5-Amino-1,2,4-thiadiazole Chemical Properties

Melting point:

112-115°C

Boiling point:

238.9±23.0 °C(Predicted)

Density 

1.495±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

pka

3.97±0.50(Predicted)

color 

Yellow

InChI

InChI=1S/C2H3N3S/c3-2-4-1-5-6-2/h1H,(H2,3,4,5)

InChIKey

VJHTZTZXOKVQRN-UHFFFAOYSA-N

SMILES

S1C(N)=NC=N1

CAS DataBase Reference

7552-07-0(CAS DataBase Reference)

NIST Chemistry Reference

5-Amino-1,2,4-thiadiazole(7552-07-0)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/22

HazardClass 

IRRITANT

HS Code 

2934999090

5-Amino-1,2,4-thiadiazole Usage And Synthesis

Physical Form

Solid

Uses

5-Amino-1,2,4-thiadiazole is a useful research chemical for organic synthesis and other chemical processes.

Synthesis

The general procedure for the synthesis of 5-amino-1,2,4-thiadiazole from the compound (CAS: 943653-32-5) is as follows: (E)-N'-carbamoyl-N,N-dimethylformamide (3.9 g, 30 mmol), hydroxylamine-O-sulphonic acid (3.7 g, 33 mmol) were mixed with anhydrous ethanol (100 mL) and reacted by heating at 80 °C for for 8 hours. Upon completion of the reaction, the mixture was cooled to room temperature, triethylamine was added and stirring was continued at room temperature for 19 hours. Subsequently, the solvent was removed by distillation under reduced pressure, and the residue was dissolved in a mixture of dichloromethane and methanol (10 mL) with a volume ratio of 9:1. Dichloromethane solution containing 5% methanol was used as the eluent, and purification was carried out by silica gel column chromatography, resulting in 1 ,2,4-thiadiazol-5-amine as a white solid (1.4 g, 47% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 7.95 (s, 2H), 7.85 (s, 1H).LC/MS analysis conditions: 10%-99% acetonitrile (containing 0.035% trifluoroacetic acid)/water (containing 0.05% trifluoroacetic acid), observed m/z (M+1) = 102.1; retention time tR = 0.39 min.

References

[1] Patent: US2009/124655, 2009, A1. Location in patent: Page/Page column 14
[2] Patent: US2009/131440, 2009, A1. Location in patent: Page/Page column 18-19
[3] Patent: US2008/27067, 2008, A1. Location in patent: Page/Page column 259

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