13178-12-6

Basic information

• Product Name: 2-AMINO-5-(4-BROMOPHENYL)-1,3,4-THIADIAZOLE
• Synonyms: 5-(4-BROMOPHENYL)-1,3,4-THIADIAZOL-2-AMINE;5-(4-BROMO-PHENYL)-[1,3,4]THIADIAZOL-2-YLAMINE;2-AMINO-5-(4-BROMOPHENYL)-1,3,4-THIADIAZOLE;IFLAB-BB F1386-0084;CHEMBRDG-BB 5310035;VITAS-BB TBB000028;2-AMINO-5-(4-BROMOPHENYL)-1,3,4-THIADIA&;2-Amino-5-(4-bromophenyl)-1,3,4-thiadiazole 97%
• CAS NO: 13178-12-6
• Molecular Formula: C₈H₆BrN₃S
• Molecular Weight: 256.12
• Product Categories: Amines;Oxadiazoles & Thiadiazoles;Oxadiazoles & Thiadiazoles;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiadiazoles;ThiadiazolesHeterocyclic Building Blocks;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 13178-12-6.mol
• Article Data: 37

Chemical Properties

• Melting Point: 228-232 °C(lit.)
• Boiling Point: 401.1 °C at 760 mmHg
• Flash Point: 196.4 °C
• Appearance: /
• Density: 1.717g/cm³
• Vapor Pressure: 1.21E-06mmHg at 25°C
• Refractive Index: 1.695
• CAS DataBase Reference: 2-AMINO-5-(4-BROMOPHENYL)-1,3,4-THIADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-(4-BROMOPHENYL)-1,3,4-THIADIAZOLE(13178-12-6)
• EPA Substance Registry System: 2-AMINO-5-(4-BROMOPHENYL)-1,3,4-THIADIAZOLE(13178-12-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 13178-12-6(Hazardous Substances Data)

Usage

General Description

2-AMINO-5-(4-BROMOPHENYL)-1,3,4-THIADIAZOLE is a chemical compound with the molecular formula C8H6BrN3S. It is classified as a thiadiazole, a type of organic compound containing a five-membered ring with sulfur, nitrogen, and two carbon atoms. 2-AMINO-5-(4-BROMOPHENYL)-1,3,4-THIADIAZOLE contains an amino group and a bromine-substituted phenyl group, which gives it unique chemical properties. It is used in various industrial and research applications, including as a building block for the synthesis of pharmaceuticals and other organic compounds. Additionally, it may have potential biological and pharmacological activities, making it a subject of interest for further research and development.

InChI:InChI=1/C8H6BrN3S/c9-6-3-1-5(2-4-6)7-11-12-8(10)13-7/h1-4H,(H2,10,12)

Upstream product

• 623-00-7 4-bromobenzenecarbonitrile 
• 79-19-6 thiosemicarbazide 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 39631-30-6 2-(4-bromobenzoyl)hydrazinecarbothioamide 
• 586-75-4 4-chlorobenzoyl chloride 
• 586-76-5 4-Bromobenzoic acid 
• 333-20-0 potassium thioacyanate 
• 1122-91-4 4-bromo-benzaldehyde 
• 36449-43-1 2-(4-bromobenzylidene)hydrazine carbothioamide 
• 94794-27-1 (2E)-2-[(4-bromophenyl)methylidene]hydrazine-1-carbothioamide 

Downstream Products

• 128627-72-5 3-[5-(4-Bromo-phenyl)-[1,3,4]thiadiazol-2-ylamino]-butyric acid 
• 128627-70-3 3-[5-(4-Bromo-phenyl)-[1,3,4]thiadiazol-2-ylamino]-2-methyl-propionic acid 
• 91660-18-3 2-Chloro-5-(4-bromophenyl)-1,3,4-thiadiazole 
• 1060691-87-3 C₂₀H₁₇BrN₄O₃S 
• 1060691-74-8 C₂₀H₁₇BrN₄O₂S 
• 1073557-80-8 (2R)-N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]-2-[(benzoyl)-amino]propanamide 
• 1073557-86-4 (2R)-N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]-2-[(phenylacetyl)amino]propanamide 
• 1072008-41-3 (2R)-N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]-2-[(phenylsulfonyl)amino]propanamide 
• 1360538-27-7 (E)-N-(5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl)-3-(p-tolyl)acrylamide 
• 1360538-25-5 (E)-N-(5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl)-3-(4-fluorophenyl)acrylamide 
• 1360538-26-6 (E)-N-(5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl)-3-(4-(trifluoromethyl)phenyl)acrylamide 
• 128627-63-4 N-<5-(4-Bromophenyl-1,3,4-thiadiazol-2-yl)>-3-phenylprop-2-en-1-one 
• 1360538-28-8 (E)-N-(5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl)-3-(4-methoxyphenyl)acrylamide 
• 1384974-74-6 C₁₆H₁₀BrN₃S 

Relevant articles and documents

The balance between hydrogen bonds, halogen bonds, and chalcogen bonds in the crystal structures of a series of 1,3,4-chalcogenadiazoles

In order to explore how specific atom-to-atom replacements change the electrostatic potentials on 1,3,4-chalcogenadiazole derivatives, and to deliberately alter the balance between inter-molecular interactions, four target molecules were synthesized and characterized. DFT calculations indicated that the atom-to-atom substitution of Br with I, and S with Se enhanced the σ-hole potentials, thus increasing the structure directing ability of halogen bonds and chalcogen bonds as compared to intermolecular hydrogen bonding. The delicate balance between these intermolecular forces was further underlined by the formation of two polymorphs of 5-(4-iodophenyl)-1,3,4-thiadiazol-2-amine; Form I displayed all three interactions while Form II only showed hydrogen and chalcogen bonding. The results emphasize that the deliberate alterations of the electrostatic potential on polarizable atoms can cause specific and deliberate changes to the main synthons and subsequent assemblies in the structures of this family of compounds.

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.

Aryl or heteroaryl substituted thiadiazole compound and antibacterial application thereof

The invention belongs to the technical field of medicines, and particularly relates to an aryl or heteroaryl substituted thiadiazole compound, a preparation method and application thereof as an antibacterial drug. The compound is represented by formula (1