| Identification | Back Directory | [Name]
2,2-DIMETHYLTHIOPROPIONAMIDE | [CAS]
630-22-8 | [Synonyms]
NSC 381432
Thiopivalamide
Neopentanethioamide
2,2-DIMETHYLTHIOPROPIOMIDE
2,2-DIMETHYLTHIOPROPIONAMIDE
2,2,2-Trimethylthioacetamide,
2,2,2-Dimethylthiopropionamide
Propanethioamide, 2,2-dimethyl- | [EINECS(EC#)]
677-829-5 | [Molecular Formula]
C5H11NS | [MDL Number]
MFCD09742834 | [MOL File]
630-22-8.mol | [Molecular Weight]
117.21 |
| Chemical Properties | Back Directory | [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) | [Fp ]
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 |
| Hazard Information | Back Directory | [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 |
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