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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: 154.169
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%
Downstream Products
79-10-7
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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.