Ethyl thiooxamate Chemical Properties

Melting point:

62-65 °C (lit.)

Boiling point:

199.2±23.0 °C(Predicted)

Density 

1.226 (estimate)

refractive index 

1.5480 (estimate)

Flash point:

74°

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

chloroform: soluble25mg/mL, clear to slightly hazy (colorless to orange)

form 

Crystalline Powder

pka

11.31±0.29(Predicted)

color 

Yellow

InChI

InChI=1S/C4H7NO2S/c1-2-7-4(6)3(5)8/h2H2,1H3,(H2,5,8)

InChIKey

YMBMCMOZIGSBOA-UHFFFAOYSA-N

SMILES

C(OCC)(=O)C(N)=S

CAS DataBase Reference

16982-21-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

RIDADR 

NA1993

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Ethyl thiooxamate Usage And Synthesis

Chemical Properties

Yellow Needles

Uses

Ethyl thiooxamate was used in the synthesis of functionalized bithiazoles.

Uses

Ethyl thiooxamate is used in a synthesis of functionalized bithiazoles.

Synthesis

The general procedure for the synthesis of ethyl thiooxalate from ethyl cyanoformate was as follows: [(cyanocarbonyl)oxy]ethane (25 g, 0.25 mol) was dissolved with triethylamine (1 ml) in ether (200 ml) and cooled to 0°C. H2S gas was drummed into the solution for 2 hours. After completion of the reaction, the mixture was stirred at room temperature overnight, followed by replacement of the gas in the reaction system with N2. A 1N HCl solution (200 ml) was added and stirring was continued for 30 minutes. The reaction mixture was separated by extraction with ether. The organic layer was washed with brine and dried with anhydrous MgSO4. The desiccant was removed by filtration and the solvent was evaporated under reduced pressure to give ethyl thiooxalate as a yellow solid (32 g, 95% yield). The product was characterized by 1H NMR (400 MHz, chloroform-d): δ 1.37 (t, J = 7.14 Hz, 3H), 4.34 (q, J = 7.14 Hz, 2H), 7.49-8.43 (m, 2H). m/z 134 (M + H)+ was shown by LC-MS (ESI) analysis.

References

[1] Patent: US2010/196321, 2010, A1. Location in patent: Page/Page column 19
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3021 - 3026
[3] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 3, p. 335 - 340
[4] Organic Syntheses, 1988, vol. 66, p. 142 - 142
[5] Patent: WO2005/37804, 2005, A1. Location in patent: Page/Page column 10

Ethyl thiooxamate(16982-21-1)Related Product Information

• Trinexapac-ethyl
• Ethanol
• Oxamide
• Ethyl formate
• Thioacetamide
• Ethyl acrylate
• Ethyl pyruvate
• Glycine
• Sodium thiosulfate
• Dithiooxamide
• 2-Thiobarbituric acid
• Ethylparaben
• Glycine ethyl ester hydrochloride
• Ethyl cyanoacetate
• Ethyl 3-aminopropanoate hydrochloride
• Ammonium thiosulfate
• Ethanethioic acid S-ethyl ester
• ISOXADIFEN-ETHYL