2-AMINO-5-(2-CHLOROPHENYL)-1,3,4-THIADIAZOLE

2-AMINO-5-(2-CHLOROPHENYL)-1,3,4-THIADIAZOLE Property

Melting point:

192-195 °C

Boiling point:

393.8±44.0 °C(Predicted)

Density 

1.461±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

2.28±0.10(Predicted)

Appearance

Light yellow to brown Solid

Safety

Hazard Codes 

Xi,T

Risk Statements 

25

Safety Statements 

45

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

2-AMINO-5-(2-CHLOROPHENYL)-1,3,4-THIADIAZOLE Chemical Properties,Usage,Production

Synthesis

5.1.1 Synthesis of 5-(2-chlorophenyl)-1,3,4-thiadiazol-2-amine (68): 2-chlorobenzoic 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 hr at 75 °C. After completion of the reaction, H2O (30 ml) was added and the mixture was heated to reflux for 4 hours. Subsequently, the reaction mixture was adjusted with 50% NaOH solution to pH 8. The precipitate was collected by filtration and the filter cake was purified by recrystallization from ethanol to give the yellow crystalline product 68 in a yield of 3.90 g, 88% yield, melting point 190-192 °C (EtOH). The product was analyzed by ESI-MS, m/z: 212.1 [M + H]+; 1H NMR (CDCl3) δ 7.45-7.50 (m, 4H), 7.60-7.62 (m, 1H), 7.99-8.01 (m, 1H). Compounds 60-81 were synthesized in the same way.

References

[1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 8, p. 998 - 1001
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 5766 - 5775
[3] Medicinal Chemistry Research, 2018, vol. 27, # 7, p. 1800 - 1821
[4] Medicinal Chemistry Research, 2012, vol. 21, # 6, p. 816 - 824
[5] Journal of Chemical Research, 2014, vol. 38, # 6, p. 347 - 350