924-42-5

Basic information

• Product Name: N-Methylolacrylamide
• Synonyms: N-(Hydroxymethyl)acrylamide solution 48 wt. % in H2O;uraminet80;Yuramin T 80;N-METHYLOLACRYLAMIDE;n-(hydroxymethyl)-2-propenamide;N-(HYDROXYMETHYL)ACRYLAMIDE;METHYLOLACRYLAMIDE;Methylolacrylamidesolution
• CAS NO: 924-42-5
• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 101.1
• EINECS: 213-103-2
• Product Categories: Acrylamide and Methacrylamide;Acrylic Monomers;Monomers;fine chemicals
• Mol File: 924-42-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 74-75°C
• Boiling Point: 277°C(lit.)
• Flash Point: 100°C
• Appearance: white crystal powder
• Density: 1.082 g/mL at 20 °C
• Vapor Pressure: 1.82E-06mmHg at 25°C
• Refractive Index: n20/D 1.413
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.25±0.10(Predicted)
• Water Solubility: <0.1 g/100 mL at 20.5℃
• Stability: Light Sensitive, Moisture Sensitive
• BRN: 506646
• CAS DataBase Reference: N-Methylolacrylamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylolacrylamide(924-42-5)
• EPA Substance Registry System: N-Methylolacrylamide(924-42-5)

Safety Data

• Hazard Codes: Xn,T
• Statements: 22-36/37/38-62-48/20/21/22-43-46-45
• Safety Statements: 26-45-36/37-53
• RIDADR: 2810
• WGK Germany: 3
• RTECS: AS3600000
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 924-42-5(Hazardous Substances Data)

Usage

Chemical Properties

White solid

General Description

A colorless or yellow aqueous solution.

Air & Water Reactions

Soluble in water.

Reactivity Profile

N-Methylolacrylamide may be sensitive to prolonged exposure to light. Polymerization and generation of heat and flames may occur on exposure to to heat or contaminants. Incompatible with strong oxidizers.

Fire Hazard

Literature sources indicate that N-Methylolacrylamide is nonflammable.

InChI:InChI=1/C4H7NO2/c1-3(2-6)4(5)7/h6H,1-2H2,(H2,5,7)

Synthetic route

formaldehyd (50-00-0) + 2-propenamide (79-06-1) → N-Methylolacrylamid (924-42-5)

Conditions	Yield
In water at 35 - 40℃; pH=7 - 9;	72%
Stage #1: formaldehyd; 2-propenamide With tetramethyl ammoniumhydroxide; 4-methoxy-phenol In water at 60℃; for 3h; Stage #2: With sulfuric acid In water for 24h; pH=7.5 - 8; Catalytic behavior; Reagent/catalyst; Temperature;	66.72%
With copper; potassium carbonate

formaldehyd (50-00-0) + 1,2-dichloro-ethane (107-06-2) + 2-propenamide (79-06-1) → N-Methylolacrylamid (924-42-5)

Conditions	Yield
With sodium; xylene

formaldehyd (50-00-0) + triethylamine (121-44-8) + 2-propenamide (79-06-1) → N-Methylolacrylamid (924-42-5)

formaldehyd (50-00-0) + 2-propenamide (79-06-1) → N,N-dimethylolacrylamide + N-Methylolacrylamid (924-42-5)

Conditions	Yield
With 4-methoxy-phenol; sodium hydroxide In water at 20 - 60℃; for 1h; pH=10.5;

4-ethylpiperazine (5308-25-8) + N-Methylolacrylamid (924-42-5) → 3-(4-ethylpiperazin-1-yl)-N-(hydroxymethyl)propanamide (1610610-01-9)

Conditions	Yield
at 20℃; for 1h; Michael Addition; Ionic liquid;	94%
With triethylamine In water at 20℃; for 1h; Michael Addition; Green chemistry;	92%
With [ADPQ][CH3COO] at 20℃; for 1h; Michael Addition;	90%

methyl galloate (99-24-1) + N-Methylolacrylamid (924-42-5) → C12H13NO6

Conditions	Yield
With sulfuric acid In ethanol at 35℃; for 96h; Friedel-Crafts Alkylation;	93.27%

4-methylpiperidin (626-58-4) + N-Methylolacrylamid (924-42-5) → N-(hydroxymethyl)-3-(4-methylpiperidin-1-yl)propanamide (1610610-02-0)

Conditions	Yield
With [DABCO-PDO][OAc] In neat (no solvent) at 20℃; for 1h; Michael Addition; Green chemistry;	93%
With triethylamine In water at 20℃; for 1h; Michael Addition; Green chemistry;	91%

Ethyl gallate (831-61-8) + N-Methylolacrylamid (924-42-5) → C13H15NO6

Conditions	Yield
With sulfuric acid In ethanol at 35℃; for 96h; Friedel-Crafts Alkylation;	92.38%

morpholine (110-91-8) + N-Methylolacrylamid (924-42-5) → N-(hydroxymethyl)-3-morpholinopropanamide (63737-25-7)

