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N,N'-Ethylenebisacrylamide
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Name

N,N'-Ethylenebisacrylamide

 EINECS N/A
CAS No. 2956-58-3 Density 1.034 g/cm3
PSA 58.20000 LogP 0.37260
Solubility Soluble in water and methanol. Melting Point 138-140 °C(lit.)
Formula C8H12N2O2 Boiling Point 456.3 °C at 760 mmHg
Molecular Weight 168.195 Flash Point 213 °C
Transport Information N/A Appearance WHITE TO OFF-WHITE TO FAINT RED POWDER,CRYSTALS OR CRYSTALLINE POWDER
Safety 26-36/37/39-20 Risk Codes 36/37/38-40-11
Molecular Structure Molecular Structure of 2956-58-3 (N,N'-ETHYLENEBISACRYLAMIDE) Hazard Symbols IrritantXi,HarmfulXn,FlammableF
Synonyms

Acrylamide,N,N'-ethylenebis- (6CI,7CI,8CI);Ethylenebisacrylamide;N,N'-Bisacryloylethylenediamine;N,N'-Diacryloyl-1,2-diaminoethane;N,N'-Ethylenebisacrylamide;

Article Data 13

N,N'-Ethylenebisacrylamide Synthetic route

107-15-3

ethylenediamine

814-68-6

acryloyl chloride

A

2956-58-3

N,N'-ethylenebisacrylamide

B

333-18-6

1,2-diaminoethane dihydrochloride

Conditions
ConditionsYield
In acetonitrile for 2h; Ambient temperature;A 85%
B n/a
107-15-3

ethylenediamine

814-68-6

acryloyl chloride

2956-58-3

N,N'-ethylenebisacrylamide

Conditions
ConditionsYield
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
107-15-3

ethylenediamine

79-10-7

acrylic acid

74-86-2

acetylene

2956-58-3

N,N'-ethylenebisacrylamide

Conditions
ConditionsYield
With carbon monoxide; tetracarbonyl nickel; acetone
N.N'-bis-<3-chloro-propionyl>-ethylenediamine

N.N'-bis-<3-chloro-propionyl>-ethylenediamine

2956-58-3

N,N'-ethylenebisacrylamide

Conditions
ConditionsYield
With potassium hydroxide at 85 - 90℃;
2680-03-7

N,N-Dimethylacrylamide

2956-58-3

N,N'-ethylenebisacrylamide

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

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
ConditionsYield
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%
591-50-4

iodobenzene

2956-58-3

N,N'-ethylenebisacrylamide

37946-57-9

N,N'-Dicinnamoyl-ethylendiamin

Conditions
ConditionsYield
With PNODAM-5 catalyst In n-heptane; N,N-dimethyl acetamide at 100℃; Heck reaction;96%
2680-03-7

N,N-Dimethylacrylamide

2956-58-3

N,N'-ethylenebisacrylamide

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

polymer, reverse-phase suspension copolymerization, NH2 content 932 μmol/g; monomer(s): 4-(2-aminoethyl)styrene hydrochloride; N,N-dimethylacrylamide; N,N-ethylenebisacrylamide

Conditions
ConditionsYield
With sorbitol tri-oleate; N,N,N,N,-tetramethylethylenediamine; adenosine 5'-phosphosulfate In tetrachloromethane; hexane; water at 35℃; for 1.75h;92%
2680-03-7

N,N-Dimethylacrylamide

2956-58-3

N,N'-ethylenebisacrylamide

4-aminomethylstyrene hydrochloride

polymer, reverse-phase suspension copolymerization, NH2 content 696 μmol/g; monomer(s): 4-aminomethylstyrene hydrochloride; N,N-dimethylacrylamide; N,N-ethylenebisacrylamide

polymer, reverse-phase suspension copolymerization, NH2 content 696 μmol/g; monomer(s): 4-aminomethylstyrene hydrochloride; N,N-dimethylacrylamide; N,N-ethylenebisacrylamide

Conditions
ConditionsYield
With sorbitol tri-oleate; N,N,N,N,-tetramethylethylenediamine; adenosine 5'-phosphosulfate In tetrachloromethane; hexane; water at 35℃; for 1.5h;92%
2680-03-7

N,N-Dimethylacrylamide

2956-58-3

N,N'-ethylenebisacrylamide

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

polymer, reverse-phase suspension copolymerization, NH2 content 894 μmol/g; monomer(s): 4-(4-aminobutyl)styrene hydrochloride; N,N-dimethylacrylamide; N,N-ethylenebisacrylamide

Conditions
ConditionsYield
With sorbitol tri-oleate; N,N,N,N,-tetramethylethylenediamine; adenosine 5'-phosphosulfate In tetrachloromethane; hexane; water at 35℃; for 1.5h;92%
295-37-4

1,4,8,11-Tetraazacyclotetradecane

2956-58-3

N,N'-ethylenebisacrylamide

3-(1,4,8,11tetraaza-cyclotetradec-1-yl)-N-[2-(3-1,4,8,11tetraaza-cyclotetradec-1-yl-propionylamino)-ethyl]-propionamide

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

N,N'-Ethylenebisacrylamide Specification

The 2-Propenamide,N,N'-1,2-ethanediylbis-, with the CAS registry number 2956-58-3, is also known as N,N'-Ethylenebis(acrylamide). It belongs to the product category of Anilines, Aromatic Amines and Nitro Compounds. This chemical's molecular formula is C8H12N2O2 and molecular weight is 168.19308. Its IUPAC name is called N-[2-(prop-2-enoylamino)ethyl]prop-2-enamide. The product should be sealed and stored in cool and dry place at temperature of 2-8 °C.

Physical properties of 2-Propenamide,N,N'-1,2-ethanediylbis-: (1)ACD/LogP: -1.28; (2)ACD/LogD (pH 5.5): -1.28; (3)ACD/LogD (pH 7.4): -1.28; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 4.82; (7)ACD/KOC (pH 7.4): 4.82; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 5; (11)Index of Refraction: 1.475; (12)Molar Refractivity: 45.81 cm3; (13)Molar Volume: 162.6 cm3; (14)Surface Tension: 34.6 dyne/cm; (15)Density: 1.034 g/cm3; (16)Flash Point: 213 °C; (17)Enthalpy of Vaporization: 71.63 kJ/mol; (18)Boiling Point: 456.3 °C at 760 mmHg; (19)Vapour Pressure: 1.63E-08 mmHg at 25°C.

Preparation: this chemical can be prepared by acryloyl chloride and ethane-1,2-diamine. This reaction will need reagent Et3N and solvent CHCl3.

Uses of 2-Propenamide,N,N'-1,2-ethanediylbis-: it can be used to produce N,N'-Dicinnamoyl-ethylendiamin at temperature of 100 °C. This reaction is a kind of Heck reaction. It will need reagent PNODAM-5 catalyst and solvent heptane, N,N-dimethyl-acetamide. The yield is about 96%.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C=CC(=O)NCCNC(=O)C=C
(2)InChI: InChI=1S/C8H12N2O2/c1-3-7(11)9-5-6-10-8(12)4-2/h3-4H,1-2,5-6H2,(H,9,11)(H,10,12)
(3)InChIKey: AYGYHGXUJBFUJU-UHFFFAOYSA-N

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