1698028-11-3 | 7-bromo-2,4,6-trichloro-8-fluoroquinazoline

CAS:1698028-11-3 | 7-bromo-2,4,6-trichloro-8-fluoroquinazoline,Description

Molecular Structure Analysis

The molecular formula of 7-Bromo-2,4,6-trichloro-8-fluoroquinazoline is C8HBrCl3FN2. The InChI code for this compound is 1S/C8HBrCl3FN2/c9-4-3(10)1-2-6(5(4)13)14-8(12)15-7(2)11/h1H.

Physical And Chemical Properties Analysis

7-Bromo-2,4,6-trichloro-8-fluoroquinazoline is a white, crystalline powder. It is relatively insoluble in water but soluble in organic solvents such as DMSO and DMF. The compound should be stored in an inert atmosphere, under -20°C.

Scientific Research Applications

Synthesis and Chemical Transformations

• Synthesis of Halogenated Quinazolines : Quinazolines, such as 7-Bromo-2,4,6-trichloro-8-fluoroquinazoline, are synthesized through various chemical reactions. For example, Tomažič and Hynes (1992) explored the synthesis of novel 2,4-diaminoquinazolines through reactions involving trifluorobenzonitrile and guanidine carbonate, leading to compounds like 6-chloro-2,4-diamino-8-fluoroquinazoline and 6-chloro-2,4-diamino-7-fluoroquinazoline (Tomažič & Hynes, 1992) .
• Rapid Synthetic Methods for Anticancer Intermediates : Zhou et al. (2019) established a rapid method for synthesizing 7-fluoroquinazoline-2, 4-diol, a significant intermediate in small molecule anticancer drugs. They utilized a three-step process involving cyclization, chlorination, and nucleophilic substitution, starting from 2-amino-4-fluoro benzoic acid and urea (Zhou et al., 2019).
• Telescoping Process in Drug Synthesis : Nishimura and Saitoh (2016) improved the synthesis of a key intermediate in drug discoveries, 5-bromo-2-methylamino-8-methoxyquinazoline, by reducing the number of isolation processes. This approach increased the total yield by 18% and maintained purity, showcasing the efficiency of the telescoping process in the synthesis of quinazoline derivatives (Nishimura & Saitoh, 2016).

Photoremoval in Biological Studies

• Photoremovable Protecting Groups : Zhu et al. (2006) investigated 8-Bromo-7-hydroxyquinoline (BHQ) as a photoremovable protecting group for biological studies. BHQ showed efficient photolysis under simulated physiological conditions, making it a valuable tool for the study of cell physiology and the temporal and spatial relevance of physiological functions (Zhu et al., 2006).

Antitumor Applications

• Fluoromethyl Analogs of Antitumor Alkaloids : Golubev et al. (2010) developed a method for synthesizing fluoromethyl-containing analogs of luotonin A, an antitumor alkaloid. They found that 7-trifluoromethylluotonin, derived from 3-bromomethyl-2-chloro-4-fluoromethylquinolines, retained antitumor activity, including apoptosis in cultured tumor cells and inhibiting DNA-topoisomerase I (Golubev et al., 2010).

Safety And Hazards

The compound is labeled with the GHS07 pictogram and the signal word "Warning". Hazard statements include H302, H315, H319, H335, indicating that it is harmful if swallowed, causes skin irritation, causes serious eye irritation, and may cause respiratory irritation. Precautionary statements include recommendations to avoid breathing dust/fume/gas/mist/vapors/spray, wash thoroughly after handling, and wear protective gloves/protective clothing/eye protection/face protection.

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