3,4-DIMETHYL-5-(2-HYDROXYETHYL)THIAZOLIUM IODIDE Chemical Properties

Melting point:

82-85 °C(lit.)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

Appearance

Light brown to brown Solid

InChI

InChI=1S/C7H12NOS.HI/c1-6-7(3-4-9)10-5-8(6)2;/h5,9H,3-4H2,1-2H3;1H/q+1;/p-1

InChIKey

GDNOYVMHHMSZJV-UHFFFAOYSA-M

SMILES

C1(CCO)SC=[N+](C)C=1C.[I-]

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

3-8-10

MSDS

• Language:English Provider:SigmaAldrich

3,4-DIMETHYL-5-(2-HYDROXYETHYL)THIAZOLIUM IODIDE Usage And Synthesis

Synthesis

General procedure: 4-methyl-5-hydroxyethyl thiazole (3.0 g, 21.0 mmol) was mixed with iodomethane (2.64 mL, 42.0 mmol) and heated to reflux for 2 hours. Upon completion of the reaction, excess iodomethane was removed by evaporation. Ether (50 mL) was added to the residual brown slurry and stirred for 30 minutes to promote crystallization. The precipitate was collected by filtration to afford 5-(2-hydroxyethyl)-3,4-dimethylthiazol-3-ium iodide (17) as a light yellow solid (5.76 g, 96.3% yield). The melting point of the product was 82-84 °C; 1H NMR (D2O, ppm): δ 4.14 (s, 3H, CH3N), 3.90 (t, 2H, CH2CH2O, J = 5.6 Hz), 3.19 (t, 2H, CH2CH2O, J = 6.0 Hz), 2.53 (s, 3H, CCH3).

References

[1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 3651 - 3661
[2] Molecules, 2016, vol. 21, # 4,
[3] Patent: CN106543194, 2017, A. Location in patent: Paragraph 0079; 0080; 0081
[4] Tetrahedron, 2008, vol. 64, # 37, p. 8797 - 8800
[5] Journal of the American Chemical Society, 1935, vol. 57, p. 1849

3,4-DIMETHYL-5-(2-HYDROXYETHYL)THIAZOLIUM IODIDE(16311-69-6)Related Product Information

• 5-ethyl-4-methylthiazole
• 3,4-DIMETHYL-5-(2-HYDROXYETHYL)THIAZOLIUM IODIDE
• 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methylthiazolium iodide
• 5-Methylthiazole
• 5-(2-Hydroxyethyl)-4-methylthiazole
• 4,5-Dimethylthiazole