2-AMINO-5-(4-METHOXYPHENYL)-1,3,4-THIADIAZOLE Chemical Properties

Melting point:

185-187 °C

Boiling point:

393.1±44.0 °C(Predicted)

Density 

1.320±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

3.37±0.10(Predicted)

Appearance

White to light yellow Solid

CAS DataBase Reference

1014-25-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

2-AMINO-5-(4-METHOXYPHENYL)-1,3,4-THIADIAZOLE Usage And Synthesis

Uses

2-Amino-5-(4-methoxyphenyl)-1,3,4-thiadiazole is a thiadiazole derivative that is potent and selective human adenosine A3 receptor antagonist. It is also used as a reactant in the synthesis of substituted thiadiazolyl(styryl)quinazolinones with anticonvulsant, sedative-hypnotic, and CNS depressant activities.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 906, 1951 DOI: 10.1021/ja01147a007

Synthesis

5.1.1 Synthesis of 5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-amine (61): p-Methoxybenzoic acid (5.18 g, 25 mmol) and aminothiourea (2.28 g, 25 mmol) were dissolved in POCl3 (7 mL) and stirred vigorously for 0.5 hours at 75°C. After the reaction was completed, H2O (30 mL) was added and the reaction mixture was heated to reflux for 4 hours. Subsequently, the pH of the reaction mixture was adjusted with 50% NaOH solution to 8. The precipitate was collected by filtration and the filter cake was recrystallized with ethanol to afford yellow crystals of the target compound 61 in 82% yield with a melting point of 219-220 °C (EtOH).ESI-MS m/z: 208.2 [M + H]+; 1H NMR (DMSO-d6) δ 3.80 (s, 3H ), 7.01-7.03 (m, 2H), 7.23 (s, 2H), 7.67-7.69 (m, 2H). Compounds 60-81 were synthesized in the same way.

References

[1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 14, p. 6663 - 6668
[2] Tetrahedron, 2018, vol. 74, # 31, p. 4161 - 4167
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 5766 - 5775
[4] Medicinal Chemistry, 2014, vol. 10, # 4, p. 376 - 381
[5] Medicinal Chemistry Research, 2012, vol. 21, # 6, p. 816 - 824

2-AMINO-5-(4-METHOXYPHENYL)-1,3,4-THIADIAZOLE(1014-25-1)Related Product Information

• 2-AMINO-5-(4-METHOXYPHENYL)-1,3,4-THIADIAZOLE
• 5-Amino-4-(4-methoxyphenyl)-1,2,3-thiadiazole
• 2-Chloro-N-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]acetamide
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• 2-FLUORO-N-(2-METHOXY-ETHYL)-N-[5-(4-METHOXY-PHENYL)-[1,3,4]THIADIAZOL-2-YL]-BENZAMIDE
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• 5-(3,4-diethoxyphenyl)-1,3,4-thiadiazol-2-amine
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• [4-(5-AMINO-[1,3,4]THIADIAZOL-2-YL)-PHENOXY]-ACETIC ACID
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• 5-(4-BUTOXY-PHENYL)-[1,3,4]THIADIAZOL-2-YLAMINE
• 5-(4-PROPOXY-PHENYL)-[1,3,4]THIADIAZOL-2-YLAMINE
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• Acetamide, N-(4-(((imino((imino((5-(4-methoxyphenyl)-1,3,4-thiadiazol- 2-yl)amino)methyl)amino)methyl)amino)sulfonyl)-2-methylphenyl)-, monoh ydrochloride
• N-[5-(4-METHOXYPHENYL)-1,3,4-THIADIAZOL-2-YL]-1-NAPHTHAMIDE