2-ACETAMIDO-5-NITROTHIAZOLE Chemical Properties

Melting point:

263°C (dec.)

Boiling point:

421°

Density 

1.546 (estimate)

refractive index 

1.6560 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMF:3.0(Max Conc. mg/mL);16.03(Max Conc. mM)
DMSO:10.0(Max Conc. mg/mL);53.43(Max Conc. mM)

form 

solid

pka

8.78±0.50(Predicted)

color 

White to Amber

Merck 

14,410

BRN 

167361

InChI

InChI=1S/C5H5N3O3S/c1-3(9)7-5-6-2-4(12-5)8(10)11/h2H,1H3,(H,6,7,9)

InChIKey

UJRRDDHEMZLWFI-UHFFFAOYSA-N

SMILES

C(NC1=NC=C([N+]([O-])=O)S1)(=O)C

CAS DataBase Reference

140-40-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

22-36/37-24/25

RTECS 

XJ1570000

HS Code 

29341000

Toxicity

chicken,LD50,oral,800mg/kg (800mg/kg),Antibiotics and Chemotherapy Vol. 5, Pg. 540, 1955.

MSDS

• Language:English Provider:ALFA

2-ACETAMIDO-5-NITROTHIAZOLE Usage And Synthesis

Chemical Properties

Yellow-brown solid

Uses

antiinflammatory, glucocorticoid

Uses

Nithiamide is a drug for chemotherapy. A protistocide drug with antibacterial activity.

Definition

ChEBI: Aminitrozole is an aromatic amide and a member of acetamides.

Safety Profile

Poison by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of SO, and NOx,.

Synthesis

General method: 2-amino-5-nitrothiazole (0.3 g, 2.0 mmol) was dissolved in dichloromethane, followed by the addition of 1.2 molar equivalents of triethylamine (TEA). The reaction mixture was stirred at 5 °C for 15 min, then acetic anhydride (10.0 mmol, 5 eq.) or the corresponding chloride (2.2 mmol, 1.1 eq.) was added slowly and dropwise. The reaction mixture was continued to be stirred at room temperature for 4 to 24 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue is neutralized with saturated sodium bicarbonate (NaHCO3) solution and the resulting solid is purified by recrystallization from the appropriate solvent mixture.

Purification Methods

Recrystallise acinitrazole from EtOH or AcOH. [Hurd & Wehrmeister J Am Chem Soc 71 4007 1949, Beilstein 27 III/IV 4676.]

References

[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 5, p. 1626 - 1633

2-ACETAMIDO-5-NITROTHIAZOLE(140-40-9)Related Product Information

• 5-NITRO-1,3-THIAZOLE 96
• Dinitolmide
• 2-Acetamido-5-nitrothiazole VETRANAL
• 2-ACETAMIDO-5-NITROTHIAZOLE
• tenonitrozole
• Nitazoxanide
• 2-ACETAMIDOTHIAZOLE
• TIZOXANIDE
• 2-CHLORO-N-(5-NITRO-THIAZOL-2-YL)-ACETAMIDE
• TIZOXANIDE GLUCURONIDE, SODIUM SALT
• ACETAMIDO-5-NITROTHIAZOLE
• 2-ACETAMIDO-5-NITROTHIAZOLE 1G [R]
• N-(5-NITRO-1,3-THIAZOL-2-YL)-2-FURAMIDE
• 4-CHLORO-N-(5-NITRO-1,3-THIAZOL-2-YL)BENZENECARBOXAMIDE
• N-(5-NITRO-1,3-THIAZOL-2-YL)BENZENECARBOXAMIDE
• AURORA 22569
• AURORA 22570
• N-(3-NITRO(2,5-THIAZOLYL))(PHENYLCYCLOPENTYL)FORMAMIDE