5202-78-8

Basic information

• Product Name: N-VINYLACETAMIDE 97
• Synonyms: n-ethenyl-acetamid;n-vinylacetamide;N-VINYLACETAMIDE 97;N-VINYLACETAMIDE 97%;N-Ethenylacetamide;Acetamide, N-ethenyl-;Einecs 225-989-8;Vinylacetamide
• CAS NO: 5202-78-8
• Molecular Formula: C₄H₇NO
• Molecular Weight: 85.10448
• EINECS: 225-989-8
• Mol File: 5202-78-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 51-54 °C(lit.)
• Boiling Point: 96°C/10mmHg(lit.)
• Flash Point: 109 °C
• Appearance: /
• Density: 0.89g/cm³
• Vapor Pressure: 0.222mmHg at 25°C
• Refractive Index: 1.414
• PKA: 14.82±0.46(Predicted)
• Water Solubility: Soluble in water
• CAS DataBase Reference: N-VINYLACETAMIDE 97(CAS DataBase Reference)
• NIST Chemistry Reference: N-VINYLACETAMIDE 97(5202-78-8)
• EPA Substance Registry System: N-VINYLACETAMIDE 97(5202-78-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/38
• Safety Statements: 26-36
• Hazardous Substances Data: 5202-78-8(Hazardous Substances Data)

Usage

General Description

N-Vinylacetamide 97 is a high-purity (97%) organic compound that is typically used as a reactive monomer in the production of polymers. Its chemical formula is C4H7NO, and it appears as a clear, colorless liquid. N-VINYLACETAMIDE 97 can undergo various chemical reactions due to the presence of a vinyl group, which makes it useful in creating a broad range of polymers with different properties. Polymers derived from N-Vinylacetamide 97 are commonly used in various industries including textiles, paper, and water treatment. It should be handled with care as it can potentially cause skin, eye, and respiratory irritation.

InChI:InChI=1/C4H7NO/c1-3-5-4(2)6/h3H,1H2,2H3,(H,5,6)

Synthetic route

2-acetylaminoethanol (142-26-7) → acetylaminoethylene (5202-78-8)

Conditions	Yield
With succinic acid anhydride at 40 - 75℃; for 15h; Time; Inert atmosphere;	82.2%

N-(1-methoxyethyl)acetamide (55204-51-8) → acetylaminoethylene (5202-78-8)

Conditions	Yield
at 550℃;	70%
at 440℃; under 100 Torr;

2-methyl-4-methyl-4H-oxazolin-5-one (69773-71-3) → acetylaminoethylene (5202-78-8)

Conditions	Yield
at 550℃; under 0.1 - 0.2 Torr;	32%

N-(2-chloro-ethyl)-acetamide (7355-58-0) → acetylaminoethylene (5202-78-8)

Conditions	Yield
With sodium hydroxide; hexane
With sodium hydroxide; hexane
With sodium hydroxide; hexane

1,1-bis-acetylamino-ethane (5335-91-1) → acetylaminoethylene (5202-78-8)

Conditions	Yield
at 220℃;

N-(1-cyanoethyl)acetamide (19861-71-3) → acetylaminoethylene (5202-78-8)

Conditions	Yield
at 450℃; under 13 Torr;

C18H17NO (58286-92-3) → acetylaminoethylene (5202-78-8) + anthracene (120-12-7)

Conditions	Yield
In diphenylether at 250℃; Rate constant;

acetamide (60-35-5) + ethylidene diacetate (542-10-9) → 1,1-bis-acetylamino-ethane (5335-91-1) + N-acetylacetamide (625-77-4) + acetylaminoethylene (5202-78-8)

Conditions	Yield
With caesium carbonate In acetonitrile at 50℃; for 3h;	A 12.1 % Chromat. B 17.2 % Chromat. C 23.8 % Chromat.

acetamide (60-35-5) + ethylidene diacetate (542-10-9) → 1,1-bis-acetylamino-ethane (5335-91-1) + N-acetylacetamide (625-77-4) + acetylaminoethylene (5202-78-8) + N-(1-Acetylamino-ethyl)-N-vinyl-acetamide

Conditions	Yield
With caesium carbonate In acetonitrile at 50℃; for 3h; Product distribution; reactions in presence of further bases or Lewis acids;	A 12.1 % Chromat. B 17.2 % Chromat. C 23.8 % Chromat. D 1.6 % Chromat.

