174566-15-5

Basic information

• Product Name: 2,4-Dichloro-7-fluoroquinazoline
• Synonyms: 2,4-DICHLORO-7-FLUOROQUINAZOLINE;7-Fluoro-2,4-dichloroquinazoline;2,4-Dichloro-7-fluoroquinazolin;4-dichloro-7-fluoroquinazoline;2,4-Dichloro-7-fluoroquizoline
• CAS NO: 174566-15-5
• Molecular Formula: C₈H₃Cl₂FN₂
• Molecular Weight: 217.03
• Mol File: 174566-15-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 277 °C
• Flash Point: 121 °C
• Appearance: /
• Density: 1.571
• Vapor Pressure: 0.43mmHg at 25°C
• Refractive Index: 1.644
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.91±0.30(Predicted)
• CAS DataBase Reference: 2,4-Dichloro-7-fluoroquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloro-7-fluoroquinazoline(174566-15-5)
• EPA Substance Registry System: 2,4-Dichloro-7-fluoroquinazoline(174566-15-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 174566-15-5(Hazardous Substances Data)

Usage

Description

2,4-Dichloro-7-fluoroquinazoline is a chemical compound characterized by the presence of two chlorine atoms at the 2nd and 4th positions and a fluorine atom at the 7th position on a quinazoline ring. It serves as a key intermediate in the synthesis of various organic compounds and pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
2,4-Dichloro-7-fluoroquinazoline is used as a precursor in the preparation of piperazine derivatives, specifically as Monoacylglycerol Lipase (MAGL) inhibitors. These MAGL inhibitors are of interest in the development of therapeutic agents for the treatment of various conditions, including neuroinflammation and pain management, due to their role in modulating endocannabinoid signaling pathways.

InChI:InChI=1/C8H3Cl2FN2/c9-7-5-2-1-4(11)3-6(5)12-8(10)13-7/h1-3H

Upstream product

• 76088-98-7 7-fluoro-2,4-dioxo-1,2,3,4-tetrahydroquinazoline 
• 76088-98-7 7-fluoroquinazoline-2,4-diol 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 80517-22-2 2-amino-4-fluorobenzonitrile 
• 446-32-2 4-fluoroanthranilic acid 

Downstream Products

• 956101-10-3 2-chloro-7-fluoro-quinazoline 

Relevant articles and documents

Targeting sars-cov-2 polymerase with new nucleoside analogues

Despite the fact that COVID-19 vaccines are already available on the market, there have not been any effective FDA-approved drugs to treat this disease. There are several already known drugs that through drug repositioning have shown an inhibitory activity against SARS-CoV-2 RNA-dependent RNA polymerase. These drugs are included in the family of nucleoside analogues. In our efforts, we synthesized a group of new nucleoside analogues, which are modified at the sugar moiety that is replaced by a quinazoline entity. Different nucleobase derivatives are used in order to increase the inhibition. Five new nucleoside analogues were evaluated with in vitro assays for targeting polymerase of SARS-CoV-2.

One-pot cascade ring enlargement of isatin-3-oximes to 2,4-dichloroquinazolines mediated by bis(trichloromethyl)carbonate and triarylphosphine oxide

An efficient and convenient one-pot cascade synthesis of 2,4-dichloroquinazolines directly from isatin-3-oximes with the addition of bis(trichloromethyl)carbonate and triarylphosphine oxide was developed, leading to substituted quinazolines in moderate to excellent yields. The efficiency of this transformation was demonstrated by compatibility with a range of functional groups. Thus, the method represents a convenient and practical strategy for the synthesis of substituted 2,4-dichloroquinazolines.

Eco-efficient one-pot synthesis of quinazoline-2,4(1H,3H)-diones at room temperature in water

An efficient one-pot synthesis of quinazoline-2,4(1H,3H)-diones was developed. First, the reactions of anthranilic acid derivatives with potassium cyanate afforded the corresponding urea derivatives. Then, cyclization of the urea derivatives with NaOH afforded the monosodium salts of benzoylene urea. Finally, HCl treatment afforded the desired products in near-quantitative yields. This is an eco-efficient method because all the reactions were carried out in water, and the desired products were obtained simply by filtration. The aqueous filtrate was the only waste generated from the reaction. We scaled up the reaction to 1 kg starting material, thus establishing an alternative approach for the green synthesis of quinazoline-2,4(1H,3H)-diones in the chemical and pharmaceutical industries.