5205-93-6

Basic information

• Product Name: Dimethylamino propyl methacrylamide
• Synonyms: 3-DIMETHYLAMINOPROPYL METHACRYLAMIDE;3-DIMETHYLAMINOPROPYL-METHYLACRYLAMIDE;N-[3-(N,N-DIMETHYLAMINO)PROPYL]METHACRYLAMIDE;n-[3-(dimethylamino)propyl]-2-methacrylamide;N-[3-(DIMETHYLAMINO)PROPYL]METHACRYLAMIDE;dimethylaminopropylmethacrylamide(dmapma);n-[3-(dimethylamino)propyl]-2-methyl-2-propenamid;N-[3-(dimethylamino)propyl]-2-methyl-2-Propenamide
• CAS NO: 5205-93-6
• Molecular Formula: C₉H₁₈N₂O
• Molecular Weight: 170.25
• EINECS: 226-002-3
• Product Categories: API intermediates;Acrylamide and Methacrylamide;Acrylic Monomers;Monomers
• Mol File: 5205-93-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: <-60°C
• Boiling Point: 134 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear liquid
• Density: 0.94 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000979mmHg at 25°C
• Refractive Index: n20/D 1.479(lit.)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 15.01±0.46(Predicted)
• CAS DataBase Reference: Dimethylamino propyl methacrylamide(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethylamino propyl methacrylamide(5205-93-6)
• EPA Substance Registry System: Dimethylamino propyl methacrylamide(5205-93-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36-38-43-41
• Safety Statements: 26-36/37/39
• WGK Germany: 1
• Hazardous Substances Data: 5205-93-6(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C9H18N2O/c1-8(2)9(12)10-6-5-7-11(3)4/h1,5-7H2,2-4H3,(H,10,12)

Synthetic route

2-(N,N-dimethylamino)ethanol (108-01-0) + 1-amino-3-(dimethylamino)propane (109-55-7) + methacrylic acid methyl ester (80-62-6) → 2-(dimethylamino)ethyl methacrylate (2867-47-2) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6)

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 %

p-toluenesulfonic acid 3-dimethylamino-n-propyl ester (39743-22-1) + 2-propenamide (79-06-1) → 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6)

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%

1-amino-3-(dimethylamino)propane (109-55-7) + methacrylic acid methyl ester (80-62-6) → 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6)

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.

3-(Dimethylamino)propyl chloride (109-54-6) + 2-propenamide (79-06-1) → 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6)

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%

β-methoxy-isobutyric acid amide (75407-20-4) + 1-amino-3-(dimethylamino)propane (109-55-7) → 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6)

Conditions	Yield
With sodium hydroxide	72%

methacrylic acid methyl ester (80-62-6) → 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6)

Conditions	Yield
With carbon dioxide	7%

1-amino-3-(dimethylamino)propane (109-55-7) + methacrylic acid methyl ester (80-62-6) → 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) + methyl 2-methyl-3-(3-dimethylaminopropylamino)propionate + N-(3-dimethylaminopropyl)-3-(3-dimethylaminopropylamino)-2-methylpropionamide

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

1,2-propanediene (463-49-0) + carbon monoxide (201230-82-2) + 1-amino-3-(dimethylamino)propane (109-55-7) → 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6)

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

β-alaninamide (4726-85-6) + poly(methacrylic acid) (79-41-4) → N-(dimethylaminopropyl)-methacrylamide + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6)

Conditions	Yield
In water

poly(methacrylic acid) (79-41-4) + 1-amino-3-(dimethylamino)propane (109-55-7) → 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6)

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 + 1-amino-3-(dimethylamino)propane (109-55-7) → 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6)

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

3-Dimethylamino-1-propanol (3179-63-3) → 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6)

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

1,3-propanesultone (1120-71-4) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) → N,N-dimethyl-N-(3-sulfopropyl)-3'-methacrylamidopropanaminium inner salt (5205-95-8)

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%

ethyleneglycol sulfate (1072-53-3) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) → 2-((3-methacrylamidopropyl)dimethylammonio)ethyl sulfate

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

1,12-dibromododecane (3344-70-5) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) → C30H60N4O2(2+)*2Br(1-)

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

4-methyl-2-oxo-1,3,2-dioxathiolane (1469-73-4, 20772-55-8, 20772-56-9, 40811-14-1, 40811-15-2, 51260-40-3, 51260-41-4) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) → C12H24N2O4S

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

1-bromo-butane (109-65-9) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) → (2-methacrylamido) propyltetrahexyldimethylammonium bromide

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

2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) + 1,3,2-dioxathiane 2,2-dioxide (1073-05-8) → 3-((3-methacrylamidopropyl)dimethylammonio)propyl sulfate

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

N,N'-Methylenebisacrylamide (110-26-9) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) + 2-propenamide (79-06-1) + (3-acrylamidophenyl)boronic acid (99349-68-5) → copolymer; monomer(s): 3-acrylamidophenylboronic acid; N-(3-dimethylaminopropyl)methacrylamide; N,N'-methylenebisacrylamide; acrylamide

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

2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) + benzyl chloride (100-44-7) → C16H25N2O(1+)*Br(1-)

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

β-Propiolactone (57-57-8) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) → N,N-dimethyl-N-(3-methacrylamidopropyl)propiobetaine (80921-09-1)

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

2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) + 4-cyano-4-(thiobenzoylthio)pentanoic acid (201611-92-9) → 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	Yield
With hydrogenchloride; 4,4'-dicyano-4,4'-azo-di-valeric acid In acetate buffer at 70℃; for 1h; pH=5;	78.77%

