13162-05-5

Basic information

• Product Name: N-VINYLFORMAMIDE
• Synonyms: SR-497;N-VinylforMaMide 98%;ForMaMide, N-ethenyl-;N-Vinylformamide (stabilized with BHT);N-Vinylformamide,contain BHT as stabilizer;N-Vinylformamide (stabilized with BHT);n-ethenyl-formamid;N-ethenyl-Formamide
• CAS NO: 13162-05-5
• Molecular Formula: C₃H₅NO
• Molecular Weight: 71.08
• EINECS: 236-102-9
• Product Categories: Monomers;Polymer Science;Vinyl Halides, Amines, Amides, and Other Vinyl Monomers
• Mol File: 13162-05-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: −16 °C(lit.)
• Boiling Point: 210 °C(lit.)
• Flash Point: 216 °F
• Appearance: /
• Density: 1.014 g/mL at 25 °C(lit.)
• Vapor Pressure: ~0.1 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.494(lit.)
• Storage Temp.: 2-8°C
• PKA: 14.70±0.23(Predicted)
• Water Solubility: Soluble in water
• CAS DataBase Reference: N-VINYLFORMAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-VINYLFORMAMIDE(13162-05-5)
• EPA Substance Registry System: N-VINYLFORMAMIDE(13162-05-5)

Safety Data

• Hazard Codes: T
• Statements: 61-22-37/38-41-40
• Safety Statements: 53-26-36/37/39-45
• Hazardous Substances Data: 13162-05-5(Hazardous Substances Data)

Usage

Uses

NVF can be used in the free radical polymerization formation of poly(NVF) with a molecular weight ranging from 104 to 106.

General Description

N-Vinylformamide (NVF) is a class of N-vinylamide that is a precursor to amide and amine functional polymer. It has attractive properties that include high reactivity in polymerization and hydrolysis.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C3H5NO/c1-2-4-3-5/h2-3H,1H2,(H,4,5)

Synthetic route

N-(1-methoxyethyl)-formamide (38591-94-5) → n-vinylformamide (13162-05-5)

Conditions	Yield
	92%

(2-hydroxyethyl)-formamide (693-06-1) → n-vinylformamide (13162-05-5)

Conditions	Yield
With acetic anhydride at 35 - 60℃; for 13.5h; Time; Inert atmosphere;	75.8%

N-(α-cyanoethyl)formamide (27394-99-6) → n-vinylformamide (13162-05-5)

Conditions	Yield
at 410 - 420℃; under 10 - 15 Torr;
alumina activated with potassium ions at 330℃; under 7.50075 Torr; Gas phase; Industry scale; Pyrolysis;

ethylidene diacetate (542-10-9) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 1,1-bis-acetylamino-ethane (5335-91-1) + n-vinylformamide (13162-05-5) + 1,1-Bis(formamido)ethane (20602-52-2) + N-(1-Formylamino-ethyl)-acetamide

Conditions	Yield
With caesium carbonate In acetonitrile at 25℃; for 23h; Further byproducts given;	A 9.4 % Chromat. B 10.5 % Chromat. C 5.4 % Chromat. D 21.2 % Chromat.

acetaldehyde (75-07-0) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → n-vinylformamide (13162-05-5)

Conditions	Yield
With acetic anhydride; potassium carbonate at 10 - 70℃; for 3h;
With acetic anhydride; potassium carbonate In 2,2,4-trimethylpentane at 10 - 70℃; for 3h;
Stage #1: acetaldehyde; formamide; potassium carbonate In 1,4-dioxane at 10 - 15℃; for 2h; Stage #2: With poly(styrene-co-maleic anhydride) In 1,4-dioxane

N-(α-hydroxyethyl)formamide (102904-85-8) → n-vinylformamide (13162-05-5)

Conditions	Yield
With C13H24O6SSi; silica gel In 1,4-dioxane at 80 - 100℃; for 6h;

N-(1-Acetoxyethyl)-formamide (74769-49-6) → n-vinylformamide (13162-05-5)

Conditions	Yield
Heating / reflux;

1,1-Bis(formamido)ethane (20602-52-2) → n-vinylformamide (13162-05-5) + formamide (77287-34-4, 77287-35-5, 60100-09-6)

Conditions	Yield
With calcium carbonate at 210℃;

quartz + 1,1-Bis(formamido)ethane (20602-52-2) → n-vinylformamide (13162-05-5)

