| Identification | More | [Name]
Ethyl thiooxamate | [CAS]
16982-21-1 | [Synonyms]
ETHYL AMINOTHIOXOACETATE
ETHYL THIOOXAMATE
ETHYL THIOOXAMIDATE
ETHYL THIOXAMATE
aminothioxoacetic acid ethyl ester
thiooxamic acid ethyl ester
Acetic acid, 2-amino-2-thioxo-, ethyl ester
Ethyl thiooxamate, 98 %
2-Amino-2-thioxoacetic acid ethyl ester
O-Ethy1 thioxamate | [Molecular Formula]
C4H7NO2S | [MDL Number]
MFCD00074903 | [Molecular Weight]
133.17 | [MOL File]
16982-21-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow Needles | [Melting point ]
62-65 °C (lit.) | [Boiling point ]
199.2±23.0 °C(Predicted) | [density ]
1.226 (estimate) | [refractive index ]
1.5480 (estimate) | [storage temp. ]
Freezer (-20°C) | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29309090 |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Needles | [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 |
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