| Identification | More | [Name]
2-AMINO-5-(4-METHOXYPHENYL)-1,3,4-THIADIAZOLE | [CAS]
1014-25-1 | [Synonyms]
1014-25-1
AKOS B014673
BUTTPARK 24\04-30
ART-CHEM-BB B014673
TIMTEC-BB SBB000467
IFLAB-BB F1386-0072
2-AMINO-5-(METHOXYPHENYL)-1,3,4-THIADIA&
5-(4-METHOXYPHENYL)-1,3,4-THIADIAZOL-2-AMINE
2-AMINO-5-(4-METHOXYPHENYL)-1,3,4-THIADIAZOLE
1,3,4-Thiadiazol-2-aMine, 5-(4-Methoxyphenyl)-
5-(4-METHOXY-PHENYL)-[1,3,4]THIADIAZOL-2-YLAMINE
2-Amino-5-(4-methoxyphenyl)-1,3,4-thiadiazole 97%
5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-amine(SALTDATA: FREE)
JRH-02708, 5-(4-Methoxyphenyl)-1,3,4-thiadiazol-2-amine, 97% | [Molecular Formula]
C9H9N3OS | [MDL Number]
MFCD00813220 | [Molecular Weight]
207.25 | [MOL File]
1014-25-1.mol |
| Chemical Properties | Back Directory | [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 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 .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT |
| Hazard Information | Back Directory | [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 |
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