7659-06-5

Basic information

• Product Name: 5-FURAN-2-YL-1,3,4-OXADIAZOL-2-YLAMINE
• Synonyms: 5-(2-Furanyl)-1,3,4-oxadiazole-2-amine;5-(furan-2-yl)-1,3,4-oxadiazol-2-amine;5-(Furan-2-yl);4-oxadiazole,2-amino-5-(2-furyl)-3;2-AMINO-5-(2-FURYL)-1,3,4-OXADIAZOLE;5-(2-FURYL)-1,3,4-OXADIAZOL-2-AMINE;5-FURAN-2-YL-1,3,4-OXADIAZOL-2-YLAMINE
• CAS NO: 7659-06-5
• Molecular Formula: C₆H₅N₃O₂
• Molecular Weight: 151.12
• Product Categories: Oxadiazoles & Thiadiazoles;Amines
• Mol File: 7659-06-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 225-226 °C
• Boiling Point: 318.5°Cat760mmHg
• Flash Point: 146.4°C
• Appearance: /
• Density: 1.385g/cm³
• Vapor Pressure: 0.00036mmHg at 25°C
• Refractive Index: 1.571
• PKA: -1.53±0.13(Predicted)
• CAS DataBase Reference: 5-FURAN-2-YL-1,3,4-OXADIAZOL-2-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-FURAN-2-YL-1,3,4-OXADIAZOL-2-YLAMINE(7659-06-5)
• EPA Substance Registry System: 5-FURAN-2-YL-1,3,4-OXADIAZOL-2-YLAMINE(7659-06-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• Hazardous Substances Data: 7659-06-5(Hazardous Substances Data)

Usage

Uses

5-Furan-2-yl-1,3,4-oxadiazol-2-ylamine, can be used in the synthesis of various chemical compounds having therapeutic activity, such as N-[5-(2-Furanyl)-1,3,4-oxadiazol-2-yl]-2-phenyl-4-quinolinecarboxamide (F863670), a small molecular inhibitor of STAT3, a cancer therapeutic agent against Glioblastoma multiforme tumor cells, and a drug target.

InChI:InChI=1/C6H5N3O2/c7-6-9-8-5(11-6)4-2-1-3-10-4/h1-3H,(H2,7,9)

Upstream product

• 3326-71-4 2-furoic acid hydrazide 
• 506-68-3 bromocyane 
• 35771-64-3 1-(2-furoyl)-3-thiosemicarbazide 
• 88-14-2 2-furanoic acid 
• 4426-72-6 hydrazine carboxamide 
• 527-69-5 2-furancarbonyl chloride 
• 98-01-1 furfural 
• 563-41-7 semicarbazide hydrochloride 

Downstream Products

• 27049-79-2 1-(4-chloro-phenyl)-3-(5-furan-2-yl-[1,3,4]oxadiazol-2-yl)-urea 
• 27049-80-5 1-(3,4-dichloro-phenyl)-3-(5-furan-2-yl-[1,3,4]oxadiazol-2-yl)-urea 
• 851095-32-4 STX-0119 
• 1204212-18-9 6-cyano-N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-2-phenyl-4-quinolinecarboxamide 
• 1204211-67-5 2-(4-fluorophenyl)-N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-4-quinolinecarboxamide 
• 1313756-45-4 N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-4-iodobenzenecarboxamide 
• 1313756-19-2 5-(2-fluorophenyl)-N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-2-furancarboxamide 
• 1430330-66-7 5-chloro-N-(5-furan-2-yl-[1,3,4]oxadiazol-2-yl)-2-hydroxybenzamide 
• 1204211-92-6 N-[5-(2-furanyl)-1,3,4-oxadiazol-2-yl]-6-iodo-2-phenylquinoline-4-carboxamide 
• 1204211-93-7 N-(5-(furan-2-yl)-1,3,4-oxadiazol-2-yl)-6-methyl-2-phenylquinoline-4-carboxamide 

Relevant articles and documents

Synthesis of a Series of Novel 2-Amino-5-substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole Derivatives as Potential Anticancer, Antifungal and Anti-bacterial Agents

Objective: The objective of the present study was to prepare the 5-substituted 2-amino-1,3,4-oxadiazole and 2-amino-1,3,4-thiadiazole derivatives and evaluate their potential anticancer, antibac-terial and antifungal activities. Methods: Twenty-seven derivatives were synthesized by iodine-mediated cyclization of semicarba-zones or thiosemicarbazones obtained from condensation of semicarbazide or thiosemicarbazide and aldehydes. The structures were confirmed by1H-NMR,13C-NMR and MS spectra. The antibacterial and antifungal activities were evaluated by diffusion method and the anticancer activities were evaluated by MTT assay. Results: Twenty-seven derivatives have been synthesized in moderate to good yields. A number of derivatives exhibited potential antibacterial, antifungal and anticancer activities. Conclusion: Compounds (1b, 1e and 1g) showed antibacterial activity against Streptococcus faecal-is, MSSA and MRSA with MIC value ranging between 4 to 64 μg/mL. Compound (2g) showed anti-fungal activity against Candida albicans (8 μg/mL) and Aspergillus niger (64 μg/mL). Compound (1o) exhibited high cytotoxic activity against HepG2 cell line (IC50 value 8.6 μM) which is compara-ble to the activity of paclitaxel, and is non-toxic on LLC-PK1 normal cell line. The structure activity relationship and molecular docking study of the synthesized compounds have also been reported.

Direct C-C Bond Cleavage of 1,3-Dicarbonyl Compounds as a Single-Carbon Synthon: Synthesis of 2-Aryl-4-quinolinecarboxylates

A novel [2 + 1 + 3] cyclization reaction for the synthesis of 2-aryl-4-quinolinecarboxylates from aryl methyl ketones, arylamines, and 1,3-dicarbonyl compounds has been established. This metal-free process achieved the C-C bond cleavage of 1,3-dicarbonyl compounds directly as a single-carbon synthon. The reaction is highly efficient and has good substrate compatibility while operating under mild conditions. This method has good practicability and successfully realized the synthesis of bioactive molecules.

Synthesis of 2-amino-1,3,4-oxadiazoles and 2-Amino-1,3,4-thiadiazoles via sequential condensation and I2-mediated oxidative C-O/C-S bond formation

2-Amino-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were synthesized via condensation of semicarbazide/thiosemicarbazide and the corresponding aldehydes followed by I2-mediated oxidative C-O/C-S bond formation. This transition-metal-free sequential synthesis process is compatible with aromatic, aliphatic, and cinnamic aldehydes, providing facile access to a variety of diazole derivatives bearing a 2-amino substituent in an efficient and scalable fashion.