5-AMINO-3-METHYL-1,2,4-THIADIAZOLE Chemical Properties

Melting point:

202 °C

Boiling point:

261.2±23.0 °C(Predicted)

Density 

1.372±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

4.56±0.50(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C3H5N3S/c1-2-5-3(4)7-6-2/h1H3,(H2,4,5,6)

InChIKey

DJKUIGPCSNRFRK-UHFFFAOYSA-N

SMILES

S1C(N)=NC(C)=N1

CAS DataBase Reference

17467-35-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

26-36

HazardClass 

IRRITANT

HS Code 

2934999090

5-AMINO-3-METHYL-1,2,4-THIADIAZOLE Usage And Synthesis

Chemical Properties

prism

Uses

3-methyl-1,2,4-thiadiazol-5-amine is a useful intermediate used in the preparation of 1,2,4-thiadiazole analogue that functions as a non-peptide inhibitor of beta-secretase.

Synthesis

The general procedure for the synthesis of 5-amino-3-methyl-1,2,4-thiadiazole from potassium thiocyanate and chloroacetamidine was as follows: chloroacetamidine (5.1 g, 55 mmol) was dissolved in methanol (250 mL) and the resulting solution was cooled to 0 °C. Subsequently, potassium thiocyanate (5.3 g, 55 mmol) was added to the solution. The reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the solution was concentrated under reduced pressure, diluted with ethyl acetate (200 mL) and insoluble solids were removed by filtration under reduced pressure. The filtrate was further concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography (silica gel, n-hexane:ethyl acetate = 4:1) to afford finally 5-amino-3-methyl-1,2,4-thiadiazole (2 g, 32% yield). The structure of the product was confirmed by 1H NMR (600 MHz, CD3OD), δ 3.27 (s, 3H).

References

[1] Patent: US2012/264727, 2012, A1. Location in patent: Page/Page column 53
[2] Patent: EP2706062, 2014, A2. Location in patent: Paragraph 0199

5-AMINO-3-METHYL-1,2,4-THIADIAZOLE(17467-35-5)Related Product Information

• 5-AMINO-3-PHENYL-1,2,4-THIADIAZOLE
• 5-AMINO-3-ETHYL-1,2,4-THIADIAZOLE
• 5-Hydrazino-3-(2-thienyl)-1,2,4-thiadiazole
• Cefozopran
• 5-AMINO-3-METHYL-1,2,4-THIADIAZOLE
• 3-PHENYL-5-PIPERAZINO-1,2,4-THIADIAZOLE
• 1-(5-METHYLAMINO-[1,2,4]THIADIAZOL-3-YL)-PROPAN-2-ONE
• JNJ 1661010
• 5-AMINO-3-ISOPROPYL-1,2,4-THIADIAZOLE
• 3-Amino-5-methyl-1,2,4-thiadiazole
• 2-AMINO-5-METHYL-1,3,4-THIADIAZOLE,2-AMINO-5-METHYL-1,3,4-THIADIAZOLE 97%
• Cefclidin
• 5-(1,4-DIAZEPAN-1-YL)-3-PHENYL-1,2,4-THIADIAZOLE
• 3-(Trichloromethyl)1,2,4-thiadiazol-5-amine
• Cefluprenam
• 2-(4-CARBOXYBUTYRYL)AMINO-5-METHYL-1,3,4-THIADIAZOLE
• N,3-DIPHENYL-1,2,4-THIADIAZOL-5-AMINE
• 1-(5-ANILINO-1,2,4-THIADIAZOL-3-YL)ACETONE