Product Name

  • Name

    N-Methylolacrylamide

  • EINECS 213-103-2
  • CAS No. 924-42-5
  • Article Data17
  • CAS DataBase
  • Density 1.074 g/cm3
  • Solubility <0.1 g/100 mL at 20.5 °C
  • Melting Point 74-75 °C
  • Formula C4H7NO2
  • Boiling Point 318.1 °C at 760 mmHg
  • Molecular Weight 101.105
  • Flash Point 146.2 °C
  • Transport Information
  • Appearance white crystal powder
  • Safety 26
  • Risk Codes 22-36/37/38
  • Molecular Structure Molecular Structure of 924-42-5 (N-Methylolacrylamide)
  • Hazard Symbols HarmfulXn
  • Synonyms Acrylamide,N-(hydroxymethyl)- (6CI,8CI);MH 100;MH 100 (amide);Monomethylolacrylamide;N-(Hydroxymethyl)acrylamide;N-MAM;N-MAM P;NMA 60;NSC 553;Rocagil BT;U-Ramin T 80;
  • PSA 49.33000
  • LogP -0.37070

Synthetic route

formaldehyd
50-00-0

formaldehyd

2-propenamide
79-06-1

2-propenamide

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

Conditions
ConditionsYield
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

formaldehyd

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

2-propenamide
79-06-1

2-propenamide

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

Conditions
ConditionsYield
With sodium; xylene
...Expand
formaldehyd
50-00-0

formaldehyd

triethylamine
121-44-8

triethylamine

2-propenamide
79-06-1

2-propenamide

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

...Expand
formaldehyd
50-00-0

formaldehyd

2-propenamide
79-06-1

2-propenamide

A

N,N-dimethylolacrylamide

N,N-dimethylolacrylamide

B

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

Conditions
ConditionsYield
With 4-methoxy-phenol; sodium hydroxide In water at 20 - 60℃; for 1h; pH=10.5;
...Expand
4-ethylpiperazine
5308-25-8

4-ethylpiperazine

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

3-(4-ethylpiperazin-1-yl)-N-(hydroxymethyl)propanamide
1610610-01-9

3-(4-ethylpiperazin-1-yl)-N-(hydroxymethyl)propanamide

Conditions
ConditionsYield
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

methyl galloate

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

C12H13NO6

C12H13NO6

Conditions
ConditionsYield
With sulfuric acid In ethanol at 35℃; for 96h; Friedel-Crafts Alkylation;93.27%
4-methylpiperidin
626-58-4

4-methylpiperidin

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

N-(hydroxymethyl)-3-(4-methylpiperidin-1-yl)propanamide
1610610-02-0

N-(hydroxymethyl)-3-(4-methylpiperidin-1-yl)propanamide

Conditions
ConditionsYield
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

Ethyl gallate

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

C13H15NO6

C13H15NO6

Conditions
ConditionsYield
With sulfuric acid In ethanol at 35℃; for 96h; Friedel-Crafts Alkylation;92.38%
morpholine
110-91-8

morpholine

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

N-(hydroxymethyl)-3-morpholinopropanamide
63737-25-7

N-(hydroxymethyl)-3-morpholinopropanamide

Conditions
ConditionsYield
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

1-(2-hydroxyethyl)piperazine

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

3-(4-(2-hydroxyethyl)piperazin-1-yl)-N-(hydroxymethyl)propanamide
1616578-06-3

3-(4-(2-hydroxyethyl)piperazin-1-yl)-N-(hydroxymethyl)propanamide

Conditions
ConditionsYield
With [DABCO-PDO][OAc] In neat (no solvent) at 20℃; for 2.5h; Michael Addition; Green chemistry;88%
N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

β-naphthol
135-19-3

β-naphthol

α-N-methacrylamide-β-naphthol
13579-22-1

α-N-methacrylamide-β-naphthol

Conditions
ConditionsYield
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-(hydroxymethyl)piperazine

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

N-(hydroxymethyl)-3-(4-(hydroxymethyl)piperazin-1-yl)propanamide

N-(hydroxymethyl)-3-(4-(hydroxymethyl)piperazin-1-yl)propanamide

Conditions
ConditionsYield
With [ADPQ][CH3COO] at 20℃; for 3h; Michael Addition;86%
Propyl gallate
121-79-9

