysis; Heating;

N,N-diethylacrylamide (2675-94-7) + N,N'-ethylenebisacrylamide (2956-58-3) + Acrylic acid 6-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexyl ester (255375-05-4) → poly(N,N-diethylacrylamide)

Conditions	Yield
Stage #1: N,N-diethylacrylamide; N,N'-ethylenebisacrylamide; Acrylic acid 6-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexyl ester With 2,2'-azobis(isobutyronitrile); acetonitrile Polymerization; Stage #2: With N,N`-dimethylethylenediamine for 24h; aminolysis; Heating;

N,N-Dimethylacrylamide (2680-03-7) + N,N'-ethylenebisacrylamide (2956-58-3) + Acrylic acid 6-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexyl ester (255375-05-4) → poly(N,N-dimethylacrylamide)

Conditions	Yield
Stage #1: N,N-Dimethylacrylamide; N,N'-ethylenebisacrylamide; Acrylic acid 6-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexyl ester With 2,2'-azobis(isobutyronitrile); acetonitrile Polymerization; Stage #2: With N,N`-dimethylethylenediamine for 24h; aminolysis; Heating;

N-Isopropylacrylamide (2210-25-5) + N,N'-ethylenebisacrylamide (2956-58-3) + Acrylic acid 6-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexyl ester (255375-05-4) → poly(N-isopropylacrylamide)

Conditions	Yield
Stage #1: N-Isopropylacrylamide; N,N'-ethylenebisacrylamide; Acrylic acid 6-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexyl ester With 2,2'-azobis(isobutyronitrile); acetonitrile Polymerization; Stage #2: With N,N`-dimethylethylenediamine at 20℃; aminolysis;

N-methylacrylamide (1187-59-3) + N,N'-ethylenebisacrylamide (2956-58-3) + Acrylic acid 6-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexyl ester (255375-05-4) → poly(N-methylacrylamide)

Conditions	Yield
Stage #1: N-methylacrylamide; N,N'-ethylenebisacrylamide; Acrylic acid 6-[(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-hexyl ester With 2,2'-azobis(isobutyronitrile); acetonitrile Polymerization; Stage #2: With N,N`-dimethylethylenediamine at 20℃; aminolysis;

N-Isopropylacrylamide (2210-25-5) + N,N'-ethylenebisacrylamide (2956-58-3) + N-(acryloyl)-L-phenylalanine (16069-16-2) → polymer; monomer(s): N-acryloyl-L-phenylalanine; N-isopropylacrylamide; N,N\-ethylene-bis-acrylamide, incorporation content 2 mol percent

Conditions	Yield
With ammonium persulfate; triethylamine In water at 20℃; for 24h;

N,N'-ethylenebisacrylamide (2956-58-3) + N-(acryloyl)-L-phenylalanine (16069-16-2) → polymer; monomer(s): N-acryloyl-L-phenylalanine; N,N\-ethylene-bis-acrylamide, incorporation content 9 mol percent

Conditions	Yield
With ammonium persulfate; triethylamine In water at 20℃; for 24h;

N,N'-ethylenebisacrylamide (2956-58-3) + diphenyltin (1011-95-6) → {Sn(C6H5)2CH2CH2CONH(CH2)2NHCOCH2CH2}n

Conditions	Yield
In not given

sodium {3-aminooxalyl-2-methyl-1-[2-(pyrazole-1-carbothioylsulfanyl)propionyl]-1H-indol-4-yloxy}-acetate + N,N-Dimethylacrylamide (2680-03-7) + acrylic acid n-butyl ester (141-32-2) + N,N'-ethylenebisacrylamide (2956-58-3) → poly(n-butyl acrylate-co-dimethyl acrylamide-co-ethylene bis-diacrylamide-co-sodium {3-aminooxalyl-2-methyl-1-[2-(pyrazole-1-carbothioylsulfanyl)propionyl]-1H-indol-4-yloxy}-acetate)

Conditions	Yield
Stage #1: sodium {3-aminooxalyl-2-methyl-1-[2-(pyrazole-1-carbothioylsulfanyl)propionyl]-1H-indol-4-yloxy}-acetate; N,N-Dimethylacrylamide; acrylic acid n-butyl ester With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 75℃; for 8h; Stage #2: N,N-Dimethylacrylamide; N,N'-ethylenebisacrylamide In N,N-dimethyl-formamide for 8h;

ethenesulfonic acid (1184-84-5) + N,N'-ethylenebisacrylamide (2956-58-3) → C30H60N2O29S9

Conditions	Yield
With 2-hydroxy-2-methylpropiophenone UV-irradiation;

Malondialdehyde (542-78-9) + N,N'-ethylenebisacrylamide (2956-58-3) → C11H16N2O4

Conditions	Yield
Stage #1: Malondialdehyde; N,N'-ethylenebisacrylamide at 60 - 65℃; for 2h; Stage #2: With 4-methoxy-phenol at 68 - 70℃; for 10h;

N,N'-ethylenebisacrylamide (2956-58-3) + Glutaraldehyde (111-30-8) → C14H22N2O4

Conditions	Yield
Stage #1: N,N'-ethylenebisacrylamide; Glutaraldehyde With acetic acid at 60 - 65℃; for 2h; Stage #2: With 4-methoxy-phenol at 68 - 70℃; for 10h;

butanedial (638-37-9) + N,N'-ethylenebisacrylamide (2956-58-3) → C12H18N2O4

Conditions	Yield
Stage #1: butanedial; N,N'-ethylenebisacrylamide With acetic acid at 60 - 65℃; for 2h; Stage #2: With 4-methoxy-phenol at 68 - 70℃; for 10h;

Upstream product

• 107-15-3 ethylenediamine 
• 79-10-7 acrylic acid 
• 74-86-2 acetylene 
• 814-68-6 acryloyl chloride 

Downstream Products

• 37946-57-9 N,N'-Dicinnamoyl-ethylendiamin 
• 113410-75-6 2-(2'-phenylsulphonylethyl)-3,3-spirotetramethylene-5-phenylsulphonylisoxazolidine 

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