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5205-93-6

Basic Information
CAS No.: 5205-93-6
Name: Dimethylamino propyl methacrylamide
Article Data: 15
Molecular Structure:
Molecular Structure of 5205-93-6 (Dimethylamino propyl methacrylamide)
Formula: C9H18N2O
Molecular Weight: 170.255
Synonyms: Acrylamide,N-[3-(dimethylamino)propyl]-2-methyl- (7CI,8CI);Dimethyl[3-(methacryloylamino)propyl]amine;Mhoromer BM 611;N-[3-(Dimethylamino)propyl]methacrylamide;N-[3-(N,N-Dimethylamino)propyl]methacrylamide;
EINECS: 226-002-3
Density: 0.919 g/cm3
Melting Point: <-60 °C
Boiling Point: 302.6 °C at 760 mmHg
Flash Point: 136.8 °C
Solubility: soluble in water and most organic solvents
Appearance: clear liquid
Hazard Symbols: IrritantXi
Risk Codes: 36-38
Safety: 26-36/37/39
PSA: 32.34000
LogP: 1.02130
Synthetic route
108-01-0

2-(N,N-dimethylamino)ethanol

109-55-7

1-amino-3-(dimethylamino)propane

80-62-6

methacrylic acid methyl ester

A

2867-47-2

2-(dimethylamino)ethyl methacrylate

B

5205-93-6

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

Conditions
ConditionsYield
Stage #1: methacrylic acid methyl ester With 10H-phenothiazine; 4-methoxy-phenol Heating / reflux; Neat (no solvent);
Stage #2: di(n-butyl)tin oxide at 70 - 101℃; Heating / reflux; Neat (no solvent);
Stage #3: 2-(N,N-dimethylamino)ethanol; 1-amino-3-(dimethylamino)propane; titanium(IV) isopropylate Product distribution / selectivity; more than 3 stages;
A 87%
B 99.2%
Stage #1: methacrylic acid methyl ester With 10H-phenothiazine; 4-methoxy-phenol In hexane Heating / reflux;
Stage #2: di(n-butyl)tin oxide In hexane at 70 - 101℃; Heating / reflux;
Stage #3: 2-(N,N-dimethylamino)ethanol; 1-amino-3-(dimethylamino)propane; titanium(IV) isopropylate Product distribution / selectivity; more than 3 stages;
A 92.3%
B 99.6%
Stage #1: methacrylic acid methyl ester With 10H-phenothiazine; 4-methoxy-phenol Heating / reflux; Neat (no solvent);
Stage #2: dioctyltin(IV) oxide at 70 - 101℃; Heating / reflux; Neat (no solvent);
Stage #3: 2-(N,N-dimethylamino)ethanol; 1-amino-3-(dimethylamino)propane Product distribution / selectivity; more than 3 stages;
A 86.1%
B 84.4%
Stage #1: methacrylic acid methyl ester With 10H-phenothiazine Heating / reflux; Neat (no solvent);
Stage #2: di(n-butyl)tin oxide at 70 - 101℃; Heating / reflux; Neat (no solvent);
Stage #3: 2-(N,N-dimethylamino)ethanol; 1-amino-3-(dimethylamino)propane; titanium(IV) isopropylate Product distribution / selectivity; more than 3 stages;
A 82.5%
B 90 %Chromat. - 100 %
39743-22-1

p-toluenesulfonic acid 3-dimethylamino-n-propyl ester

79-06-1

2-propenamide

5205-93-6

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

Conditions
ConditionsYield
Stage #1: 2-propenamide With potassium hydroxide In N,N-dimethyl-formamide at 60℃; for 1h;
Stage #2: p-toluenesulfonic acid 3-dimethylamino-n-propyl ester In N,N-dimethyl-formamide at 100℃; for 6h;
95%
109-55-7

1-amino-3-(dimethylamino)propane

80-62-6

methacrylic acid methyl ester

5205-93-6

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

Conditions
ConditionsYield
Stage #1: methacrylic acid methyl ester With 10H-phenothiazine; 4-methoxy-phenol In xylene at 70℃; Heating / reflux;
Stage #2: titanium(IV) isopropylate; di(n-butyl)tin oxide In xylene at 70 - 103℃; Heating / reflux;
Stage #3: 1-amino-3-(dimethylamino)propane In xylene at 103 - 150℃; for 4h; Product distribution / selectivity; Heating / reflux;
93%
Stage #1: methacrylic acid methyl ester With 10H-phenothiazine In xylene Heating / reflux;
Stage #2: di(n-butyl)tin oxide In xylene at 70 - 103℃; Heating / reflux;
Stage #3: 1-amino-3-(dimethylamino)propane In xylene at 103 - 150℃; for 5.5h; Product distribution / selectivity; Heating / reflux;
96.9 - 97.4 %Chromat.
Stage #1: methacrylic acid methyl ester With 10H-phenothiazine Heating / reflux; Neat (no solvent);
Stage #2: di(n-butyl)tin oxide at 70 - 103℃; Heating / reflux; Neat (no solvent);
Stage #3: 1-amino-3-(dimethylamino)propane at 103 - 150℃; for 5.5h; Product distribution / selectivity; Heating / reflux; Neat (no solvent);
95.2 %Chromat.
109-54-6

