N-ACRYLOYLTRIS(HYDROXYMETHYL)AMINOMETHANE Chemical Properties

Melting point:

136-141 °C(lit.)

Boiling point:

510.8±50.0 °C(Predicted)

Density 

1.272±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

12.74±0.46(Predicted)

form 

solid

Water Solubility 

Soluble in water.

Sensitive 

Light Sensitive & Hygroscopic

BRN 

2081162

InChI

InChI=1S/C7H13NO4/c1-2-6(12)8-7(3-9,4-10)5-11/h2,9-11H,1,3-5H2,(H,8,12)

InChIKey

MVBJSQCJPSRKSW-UHFFFAOYSA-N

SMILES

C(NC(CO)(CO)CO)(=O)C=C

CAS DataBase Reference

13880-05-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

F 

8-10-21

HS Code 

29241900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N-ACRYLOYLTRIS(HYDROXYMETHYL)AMINOMETHANE Usage And Synthesis

Chemical Properties

White crystals or crystalline powder

Uses

N-[Tris(hydroxymethyl)methyl] acrylamide is used to prepare N-(5-hydroxymethyl-2-phenyl-[1,3]dioxan-5-yl)-acrylamide by reaction with benzaldehyde.

Synthesis

N-Acryloyl(tris(hydroxymethyl)aminomethane was synthesized from acryloyl chloride and tris(hydroxymethyl)aminomethane according to the method reported by Pucci et al. (Eur. Polym. J. 1991, 27, 1101). The procedure was as follows: to a stirred 3N potassium hydroxide methanol solution of tris(hydroxymethyl)aminomethane (3.00 g, 24.8 mmol), acryloyl chloride (3.60 mL, 44.6 mmol) was added slowly and dropwise at 0 °C, keeping the pH of the reaction system between 8 and 8. The reaction mixture was continued to be stirred at 0 °C for 3 h. The reaction was then naturally warmed to room temperature and continued for 4 h. The reaction was carried out at 0 °C. After completion of the reaction, the mixture was filtered and the filtrate was evaporated to dryness under vacuum. The resulting solid was purified by recrystallization from methanol to afford the target compound, N-acryloyl(trimethylol)aminomethane (3.78 g, 87%), as a white powder with a melting point of 205 °C. The product was purified by recrystallization from methanol. The product was characterized by the following data: IR (NaCl, cm^-1): 3420 (br, s), 1653 (s), 1560 (m), 1540 (m), 1018 (m); 1H NMR (300 MHz, DMSO-d6): δ 3.56 (d, 6H, J = 5.7 Hz, CH2), 4.76 (t, 3H, J = 5.7 Hz, OH), 5.54 (dd, 1H, J = 2.4, 9.9 Hz, Ha), 6.02 (dd, 1H, J = 2.4, 17.1 Hz, Hb), 6.37 (dd, 1H, J = 9.9, 17.1 Hz, Hc), 7.42 (s, 1H, NH).

References

[1] Journal of Organic Chemistry, 2008, vol. 73, # 14, p. 5602 - 5605
[2] Patent: WO2016/185425, 2016, A1. Location in patent: Page/Page column 57
[3] Macromolecular Bioscience, 2013, vol. 13, # 4, p. 512 - 522
[4] Tetrahedron, 2001, vol. 57, # 50, p. 9979 - 9987
[5] Tetrahedron Letters, 1991, vol. 32, # 11, p. 1437 - 1440

N-ACRYLOYLTRIS(HYDROXYMETHYL)AMINOMETHANE(13880-05-2)Related Product Information

• Stannous oxalate
• Tris(hydroxymethyl)aminomethane
• Methacrylamide
• N-TERT-BUTYLACRYLAMIDE
• N-ACRYLOYLTRIS(HYDROXYMETHYL)AMINOMETHANE