Name | 2,4,6-Trichloroquinazoline |
Synonyms | 2,4,6-trichlroquinazoline 2,4,6-TRICHLOROQUINAZOLINE 2,4,6-Trichloroquinazoline 2,4,6-TRICHLOROQUINOXALINE Quinazoline, 2,4,6-trichloro- quinazoline, 2,4,6-trichloro- |
CAS | 20028-68-6 |
InChI | InChI=1/C8H3Cl3N2/c9-4-1-2-6-5(3-4)7(10)13-8(11)12-6/h1-3H |
Molecular Formula | C8H3Cl3N2 |
Molar Mass | 233.48 |
Density | 1.600±0.06 g/cm3(Predicted) |
Melting Point | 131 °C |
Boling Point | 230-240 °C(Press: 15 Torr) |
Flash Point | 162.566°C |
Vapor Presure | 0.002mmHg at 25°C |
pKa | -1.15±0.30(Predicted) |
Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
Refractive Index | 1.678 |
Risk Codes | R25 - Toxic if swallowed R37/38 - Irritating to respiratory system and skin. R41 - Risk of serious damage to eyes |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
Introduction | quinazoline is an important class of benzo-heterocyclic compounds containing two nitrogen atoms, its derivatives have a variety of biological activities, such as anti-malaria, anti-fungal, anti-inflammatory, anti-hypertension, hypoglycemic, anti-tumor and anti-HIV activity. Therefore, the synthesis of quinazoline derivatives has received extensive attention. 2, 4, 6-trichloroquinazoline is an important quinazoline derivatives, can be prepared by a variety of synthetic routes, for example, 2, 4, 6-trichloroquinazoline is prepared by using 2-amino-5-chlorobenzoic acid as a starting material through cyclization reaction and chlorination reaction. |
Use | 2,4, 6-trichloroquinazoline is a heterocyclic organic compound and can be used as a pharmaceutical intermediate. |
preparation | 2, 4-dichloroquinazoline derivatives are synthesized 2, an important intermediate of 4-disubstituted quinazoline, via nucleophilic substitution reactions or transition metal-catalyzed coupling reactions, A variety of functional groups can be introduced at the 2-and 4-positions of the quinazoline ring. The synthesis of 2, 4-dichloroquinazoline derivatives is generally obtained by chloro reaction of quinazoline 2, 4-dione. There are many synthetic methods of quinazoline 2, 4-dione, such as: the condensation of anthranilic acid with excess urea at 150 ℃ ~ 200 ℃, condensation of anthranilic acid derivatives with cyanates under acidic conditions, reaction of anthranilic acid amide with phosgene, reaction of anthranilic acid acetonitrile with carbon dioxide in 1, 8-diazacyclo-bicyclo [5, 4, catalytic condensation of 0] -7-undecene, etc. However, the above method has the disadvantages of large amount of urea, harsh reaction conditions, long reaction time or low reaction yield. Recently, Lee et al used O-aminophenylacetonitrile and diphosgene reaction, using acetonitrile as solvent, in a sealed tube pressure reaction for 12 hours, one-step reaction synthesis of 2, 4-dichloroquinazoline derivative [1]. However, the application of this method is greatly limited due to the great toxicity of diphosgene. In this paper, phosphorus oxychloride (POCl3) as solvent, in the presence of phosphorus pentachloride ( PCl5), 2-amino-5-chlorobenzoic acid and urea condensation, one-pot reaction directly synthesized 2, 4, 6-trichloroquinazoline. The synthesis reaction scheme is shown in the following figure. Fig.1 reaction formula for synthesis of 2, 4, 6-trichloroquinazoline |