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924-42-5

Basic Information
CAS No.: 924-42-5
Name: N-Methylolacrylamide
Article Data: 17
Molecular Structure:
Molecular Structure of 924-42-5 (N-Methylolacrylamide)
Formula: C4H7NO2
Molecular Weight: 101.105
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;
EINECS: 213-103-2
Density: 1.074 g/cm3
Melting Point: 74-75 °C
Boiling Point: 318.1 °C at 760 mmHg
Flash Point: 146.2 °C
Solubility: <0.1 g/100 mL at 20.5 °C
Appearance: white crystal powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38
Safety: 26
PSA: 49.33000
LogP: -0.37070
Synthetic route
50-00-0

formaldehyd

79-06-1

2-propenamide

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
50-00-0

formaldehyd

107-06-2

1,2-dichloro-ethane

79-06-1

2-propenamide

924-42-5

N-Methylolacrylamid

Conditions
ConditionsYield
With sodium; xylene
50-00-0

formaldehyd

121-44-8

triethylamine

79-06-1

2-propenamide

924-42-5

N-Methylolacrylamid

50-00-0

formaldehyd

79-06-1

2-propenamide

A

N,N-dimethylolacrylamide

B

924-42-5

N-Methylolacrylamid

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

4-ethylpiperazine

924-42-5

N-Methylolacrylamid

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%
99-24-1

methyl galloate

924-42-5

N-Methylolacrylamid

C12H13NO6

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

4-methylpiperidin

924-42-5

N-Methylolacrylamid

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%
831-61-8

Ethyl gallate

924-42-5

N-Methylolacrylamid

C13H15NO6

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

morpholine

924-42-5

N-Methylolacrylamid

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%
103-76-4

1-(2-hydroxyethyl)piperazine

924-42-5

N-Methylolacrylamid

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%
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    CAS No.: 924-42-5 Other Names: N-(Hydroxymethyl)-2-Propenamide MF: C4H7NO2 EINECS No.: 213-103-2 Place of Origin:

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    Chemical Name: N-Methylolacrylamide CAS No.: 924-42-5 Molecular Fomula: C4H7NO2 Chemical Structure: Molecular weight: 101.1 Appearance: white crystalline powder Assay: 98% Appearance:White powder Storage:Store in cool

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Consensus Reports

Reported in EPA TSCA Inventory.

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.