N-(α-isopropoxyethyl)acetamide → acetylaminoethylene (5202-78-8)

N-(1-methoxyethyl)acetamide (55204-51-8) → acetamide (60-35-5) + acetylaminoethylene (5202-78-8)

Conditions	Yield
at 330 - 350℃; Product distribution / selectivity;

Acetaldehyde oxime (107-29-9) + acetic anhydride (108-24-7) → acetylaminoethylene (5202-78-8)

Conditions	Yield
With copper(l) iodide; sodium hydrogensulfite In 1,2-dichloro-ethane at 120℃; for 12h; Inert atmosphere;

acetylaminoethylene (5202-78-8) + 4-Aminoacetophenone (99-92-3) → N-(6-acetyl-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)acetamide

Conditions	Yield
With sodium dodecyl-sulfate In water at 20℃; for 1h; pH=1; Reagent/catalyst; Solvent; Temperature; Time; Green chemistry; diastereospecific reaction;	99%
With cerium(IV) sulphate In acetonitrile at 20℃; under 760.051 Torr; for 6h; Catalytic behavior; Temperature; diastereoselective reaction;	89%

acetylaminoethylene (5202-78-8) + 4.-brorno-thiophene-3-carboxylic acid ethyl ester (224449-33-6) → ethyl 4-(2-acetamidovinyl)thiophene-3-carboxylate

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;	99%

acetylaminoethylene (5202-78-8) + 1-Bromo-3-phenylpropane (637-59-2) → N-ethenyl-N-(3-phenylpropyl)acetamide (1105508-27-7)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide Inert atmosphere;	98%

C6H4NCH2CHCCH2 (491-35-0) + acetylaminoethylene (5202-78-8) + Benzyl bromoacetate (5437-45-6) → benzyl (S)-4-acetamido-4-(4-methylquinolin-2-yl)butanoate

Conditions	Yield
With potassium phosphate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; water In toluene at 25℃; for 15h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation; enantioselective reaction;	96%

acetylaminoethylene (5202-78-8) + p-methylbenzaldehyde oxime (3717-15-5) → (E)-4-methylbenzaldehyde O-1-(N-acetyl)aminoethyloxime (1140531-49-2)

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; tris(4-bromophenyl)aminium hexachloroantimonate In dichloromethane at 20℃; for 0.166667h;	95%

acetylaminoethylene (5202-78-8) + Ac-FQPKCG-NH2 (1352790-18-1) → C36H56N10O9S (1352790-23-8)

Conditions	Yield
With GLUTATHIONE; 2,2’-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride for 1h; pH=4; Product distribution / selectivity; Acetate buffer; UV-irradiation;	95%
With GLUTATHIONE for 1h; pH=4; aq. acetate buffer; UV-irradiation;

acetylaminoethylene (5202-78-8) + Ethyl bromodifluoroacetate (667-27-6) + phenylboronic acid (98-80-6) → ethyl 4-acetamido-2,2-difluoro-4-phenylbutanoate

Conditions	Yield
With nickel(II) triflate; potassium carbonate; 5,5′-bis(trifluoromethyl)-2,2′-bipyridine In 1,4-dioxane at 80℃; for 8h; Inert atmosphere; Schlenk technique;	92%

p-toluene sulfinic acid (536-57-2) + acetylaminoethylene (5202-78-8) → N-[1-(p-toluenesulfonyl)ethyl]acetamide (1578252-28-4)

Conditions	Yield
With photoredox catalyst Ni/TiO2 In acetonitrile at 20℃; for 3.5h; Molecular sieve; Irradiation;	92%

6-methyl-4-tosyloxy-2(2H)-pyranone (31913-41-4) + acetylaminoethylene (5202-78-8) → N-(1-(6-methyl-2-oxo-2H-pyran-4-yl)vinyl)acetamide