1,1-Bis(formamido)ethane (20602-52-2) → n-vinylformamide (13162-05-5)

formamide (77287-34-4, 77287-35-5, 60100-09-6) + acetylene (74-86-2) → n-vinylformamide (13162-05-5)

Conditions	Yield
decacarbonyldirhenium(0) In 1,4-dioxane at 170℃; under 13501.4 Torr; for 0.2h;

N-(1-ethoxyethyl)-formamide → n-vinylformamide (13162-05-5)

Conditions	Yield
With magnesium oxide In ethanol at 185 - 400℃; under 262.526 Torr; Pyrolysis; Inert atmosphere;

1-methylindole (603-76-9) + n-vinylformamide (13162-05-5) → N-(1-(1-methyl-1H-indol-3-yl)ethyl)formamide (1262894-65-4)

Conditions	Yield
With iron(III) chloride In dichloromethane at 40℃; for 0.5h; regioselective reaction;	99%

n-vinylformamide (13162-05-5) + methyl indolizine-1-carboxylate (316375-85-6) → methyl 3-(1-formamidoethyl)indolizine-1-carboxylate (1262894-66-5)

Conditions	Yield
With iron(III) chloride In dichloromethane at 40℃; for 0.5h; regioselective reaction;	99%

n-vinylformamide (13162-05-5) → poly(vinyl formamide), [η] = 0.42 dl/g at 25 deg C in 0.1 mol/l sodium acetate; monomer(s): N-vinylformamide

Conditions	Yield
With ammonia; dihydrogen peroxide In water at 60℃; for 4.5h;	98%

n-vinylformamide (13162-05-5) + 2-Methacrylamido-2-deoxy-D-glucose (17377-64-9) → polymer, molar ratio N-vinylformamide:N-methacryloyl-D-glucosamine = 45:55; monomer(s): N-vinylformamide; N-methacryloyl-D-glucosamine

Conditions	Yield
With 2,2-azobis(2-amidinopropane)dihydrochloride In water at 60℃; for 5h;	98%

indole (120-72-9) + n-vinylformamide (13162-05-5) → N-(1-(1H-indol-3-yl)ethyl)acetamide

Conditions	Yield
With iron(III) chloride In dichloromethane at 40℃; for 0.5h; regioselective reaction;	97%

n-vinylformamide (13162-05-5) + methyl iodide (74-88-4) → N-vinyl-N-methyl-formamide (2867-48-3)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 15℃; Methylation;	96%

formic acid (64-18-6) + n-vinylformamide (13162-05-5) → N-(α-formoxyethyl)formamide

Conditions	Yield
at 25℃; for 1h; Addition;	95%

n-vinylformamide (13162-05-5) + 4-(vinylformylamino)-2-butanone (281205-60-5) → polymer, 4-(vinylformylamino)-2-butanone-(vinyl formamide) copolymer, vinyl formamide 84 percent, 4-(vinylformylamino)-2-butanone 16 percent, intrinsic viscosity 0.40 dl/g; monomer(s): vinyl formamide; 4-(vinylformylamino)-2-butanone

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In isopropyl alcohol at 60℃;	95%

n-vinylformamide (13162-05-5) + p-methylbenzaldehyde oxime (3717-15-5) → (E)-4-methylbenzaldehyde O-1-(N-formyl)aminoethyloxime (1140531-50-5)

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

methanol (67-56-1) + n-vinylformamide (13162-05-5) → N-(1-methoxyethyl)-formamide (38591-94-5)

Conditions	Yield
With sodium methylate at 25℃; for 18h; Addition;	93%

n-vinylformamide (13162-05-5) → N-[α-(N'-vinyl-N'-formamido)ethyl]formamide

Conditions	Yield
With trimethylamine at 25℃; for 42h; Dimerization;	93%

n-vinylformamide (13162-05-5) + p-methoxybenzyl chloride (824-94-2) → N-(p-methoxybenzyl)-N-vinylformamide (1352951-39-3)

Conditions	Yield
Stage #1: n-vinylformamide With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: p-methoxybenzyl chloride In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere;	93%

n-vinylformamide (13162-05-5) + di-tert-butyl dicarbonate (24424-99-5) → N-formyl-N-vinyl-carbamic acid tert-butyl ester (1321892-09-4)