Propyl gallate

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

C14H17NO6

C14H17NO6

Conditions
ConditionsYield
With sulfuric acid In ethanol at 35℃; for 96h; Friedel-Crafts Alkylation;85.92%
2,4-dihydroxybenzophenone
131-56-6

2,4-dihydroxybenzophenone

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

(3,5-dimethacrylamide-2,4-dihydroxyphenyl) (phenyl)methanone

(3,5-dimethacrylamide-2,4-dihydroxyphenyl) (phenyl)methanone

Conditions
ConditionsYield
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

N-Methylolacrylamid

benzylamine
100-46-9

benzylamine

3-(benzylamino)-N-(hydroxymethyl)propanamide
1610610-03-1

3-(benzylamino)-N-(hydroxymethyl)propanamide

Conditions
ConditionsYield
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

N-Methylolacrylamid

9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide
35948-25-5

9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide

10‐(4‐hydroxy‐3‐(hydroxymethyl)amino‐3‐oxopropyl)‐9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide

10‐(4‐hydroxy‐3‐(hydroxymethyl)amino‐3‐oxopropyl)‐9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide

Conditions
ConditionsYield
In tetrahydrofuran at 120℃; for 8h; Temperature; Inert atmosphere;79.9%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

N,N'-[(4,5-dihydroxy-1,2-phenylene)bis(methylene)]bisacrylamide

N,N'-[(4,5-dihydroxy-1,2-phenylene)bis(methylene)]bisacrylamide

Conditions
ConditionsYield
With sulfuric acid In ethanol at 20 - 35℃; Friedel-Crafts Alkylation; Sonication;73%
phenolphthalein
77-09-8

phenolphthalein

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

N-(2-hydroxy-5-(1-(4-hydroxyphenyl)-3-oxo-1,3-dihydroisobenzofuran-1-yl)benzyl)acrylamide
1383627-29-9

N-(2-hydroxy-5-(1-(4-hydroxyphenyl)-3-oxo-1,3-dihydroisobenzofuran-1-yl)benzyl)acrylamide

Conditions
ConditionsYield
With aluminum (III) chloride In acetone at 40℃;32%
In trifluoroacetic acid
N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

2-methoxy-phenol
90-05-1

2-methoxy-phenol

N-(4-hydroxy-3-methoxybenzyl)acrylamide
852923-26-3

N-(4-hydroxy-3-methoxybenzyl)acrylamide

Conditions
ConditionsYield
With sulfuric acid In ethanol at 35℃; Friedel Crafts alkylation; Cooling with ice;31%
N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

N-hydroxy-4-methoxybenzenecarboximidoyl chloride
74903-79-0

N-hydroxy-4-methoxybenzenecarboximidoyl chloride

3-(4-methoxy-phenyl)-4,5-dihydro-isoxazole-5-carboxylic acid hydroxymethyl-amide

3-(4-methoxy-phenyl)-4,5-dihydro-isoxazole-5-carboxylic acid hydroxymethyl-amide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; water for 0.333333h;26%
N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

phenol
108-95-2

phenol

N-(4-hydroxybenzyl)acrylamide

N-(4-hydroxybenzyl)acrylamide

Conditions
ConditionsYield
With aluminum (III) chloride; 10H-phenothiazine In acetone at 0 - 40℃; for 16h;26%
benzoyl chloride
98-88-4

benzoyl chloride

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

acryloylamino-benzoyloxy-methane
22636-63-1

acryloylamino-benzoyloxy-methane

methanol
67-56-1

methanol

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

N-methoxymethyl-acrylamide
3644-11-9

N-methoxymethyl-acrylamide

Conditions
ConditionsYield
With hydrogenchloride
N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

N,N'-Methylenebisacrylamide
110-26-9

N,N'-Methylenebisacrylamide

Conditions
ConditionsYield
With hydrogenchloride
N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

2,3-dibromo-propionic acid-(hydroxymethyl-amide)
17354-02-8

2,3-dibromo-propionic acid-(hydroxymethyl-amide)