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; N-ethyl-N,N-diisopropylamine; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 85℃; for 4h; Heck reaction;	91%

4-methyl-N-(2-methylallyl)-N-(3-phenylprop-2-yn-1-yl)benzenesulfonamide (869938-32-9) + acetylaminoethylene (5202-78-8) → (+)-N-[(5S*,7aR*)-7a-methyl-4-phenyl-2-tosyl-2,3,5,6,7,7a-hexahydro-1H-isoindol-5-yl]acetamide

Conditions	Yield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; (R)-segphos In dichloromethane at 20℃; for 72h; Schlenk technique; stereoselective reaction;	91%

acetylaminoethylene (5202-78-8) + Ethyl bromodifluoroacetate (667-27-6) + 4-fluoroboronic acid (1765-93-1) → ethyl 2,2-difluoro-3-(4-fluorophenyl)-3-oxopropanoate (2262-04-6) + ethyl 4-acetamido-2,2-difluoro-5-(4-fluorophenyl)-5-oxopentanoate

Conditions	Yield
With carbon monoxide; water; C19H16ClFN2NiO3; potassium carbonate In 1,4-dioxane at 50℃; under 760.051 Torr; for 18h; Time; Schlenk technique; Sealed tube;	A 38 %Spectr. B 91%

9H-thioxanthen-9-ol (6783-74-0) + acetylaminoethylene (5202-78-8) → (9H-thioxanthen-9-yl)-acetaldehyde

Conditions	Yield
Stage #1: 9H-thioxanthen-9-ol; acetylaminoethylene With acetic acid at 20℃; for 1h; Stage #2: With hydrogenchloride for 1h;	90%

acetylaminoethylene (5202-78-8) → N-(1-methoxyethyl)acetamide (55204-51-8)

Conditions	Yield
With acetamide	90%
In methanol

acetylaminoethylene (5202-78-8) + histone H3 K27C → H3 Ks27Ac

Conditions	Yield
With GLUTATHIONE; 2,2’-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride for 2h; pH=4; Acetate buffer; UV-irradiation;	90%

acetylaminoethylene (5202-78-8) + histone H4 K16C → H4 Ks16Ac

Conditions	Yield
With dimethylsulfide; GLUTATHIONE; 2,2’-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride for 2h; pH=4; Product distribution / selectivity; Acetate buffer; UV-irradiation;	90%

acetylaminoethylene (5202-78-8) + thiophenol (108-98-5) → C10H13NOS

Conditions	Yield
With tris(bipyridine)ruthenium(II) dichloride hexahydrate In acetonitrile at 20℃; for 2h; Catalytic behavior; Solvent; Irradiation; regioselective reaction;	90%

acetylaminoethylene (5202-78-8) + phenylmethanethiol (100-53-8) → C11H15NOS

Conditions	Yield
With tris(bipyridine)ruthenium(II) dichloride hexahydrate In acetonitrile at 20℃; for 18h; Irradiation; regioselective reaction;	90%

acetylaminoethylene (5202-78-8) + 4-acetophenyl triflate (109613-00-5) → N-acetyl-1-(4'-acetylphenyl)ethenamine (823790-71-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; 1,1'-bis-(diphenylphosphino)ferrocene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 85℃; for 1.75h; Heck coupling;	89%
With 1,3-bis-(diphenylphosphino)propane; triethylamine; palladium diacetate In N,N-dimethyl-formamide at 100℃; Heck reaction;	40%

acetylaminoethylene (5202-78-8) + Ethyl 4-bromobenzoate (5798-75-4) → ethyl 4-(1-acetamidovinyl)benzoate (1028431-82-4)

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; triethylamine; palladium diacetate In isopropyl alcohol for 12h; Heck arylation; Heating;	89%

acetylaminoethylene (5202-78-8) + phenylmethanethiol (100-53-8) → 1-acetamido-2-benzylthioethane (60116-67-8)

