54464-14-1

Basic information

• Product Name: 5-(4-Methoxyphenyl)-4H-1,2,4-triazol-3-amine
• Synonyms: 5-(4-methoxyphenyl)-1H-1,2,4-triazol-3-amine;5-(4-Methoxyphenyl)-4H-1,2,4-triazol-3-amine;5-(4-Methoxyphenyl)-4H-1,2,4-triazol-3-ylamine;5-(4-methoxyphenyl)-4H-1,2,4-triazol-3-amine(SALTDATA: 0.1H2O);5-(4-methoxyphenyl)-4H-1,2,4-triazol-3-amine 0.1H2O;[5-(4-methoxyphenyl)-1H-1,2,4-triazol-3-yl]amine;5-(4-Methoxyphenyl)-2H-1,2,4-triazol-3-amine
• CAS NO: 54464-14-1
• Molecular Formula: C₉H₁₀N₄O
• Molecular Weight: 190.2
• Mol File: 54464-14-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 441.8 °C at 760 mmHg
• Flash Point: 221 °C
• Appearance: /
• Density: 1.304 g/cm³
• Vapor Pressure: 5.3E-08mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: 5-(4-Methoxyphenyl)-4H-1,2,4-triazol-3-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-Methoxyphenyl)-4H-1,2,4-triazol-3-amine(54464-14-1)
• EPA Substance Registry System: 5-(4-Methoxyphenyl)-4H-1,2,4-triazol-3-amine(54464-14-1)

Safety Data

• Hazardous Substances Data: 54464-14-1(Hazardous Substances Data)

Usage

General Description

5-(4-Methoxyphenyl)-4H-1,2,4-triazol-3-amine is a chemical compound with the molecular formula C10H10N4O. It is a triazole derivative that has a 1,2,4-triazole core structure with an amine group attached to it. The compound also contains a methoxyphenyl group attached to the triazole ring. It is primarily used in the field of medicinal chemistry and drug discovery, where it may be used as a building block for the synthesis of various pharmaceutical compounds. Its specific roles and applications may vary depending on the specific research or industrial context in which it is used.

InChI:InChI=1/C9H10N4O/c1-14-7-4-2-6(3-5-7)8-11-9(10)13-12-8/h2-5H,1H3,(H3,10,11,12,13)

Upstream product

• 23524-07-4 3-chloro-5-(4-methoxy-phenyl)-[1,2,4]oxadiazole 
• 1937-19-5 1-aminoguanidine hydrochloride 
• 100-07-2 4-methoxy-benzoyl chloride 
• 100-09-4 4-methoxybenzoic acid 
• 168893-38-7 C₉H₁₂N₄O₂ 
• 3290-99-1 4-methoxybenzoic acid hydrazide 
• 168893-38-7 N-(4-methoxybenzamido)-guanidine 
• 420-04-2 CYANAMID 
• 19350-72-2 N'-(4-methoxybenzylidene)-4-methylbenzenesulfonohydrazide 
• 123-11-5 4-methoxy-benzaldehyde 
• 121-98-2 methyl 4-methoxybenzoate 

Downstream Products

• 74258-84-7 3-{1-[(Z)-5-(4-Methoxy-phenyl)-2H-[1,2,4]triazol-3-ylimino]-ethyl}-dihydro-furan-2-one 
• 74258-04-1 2-(4-Methoxy-phenyl)-5,8-dimethyl-7,8-dihydro-6H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-a]pyrimidine 
• 66045-41-8 6-(2-Hydroxy-ethyl)-2-(4-methoxy-phenyl)-5-methyl-4H-[1,2,4]triazolo[1,5-a]pyrimidin-7-one 
• 74258-68-7 7-Chloro-6-(2-chloro-ethyl)-2-(4-methoxy-phenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine 
• 74258-07-4 8-Isopropyl-2-(4-methoxy-phenyl)-5-methyl-7,8-dihydro-6H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-a]pyrimidine 
• 74258-12-1 8-tert-Butyl-2-(4-methoxy-phenyl)-5-methyl-7,8-dihydro-6H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-a]pyrimidine 
• 74258-37-0 2-(4-Methoxy-phenyl)-5-methyl-8-(3-pyrrolidin-1-yl-propyl)-7,8-dihydro-6H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-a]pyrimidine 
• 1456613-86-7 2-(4-methoxyphenyl)-5-thioxo-5,6-dihydro-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7(4H)-one 
• 924867-16-3 2-(4-methoxyphenyl)-5-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-one 

Relevant articles and documents

Discovery of highly potent tubulin polymerization inhibitors: Design, synthesis, and structure-activity relationships of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidines

By removing 5-methyl and 6-acetyl groups in our previously reported compound 3, we designed a series of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine derivatives as potential tubulin polymerization inhibitors. Among them, compound 5e displayed low nanomolar antiproliferative efficacy on HeLa cells which was 166-fold higher than the lead analogue 3. Interestingly, 5e displayed significant selectivity in inhibiting cancer cells over HEK-293 (normal human embryonic kidney cells). In addition, 5e dose-dependently arrested HeLa in G2/M phase through the alterations of the expression levels of p-cdc2 and cyclin B1, and caused HeLa cells apoptosis by regulation of expressions of cleaved PARP. Further evidence demonstrated that 5e effectively inhibited tubulin polymerization and was 3-fold more powerful than positive control CA-4. Moreover, molecular docking analysis indicated that 5e overlapped well with CA-4 in the colchicine-binding site. These studies demonstrated that 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine skeleton might be used as the leading unit to develop novel tubulin polymerization inhibitors as potential anticancer agents.

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.

Synthesis and in vitro anti-epileptic activities of novel [1,2,4]-triazolo[1,5-a]pyrimidin-7(4H)-one derivatives

In this investigation, eight novel 2,5-disubstituted [1,2,4]-triazolo[1,5-a]pyrimidin-7(4H)-one and eight novel 2,5-disubstituted [1,2,4]-triazolo[1,5-a]pyrimidine amine derivatives were synthesized based on the novel marine natural product Essramycin. Their anti-epileptic activities were evaluated by 4-aminopyridine (4-AP)-induced hyper excitability model in primary cultured neocortical neurons. Five compounds with [1,2,4]-triazolo[1,5-a]pyrimidin-7(4H)-one skeleton showed remarkable anti-epileptic activities. The preliminary structure–activity relationship (SAR) showed that the pyrimidine-7(4H)-one motif is the necessary “active core” of anti-epileptic activity. To understand the action mechanism of anti-epileptic activity of [1,2,4]-triazolo[1,5-a]pyrimidin-7(4H)-one compounds, docking studies using the model of GABAA as docking scaffolds were performed and the docking results were in concordance with the experiment observations. (Figure presented.).