20028-68-6

Basic information

• Product Name: 2,4,6-TRICHLOROQUINAZOLINE
• Synonyms: 2,4,6-TRICHLOROQUINAZOLINE;2,4,6-TRICHLOROQUINOXALINE;2,4,6-Trichloroquinazoline 98%;2,4,6-trichlroquinazoline
• CAS NO: 20028-68-6
• Molecular Formula: C₈H₃Cl₃N₂
• Molecular Weight: 233.48
• Mol File: 20028-68-6.mol
• Article Data: 43

Chemical Properties

• Melting Point: 131 °C
• Boiling Point: 298.549 °C at 760 mmHg
• Flash Point: 162.566 °C
• Appearance: /
• Density: 1.601 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.678
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.15±0.30(Predicted)
• CAS DataBase Reference: 2,4,6-TRICHLOROQUINAZOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRICHLOROQUINAZOLINE(20028-68-6)
• EPA Substance Registry System: 2,4,6-TRICHLOROQUINAZOLINE(20028-68-6)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25-37/38-41
• Safety Statements: 26-36
• Hazardous Substances Data: 20028-68-6(Hazardous Substances Data)

Usage

General Description

2,4,6-Trichloroquinazoline is a chemical compound with the molecular formula C8H3Cl3N2. It is a white to light yellow crystalline solid with a melting point of 187-191°C. It is primarily used as an intermediate in the synthesis of pharmaceuticals and agrochemicals, and as a building block in the production of various organic compounds. 2,4,6-Trichloroquinazoline may also have potential applications in the field of materials science, as well as in research and development for new chemical processes and products. It is important to handle this chemical with caution, as it may cause skin and eye irritation and should be used in a well-ventilated area with appropriate personal protective equipment.

InChI:InChI=1/C8H3Cl3N2/c9-4-1-2-6-5(3-4)7(10)13-8(11)12-6/h1-3H

Upstream product

• 1640-60-4 6-chloro-1,2,3,4-tetrahydroquinazoline-2,4-dione 
• 5922-60-1 2-amino-5-chlorobenzonitrile 
• 503-38-8 trichloromethyl chloroformate 
• 618889-14-8 N-(4-Chloro-2-cyanophenyl)-2,2,2-trifluoroacetamide 
• 63069-48-7 p-chloro-o-iodoaniline 
• 784183-51-3 N-(4-chloro-2-iodophenyl)-2,2,2-trifluoroacetamide 
• 1640-60-4 2,4-dihydroxy-6-chloroquinazoline 
• 1095657-56-9 6-chloroquinazoline-2,4(1H,3H)-dione monopotassium salt 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 635-21-2 5-chloroanthranilic acid 
• 57-13-6 urea 
• 5202-89-1 4-chlorobenzenesulfonyl chloride 
• 134-20-3 2-carbomethoxyaniline 
• 2516-95-2 5-chloro-2-nitrobenzoic acid 

Downstream Products

• 1640-60-4 6-chloro-1,2,3,4-tetrahydroquinazoline-2,4-dione 
• 76004-42-7 N-(2,6-Dichloro-quinazolin-4-yl)-N',N'-diethyl-cyclohexane-1,4-diamine; hydrochloride 
• 150450-96-7 N-benzyl-2,6-dichloroquinazolin-4-amine 
• 20197-87-9 2,6-dichloro-3H-quinazolin-4-one 
• 61741-56-8 6-chloro-2-phenethylamino-3H-quinazolin-4-one 
• 769158-24-9 2-((2,6-dichloro-4-oxoquinazolin-3(4H)-yl)methyl)benzonitrile 
• 33017-92-4 6-chloro-2-(4-methylpiperazin-1-yl)quinazolin-4(3H)-one 
• 76004-86-9 NCI 151998 
• 76004-87-0 6-Chloro-N²-(3,5-dichloro-phenyl)-N⁴-[2-(1-methyl-pyrrolidin-2-yl)-ethyl]-quinazoline-2,4-diamine; hydrochloride 
• 76004-90-5 NCI 152189 
• 76004-88-1 6-Chloro-N²-(3,4-dichloro-phenyl)-N⁴-(1-ethyl-piperidin-3-yl)-quinazoline-2,4-diamine; hydrochloride 
• 76004-94-9 6-Chloro-N²-(3,4-dichloro-phenyl)-N⁴-(4-diethylamino-cyclohexyl)-quinazoline-2,4-diamine; hydrochloride 
• 76005-03-3 7-Chloro-N⁴-(2-diethylamino-ethyl)-N²-(3-diethylaminomethyl-4-ethoxy-phenyl)-quinazoline-2,4-diamine; hydrochloride 
• 76005-02-2 6-Chloro-N⁴-(2-diethylamino-ethyl)-N²-(3-diethylaminomethyl-4-ethoxy-phenyl)-quinazoline-2,4-diamine; hydrochloride 