Conditions	Yield
In water at 20℃; for 18h; Green chemistry; regioselective reaction;	88%
With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate In acetonitrile at 20℃; for 6h; Irradiation; Sealed tube;	82%
With 2,2’-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride at 20℃; for 0.5h; pH=4; Acetate buffer; UV-irradiation;

C6H4NCH2CHCCH2 (491-35-0) + acetylaminoethylene (5202-78-8) + bromoacetic acid methyl ester (96-32-2) → methyl (S)-4-acetamido-4-(4-methylquinolin-2-yl)butanoate

Conditions	Yield
With potassium phosphate; (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; water In toluene at 25℃; for 15h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation; enantioselective reaction;	88%

Upstream product

• 55204-51-8 N-(1-methoxyethyl)acetamide 
• 60-35-5 acetamide 
• 542-10-9 ethylidene diacetate 
• 142-26-7 2-acetylaminoethanol 
• 107-29-9 Acetaldehyde oxime 
• 108-24-7 acetic anhydride 
• 69773-71-3 2-methyl-4-methyl-4H-oxazolin-5-one 
• 58286-92-3 C₁₈H₁₇NO 
• 19861-71-3 N-(1-cyanoethyl)acetamide 
• 5335-91-1 1,1-bis-acetylamino-ethane 
• 7355-58-0 N-(2-chloro-ethyl)-acetamide 

Downstream Products

• 18793-44-7 N-β-styrylacetamid 
• 177750-24-2 N-(1-(naphthalen-2-yl)vinyl)acetamide 
• 57957-24-1 N-(1-phenylvinyl)acetamide 
• 872452-07-8 N-(1-(3,6-dihydro-2-methyl-6-oxo-2H-pyran-4-yl)vinyl)acetamide 
• 872452-02-3 N-(1-(3-oxocyclohex-1-enyl)vinyl)acetamide 
• 1105508-27-7 N-ethenyl-N-(3-phenylpropyl)acetamide 
• 1105508-25-5 N-(4-methoxybenzyl)-N-vinylacetamide 

Relevant articles and documents

Access to multi-functionalized oxazolines via silver-catalyzed heteroannulation of enamides with sulfoxonium ylides

Disclosed herein is an efficient Ag-catalyzed [4 + 1] heteroannulation reaction of enamides with α-carbonyl sulfoxonium ylides. The diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline derivatives. The synthetic utility of the resultant tetra-substituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical relevance.

Preparation method of N-vinyl alkylamide

The invention relates to the technical field of vinyl compound production, in particular to a preparation method of Nvinyl alkyl amide. The preparation method comprises the following steps: A) under the action of a composite basic catalyst, reacting acetaldehyde with alkylamide to obtain Nhydroxyethyl alkylamide, and carrying out esterification reaction on the obtained Nhydroxyethyl alkylamide andacid anhydride to obtain an ester compound; wherein the composite basic catalyst comprises an inorganic base and an amine compound; and B) carrying out medium-temperature cracking on the ester compound, and carrying out vacuum distillation to obtain the Nvinyl alkylamide. Research finds that inorganic base and amine compounds are adopted as catalysts at the same time, so that the dosage of a basic catalyst required by reaction of Nhydroxyethyl alkylamide and anhydride can be remarkably reduced, the temperature required by subsequent cracking reaction is reduced, a reaction system tends to bemilder, and the reaction yield is improved. The yield and the purity of a reaction product can be remarkably improved while the energy consumption is reduced.

PROCESS FOR PRODUCING HIGH-PURITY N-VINYLCARBOXAMIDES

Disclosed is a process for producing high-purity N-vinylcarboxamides comprising: (A) a step of dissolving a crude N-vinylcarboxamide in an alcohol having 1 to 3 carbon atoms, the crude N-vinylcarboxamide containing 50 to 97% by mass of an N-vinylcarboxamide; (B) a step of adding an aliphatic hydrocarbon having 5 to 10 carbon atoms to the composition obtained in the step (A) to precipitate a crystal of the N-vinylcarboxamide; and (C) a step of separating the crystal of the N-vinylcarboxamide precipitated in the step (B).