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

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

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

Safety Statements 

22-24/25

WGK Germany 

3

F 

3-8-10

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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

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