Conditions	Yield
With [DABCO-PDO][OAc] In neat (no solvent) at 20℃; for 2h; Michael Addition; Green chemistry;	90%
at 20℃; for 2h; Michael Addition; Ionic liquid;	90%
With [ADPQ][CH3COO] at 20℃; for 2h; Michael Addition;	87%

1-(2-hydroxyethyl)piperazine (103-76-4) + N-Methylolacrylamid (924-42-5) → 3-(4-(2-hydroxyethyl)piperazin-1-yl)-N-(hydroxymethyl)propanamide (1616578-06-3)

Conditions	Yield
With [DABCO-PDO][OAc] In neat (no solvent) at 20℃; for 2.5h; Michael Addition; Green chemistry;	88%

N-Methylolacrylamid (924-42-5) + β-naphthol (135-19-3) → α-N-methacrylamide-β-naphthol (13579-22-1)

Conditions	Yield
With sulfuric acid In ethanol for 5h; Friedel-Crafts Acylation; Heating; Green chemistry;	86%
With sulfuric acid at 50℃; for 5h; Friedel-Crafts Alkylation;	86%

N-(hydroxymethyl)piperazine (90324-69-9) + N-Methylolacrylamid (924-42-5) → N-(hydroxymethyl)-3-(4-(hydroxymethyl)piperazin-1-yl)propanamide

Conditions	Yield
With [ADPQ][CH3COO] at 20℃; for 3h; Michael Addition;	86%

Propyl gallate (121-79-9) + N-Methylolacrylamid (924-42-5) → C14H17NO6

Conditions	Yield
With sulfuric acid In ethanol at 35℃; for 96h; Friedel-Crafts Alkylation;	85.92%

2,4-dihydroxybenzophenone (131-56-6) + N-Methylolacrylamid (924-42-5) → (3,5-dimethacrylamide-2,4-dihydroxyphenyl) (phenyl)methanone

Conditions	Yield
With alchlor In [(2)H6]acetone at 35℃; for 48h;	83%
With sulfuric acid In ethanol at 44℃; for 96h; Solvent; Reagent/catalyst; Temperature; Friedel-Crafts Alkylation;	73%

N-Methylolacrylamid (924-42-5) + benzylamine (100-46-9) → 3-(benzylamino)-N-(hydroxymethyl)propanamide (1610610-03-1)

Conditions	Yield
With [ADPQ][CH3COO] at 20℃; for 3h; Michael Addition;	80%
With [DABCO-PDO][OAc] In neat (no solvent) at 20℃; for 4.5h; Michael Addition; Green chemistry;	70%
With triethylamine In water at 20℃; for 5h; Michael Addition; Green chemistry;	65%

N-Methylolacrylamid (924-42-5) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → 10‐(4‐hydroxy‐3‐(hydroxymethyl)amino‐3‐oxopropyl)‐9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide

Conditions	Yield
In tetrahydrofuran at 120℃; for 8h; Temperature; Inert atmosphere;	79.9%

benzene-1,2-diol (120-80-9) + N-Methylolacrylamid (924-42-5) → N,N'-[(4,5-dihydroxy-1,2-phenylene)bis(methylene)]bisacrylamide

Conditions	Yield
With sulfuric acid In ethanol at 20 - 35℃; Friedel-Crafts Alkylation; Sonication;	73%

phenolphthalein (77-09-8) + N-Methylolacrylamid (924-42-5) → N-(2-hydroxy-5-(1-(4-hydroxyphenyl)-3-oxo-1,3-dihydroisobenzofuran-1-yl)benzyl)acrylamide (1383627-29-9)

Conditions	Yield
With aluminum (III) chloride In acetone at 40℃;	32%
In trifluoroacetic acid

N-Methylolacrylamid (924-42-5) + 2-methoxy-phenol (90-05-1) → N-(4-hydroxy-3-methoxybenzyl)acrylamide (852923-26-3)

Conditions	Yield
With sulfuric acid In ethanol at 35℃; Friedel Crafts alkylation; Cooling with ice;	31%

N-Methylolacrylamid (924-42-5) + N-hydroxy-4-methoxybenzenecarboximidoyl chloride (74903-79-0) → 3-(4-methoxy-phenyl)-4,5-dihydro-isoxazole-5-carboxylic acid hydroxymethyl-amide

Conditions	Yield
With triethylamine In tetrahydrofuran; water for 0.333333h;	26%

N-Methylolacrylamid (924-42-5) + phenol (108-95-2) → N-(4-hydroxybenzyl)acrylamide

Conditions	Yield
With aluminum (III) chloride; 10H-phenothiazine In acetone at 0 - 40℃; for 16h;	26%

benzoyl chloride (98-88-4) + N-Methylolacrylamid (924-42-5) → acryloylamino-benzoyloxy-methane (22636-63-1)

methanol (67-56-1) + N-Methylolacrylamid (924-42-5) → N-methoxymethyl-acrylamide (3644-11-9)

