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% |
Conditions | Yield |
---|---|
With hydrogenchloride |
formaldehyd
1,2-dichloro-ethane
2-propenamide
N,N'-Methylenebisacrylamide
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
With sulfuric acid; water | |
With hydroquinone | |
With sulfuric acid |
formaldehyd
sulfuric acid
acrylonitrile
N,N'-Methylenebisacrylamide
Pentaerythritol
N-Methylolacrylamid
B
C13H22N2O6
I
N,N'-Methylenebisacrylamide
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 |
Conditions | Yield |
---|---|
With sodium hydroxide; potassium carbonate; triethylamine In 1,4-dioxane; methanol; water; ethyl acetate | 200 mg (58%) |
N,N'-Methylenebisacrylamide
bis(mesityleneformyl)phosphine
N,N-methylene(bis(bis(2,4,6-trimethylbenzoyl)phosphino)propanamide)
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
N,N'-Methylenebisacrylamide
C136H158N22O24
Conditions | Yield |
---|---|
In methanol; water at 50℃; for 48h; Michael Addition; Inert atmosphere; | 95% |
N,N'-Methylenebisacrylamide
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
Conditions | Yield |
---|---|
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine In water at 30℃; for 1h; | 93% |
Conditions | Yield |
---|---|
With triethylamine at 20℃; for 24h; Michael Addition; | 93% |
N,N'-Methylenebisacrylamide
dimethyl acetylenedicarboxylate
triethyl phosphite
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction; | 92% |
N,N'-Methylenebisacrylamide
ammonium thiocyanate
benzenediazonium tetrafluoroborate
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
trisodium (S,S)-ethylenediamine-N,N’-disuccinic acid
Conditions | Yield |
---|---|
With lithium hydroxide at 20℃; for 48h; | 90.1% |
Conditions | Yield |
---|---|
With 2,4-di-tert-Butylphenol; toluene-4-sulfonic acid In chloroform Ambient temperature; 2-4d; | 90% |
N,N'-Methylenebisacrylamide
ammonium thiocyanate
Conditions | Yield |
---|---|
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 10 - 15℃; | 90% |
N,N'-Methylenebisacrylamide
acetylenedicarboxylic acid diethyl ester
phosphorous acid trimethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction; | 90% |
N,N'-Methylenebisacrylamide
N-Isopropylacrylamide
N-propylacrylamide
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
Conditions | Yield |
---|---|
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine; sodium dodecyl-sulfate at 70℃; for 4h; | 88.3% |
N,N'-Methylenebisacrylamide
dimethyl acetylenedicarboxylate
phosphorous acid trimethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction; | 87% |
N,N'-Methylenebisacrylamide
potassium thioacyanate
benzenediazonium tetrafluoroborate
Conditions | Yield |
---|---|
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 15℃; for 1.75h; | 86% |
N,N'-Methylenebisacrylamide
4-methoxybenzenediazonium tetrafluoroborate
ammonium thiocyanate
N-{[3-(4-methoxy-phenyl)-2-thiocyanato-propionylamino]-methyl}-acrylamide
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
ammonium thiocyanate
4-methylbenzenediazonium tetrafluoroborate
N-[(2-thiocyanato-3-p-tolyl-propionylamino)-methyl]-acrylamide
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
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
Conditions | Yield |
---|---|
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine In water at 50℃; for 1h; | 85% |
N,N'-Methylenebisacrylamide
Di-tert-butyl acetylenedicarboxylate
phosphorous acid trimethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction; | 85% |
N,N'-Methylenebisacrylamide
N-Isopropylacrylamide
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
Conditions | Yield |
---|---|
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine; sodium dodecyl-sulfate at 70℃; for 4h; | 84.9% |
N,N'-Methylenebisacrylamide
N-isopropylmethacrylamide
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
Conditions | Yield |
---|---|
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine; sodium dodecyl-sulfate at 70℃; for 4h; | 84.9% |
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
Di-tert-butyl acetylenedicarboxylate
triethyl phosphite
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction; | 84% |
N,N'-Methylenebisacrylamide
2-methyl-acrylic acid 3-dimethylamino-propyl amide
2-propenamide
(3-acrylamidophenyl)boronic acid
Conditions | Yield |
---|---|
With α,α'-azodiizobutyramidine-dihydrochloride In water; dimethyl sulfoxide at 60℃; for 20h; | 83.7% |
N,N'-Methylenebisacrylamide
2-methylphenyl diazonium tetrafluoroborate
ammonium thiocyanate
Conditions | Yield |
---|---|
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 10 - 15℃; | 82% |
N,N'-Methylenebisacrylamide
fullerene-C60
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
Conditions | Yield |
---|---|
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine In water at 50℃; for 1.4h; | 82% |
triphenyl phosphite
N,N'-Methylenebisacrylamide
Di-tert-butyl acetylenedicarboxylate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction; | 82% |
Conditions | Yield |
---|---|
With copper(II) bis(tetrafluoroborate) In water; N,N-dimethyl-formamide at 15℃; | 81% |
N,N'-Methylenebisacrylamide
acetylenedicarboxylic acid diethyl ester
triethyl phosphite
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction; | 81% |
N,N'-Methylenebisacrylamide
fullerene-C60
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
Conditions | Yield |
---|---|
With ammonium persulfate; N,N,N,N,-tetramethylethylenediamine In water at 50℃; for 1.5h; | 80% |
triphenyl phosphite
N,N'-Methylenebisacrylamide
acetylenedicarboxylic acid diethyl ester
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 5.25h; diastereoselective reaction; | 80% |
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 (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.
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. |
Reported in EPA TSCA Inventory.
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, Xi
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 (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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