2002-03-1

Basic information

• Product Name: 2-AMINO-5-PHENYL-1 3 4-THIADIAZOLE 96
• Synonyms: 5-Phenyl-1,3,4-thiadiazole-2-amine;5-Phenyl-2-amino-1,3,4-thiadiazole;NSC 677;2-AMino-5-phenyl-1,3,4-thiadiazole 96%;2-Amino-5-phenyl-1,3,4-thiazole;2-AMINO-5-PHENYL-1 3 4-THIADIAZOLE 96;1,3,4-thiadiazol-2-amine, 5-phenyl-
• CAS NO: 2002-03-1
• Molecular Formula: C₈H₇N₃S
• Molecular Weight: 177.23
• Product Categories: Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Building Blocks;Heterocyclic Building Blocks;Thiadiazoles
• Mol File: 2002-03-1.mol

Chemical Properties

• Melting Point: 223-227 °C(lit.)
• Boiling Point: 569.8°C at 760 mmHg
• Flash Point: 298.4°C
• Appearance: /
• Density: 1.333±0.06 g/cm3(Predicted)
• Vapor Pressure: 8.05E-14mmHg at 25°C
• Solubility: soluble in Dimethylformamide
• PKA: 2.90±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-5-PHENYL-1 3 4-THIADIAZOLE 96(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-PHENYL-1 3 4-THIADIAZOLE 96(2002-03-1)
• EPA Substance Registry System: 2-AMINO-5-PHENYL-1 3 4-THIADIAZOLE 96(2002-03-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2002-03-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Amino-5-phenyl-1,3,4-thiadiazole is used as a key intermediate in the synthesis of various 1,3,4-thiadiazole derivatives. These derivatives have potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.
Used in Corrosion Inhibition:
2-Amino-5-phenyl-1,3,4-thiadiazole is used as a corrosion inhibitor for mild steel in acidic environments. Its corrosion inhibition properties have been examined using potentiodynamic polarization and electrochemical impedance spectroscopy (EIS), demonstrating its effectiveness in protecting mild steel from corrosion in 0.5M H2SO4 and 1.0M HCl.
Used in Schiff Base Synthesis:
2-Amino-5-phenyl-1,3,4-thiadiazole can be condensed with various aldehydes, such as benzaldehyde (SPT), 4-nitrobenzaldehyde (SNT), 4-methoxybenzaldehyde (SMT), and 2-hydroxybenzaldehyde (SSTH), as well as 2-hydroxyacetophenone, to form Schiff's bases. These Schiff's bases have potential applications in various fields, including as ligands in coordination chemistry, catalysts, and sensors.

InChI:InChI=1/C8H7N3S.H2O4S/c9-8-11-10-7(12-8)6-4-2-1-3-5-6;1-5(2,3)4/h1-5H,(H2,9,11);(H2,1,2,3,4)

Upstream product

• 1627-73-2 1-benzylidene thiosemicarbazide 
• 5351-66-6 benzoyl thiosemicarbazide 
• 91135-71-6 5-benzoyl-pyrimidine-2,4,6-trione 
• 79-19-6 thiosemicarbazide 
• 117891-38-0 1-thiobenzoyl-thiosemicarbazide 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 5442-13-7 thiobenzimidic acid ethyl ester; hydrochloride 
• 100-47-0 benzonitrile 
• 75-08-1 ethanethiol 
• 75-36-5 acetyl chloride 
• 109142-08-7 1-thiobenzoyl semicarbazide 
• 4291-14-9 phenyl-1,3,4-thiadiazole 
• 19430-40-1 cyclopentanecarboxylic acid 5-phenyl-[1,3,4]thiadiazol-2-ylamide 
• 70027-43-9 ethyl (5-phenyl-[1,3,4]thiadiazol-2-yl)carbamate 

