1-ACETYL-3-THIOSEMICARBAZIDE

1-ACETYL-3-THIOSEMICARBAZIDE Property

Melting point:

165-170 °C

Density 

1.280 (estimate)

refractive index 

1.7490 (estimate)

storage temp. 

2-8°C(protect from light)

solubility 

DMSO (Sparingly), Methanol (Sparingly)

pka

10.30±0.70(Predicted)

form 

solid

Appearance

Off-white to light yellow Solid

Water Solubility 

Partly soluble in water.

Stability:

Hygroscopic

CAS DataBase Reference

2302-88-7(CAS DataBase Reference)

Safety

Hazard Codes 

T

Risk Statements 

25-36/37/38

Safety Statements 

24/25-45

RIDADR 

2811

HazardClass 

6.1

PackingGroup 

III

HS Code 

29309099

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P330Rinse mouth.

1-ACETYL-3-THIOSEMICARBAZIDE Chemical Properties,Usage,Production

Chemical Properties

white to slightly beige crystalline powder

Uses

1-Acetyl-3-thiosemicarbazide is applied in pharmaceutical industry as an intermediate.

Synthesis

General procedure for the synthesis of acetylthiosemicarbazone from aminothiourea and acetyl chloride: preparation of the intermediate 2-acetylcarbazinethioformamide; Acetyl chloride (8.64 g, 0.11 mol) was added slowly and dropwise to an anhydrous tetrahydrofuran (THF, 100 mL) solution of aminothiourea (9.10 g, 0.10 mol) at 0 °C. The reaction mixture was heated to reflux and maintained for 3 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction was quenched by the addition of water (100 mL) followed by extraction with ethyl acetate (3 x 100 mL). The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography (eluent: methanol/dichloromethane=1/1, v/v) to afford the target compound acetylthiosemicarbazone (8.64 g, 65% yield). The results of mass spectrometry (electrospray ionization, ESI) analysis: m/z calculated value C3H7N3OS [M+H]+ 133.03, measured value 134.0 (MH+).

References

[1] Patent: WO2009/87220, 2009, A1. Location in patent: Page/Page column 57
[2] Yakugaku Zasshi, 1952, vol. 72, p. 376
[3] Chem.Abstr., 1953, p. 3856
[4] Synthetic Communications, 2004, vol. 34, # 22, p. 4189 - 4198
[5] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2010, vol. 76, # 5, p. 531 - 536