3-(Dimethylamino)propyl chloride

79-06-1

2-propenamide

5205-93-6

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

Conditions
ConditionsYield
Stage #1: 2-propenamide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 60℃; for 1h;
Stage #2: 3-(Dimethylamino)propyl chloride In N,N-dimethyl-formamide; mineral oil at 80℃; for 4h;
90%
75407-20-4

β-methoxy-isobutyric acid amide

109-55-7

1-amino-3-(dimethylamino)propane

5205-93-6

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

Conditions
ConditionsYield
With sodium hydroxide72%
80-62-6

methacrylic acid methyl ester

5205-93-6

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

Conditions
ConditionsYield
With carbon dioxide7%
109-55-7

1-amino-3-(dimethylamino)propane

80-62-6

methacrylic acid methyl ester

A

5205-93-6

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

B

methyl 2-methyl-3-(3-dimethylaminopropylamino)propionate

C

N-(3-dimethylaminopropyl)-3-(3-dimethylaminopropylamino)-2-methylpropionamide

Conditions
ConditionsYield
at 200℃; Product distribution; also with methyl acrylate; var. temp. and reaction time; also in the presence of amidation catalysts;
463-49-0

1,2-propanediene

201230-82-2

carbon monoxide

109-55-7

1-amino-3-(dimethylamino)propane

5205-93-6

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

Conditions
ConditionsYield
dodecacarbonyl-triangulo-triruthenium In 1,4-dioxane at 100℃; under 9880 Torr; for 18h;10 % Chromat.
4726-85-6

β-alaninamide

79-41-4

poly(methacrylic acid)

A

N-(dimethylaminopropyl)-methacrylamide

B

5205-93-6

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

Conditions
ConditionsYield
In water
79-41-4

poly(methacrylic acid)

109-55-7

1-amino-3-(dimethylamino)propane

5205-93-6

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

Conditions
ConditionsYield
at 150℃; under 7500.75 Torr; Microwave irradiation;
Stage #1: poly(methacrylic acid); 1-amino-3-(dimethylamino)propane With 10H-phenothiazine In toluene at 35℃; Cooling with ice; Industry scale;
Stage #2: at 253℃; under 15001.5 Torr; for 0.0208333h; Microwave irradiation; Industry scale;
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Specification

The IUPAC name of Dimethylamino propyl methacrylamide is N-[3-(dimethylamino)propyl]-2-methylprop-2-enamide. With the CAS registry number 5205-93-6 and EINECS 226-002-3, it is also named as N-(3-(Dimethylamino)propyl)methacrylamide. The product's categories are API Intermediates; Acrylamide and Methacrylamide; Acrylic Monomers; Monomers. It is clear liquid which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.21; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.78; (4)ACD/LogD (pH 7.4): -1.53; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 23.55 Å2; (13)Index of Refraction: 1.459; (14)Molar Refractivity: 50.65 cm3; (15)Molar Volume: 185.1 cm3; (16)Surface Tension: 30.2 dyne/cm; (17)Enthalpy of Vaporization: 54.28 kJ/mol; (18)Vapour Pressure: 0.000979 mmHg at 25°C; (19)Rotatable Bond Count: 5; (20)Tautomer Count: 2; (21)Exact Mass: 170.141913; (22)MonoIsotopic Mass: 170.141913; (23)Topological Polar Surface Area: 32.3; (24)Heavy Atom Count: 12; (25)Complexity: 164.

Preparation and Uses of Dimethylamino propyl methacrylamide: It can be obtained by the reaction of methyl methacrylate and N,N-Dimethyl-1,3-propane diamine. It is used as fiber modifier, pulp additives and agglutinant. It alsocan react with 2-acrylamido-2-methylpropanesulfonic acid to get N,N-dimethyl-N-(3-methacrylamidopropyl)-N-[N'-(1,1-dimethyl-2-sulfonatoethyl)propionamido]betaine. This reaction needs reagent hydroquinone and solvent H2O at temperature of 20 °C. The reaction time is 3 days. The yield is 71%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C(\C(=C)C)NCCCN(C)C
2. InChI:InChI=1/C9H18N2O/c1-8(2)9(12)10-6-5-7-11(3)4/h1,5-7H2,2-4H3,(H,10,12)
3. InChIKey:GDFCSMCGLZFNFY-UHFFFAOYAE