13229-03-3

Basic information

• Product Name: 2-hydrazinyl-5-phenyl-1,3,4-thiadiazole
• CAS NO: 13229-03-3
• Molecular Formula: C₈H₈N₄S
• Molecular Weight: 192.2409
• Mol File: 13229-03-3.mol

Chemical Properties

• Boiling Point: 375.7°C at 760 mmHg
• Flash Point: 181°C
• Density: 1.4g/cm³
• Vapor Pressure: 7.64E-06mmHg at 25°C
• Refractive Index: 1.714
• CAS DataBase Reference: 2-hydrazinyl-5-phenyl-1,3,4-thiadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydrazinyl-5-phenyl-1,3,4-thiadiazole(13229-03-3)
• EPA Substance Registry System: 2-hydrazinyl-5-phenyl-1,3,4-thiadiazole(13229-03-3)

Safety Data

• Hazardous Substances Data: 13229-03-3(Hazardous Substances Data)

Upstream product

• 49579-94-4 nitroso-(5-phenyl-[1,3,4]thiadiazol-2-yl)-amine 
• 86738-35-4 2-(methylsulfonyl)-5-phenyl-1,3,4-thiadiazole 
• 13373-11-0 2-chloro-5-phenyl-[1,3,4]thiadiazole 
• 5585-19-3 5-phenyl-1,3,4-thiadiazole-2-thiol 
• 93-58-3 benzoic acid methyl ester 
• 613-94-5 benzoic acid hydrazide 
• 65-85-0 benzoic acid 
• 6956-33-8 dibenzylidenethiocarbohydrazide 
• 100-52-7 benzaldehyde 
• 1627-73-2 1-benzylidene thiosemicarbazide 
• 2002-03-1 2-amino-5-phenyl-1,3,4-thiadiazole 
• 53645-95-7 2-bromo-5-phenyl-1,3,4-thiadiazole 
• 49580-00-9 2-benzylidene-1-(5-phenyl-1,3,4-thiadiazol-2-yl)hydrazine 

Downstream Products

• 100882-31-3 3-(5-phenyl-[1,3,4]thiadiazol-2-ylhydrazono)-butyric acid ethyl ester 
• 106477-33-2 4-nitro-benzaldehyde-(5-phenyl-[1,3,4]thiadiazol-2-ylhydrazone) 
• 108483-89-2 N'-(phenyl-[1,3,4]thiadiazol-2-yl)-acetohydrazonic acid ethyl ester 
• 43029-38-5 6-phenyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 59758-43-9 2-[(5-phenyl-[1,3,4]thiadiazol-2-yl)-hydrazono]-propionic acid 
• 13228-96-1 6-phenyl-2H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-3-thione 
• 13228-95-0 6-phenyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-ylamine 
• 59758-64-4 5-phenyl-2-(5-phenyl-[1,3,4]thiadiazol-2-yl)-2H-pyrazol-3-ylamine 
• 13229-05-5 benzoic acid N'-(5-phenyl-[1,3,4]thiadiazol-2-yl)-hydrazide 
• 59758-50-8 phenyl-[(5-phenyl-[1,3,4]thiadiazol-2-yl)-hydrazono]-acetic acid 
• 91096-53-6 potassium-5-phenyl-1,3,4-thiadiazol-2-yl dithiocarbazate 
• 91096-42-3 N'-(5-Phenyl-[1,3,4]thiadiazol-2-yl)-hydrazinecarboxylic acid ethyl ester 
• 91096-46-7 C₁₄H₁₆N₄O₄S 
• 108005-08-9 3-p-toluidino-6-phenyl-s-triazolo<3,4-b><1,3,4>thiadiazole 

Relevant articles and documents

Synthesis and antitrypanosomal profile of new functionalized 1,3,4-thiadiazole-2-arylhydrazone derivatives, designed as non-mutagenic megazol analogues

The synthesis of the new powerful trypanocidal agent brazilizone A (4k) (IC50/24 h = 5.3 μM) is reported. In this work we reported the synthesis and the trypanocidal profile of new 1,3,4-thiadiazole-2-arylhydrazone derivatives of nitroimidazole

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.

