10185-68-9

Basic information

• Product Name: 4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)ANILINE
• Synonyms: 4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)ANILINE;4-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline 97%;3-(4-Aminophenyl)-5-methyl-1,2,4-oxadiazole;4-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline97%;4-(5-Methyl-1,2,4-oxadiazol-3-yl)
• CAS NO: 10185-68-9
• Molecular Formula: C₉H₉N₃O
• Molecular Weight: 175.19
• Mol File: 10185-68-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 113 °C
• Boiling Point: 357.8°Cat760mmHg
• Flash Point: 170.2°C
• Appearance: /
• Density: 1.229g/cm³
• Vapor Pressure: 2.66E-05mmHg at 25°C
• Refractive Index: 1.594
• CAS DataBase Reference: 4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)ANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)ANILINE(10185-68-9)
• EPA Substance Registry System: 4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)ANILINE(10185-68-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 10185-68-9(Hazardous Substances Data)

Usage

General Description

4-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline is a chemical compound with the molecular formula C9H9N3O. It is a derivative of aniline, with a methyl group and an oxadiazole ring attached to the carbon atom in the para position of the aniline ring. 4-(5-METHYL-1,2,4-OXADIAZOL-3-YL)ANILINE is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals due to its potential for biological activity. It has also been studied for its potential use in organic electronic materials and as a fluorescent probe in biological imaging. Additionally, 4-(5-Methyl-1,2,4-oxadiazol-3-yl)aniline has been reported to exhibit antimicrobial and antiviral properties in certain studies.

InChI:InChI=1/C9H9N3O/c1-6-11-9(12-13-6)7-2-4-8(10)5-3-7/h2-5H,10H2,1H3

Upstream product

• 937-31-5 (4-Nitrophenyl)acetylene 
• 192332-48-2 (Z)-4-nitrobenzamidoxime 
• 619-72-7 4-nitrobenzonitrile 
• 555-16-8 4-nitrobenzaldehdye 
• 277319-62-7 4-amino-N'-hydroxybenzimidamide 
• 141-78-6 ethyl acetate 
• 25283-96-9 3-(4-methoxyphenyl)-5-methyl-1,2,4-oxadiazole 
• 918967-52-9 tert-butyl (4-(N’-hydroxycarbamimidoyl)phenyl)carbamate 
• 873-74-5 4-Aminobenzonitrile 
• 143090-18-0 tert-butyl N-(4-cyanophenyl)carbamate 
• 643744-95-0 [4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-carbamic acid tert-butyl ester 

Downstream Products

• 1160931-81-6 2-(5-((5-(4-chlorophenyl)furan-2-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)-N-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)acetamide 

Relevant articles and documents

The first one-pot ambient-temperature synthesis of 1,2,4-oxadiazoles from amidoximes and carboxylic acid esters

The first one-pot room-temperature protocol for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles via the condensation between amidoximes and carboxylic acid esters in superbase medium MOH/DMSO is reported. A broad spectrum of alkyl, aryl and hetaryl amidoximes and esters was examined. This reaction route provides convenient access to 1,2,4-oxadiazoles, which is highly desirable because in the light of this privileged scaffold is recognized as an important core in the design of novel therapeutic agents and high-tech materials.

Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides

A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia - with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed within each series, with 1,2,4-oxadiazole 3 (metHb% = 61.0 ± 3.6) and 1,3,4-oxadiazole 10 (metHb% = 52.4 ± 0.9) demonstrating the greatest activity. Of the 5 candidates (compounds 3, 10, 11, 13 and 23) evaluated in vivo, failure to induce a lethal end-point at doses of 120 mg/kg was observed in all cases. Inadequate metabolic stability, particularly towards hepatic enzymes such as the CYPs, was postulated as one reason for their failure.

Synthesis of some unusual (1,2,4-oxadiazole)-linked hexenopyranosides and mannopyranosides

A copper-catalyzed reaction of propargyl 4,6-di-O-acetyl-2,3-dideoxy- α-D-erythro-hex-2-enopyranoside with 3-(4-azidophenyl)-1,2,4-oxadiazoles gave the corresponding hexenopyranosides bearing an 1,2,4-oxadiazole subunit in the aglyconic part of the molecu