1-bromo-hexane (111-25-1) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) → (2-methacrylamido) propyltetrabenzyldimethylammonium chloride

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

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) → N,N-dimethyl-N-(3-methacrylamidopropyl)-N-[N'-(1,1-dimethyl-2-sulfonatoethyl)propionamido]betaine

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

2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) + acrylic acid (79-10-7) → N,N-dimethyl-N-(3-methacrylamidopropyl)propiobetaine (80921-09-1)

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;

1,3-propanesultone (1120-71-4) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) → [3-(methacryloylamino)propyl]dimethyl(3-sulfopropyl)ammonium hydroxide

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

2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) → poly(N-(3-dimethylammoniopropyl)methacrylamide sulfate); monomer(s): N-(3-dimethylaminopropyl)methacrylamide

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;

methyl 2-iodopropionate (56905-18-1, 114438-55-0, 114438-56-1) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) → (3-methacryloylamino-propyl)-(1-methoxycarbonyl-ethyl)-dimethyl-ammonium; iodide (108899-87-2)

Conditions	Yield
With acetone

2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) + Ethyl 2-bromopropionate (535-11-5, 41978-69-2) → (1-ethoxycarbonyl-ethyl)-(3-methacryloylamino-propyl)-dimethyl-ammonium; bromide (109337-30-6)

Conditions	Yield
With acetone

piperidine (110-89-4) + 2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) → N-(3-dimethylamino-propyl)-2-methyl-3-piperidin-1-yl-propionamide

Conditions	Yield
In water at 70℃; Rate constant;

2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) + 2-propenamide (79-06-1) → (2-carbamoyl-ethyl)-dimethyl-[3-(2-methyl-acryloylamino)-propyl]-ammonium; chloride

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

2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) + haloacetic acid methyl ester → (3-methacryloylamino-propyl)-methoxycarbonylmethyl-dimethyl-ammonium; iodide (108322-54-9)

2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) + haloacetic acid ethyl ester → ethoxycarbonylmethyl-(3-methacryloylamino-propyl)-dimethyl-ammonium; iodide (108899-89-4)

2-methyl-acrylic acid 3-dimethylamino-propyl amide (5205-93-6) + haloacetic acid methyl ester → (3-methacryloylamino-propyl)-methoxycarbonylmethyl-dimethyl-ammonium; bromide (108480-06-4)

Upstream product

• 109-55-7 1-amino-3-(dimethylamino)propane 
• 80-62-6 methacrylic acid methyl ester 
• 463-49-0 1,2-propanediene 
• 201230-82-2 carbon monoxide 
• 4726-85-6 β-alaninamide 
• 79-41-4 poly(methacrylic acid) 
• 75407-20-4 β-methoxy-isobutyric acid amide 
• 3179-63-3 3-Dimethylamino-1-propanol 
• 39743-22-1 p-toluenesulfonic acid 3-dimethylamino-n-propyl ester 
• 79-06-1 2-propenamide 
• 109-54-6 3-(Dimethylamino)propyl chloride 
• 28805-15-4 methacrylic acid ammonium salt 
• 108-01-0 2-(N,N-dimethylamino)ethanol 

Downstream Products

• 5205-95-8 N,N-dimethyl-N-(3-sulfopropyl)-3'-methacrylamidopropanaminium inner salt 
• 83623-32-9 4-sulfonatobutyl[3-(methacryloylamino)propyl]dimethylammonium 

Relevant articles and documents

Preparation method of N-dimethylaminopropyl(meth)acrylamide

The invention discloses a preparation method of N-dimethylaminopropyl(meth)acrylamide. The preparation method comprises the following steps: firstly, carrying out alcohol derivatization on 3-dimethylamino-1-propanol; reacting the derivatization product with (meth)acrylamide in the presence of an organic solvent and an alkali to obtain the N-dimethylaminopropyl(meth)acrylamide. Compared with a conventional preparation method adopted in the market, the preparation method disclosed by the invention has the advantages that the reaction conditions are mild, the operation is simple and convenient, the control is easy, the preparation cost is relatively low, and the commercial value is relatively high.

Continuous Method for Producing Amides of Ethylenically Unsaturated Carboxylic Acids

The invention relates to a continuous method for producing amides, according to which at least one carboxylic acid of formula (I) R3-COON (I), wherein R3 is an optionally substituted alkenyl group comprising between 2 and 4 carbon atoms, is reacted with at least one amine of formula (II) HNR1R2 (II), wherein R1 and R2 are independently hydrogen or a hydrocarbon radical comprising between 1 and 100 C atoms, to form an ammonium salt and/or a Michael adduct, and said ammonium salt is then reacted to form a carboxylic acid amide. under microwave irradiation in a reaction pipe, the longitudinal axis of the pipe being oriented in the direction of propagation of the microwaves of a monomode microwave applicator.

Method For Producing Alkaline (Meth)Acrylamides

The invention relates to a method for producing alkaline amides or imides of ethylenically unsaturated C3 to C6 carboxylic acids by reacting amines that contain at least one primary and/or secondary amino group and at least one tertiary amino group with ethylenically unsaturated C3 to C6 carboxlic acids to form an ammonium salt and said ammonium salt is subsequently converted into the alkaline amide or imide by means of microwave radiation, with the proviso that the primary and/or secondary amino group is devoid of alkoxy groups.