Design, Synthesis, and Biological Evaluation of Novel 1,3,4-Thiadiazolylpyrazolines Compounds Containing Ferrocene

The synthesis of 1,3,4-thiadiazole skeleton compounds exhibiting high fungicidal activities has been demonstrated. Thirteen novel 1,3,4-thiadiazolyl-pyrazolines compounds containing ferrocene were designed and synthesized from the ferrocenylchalcones intermediates 3a–3m and the 2-hydrazino-5-phenyl-1,3,4-thiadiazole intermediate 8. All compounds were characterized by 1H NMR, 13C NMR, FT-IR spectra, and HR-MS, and the structure of one of the new compounds N-(4-phenyl-1,3,4-thiadiazol-2-yl)-3-ferrocenyl-5-phenyl-pyrazoline 9a was further determined by X-ray diffraction analysis. The preliminary results of a biological activity assay indicated that all the title compounds exhibited significant fungicidal activities against Pythium solani, Gibberella saubinetii, and Gibberella nicotiancola. Furthermore, compounds 9e and 9h displayed even higher fungicidal activities against the three fungal species compared with the control drug pyraclostrobin.

Synthesis and spectral characterization of Zn(II) microsphere series for antimicrobial application

Microsphere series have been synthesized by reacting zinc(II) acetate dihydrate with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole/oxadiazole/triazole with salicylaldehyde. Elemental analysis suggests that the complexes have 1:2 and 1:1 stoichiometry of the type [Zn(L)2(H2O)2] and [Zn(L′)(H 2O)2]; LH = Schiff bases derived from 2-hydrazino-5- [substituted phenyl]-1,3,4-thia/oxadiazole with salicylaldehyde; L′H 2 = Schiff bases derived from 3-(substituted phenyl)-4-amino-5- hydrazino-1,2,4-triazole and salicylaldehyde and were characterized by elemental analyses, IR, 1H NMR and 13C NMR spectral data. Scanning electron microscopy (SEM) showed that synthesized materials have microsphere like structure and there EDX analysis comparably matches with elemental analysis. For the antimicrobial application Schiff bases and their zinc(II) complexes were screened for four bacteria e.g. Bacillus subtilis, Pseudomonas aeruginosa, Salmonella typhi, Streptococcus pyogenes and four fungi e.g. Cyrtomium falcatum, Aspergillus niger, Fusarium oxysporium and Curvularia pallescence by the reported method. Schiff base and Zn(II) compounds showed significant antimicrobial activities. However, activities increase upon chelation. Thermal analysis (TGA) data of compound (10) showed its stability up to 300 °C.

Synthesis, spectral and antimicrobial activity of Zn(II) complexes with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and benzaldehyde/2-hydroxyacetophenone/indoline-2,3-dione

(Chemical Equation Presented) Zn(II) complexes have been synthesized by reacting zinc acetate with Schiff bases derived from 2-hydrazino- 5-[substituted phenyl]-1,3,4-thiadiazole and 2-hydroxyacetophenone/benzaldehyde/indoline-2, 3-dione. All these comple

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Unsaturated Compounds containing Nitrogen. Part 4. Further Reactions of 1-Chloro-2,3-diazabutadienes with S-Nucleophiles

1-Chloro-1,4-diaryl-2,3-diazabutadienes (Ar1CCl=NN=CHAr2), prepared by the reaction of thionyl chloride with aroylhydrazones (Ar1CONHN=CHAr2), react with thiosemicarbazide or thiocarbohydrazide to give 2-arylidenehydrazino-5-aryl-1,3,4-thiadiazoles, and with potassium thiocyanate to give 1-thiocyanato-1,4-diaryl-2,3-diazabutadienes which isomerize thermally to arylideneamino-5-aryl-1,3,4-thiadiazoles. 1-Chloro-1,4-diphenyl-2,3-diazabutadiene reacts with potassium ethylxanthate to give a 1-ethylxanthyl-2,3-diazabutadiene which on pyrolysis yields 2,5-diphenyl-1,3,4-thiadiazole.