Dimethylamino propyl methacrylamide supplier

Name
Dimethylamino propyl methacrylamide
EINECS 226-002-3
CAS No. 5205-93-6
Article Data15
CAS DataBase
Density 0.919 g/cm³
Solubility soluble in water and most organic solvents
Melting Point <-60 °C
Formula C₉H₁₈N₂O
Boiling Point 302.6 °C at 760 mmHg
Molecular Weight 170.255
Flash Point 136.8 °C
Transport Information
Appearance clear liquid
Safety 26-36/37/39
Risk Codes 36-38
Molecular Structure
Hazard Symbols Xi
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;
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

Conditions	Yield
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 %

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide	72%

: 80-62-6
methacrylic acid methyl ester

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

Conditions

Conditions	Yield
With carbon dioxide	7%

: 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

Conditions	Yield
at 200℃; Product distribution; also with methyl acrylate; var. temp. and reaction time; also in the presence of amidation catalysts;

...Expand

: 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

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

...Expand

: 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

Conditions	Yield
In water

...Expand

: 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

Conditions	Yield
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;

: methacrylic acid ammonium salt

: 109-55-7
1-amino-3-(dimethylamino)propane

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

Conditions

Conditions	Yield
With 10H-phenothiazine In toluene at 175 - 185℃; for 0.0333333h; Microwave irradiation;

: 3179-63-3
3-Dimethylamino-1-propanol

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide / 6 h / 20 - 50 °C 2.1: potassium hydroxide / N,N-dimethyl-formamide / 1 h / 60 °C 2.2: 6 h / 100 °C View Scheme

: 1120-71-4
1,3-propanesultone

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: 5205-95-8
N,N-dimethyl-N-(3-sulfopropyl)-3'-methacrylamidopropanaminium inner salt

Conditions

Conditions	Yield
In acetone at 20℃; for 48h;	98%
With oxygen; 4-methoxy-phenol In methanol; acetone at 40 - 45℃; for 2h; Temperature; Reagent/catalyst;	97.41%
at 25℃; for 3h; Temperature; Heating;	93.4%
In diethyl ether at 20℃; for 24h;	86%

: 1072-53-3
ethyleneglycol sulfate

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: 2-((3-methacrylamidopropyl)dimethylammonio)ethyl sulfate

Conditions

Conditions	Yield
With nitrobenzene In acetonitrile at 50℃; for 24h; Schlenk technique; Inert atmosphere;	95.6%

: 3344-70-5
1,12-dibromododecane

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: C30H60N4O2(2+)*2Br(1-)

Conditions

Conditions	Yield
In acetonitrile at 65℃; for 144h; Schlenk technique;	95%

: 1469-73-4, 20772-55-8, 20772-56-9, 40811-14-1, 40811-15-2, 51260-40-3, 51260-41-4
4-methyl-2-oxo-1,3,2-dioxathiolane

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: C12H24N2O4S

Conditions

Conditions	Yield
With hydroquinone In 1,4-dioxane at 97℃; for 2.5h;	94%

: 109-65-9
1-bromo-butane

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: (2-methacrylamido) propyltetrahexyldimethylammonium bromide

Conditions

Conditions	Yield
In acetone at 60℃; for 30h; Inert atmosphere;	89.6%

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: 1073-05-8
1,3,2-dioxathiane 2,2-dioxide

: 3-((3-methacrylamidopropyl)dimethylammonio)propyl sulfate

Conditions

Conditions	Yield
With nitrobenzene In acetonitrile at 50℃; for 24h; Schlenk technique; Inert atmosphere;	88.8%

: 110-26-9
N,N'-Methylenebisacrylamide

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: 79-06-1
2-propenamide

: 99349-68-5
(3-acrylamidophenyl)boronic acid

copolymer; monomer(s): 3-acrylamidophenylboronic acid; N-(3-dimethylaminopropyl)methacrylamide; N,N'-methylenebisacrylamide; acrylamide: copolymer; monomer(s): 3-acrylamidophenylboronic acid; N-(3-dimethylaminopropyl)methacrylamide; N,N'-methylenebisacrylamide; acrylamide

Conditions

Conditions	Yield
With α,α'-azodiizobutyramidine-dihydrochloride In water; dimethyl sulfoxide at 60℃; for 20h;	83.7%

...Expand

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: 100-44-7
benzyl chloride

: C16H25N2O(1+)*Br(1-)

Conditions

Conditions	Yield
In dichloromethane at 40℃; for 24h; Inert atmosphere;	81.1%

: 57-57-8
β-Propiolactone

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: 80921-09-1
N,N-dimethyl-N-(3-methacrylamidopropyl)propiobetaine

Conditions

Conditions	Yield
With 2,2-diphenyl-1-picrylhydrazyl In tetrahydrofuran at 0 - 4℃; for 27h; Inert atmosphere;	80%