Relevant articles and documents

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.

Molecular Hybridization-Inspired Optimization of Diarylbenzopyrimidines as HIV-1 Nonnucleoside Reverse Transcriptase Inhibitors with Improved Activity against K103N and E138K Mutants and Pharmacokinetic Profiles

Molecular hybridization is a powerful strategy in drug discovery. A series of novel diarylbenzopyrimidine (DABP) analogues were developed by the hybridization of FDA-approved drugs etravirine (ETR) and efavirenz (EFV) as potential HIV-1 nonnucleoside reverse transcriptase inhibitors (NNRTIs). Substituent modifications resulted in the identification of new DABPs with the combination of the strengths of the two drugs, especially compound 12d, which showed promising activity toward the EFV-resistant K103N mutant. 12d also had a favorable pharmacokinetic (PK) profile with liver microsome clearances of 14.4 μL/min/mg (human) and 33.2 μL/min/mg (rat) and an oral bioavailability of 15.5% in rat. However, its activity against the E138K mutant was still unsatisfactory; E138K is the most prevalent NNRTI resistance-associated mutant in ETR treatment. Further optimizations resulted in a highly potent compound (12z) with no substituents on the phenyl ring and a 2-methyl-6-nitro substitution pattern on the 4-cyanovinyl-2,6-disubstitued phenyl motif. The antiviral activity of this compound was much higher than those of ETR and EFV against the WT, E138K, and K103N variants (EC50 = 3.4, 4.3, and 3.6 nM, respectively), and the cytotoxicity was decreased while the selectivity index (SI) was increased. In particular, this compound exhibited acceptable intrinsic liver microsome stability (human, 34.5 μL/min/mg; rat, 33.2 μL/min/mg) and maintained the good PK profile of its parent compound EFV and showed an oral bioavailability of 16.5% in rat. Molecular docking and structure-activity relationship (SAR) analysis provided further insights into the binding of the DABPs with HIV-1 reverse transcriptase and provided a deeper understanding of the key structural features responsible for their interactions.

Discovery of 2-(4-Substituted-piperidin/piperazine-1-yl)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-quinazoline-2,4-diamines as PAK4 inhibitors with potent A549 cell proliferation, migration, and invasion inhibition activity

A series of novel 2,4-diaminoquinazoline derivatives were designed, synthesized, and evaluated as p21-activated kinase 4 (PAK4) inhibitors. All compounds showed significant inhibitory activity against PAK4 (half-maximal inhibitory concentration IC50 1 ?M). Among them, compounds 8d and 9c demonstrated the most potent inhibitory activity against PAK4 (IC50 = 0.060 ?M and 0.068 ?M, respectively). Furthermore, we observed that compounds 8d and 9c displayed potent antiproliferative activity against the A549 cell line and inhibited cell cycle distribution, migration, and invasion of this cell line. In addition, molecular docking analysis was performed to predict the possible binding mode of compound 8d. This series of compounds has the potential for further development as PAK4 inhibitors for anticancer activity.