2138-98-9

Basic information

• Product Name: 2-Amino-5-(2-chlorophenyl)-1,3,4-oxadiazole
• Synonyms: 5-(4-CHLOROPHENYL)-1,3,4-OXADIAZOL-2-AMINE;5-(4-CHLORO-PHENYL)-[1,3,4]OXADIAZOL-2-YLAMINE;2-AMINO-5-(4-CHLOROPHENYL)-1,3,4-OXADIAZOLE;2-AMINO-5-(2-CHLOROPHENYL)-1,3,4-OXADIA&;5-(2-Chorophenyl)-1,3,4-oxadiazole-2-amine;2-Amino-5-(4-chlorophenyl)-1,3-4-oxadiazole 97%;5-(2-Chlorophenyl)-1,3,4-oxadiazol-2-amine;2-Amino-5-(2-chlorophenyl)-1,3,4-oxadiazole
• CAS NO: 2138-98-9
• Molecular Formula: C₈H₆ClN₃O
• Molecular Weight: 195.61
• Product Categories: Amines;Oxadiazoles & Thiadiazoles;Oxadiazoles & Thiadiazoles
• Mol File: 2138-98-9.mol
• Article Data: 15

Chemical Properties

• Melting Point: 165-169 ºC
• Boiling Point: 358.3 °C at 760 mmHg
• Flash Point: 170.5 °C
• Appearance: /
• Density: 1.415 g/cm³
• Vapor Pressure: 0.000657mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: 2-Amino-5-(2-chlorophenyl)-1,3,4-oxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-(2-chlorophenyl)-1,3,4-oxadiazole(2138-98-9)
• EPA Substance Registry System: 2-Amino-5-(2-chlorophenyl)-1,3,4-oxadiazole(2138-98-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• RIDADR: 2811
• WGK Germany: 3
• Hazardous Substances Data: 2138-98-9(Hazardous Substances Data)

Usage

Description

2-Amino-5-(2-chlorophenyl)-1,3,4-oxadiazole is an organic compound characterized by its oxadiazole ring fused with a chlorophenyl group. It is known for its potential applications in various fields due to its unique chemical structure and properties.

Uses

Used in Pharmaceutical Industry:
2-Amino-5-(2-chlorophenyl)-1,3,4-oxadiazole is used as a reactant in the synthesis of various quinazolinone derivatives, which have been studied for their antimicrobial activity against a range of bacteria and fungi. This application is significant in the development of new drugs to combat antibiotic-resistant infections.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Amino-5-(2-chlorophenyl)-1,3,4-oxadiazole serves as a key intermediate for the production of various compounds with potential applications in different industries, such as pharmaceuticals, agrochemicals, and materials science. Its unique structure allows for further functionalization and modification to create new molecules with desired properties.

InChI:InChI=1/C9H7ClN2O/c1-6-11-12-9(13-6)7-4-2-3-5-8(7)10/h2-5H,1H3

Upstream product

• 5315-85-5 2-[(2-chlorophenyl)methylene]hydrazinecarboxamide 
• 830-86-4 4-(o-chloro)benzoylthiosemicarbazide 
• 89-98-5 2-chloro-benzaldehyde 
• 4426-72-6 hydrazine carboxamide 
• 118-91-2 ortho-chlorobenzoic acid 
• 5315-85-5 C₈H₈ClN₃O 
• 5814-05-1 2-chlorobenzoylhydrazide 
• 563-41-7 semicarbazide hydrochloride 

Downstream Products

• 14768-88-8 N-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-acetamide 
• 6694-43-5 1-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-3-phenyl-urea 
• 14632-11-2 N-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-propionamide 
• 59940-08-8 2-chloro-N-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-acetamide 
• 34257-04-0 5-(2-chloro-phenyl)-3-(3-chloro-propionyl)-3H-[1,3,4]oxadiazol-2-ylideneamine 
• 37423-09-9 N'-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-N,N-dimethyl-formamidine 
• 51324-05-1 2-<2-Chlor-phenyl>-5-oxo-7-aethoxycarbonyl-1,3,4-oxadiazolo<3,2-a>pyrimidin 
• 67454-90-4 [5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-ylamino]-methanol 
• 25433-40-3 1-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-biguanide 
• 13751-23-0 1-(2-Chlor-benzoyl)-5-carbamoyl-diaminoguanidin 
• 13751-31-0 1-(2-Chlor-benzoyl)-5-thiocarbamoyl-diaminoguanidin 
• 28037-28-7 {[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-ylamino]-methylene}-malonic acid diethyl ester 
• 89757-61-9 3-Chloro-N-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-propionamide 
• 90147-10-7 4-Chloro-N-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-butyramide 

Relevant articles and documents

Synthesis, antibacterial activities and molecular docking study of thiouracil derivatives containing oxadiazole moiety

A series of novel thiouracil derivatives 9 containing an oxadiazole moiety have been synthesized by structural modification of a lead SecA inhibitor, 2. These compounds have been evaluated for their antibacterial activities against Bacillus amyloliquefaciens, Staphylococcus aureus and Bacillus subtilis. Among them, compounds 9g and 9n exhibited promising antibacterial activities against the tested strains. Compound 9g was also tested for its inhibitory activities against SecA ATPase, and the IC50 value of compound 9g was 19.9 μg/mL, lower than that of compound 2 (20.8 μg/mL). Molecular docking work indicates that compound 9g likely occupies the pocket formed by SecA IRA2 and NBD domain.

Ultrapotent Inhibitor of Clostridioides difficile Growth, Which Suppresses Recurrence in Vivo

Clostridioides difficile is the leading cause of healthcare-associated infection in the U.S. and considered an urgent threat by the Centers for Disease Control and Prevention (CDC). Only two antibiotics, vancomycin and fidaxomicin, are FDA-approved for the treatment of C. difficile infection (CDI), but these therapies still suffer from high treatment failure and recurrence. Therefore, new chemical entities to treat CDI are needed. Trifluoromethylthio-containing N-(1,3,4-oxadiazol-2-yl)benzamides displayed very potent activities [sub-μg/mL minimum inhibitory concentration (MIC) values] against Gram-positive bacteria. Here, we report remarkable antibacterial activity enhancement via halogen substitutions, which afforded new anti-C. difficile agents with ultrapotent activities [MICs as low as 0.003 μg/mL (0.007 μM)] that surpassed the activity of vancomycin against C. difficile clinical isolates. The most promising compound in the series, HSGN-218, is nontoxic to mammalian colon cells and is gut-restrictive. In addition, HSGN-218 protected mice from CDI recurrence. Not only does this work provide a potential clinical lead for the development of C. difficile therapeutics but also highlights dramatic drug potency enhancement via halogen substitution.

Ultrasound-assisted synthesis of 2-amino-1,3,4-oxadiazoles through NBS-mediated oxidative cyclization of semicarbazones

A ultrasound-assisted oxidative cyclization of semicarbazones using N-bromosuccinimide in the presence of sodium acetate was established providing efficient and rapid access to a variety of 2-amino-1,3,4-oxadiazoles. Moreover, the new synthetic protocol provides a simple procedure utilizing a safer oxidizing system that affords the target products in high regioselectivity, satisfactory yields, and elevated purities.