Downstream Products

• 110438-44-3 3-ethyl-5-phenyl-1,3,4-thiadiazole-2(3H)-imine 
• 70027-43-9 ethyl (5-phenyl-[1,3,4]thiadiazol-2-yl)carbamate 
• 6583-41-1 benzylidene-(5-phenyl-[1,3,4]thiadiazol-2-yl)-amine 
• 19948-90-4 N-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide 
• 28898-88-6 N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 20460-58-6 2-chloro-N-[5-phenyl-[1,3,4]-thiadiazol-2-yl]-acetamide 
• 41148-24-7 nitro-(phenyl-[1,3,4]thiadiazol-2-yl)-amine 
• 16430-70-9 2-(5-phenyl-[1,3,4]thiadiazol-2-ylamino)-ethanol 
• 66181-13-3 4-(5-phenyl-[1,3,4]thiadiazol-2-yl)-3-thio-allophanic acid methyl ester 
• 66181-15-5 (5-phenyl-[1,3,4]thiadiazol-2-yl)-carbamic acid methyl ester 
• 72192-63-3 N-(5-phenyl-[1,3,4]thiadiazol-2-yl)-2-p-tolyloxy-acetamide 
• 72192-61-1 2-(2-chloro-phenoxy)-N-(5-phenyl-[1,3,4]thiadiazol-2-yl)-acetamide 
• 72192-62-2 2-(2-nitro-phenoxy)-N-(5-phenyl-[1,3,4]thiadiazol-2-yl)-acetamide 
• 6578-86-5 2-(4-fluorobenzalamino)-5-phenyl-1,3,4-thiadiazole 

Relevant articles and documents

Crystalline and molecular structure of 2-amino-5-phenyl-1,3,4-thiadiazole

The crystalline and molecular structure of 2-amino-5-phenyl-1,3,4-thiadiazole was studied by the X-ray diffraction method. C8H7N3S. Monoclinic crystals: a = 11.085 (3), b = 7.544 (3), c = 11. 180 (3) A; β = 115.22 (2)°; V

One pot synthesis and characterization of some novel Schiff bases with 1,3,4-thiadiazole unit

A series of novel benzimidazole substituted Schiff bases were synthesized by the reaction of aromatic aldehydes with the corresponding ethyl acetoacetate or methyl acetoacetate and 1,3,4-thiadiazole. These compounds have been characterized by 1

An efficient synthesis of novel spiro[indole-3,8′-pyrano[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidine derivatives via organobase-catalyzed three-component reaction of malononitrile, isatin and heterocyclic-1,3-diones

In this research, firstly, some derivatives of sulfur containing [1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one have been synthesized and then they were used for the synthesis of novel derivatives of 6′-amino-2,9′-dioxo-2′-phenyl-9′H-spiro[indoline-3,8′-pyrano[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidine]-7′-carbonitriles via a one-pot three-component condensation reaction of 7-hydroxy-2-phenyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one derivatives, malononitrile and isatin compounds in the presence of DABCO as a organocatalyst and under solvent-free conditions. In this report, a new family of spiro-pyrano-thiadiazolo-pyrimidine derivatives have been synthesized in short reaction times (10–60 min) and good to excellent yields (80–96%). The structures of all synthesized products have been confirmed by IR, 1H NMR, 13C NMR and mass spectrometry, and the structure of one selected product was characterized by single-crystal X-ray diffraction studies as well.

Design, synthesis and pharmacological evaluation of carboxamide and carbothioamide derivatives of 1,3,4-thiadiazole as the inhibitors of acetylcholinesterase and oxipiperazine)ative stress for the management of cognitive debility

Acetylcholinesterase has been a promising target for the development of putative therapeutics against cognitive decline. The deleterious effect of oxidative stress on the learning and memory paradigms of an individual has also been well documented. In vie

Non-typical fluorescence effects and biological activity in selected 1,3,4-thiadiazole derivatives: Spectroscopic and theoretical studies on substituent, molecular aggregation, and pH effects

The below article presents the results of spectroscopic research, theoretical (timedependent density functional theory (TD-DFT)), microbiological, and antioxidative calculations for three compounds from the group of 1,3,4-thiadiazoles: 2-amino-5-phenyl-1,

Synthesis, Characterization and Biological Evaluation of Some Novel Azo-Imine Compounds

The oxidative cyclization of thiosemicarbazone (III) synthesized from reaction between substituted aryl aldehydes (I) with thiosemicarbazide (II) was done using ferric chloride as oxidative agent to get 2-amino-5-phenyl-1,3,4-thiadiazole (IV). 2-Amino-5-phenyl-1,3,4-thiadiazole was introduced in condensation reactions with substituted aldehydes to obtain benzylidene imine derivatives (VI)1-5. Further these were treated with sulphanilic acid to give new 2-{[5-phenyl-1,3,4-thiadiazole-2-imino] substituted benzene}diazenyl benzene sulfonic acid derivatives (VII)1-5. These derivatives were further characterized by FT-IR, 1H NMR and 13C NMR spectral studies and were screened for antibacterial, antifungal and antioxidant activities.

