2,2-Dimethylthiopropionamide Chemical Properties

Melting point:

117-119℃ (ethyl acetate hexane )

Boiling point:

162.1±23.0℃ (760 Torr)

Density 

0.978±0.06 g/cm3 (20 ºC 760 Torr)

Flash point:

51.9±22.6℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Ethyl Acetate

form 

Solid

pka

13.33±0.29(Predicted)

color 

White

Water Solubility 

Soluble in water (10 g/L) (25°C).

InChI

InChI=1S/C5H11NS/c1-5(2,3)4(6)7/h1-3H3,(H2,6,7)

InChIKey

FJZJUSOFGBXHCV-UHFFFAOYSA-N

SMILES

C(N)(=S)C(C)(C)C

Safety Information

HS Code 

2930909899

2,2-Dimethylthiopropionamide Usage And Synthesis

Uses

2,2-Dimethylthiopropionamide is used as a reagent to synthesize Dabrafenib, an inhibitor of BRAF kinase that is used to treat BRAF V600-mutation positive carcinoma. BRAF is a gene that mediates cell growth and is activated by mutations caused by cancer. 2,2-Dimethylthiopropionamide is also used as a reagent to prepare sulfonyl-substituted 4,5-diarylthiazoles, compounds that act as cyclooxygenase-2 inhibitors (anti-inflammatory agents).

Synthesis

To a round bottom flask (250 mL) was added trimethyl amine (5.0 g, 0.049 mol) and Lawesson's reagent (8.0g, 0.020 mol), dissolved in THF (100 mL), nitrogen, 80° C oil. The reaction bath for 4 hours. TLC monitors the reaction progress. After completion of the reaction, the solvent was removed by rotary evaporation; the residue was purified by silica gel column chromatography (petroleum ether: 1: ethyl acetate = 10) to give a white solid 2,2-Dimethylthiopropionamide (3.7 g, 65percent yield).

References

[1] Chemistry - A European Journal, 2013, vol. 19, # 29, p. 9655 - 9662
[2] Phosphorus and Sulfur and the Related Elements, 1986, vol. 26, p. 169 - 184
[3] Patent: CN103936728, 2016, B. Location in patent: Paragraph 0211; 0213; 0214; 0215
[4] Canadian Journal of Chemistry, 1977, vol. 55, p. 2331 - 2335
[5] Journal of the Chemical Society [Section] C: Organic, 1966, p. 686 - 691

2,2-Dimethylthiopropionamide(630-22-8)Related Product Information

• 2,2-Dimethylthiopropionamide
• 2,2-DIMETHYLPROPANETHIOHYDRAZIDE
• 1-(aminocarbonothioyl)cyclopentanecarboxylic acid
• AKOS BBS-00006261