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: 201611-92-9
4-cyano-4-(thiobenzoylthio)pentanoic acid

poly(N-[3-(dimethylamino)propyl]methacrylamide), terminated with 4-carboxy-2-cyanobutyl-2-yl and thiobenzoylsulfanyl units, product of RAFT polymerization; monomer(s): N-[3-(dimethylamino)propyl]methacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate: poly(N-[3-(dimethylamino)propyl]methacrylamide), terminated with 4-carboxy-2-cyanobutyl-2-yl and thiobenzoylsulfanyl units, product of RAFT polymerization; monomer(s): N-[3-(dimethylamino)propyl]methacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate

Conditions

Conditions	Yield
With hydrogenchloride; 4,4'-dicyano-4,4'-azo-di-valeric acid In acetate buffer at 70℃; for 1h; pH=5;	78.77%

: 111-25-1
1-bromo-hexane

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: (2-methacrylamido) propyltetrabenzyldimethylammonium chloride

Conditions

Conditions	Yield
In acetone at 4 - 60℃; for 42h; Inert atmosphere;	73.9%

: 15214-89-8
2-acrylamido-2-methylpropanesulfonic acid

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: N,N-dimethyl-N-(3-methacrylamidopropyl)-N-[N'-(1,1-dimethyl-2-sulfonatoethyl)propionamido]betaine

Conditions

Conditions	Yield
With hydroquinone In water at 20℃; for 72h; Addition;	71%
With hydroquinone In water at 70℃; Kinetics; Concentration;

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: 79-10-7
acrylic acid

: 80921-09-1
N,N-dimethyl-N-(3-methacrylamidopropyl)propiobetaine

Conditions

Conditions	Yield
With radical inhibitor at 0 - 20℃; for 5h; Cooling with ice;	70%
In water at 70℃; Product distribution; Further Variations:; Reaction partners; Temperatures; Addition;
In water Addition;
In water-d2 Kinetics; Solvent;
With hydroquinone In water at 50℃; Kinetics; Concentration;

: 1120-71-4
1,3-propanesultone

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: [3-(methacryloylamino)propyl]dimethyl(3-sulfopropyl)ammonium hydroxide

Conditions

Conditions	Yield
In diethyl ether at 20℃; for 16h;	39%

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

poly(N-(3-dimethylammoniopropyl)methacrylamide sulfate); monomer(s): N-(3-dimethylaminopropyl)methacrylamide: poly(N-(3-dimethylammoniopropyl)methacrylamide sulfate); monomer(s): N-(3-dimethylaminopropyl)methacrylamide

Conditions

Conditions	Yield
With sulfuric acid In water at 70℃; for 4h;	35%
With sulfuric acid In water Activation energy;
With sulfuric acid In water Kinetics; Further Variations:; pH-values;

: 56905-18-1, 114438-55-0, 114438-56-1
methyl 2-iodopropionate

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: 108899-87-2
(3-methacryloylamino-propyl)-(1-methoxycarbonyl-ethyl)-dimethyl-ammonium; iodide

Conditions

Conditions	Yield
With acetone

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: 535-11-5, 41978-69-2
Ethyl 2-bromopropionate

: 109337-30-6
(1-ethoxycarbonyl-ethyl)-(3-methacryloylamino-propyl)-dimethyl-ammonium; bromide

Conditions

Conditions	Yield
With acetone

: 110-89-4
piperidine

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: N-(3-dimethylamino-propyl)-2-methyl-3-piperidin-1-yl-propionamide

Conditions

Conditions	Yield
In water at 70℃; Rate constant;

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

: 79-06-1
2-propenamide

: (2-carbamoyl-ethyl)-dimethyl-[3-(2-methyl-acryloylamino)-propyl]-ammonium; chloride

Conditions

Conditions	Yield
With hydrogenchloride In water at 20℃; for 0.5h; quaternization;	76 % Chromat.

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

haloacetic acid methyl ester: haloacetic acid methyl ester

: 108322-54-9
(3-methacryloylamino-propyl)-methoxycarbonylmethyl-dimethyl-ammonium; iodide

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

haloacetic acid ethyl ester: haloacetic acid ethyl ester

: 108899-89-4
ethoxycarbonylmethyl-(3-methacryloylamino-propyl)-dimethyl-ammonium; iodide

: 5205-93-6
2-methyl-acrylic acid 3-dimethylamino-propyl amide

haloacetic acid methyl ester: haloacetic acid methyl ester

: 108480-06-4
(3-methacryloylamino-propyl)-methoxycarbonylmethyl-dimethyl-ammonium; bromide

Dimethylamino propyl methacrylamide 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

Product Name

Dimethylamino propyl methacrylamide

Synthetic route

Dimethylamino propyl methacrylamide Specification

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