| Identification | More | [Name]
N-ACRYLOYLTRIS(HYDROXYMETHYL)AMINOMETHANE | [CAS]
13880-05-2 | [Synonyms]
2-ACRYLAMIDO-2-HYDROXYMETHYL-1,3-PROPANEDIOL
ACRYLAMIDOTRISHYDROXYMETHYLMETHANE
N-(2-HYDROXY-1,1-BIS(HYDROXYMETHYL)ETHYL)-2-PROPENAMIDE
N-ACRYLOYLTRIS(HYDROXYMETHYL)AMINOMETHANE
N-[TRIS(HYDROXYMETHYL)METHYL]ACRYLAMIDE
N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]acrylamide
NAT, TRIS-acrylamide
Acryloylaminomethylidynetrimethanol
N-[1,1-Bis(hydroxymethyl)-2-hydroxyethyl]propenamide
N-[1,1-Di(hydroxymethyl)-2-hydroxyethyl]acrylamide | [EINECS(EC#)]
237-645-4 | [Molecular Formula]
C7H13NO4 | [MDL Number]
MFCD00081045 | [Molecular Weight]
175.18 | [MOL File]
13880-05-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White crystals or crystalline powder | [Melting point ]
136-141 °C(lit.)
| [Boiling point ]
510.8±50.0 °C(Predicted) | [density ]
1.272±0.06 g/cm3(Predicted) | [storage temp. ]
0-6°C | [form ]
solid | [pka]
12.74±0.46(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [F ]
8-10-21 | [HS Code ]
29241900 |
| Hazard Information | Back Directory | [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 |
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