Conditions	Yield
With dmap In tetrahydrofuran at 20℃; for 22h; Inert atmosphere;	93%
With dmap In tetrahydrofuran at 20℃; for 22h; Inert atmosphere;	93%
With dmap In tetrahydrofuran

n-vinylformamide (13162-05-5) + isobutyryl chloride (79-30-1) → N-vinyl-2-methylpropionamide

Conditions	Yield
Stage #1: n-vinylformamide; isobutyryl chloride With triethylamine In tetrahydrofuran at 0 - 5℃; for 3h; Inert atmosphere; Stage #2: With water; sodium hydroxide In tetrahydrofuran at 0 - 5℃; Solvent; Reagent/catalyst; Temperature; Time; Inert atmosphere;	93%
Stage #1: n-vinylformamide; isobutyryl chloride With dmap; triethylamine In tetrahydrofuran at 0 - 5℃; for 2h; Stage #2: With sodium hydroxide In tetrahydrofuran at 0℃; for 2h;	59%
Stage #1: n-vinylformamide; isobutyryl chloride With triethylamine In tetrahydrofuran at 0℃; for 5h; Stage #2: With sodium hydroxide In tetrahydrofuran at 0 - 5℃; for 9h;	52%

n-vinylformamide (13162-05-5) + isopropyl alcohol (67-63-0) → N-(1-isopropoxy-ethyl)-formamide

Conditions	Yield
With hydrogenchloride at 0℃; for 2h; Addition;	92%

n-vinylformamide (13162-05-5) → N-vinylformamide potassium salt

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 4℃; for 1h;	92%

n-vinylformamide (13162-05-5) + acrylic acid methyl ester (292638-85-8) → methyl 3-(N-vinylformamido)-propionate (164144-18-7)

Conditions	Yield
With sodium methylate; p-benzoquinone	92%
With sodium methylate; p-benzoquinone	92%

n-vinylformamide (13162-05-5) + N-methoxy-4-methylbenzamide (25563-06-8) → N-(6-methyl-1-oxo-1,2,3,4-tetrahydroisoquinolin-3-yl)formamide

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; sodium acetate at 60℃; for 4h; Sealed tube;	92%

n-vinylformamide (13162-05-5) + 2-hydroxy-propionitrile (78-97-7) → N-[α-(α'-cyanoethoxy)ethyl]formamide

Conditions	Yield
With boron trifluoride at 0℃; for 18h; Addition;	91%

n-vinylformamide (13162-05-5) + methyl 3-(N-vinylformamido)-propionate (164144-18-7) → polymer, 3-(vinylformylamino)propionate-(vinyl formamide) copolymer, vinyl formamide 85 percent, methyl 3-(vinylformylamino)propionate 15 percent, intrinsic viscosity 0.27 dl/g; monomer(s): vinyl formamide; methyl 3-(vinylformylamino)propionate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In isopropyl alcohol at 60℃;	90%

n-vinylformamide (13162-05-5) + 4-chlorobenzaldehyde oxime (3717-24-6) → (E)-4-chlorobenzaldehyde O-1-(N-formyl)aminoethyloxime (1140531-46-9)

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; tris(4-bromophenyl)aminium hexachloroantimonate In dichloromethane at 20℃; for 0.166667h;	90%

n-vinylformamide (13162-05-5) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → poly(N-vinyl formamide)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In isopropyl alcohol for 4h; Heating / reflux;	89%

pentanal (110-62-3) + n-vinylformamide (13162-05-5) + 4-nitro-aniline (100-01-6) → (2-butyl-6-nitro-1,2,3,4-tetrahydroquinolin-4-yl)formamide

Conditions	Yield
With bismuth(III) chloride In acetonitrile at 20℃; for 4h; Inert atmosphere;	89%

n-vinylformamide (13162-05-5) → povinylformamide

Conditions	Yield
With C8H14N2OS2; 2,2'-azobis(isobutyronitrile) at 25 - 60℃; for 45h; Conversion of starting material; Neat (no solvent);	88%
With C8H14N2OS2; 2,2'-azobis(isobutyronitrile) at 25 - 60℃; for 12h; Conversion of starting material; Neat (no solvent);	83%
With C8H14N2OS2; 2,2'-azobis(isobutyronitrile) at 25 - 60℃; for 18h; Conversion of starting material; Neat (no solvent);	83%

n-vinylformamide (13162-05-5) + 4-nitrobenzaldehyde oxime (1129-37-9) → (E)-4-nitrobenzaldehyde O-1-(N-formyl)aminoethyloxime (1140531-43-6)