A novel approach to the synthesis of 1,3,4-thiadiazole-2-amine derivatives

The main purpose of the study was the development of a new method for synthesis of 1,3,4-thiadiazol-2-amine derivatives in a one-pot manner using the reaction between a thiosemicarbazide and carboxylic acid without toxic additives such as POCl3 or SOCl2. The reaction was investigated in the presence of polyphosphate ester (PPE). It was found that, in the presence of PPE, the reaction between the thiosemicarbazide and carboxylic acid proceeds in one-pot through three steps with the formation of corresponding 2-amino-1,3,4-thiadiazole. Using the developed approach five, 2-amino-1,3,4-thiadiazoles were synthesized. The structures of all compounds were proven by mass spectrometry, IR, and NMR spectroscopies.

COMPOUNDS HAVING PDE9A INHIBITORY ACTIVITY, AND PHARMACEUTICAL USES THEREOF

The present invention provides a compound having a specific chemical structure and having PDE9A inhibitory activity, or a pharmaceutically acceptable salt thereof. The present invention provides a composition containing the compound or a pharmaceutically acceptable salt thereof. The present invention provides a pharmaceutical use, for treating or preventing PDE9A-related diseases, of the compound according to the present invention, a salt thereof, and a composition containing the compound or salt. The present invention also provides a method for treating or preventing PDE9A-related diseases, the method comprising administering an effective amount of the compound according to the present invention, a salt thereof, or a composition containing the compound or salt to a subject in need of treatment.

Gramine-based structure optimization to enhance anti-gastric cancer activity

Gramine is a natural indole alkaloid with a wide range of biological activities, but its anti-gastric cancer activity is poor. Herein, a pharmacophore fusion strategy was adopted to design and synthesize a new series of indole-azole hybrids on the structural basis of gramine. Based on our previous studies, different nitrogen-containing five-membered heterocyclic rings and terminal alkyne group were introduced into the indole-based scaffold to investigate their effect on improving the anti-gastric cancer activity of gramine derivatives. Structure-activity relationship (SAR) studies highlighted the role played by terminal alkyne in enhancing the inhibitory effect, and compound 16h displayed the best antiproliferative activity against gastric cancer MGC803 cells with IC50 value of 3.74 μM. Further investigations displayed compound 16h could induce mitochondria-mediated apoptosis, and caused cell cycle arrest at G2/M phase. Besides, compound 16h could inhibit the metastasis ability of MGC803 cells. Our studies may provide a new strategy for structural optimization of gramine to enhance anti-gastric cancer activity, and provide a potential candidate for the treatment of gastric cancer.

Synthesis and Biological Evaluation of Oxadiazole Clubbed Thiadiazole Derivatives as Antimicrobial Agents

A series of 1,3,4-oxadiazole clubbed 1,3,4-thiadiazole derivatives were synthesized and assessed in vitro for their activity as antimicrobial agents. The target compounds 2-(5-(substituted aryl)-1, 3, 4-oxadiazol-2-ylthio)-N-(5-(substituted aryl)-1, 3, 4-thiadiazol-2-yl) acetamides (5a-5s) were synthesized using a basic condensation reaction between 5-(substituted aryl)-1,3,4-oxadiazole-2-thiol and 2-chloro-N-(5-(substituted aryl)-1,3,4-thiadiazol-2-yl)acetamide in presence of K2CO3 as a scavenging agent and acetone as reaction solvent. The titled compounds synthesized here, exhibited excellent to moderate antimicrobial activity against a broad panel of antibacterial strains of Gram-positive and Gram-negative bacteria and fungi.