942-70-1

Basic information

• Product Name: 2-AMINO-5-(4-FLUOROPHENYL)-1 3 4-THIADI&
• Synonyms: 2-AMINO-5-(4-FLUOROPHENYL)-1 3 4-THIADI&;1,3,4-Thiadiazol-2-amine, 5-(4-fluorophenyl)-;5-(4-fluorophenyl)-1,3,4-thiadiazol-2-amine(SALTDATA: FREE);5-(4-Fluorophenyl)-1,3,4-thiadiazol-2-amine, 1-(5-Amino-1,3,4-thiadiazol-2-yl)-4-fluorobenzene;2-Amino-5-(4-fluorophenyl)-1,3,4-thiadiazole 97%
• CAS NO: 942-70-1
• Molecular Formula: C₈H₆FN₃S
• Molecular Weight: 195.22
• Product Categories: API intermediates;Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;Heterocyclic Building Blocks;Heterocyclic Fluorinated Building Blocks;Other Fluorinated Heterocycles;Thiadiazoles
• Mol File: 942-70-1.mol
• Article Data: 39

Chemical Properties

• Melting Point: 238-243 °C
• Boiling Point: 351.9 °C at 760 mmHg
• Flash Point: 166.6 °C
• Appearance: /
• Density: 1.423 g/cm³
• Vapor Pressure: 3.98E-05mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: 2-AMINO-5-(4-FLUOROPHENYL)-1 3 4-THIADI&(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-(4-FLUOROPHENYL)-1 3 4-THIADI&(942-70-1)
• EPA Substance Registry System: 2-AMINO-5-(4-FLUOROPHENYL)-1 3 4-THIADI&(942-70-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 942-70-1(Hazardous Substances Data)

Usage

Uses

2-Amino-5-(4-fluorophenyl)-1,3,4-thiadiazole can be used as a substrate in the preparation of:Bithiophene based azo dyes with possible nonlinear optical (NLO) properties.4-Thiazolidinone derivatives as potent HCV NS5B polymerase inhibitors.1,3,4-Thiadiazole and phenothiazine hybrids as possible antitubercular agents.

InChI:InChI=1/C8H6FN3S/c9-6-3-1-5(2-4-6)7-11-12-8(10)13-7/h1-4H,(H2,10,12)

Upstream product

• 459-38-1 (4-fluorobenzylidenehydrazinyl)thiocarboxamide 
• 333-20-0 potassium thioacyanate 
• 459-57-4 4-fluorobenzaldehyde 
• 403-43-0 4-fluorobenzoyl chloride 
• 403-33-8 methyl 4-flurobenzoate 
• 456-22-4 4-Fluorobenzoic acid 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 456-06-4 4-fluorobenzoyl hydrazide 
• 79-19-6 thiosemicarbazide 
• 831-38-9 2-(4-fluorobenzoyl)hydrazinecarbothioamide 

Downstream Products

• 70038-95-8 N-[5-(4-fluoro-phenyl)-[1,3,4]thiadiazol-2-yl]-acetamidine 
• 980-45-0 4-acetylamino-N-[5-(4-fluoro-phenyl)-[1,3,4]thiadiazol-2-yl]-benzenesulfonamide 
• 128627-65-6 (E)-N-[5-(4-Fluoro-phenyl)-[1,3,4]thiadiazol-2-yl]-3-phenyl-acrylamide 
• 128627-54-3 N-<5-(4-Fluorophenyl)-1,3,4-thiadiazol-2-yl>acrylamide 
• 128627-71-4 3-[5-(4-Fluoro-phenyl)-[1,3,4]thiadiazol-2-ylamino]-2-methyl-propionic acid 
• 128627-61-2 N-[5-(4-Fluoro-phenyl)-[1,3,4]thiadiazol-2-yl]-2-methyl-acrylamide 
• 1060691-95-3 C₂₁H₁₉FN₄O₃S 
• 1060691-84-0 C₂₀H₁₇FN₄O₃S 
• 1060691-71-5 C₂₀H₁₇FN₄O₂S 
• 907178-54-5 C₁₅H₁₀FN₃S 
• 1431555-43-9 4-[[5-(4-fluorophenyl)-1,3,4-thiadiazol-2-ylimino]-methyl]phenol 