Conditions	Yield
With hydrogenchloride

N-Methylolacrylamid (924-42-5) + 1,2-dichloro-ethane (107-06-2) → N,N'-Methylenebisacrylamide (110-26-9)

Conditions	Yield
With hydrogenchloride

N-Methylolacrylamid (924-42-5) → 2,3-dibromo-propionic acid-(hydroxymethyl-amide) (17354-02-8)

Conditions	Yield
With tetrachloromethane; bromine

styrene (292638-84-7) + N-Methylolacrylamid (924-42-5) → 6-phenyl-2-vinyl-5,6-dihydro-4H-[1,3]oxazine (13727-35-0)

Conditions	Yield
With sulfuric acid In acetic acid

trinitromethane (517-25-9) + N-Methylolacrylamid (924-42-5) → N-Methylol-4,4,4-trinitro-butyramid (99419-19-9)

Conditions	Yield
With acetic anhydride

trinitromethane (517-25-9) + N-Methylolacrylamid (924-42-5) → N-Trinitroethyl-acrylsaeureamid (98021-49-9)

Conditions	Yield
In water

N-Methylolacrylamid (924-42-5) + isobutene (115-11-7) → 6,6-dimethyl-2-vinyl-5,6-dihydro-4H-[1,3]oxazine (13157-57-8)

Conditions	Yield
With sulfuric acid In acetic acid

N-Methylolacrylamid (924-42-5) + cyclohexene (110-83-8) → 2-vinyl-4a,5,6,7,8,8a-hexahydro-4H-benzo[e][1,3]oxazine (13670-18-3)

Conditions	Yield
With sulfuric acid In acetic acid

N-Methylolacrylamid (924-42-5) → N,N'-Oxydimethylen-diacrylsaeureamid (16958-71-7)

Conditions	Yield
With hydrogenchloride; hydroquinone In tetrachloromethane
With hydrogenchloride

Upstream product

• 50-00-0 formaldehyd 
• 107-06-2 1,2-dichloro-ethane 
• 79-06-1 2-propenamide 
• 121-44-8 triethylamine 

Downstream Products

• 22636-63-1 acryloylamino-benzoyloxy-methane 
• 3644-11-9 N-methoxymethyl-acrylamide 
• 110-26-9 N,N'-Methylenebisacrylamide 
• 64437-72-5 acrylamido methylene uree 
• 50-00-0 formaldehyd 
• 79-06-1 2-propenamide 
• 137691-13-5 3-acrylamidomethyl-4-methoxybenzophenone 
• 852923-26-3 N-(4-hydroxy-3-methoxybenzyl)acrylamide 
• 1610610-03-1 3-(benzylamino)-N-(hydroxymethyl)propanamide 
• 1383627-31-3 N,N-(((3-oxo-1,3-dihydroisobenzofuran-1,1-diyl)-bis(2-hydroxy-5,1-phenylene))-bis(methylene))diacrylamide 
• 1383627-29-9 N-(2-hydroxy-5-(1-(4-hydroxyphenyl)-3-oxo-1,3-dihydroisobenzofuran-1-yl)benzyl)acrylamide 
• 14800-18-1 N-(3,5-dimethyl-2-hydroxybenzyl)acrylamide 
• 127089-61-6 1-phenyl-2-(acrylamidomethyl)-butane-1,3-dione 

Relevant articles and documents

Synthesis method of N-hydroxymethyl acrylamide

The invention relates to a synthesis method of N-hydroxymethyl acrylamide. By taking solid acrylamide and paraformaldehyde as raw materials, adopting a supported quaternary ammonium base catalyst, and selectively activating an amino group in the acrylamide by controlling the size of a hydrocarbyl group connected with quaternary ammonium base and utilizing the steric effect of hydrocarbyl, the self-polymerization behavior in the production process of the N-hydroxymethyl acrylamide is reduced, and the N-hydroxymethyl acrylamide monomer is efficiently obtained. The supported quaternary ammonium alkali is used as the catalyst, the reaction condition is mild, the selectivity is high, system polymerization caused by the traditional inorganic alkali liquor reaction is effectively avoided, and the reaction system can realize high-efficiency conversion of raw materials without adding a large amount of water as a reaction solvent, so that the yield is improved; and the supported quaternary ammonium base catalyst has the characteristics of large specific surface area, high reaction activity and the like, greatly reduces the use amount of solvent water in the reaction process, is convenient to remove in the post-treatment process, and reduces sewage discharge.

Copolymerization of acrylic acid with acrylamide biuret derivatives

Copolymerization of acrylic acid with new acrylamide biuret derivatives obtained was investigated. Reactivity ratios r 1 and r 2 of these monomers with acrylic acid were calculated. It was found that monomers of mono- and diacrylamide biuret derivatives are of cyclic structures and this fact specifically affects their activity in the copolymerization with acrylic acid.

An efficient hydroxymethylation of lactams

N-Hydroxymethylation of lactams was achieved using paraformaldehyde in acetone in the presence of K2CO3 and water under sonication conditions.