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20028-68-6

2,4,6-Trichloroquinazoline

CAS: 20028-68-6

Molecular Formula: C8H3Cl3N2

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20028-68-6 - Names and Identifiers

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

20028-68-6 - Physico-chemical Properties

Molecular FormulaC8H3Cl3N2
Molar Mass233.48
Density1.600±0.06 g/cm3(Predicted)
Melting Point131 °C
Boling Point230-240 °C(Press: 15 Torr)
Flash Point162.566°C
Vapor Presure0.002mmHg at 25°C
pKa-1.15±0.30(Predicted)
Storage Conditionunder inert gas (nitrogen or Argon) at 2-8°C
Refractive Index1.678

20028-68-6 - Risk and Safety

Risk CodesR25 - Toxic if swallowed
R37/38 - Irritating to respiratory system and skin.
R41 - Risk of serious damage to eyes
Safety DescriptionS26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36 - Wear suitable protective clothing.

20028-68-6 - Reference Information

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
Last Update:2024-04-09 21:50:46
20028-68-6
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