26059-81-4

Basic information

• Product Name: 2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE
• Synonyms: 2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE;2-(trifluoromethyl)quinazolin-4-ol;2-(trifluoroMethyl)quinazolin-4(3H)-one;2-Trifluoromethyl-3H-quinazolin-4-one;2-(trifluoromethyl)-3,4-dihydroquinazolin-4-one
• CAS NO: 26059-81-4
• Molecular Formula: C₉H₅F₃N₂O
• Molecular Weight: 214.14
• Mol File: 26059-81-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 248-251°
• Boiling Point: 248℃
• Flash Point: 104℃
• Appearance: /
• Density: 1.51
• Vapor Pressure: 0.025mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.90±0.20(Predicted)
• CAS DataBase Reference: 2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE(26059-81-4)
• EPA Substance Registry System: 2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE(26059-81-4)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• HazardClass: IRRITANT
• Hazardous Substances Data: 26059-81-4(Hazardous Substances Data)

Usage

General Description

2-(Trifluoromethyl)-4(3H)-quinazolinone is a chemical compound with the molecular formula C9H5F3N2O. It is a quinazolinone derivative that contains a trifluoromethyl group. 2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE is mainly used in medicinal chemistry and drug discovery, where it is utilized as a building block in the synthesis of various pharmaceuticals and bioactive compounds. Its unique structure and properties make it an important intermediate in the development of new drugs for the treatment of various diseases and medical conditions. Additionally, it has potential applications in the field of agrochemicals and materials science.

InChI:InChI=1/C9H5F3N2O/c10-9(11,12)8-13-6-4-2-1-3-5(6)7(15)14-8/h1-4H,(H,13,14,15)

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 28144-70-9 anthranilic acid amide 
• 76-05-1 trifluoroacetic acid 

Downstream Products

• 927969-20-8 (2-(trifluoromethyl)quinazolin-4-yl)glycine 
• 52353-35-2 4-chloro-2-trifluoromethyl quinazoline 
• 154136-31-9 4-hydrazino-2-trifluoromethylquinazoline 

Relevant articles and documents

Quinazolines as cyclin dependent kinase inhibitors

Quinazolines have been identified as inhibitors of CDK4/D1 and CDK2/E. Aspects of the SAR were investigated using solution-phase, parallel synthesis. An X-ray crystal structure was obtained of quinazoline 51 bound in CDK2 and key interactions within the ATP binding pocket are defined.

Selective Toll-like receptor 7 agonists with novel chromeno[3,4-d]imidazol-4(1H)-one and 2-(trifluoromethyl)quinoline/ quinazoline-4-amine scaffolds

Toll-like receptors (TLRs) are promising targets for treatment of viral infections, autoimmune diseases, and cancers. Here, two new series of selective small-molecule TLR7 agonists with novel scaffolds and good selectivity over TLR8 are described, some with potencies in the low micromolar range. 8-Hydroxy-1-isobutylchromeno[3,4-d]imidazol-4(1H)-one (26) from the first series was designed and synthesized on the basis of previously described TLR7 antagonist 2, and is shown to be a selective TLR7 agonist (EC50, 1.8 μM). The second series was based on 2-(trifluoromethyl)quinolin-4-amine and 2-(trifluoromethyl)quinazolin-4-amine scaffolds, which were defined according to our in-house ligand-based virtual screening protocol. Further synthesis of a focused library of analogs, biological evaluation, and docking studies provided systematic exploration of the structure?activity relationships, which indicate that a secondary or tertiary amine with smaller flexible alkyl substituents up to three carbon atoms in length, or bulkier rigid aliphatic rings is required at position 4 on 2-(trifluoromethyl)quinoline/quinazoline scaffold for potent TLR7 agonist activity. The influence of selected TLR7 agonists on cytokine production is also reported showing that N-cyclopropyl-2-(trifluoromethyl)quinazolin-4-amine (46) is able to induce increased levels of IL-6 and IL-8. These data demonstrate successful in-silico definition of novel TLR7 versus TLR8-selective compounds as promising chemical probes for further development of potent small-molecule immunomodulators.

Microwave irradiation in solvent-free conditions: Preparation of 2-substituted- 4(3H)-quinazolinones by heterocyclisation of 2-aminobenzamide with carboxylic acids

A simple and fast preparation of 2-substituted-4(3H)-quinazolinones in high yields has been developed by microwave induced heterocyclisation of 2-aminobenzamide with carboxylic acids in solvent-free conditions. In comparison, the reactions are 40-80 times faster under microwave irradiation and the yields are much higher than conventional heating.