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; tris(4-bromophenyl)aminium hexachloroantimonate In dichloromethane at 20℃; for 0.166667h;	88%

Upstream product

• 542-10-9 ethylidene diacetate 
• 77287-34-4 formamide 
• 693-06-1 (2-hydroxyethyl)-formamide 
• 74-86-2 acetylene 
• 20602-52-2 ethylidene bis-formamide 
• 38591-94-5 N-(1-methoxyethyl)-formamide 
• 74769-49-6 N-(1-Acetoxyethyl)-formamide 
• 102904-85-8 N-(α-hydroxyethyl)formamide 
• 75-07-0 acetaldehyde 
• 27394-99-6 N-(α-cyanoethyl)formamide 

Downstream Products

• 192058-10-9 N-n-butyl-N-vinylformamide 
• 13313-25-2 N-benzoylethyleneimine 
• 1026-05-7 trans-2-methyl-N-phenyl-1,2,3,4-tetrahydroquinolin-4-amine 
• 1026-05-7 cis-2-methyl-N-phenyl-1,2,3,4-tetrahydroquinolin-4-amine 
• 1140531-50-5 (E)-4-methylbenzaldehyde O-1-(N-formyl)aminoethyloxime 
• 1140531-43-6 (E)-4-nitrobenzaldehyde O-1-(N-formyl)aminoethyloxime 
• 1140531-46-9 (E)-4-chlorobenzaldehyde O-1-(N-formyl)aminoethyloxime 
• 3195-78-6 N-vinyl-N-methylacetamide 
• 281205-60-5 4-(vinylformylamino)-2-butanone 
• 2867-48-3 N-vinyl-N-methyl-formamide 
• 102904-85-8 N-(α-hydroxyethyl)formamide 
• 38591-94-5 N-(1-methoxyethyl)-formamide 
• 40652-55-9 C₁₂H₁₄N₂O₃ 
• 40652-54-8 C₁₀H₈Cl₂N₂O₂ 

Relevant articles and documents

Reactions of ethylidene diacetate: Formation of N-vinylamide precursors ethylidene bisacetamide and ethylidene bisformamide

Ethylidene diacetate (EDA) reacts with formamide or acetamide under stoichiometric base or catalytic Lewis acid conditions to afford the corresponding ethylidene bisamides and N-vinylamides. Sn(OAc)2 afforded an overall 82.6% selectivity to the desired acetamide derivatives. Sn(OAc)2 and Zn(OAc)2 facilitate amide attack at the tertiary carbon of EDA.

SYNTHESIS OF 1-HYDROXYETHYL FORMAMIDES AND N-VINYL FORMAMIDES

Processes and systems for producing N-vinyl carboxylic acid amides are provided herein. According to some aspects of the present invention, a process for producing an N-vinyl carboxylic acid amide is described that eliminates interim solids handling steps during formation of the intermediate compounds, thereby increasing efficiency and reducing cost. The processes and system described herein may be used for the synthesis of N-vinylformamide and its intermediates, including 1-hydroxyethylformamide and 1- alkoxyethylformamide, or for the synthesis of N-methyl,N-vinylformamide and its intermediates, including N-methyl,1-hydroxyethylformamide and N- methyl,1alkoxyethylformamide.

PROCESS FOR THE PREPARATION OF N-VINYLCARBOXAMIDES

Process for the preparation of N-vinylcarboxamides by pyrolysis of a compound of the formula [in-line-formulae]CH3—CH(CN)—N(R)—CO—R1 ??(I),[/in-line-formulae]in which R and R1 are H or C1- to C6-alkyl,in the presence of solids which are doped with alkali metal or alkaline earth metal ions, under reduced pressure at a temperature of from 330 to 750° C. with elimination of hydrogen cyanide, cooling, separation and isolation of the reaction products, a solid arranged in a tubular reactor being treated at a temperature in the range from 0 to 250° C. with a solution of an alkali metal and/or alkaline earth metal base, the solution being discharged, the remaining solvent which adheres to the catalyst thus obtainbale being evaporated and said catalyst then being heated to a temperature of at least 380° C. for activation.