Conditions
ConditionsYield
With tetrachloromethane; bromine
styrene
292638-84-7

styrene

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

6-phenyl-2-vinyl-5,6-dihydro-4H-[1,3]oxazine
13727-35-0

6-phenyl-2-vinyl-5,6-dihydro-4H-[1,3]oxazine

Conditions
ConditionsYield
With sulfuric acid In acetic acid
trinitromethane
517-25-9

trinitromethane

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

N-Methylol-4,4,4-trinitro-butyramid
99419-19-9

N-Methylol-4,4,4-trinitro-butyramid

Conditions
ConditionsYield
With acetic anhydride
trinitromethane
517-25-9

trinitromethane

N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

N-Trinitroethyl-acrylsaeureamid
98021-49-9

N-Trinitroethyl-acrylsaeureamid

Conditions
ConditionsYield
In water
N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

isobutene
115-11-7

isobutene

6,6-dimethyl-2-vinyl-5,6-dihydro-4H-[1,3]oxazine
13157-57-8

6,6-dimethyl-2-vinyl-5,6-dihydro-4H-[1,3]oxazine

Conditions
ConditionsYield
With sulfuric acid In acetic acid
N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

cyclohexene
110-83-8

cyclohexene

2-vinyl-4a,5,6,7,8,8a-hexahydro-4H-benzo[e][1,3]oxazine
13670-18-3

2-vinyl-4a,5,6,7,8,8a-hexahydro-4H-benzo[e][1,3]oxazine

Conditions
ConditionsYield
With sulfuric acid In acetic acid
N-Methylolacrylamid
924-42-5

N-Methylolacrylamid

N,N'-Oxydimethylen-diacrylsaeureamid
16958-71-7

N,N'-Oxydimethylen-diacrylsaeureamid

Conditions
ConditionsYield
With hydrogenchloride; hydroquinone In tetrachloromethane
With hydrogenchloride

N-Methylolacrylamide Consensus Reports

Reported in EPA TSCA Inventory.

N-Methylolacrylamide Specification

The N-(Hydroxymethyl)prop-2-enamide with CAS registry number of 924-42-5 is also known as 2-Propenamide, N-(hydroxymethyl)-. The IUPAC name and product name are the same. It belongs to product categories of Acrylamide and Methacrylamide; Acrylic Monomers; Monomers. Its EINECS registry number is 213-103-2. In addition, the formula is C4H7NO2 and the molecular weight is 101.10. This chemcal is a white crystal powder and should be stored in sealed containers in ventilated, dry place avoid light at -20 °C for 3 months.

Physical properties about N-(Hydroxymethyl)prop-2-enamide are: (1)ACD/LogP: -1.48; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.48; (4)ACD/LogD (pH 7.4): -1.48; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 3.74; (8)ACD/KOC (pH 7.4): 3.74; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.459; (13)Molar Refractivity: 25.46 cm3; (14)Molar Volume: 93 cm3; (15)Surface Tension: 37.2 dyne/cm; (16)Density: 1.085 g/cm3; (17)Flash Point: 146.2 °C; (18)Enthalpy of Vaporization: 64.87 kJ/mol; (19)Boiling Point: 318.1 °C at 760 mmHg; (20)Vapour Pressure: 3.06E-05 mmHg at 25 °C.

Preparation of N-(Hydroxymethyl)prop-2-enamide: it is prepared by reaction of acrylamide with 37% formaldehyde solution. The reaction occurs in alkaline conditions.

N-(hydroxymethyl)prop-2-enamide is prepared by reaction of acrylamide with 37% formaldehyde solution.

Uses of N-(Hydroxymethyl)prop-2-enamide: it is a versatile cross-linking monomer. What's more, it can be used for fiber modification, resin processing, adhesives, treatment agent of paper, leather, metal surface, and also used as soil conditioner.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. Besides, it is harmful if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C=CC(=O)NCO
2. InChI: InChI=1S/C4H7NO2/c1-2-4(7)5-3-6/h2,6H,1,3H2,(H,5,7)
3. InChIKey: CNCOEDDPFOAUMB-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 420mg/kg (420mg/kg)   "Kirk-Othmer Encyclopedia of Chemical Technology," 3rd ed., Grayson, M., and D. Eckroth, eds. New York, John Wiley & Sons, Inc., 1978Vol. 1, Pg. 306, 1978.
rabbit LDLo skin 16gm/kg (16000mg/kg) BEHAVIORAL: TREMOR Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 111, 1990.
rat LD50 intraperitoneal 563mg/kg (563mg/kg)   Biochemical Pharmacology. Vol. 19, Pg. 2591, 1970.
rat LD50 oral 474mg/kg (474mg/kg)   Nippon Eiseigaku Zasshi. Japanese Journal of Hygiene. Vol. 34, Pg. 183, 1979.

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