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
• Article Data: 148

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

2-Amino-5-phenyl-1,3,4-thiadiazole may be used for the synthesis of 1,3,4-thiadiazole derivatives.

General Description

2-Amino-5-phenyl-1,3,4-thiadiazole on condensation with benzaldehyde (SPT), 4-nitrobenzaldehyde (SNT), 4-methoxybenzaldehyde (SMT), 2-hydroxybenzaldehyde (SSTH) or 2-hydroxyacetophenone affords Schiff′s bases. Its molecular geometry and vibrational frequencies have been evaluated using the Hartree-Fock and density functional method (B3LYP). 2-Amino-5-phenyl-1,3,4-thiadiazole has been reported to inhibit the corrosion of mild steel in 0.5M H2SO4 and 1.0M HCl. Corrosion inhibition has been examined using potentiodynamic polarization and electrochemical impedance spectroscopy (EIS).

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

• 5351-66-6 benzoyl thiosemicarbazide 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 79-19-6 thiosemicarbazide 
• 5442-13-7 thiobenzimidic acid ethyl ester; hydrochloride 
• 100-47-0 benzonitrile 
• 75-08-1 ethanethiol 
• 70027-43-9 ethyl (5-phenyl-[1,3,4]thiadiazol-2-yl)carbamate 
• 20605-40-7 thiobenzoylhydrazine 
• 1124-58-9 p-tolylcyanate 
• 98-88-4 benzoyl chloride 
• 96133-99-2 C₁₀H₁₃N₃OS 
• 109142-08-7 1-thiobenzoyl semicarbazide 
• 75-36-5 acetyl chloride 
• 91135-71-6 5-benzoyl-pyrimidine-2,4,6-trione 

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 
• 6578-86-5 2-(4-fluorobenzalamino)-5-phenyl-1,3,4-thiadiazole 
• 6583-42-2 (4-chloro-benzylidene)-(5-phenyl-[1,3,4]thiadiazol-2-yl)-amine 
• 6583-43-3 (2-chloro-benzylidene)-(5-phenyl-[1,3,4]thiadiazol-2-yl)-amine 
• 6578-87-6 4-[(5-phenyl-[1,3,4]thiadiazol-2-ylimino)-methyl]-phenol 
• 6578-88-7 2N-salicylidene-5-phenyl-1,3,4-thiadiazole 
• 69378-06-9 2,6-diphenyl-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5,7-dione 
• 69378-02-5 1,3-bis-(5-phenyl-[1,3,4]thiadiazol-2-yl)-urea 

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

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.

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,

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.

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.