Relevant articles and documents

Synthesis and preliminary anticancer activity assessment of n-glycosides of 2-amino-1,3,4-thiadiazoles

The addition of 2-amino-1,3,4-thiadiazole derivatives with parallel iodination of differ-ently protected glycals has been achieved using a double molar excess of molecular iodine under mild conditions. The corresponding thiadiazole derivatives of N-glycosides were obtained in good yields and anomeric selectivity. The usage of iodine as a catalyst makes this method easy, inexpen-sive, and successfully useable in reactions with sugars. Thiadiazole derivatives were tested in a panel of three tumor cell lines, MCF-7, HCT116, and HeLa. These compounds initiated biological response in investigated tumor models in a different rate. The MCF-7 is resistant to the tested com-pounds, and the cytometry assay indicated low increase in cell numbers in the sub-G1 phase. The most sensitive are HCT-116 and HeLa cells. The thiadiazole derivatives have a pro-apoptotic effect on HCT-116 cells. In the case of the HeLa cells, an increase in the number of cells in the sub-G1-phase and the induction of apoptosis was observed.

Synthesis, docking, and biological evaluation of thiazolidinone derivatives against hepatitis C virus genotype 4a

Hepatitis C virus (HCV) genotype 4a (GT4a) is prevalent in Egypt. It did not gain the necessary scientific focus despite its high resistance. Since the crystal structure NS5B (RNA-dependent RNA polymerase) of HCV GT4a has not been resolved until now, homology modeling was conducted to build and validate the 3D model of the enzyme. Ligand binding sites including the allosteric thumb II pocket were detected and used in lead optimization. Sixty new 4-thiazolidinone derivatives have been virtually designed and docked into thumb II site of HCV NS5B GT4a using rigid docking approach. Eighteen compounds (7a–r) that show good docking scores were synthesized and tested in vitro against NS5B GT4a. Compounds 7b and 7n showed the best inhibitory activity (IC50 = 0.338 and 0.342 μM, respectively). Compounds 7a, 7b, 7c, 7d, 7k, 7n, 7q, and 7r that have IC50 values less than 2 μM were assessed for cellular anti-HCV GT4a activity using human hepatoma cell line (Huh 7.5). The percentages of viral growth inhibition are between 79.67 and 94.77%. Compound 7b is the most active in the in vitro and cellular assays and could be considered a potential new lead for future anti-HCV studies. [Figure not available: see fulltext.]

Synthesis and trypanocidal activity of novel pyridinyl-1,3,4-thiadiazole derivatives

Herein, we present the design, synthesis and trypanocidal evaluation of sixteen new 1,3,4-thiadiazole derivatives from N-aminobenzyl or N-arylhydrazone series. All derivatives were assayed against the trypomastigote form of Trypanosoma cruzi, showing IC50 values ranging from 3 to 226 μM, and a better trypanocidal profile was demonstrated for the 1,3,4-thiadiazole-N-arylhydrazones (3a-g). In this series, the 2-pyridinyl fragment bound to the imine subunit of the hydrazine moiety presented pharmacophoric behavior for trypanocidal activity. Compounds 2a, 11a and 3e presented remarkable activity and excellent selectivity indexes. Compound 2a was also active against the intracellular amastigote form of T. cruzi. Moreover, its corresponding hydrochloride, compound 11a, showed the most promising profile, producing phenotypic changes similar to those caused by posaconazole, a well-known inhibitor of sterol biosynthesis. Thus, 1,3,4-thiadiazole derivative 11a could be considered a good prototype for the development of new drug candidates for Chagas disease therapy.