98554-00-8

Basic information

• Product Name: 5-(4-Chloro-phenyl)-4H-[1,2,4]triazol-3-ylamine
• Synonyms: 5-(4-Chloro-phenyl)-4H-[1,2,4]triazol-3-ylamine;3-(4-Chlorophenyl)-1H-1,2,4-Triazol-5-Amine(WX150053)
• CAS NO: 98554-00-8
• Molecular Formula: C₈H₇ClN₄
• Molecular Weight: 194.62
• Mol File: 98554-00-8.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(4-Chloro-phenyl)-4H-[1,2,4]triazol-3-ylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-Chloro-phenyl)-4H-[1,2,4]triazol-3-ylamine(98554-00-8)
• EPA Substance Registry System: 5-(4-Chloro-phenyl)-4H-[1,2,4]triazol-3-ylamine(98554-00-8)

Safety Data

• Hazardous Substances Data: 98554-00-8(Hazardous Substances Data)

Usage

Chemical Family

Triazole

Physical State

White solid

Molecular Weight

204.63 g/mol

Applications

Intermediate in the synthesis of pharmaceuticals, agrochemicals, and dyes
Known for fungicidal and herbicidal properties

Potential Activities

Studied for antitumor and antimicrobial activities

Upstream product

• 51884-13-0 2-(4-chlorobenzoyl)hydrazinecarboximidamide 
• 536-40-3 4-chlorobenzoic acid hydrazide 
• 74-11-3 para-chlorobenzoic acid 
• 122-01-0 4-chloro-benzoyl chloride 
• 51884-13-0 C₈H₉ClN₄O 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 623-03-0 4-Cyanochlorobenzene 
• 420-04-2 CYANAMID 
• 23432-96-4 3-chloro-5-(4-chlorophenyl)-1,2,4-oxadiazole 
• 19350-69-7 4-chlorobenzaldehyde p-toluenesulfonylhydrazone 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 168893-29-6 5-amino-3-(4-chlorophenyl)-1-[methylamino(thiocarbonyl)]-1H-1,2,4-triazole 
• 1456613-82-3 2-(4-chlorophenyl)-5-thioxo-5,6-dihydro-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one 
• 1252014-22-4 C₁₂H₁₂ClN₅O₂S 

Relevant articles and documents

Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N-Tosylhydrazones

The diversity-oriented synthesis of 1,2,4-triazols, 1,3,4-thiadiazols, and 1,3,4-selenadiazoles from N-tosylhydrazones was developed, and the reactions were general for a wide range of substrates, in which NH2CN, KOCN, KSCN, and KSeCN were used as odorless sources. Two different pathways were proposed, and N-tosylhydrazonoyl chlorides were formed in situ in the presence of NCS.

A Novel Iron-catalyzed One-pot Synthesis of 3-Amino-1,2,4-triazoles

A novel one-pot synthesis of 3-amino-1,2,4-triazole developed via iron (III) catalyzed route is reported. The new method is more efficient, simple, and convenient and presents a concise new strategy for the synthesis of 3-amino-1,2,4-triazole derivatives.

3-Aryl/Heteroaryl-5-amino-1-(3′,4′,5′-trimethoxybenzoyl)-1,2,4-triazoles as antimicrotubule agents. Design, synthesis, antiproliferative activity and inhibition of tubulin polymerization

Many natural and synthetic substances are known to interfere with the dynamic assembly of tubulin, preventing the formation of microtubules. In our search for potent and selective antitumor agents, a novel series of 1-(3′,4′,5′-trimethoxybenzoyl)-5-amino-1,2,4-triazoles were synthesized. The compounds had different heterocycles, including thiophene, furan or the three isomeric pyridines, and they possessed a phenyl ring bearing electron-releasing or electron-withdrawing substituents at the 3-position of the 5-amino-1,2,4-triazole system. Most of the twenty-two tested compounds showed moderate to potent antiproliferative activities against a panel of solid tumor and leukemic cell lines, with four (5j, 5k, 5o and 5p) showing strong antiproliferative activity (IC50 50 values 2-100-fold lower for Jurkat and RS4;11 cells than those for the three lines derived from solid tumors (HeLa, HT-29 and MCF-7 cells). Compound 5k strongly inhibited tubulin assembly, with an IC50 value of 0.66 μM, half that obtained in simultaneous experiments with CA-4 (IC50 = 1.3 μM).