6484-24-8

Basic information

• Product Name: 4-chloro-2-methylquinazoline
• Synonyms: 4-chloro-2-methylquinazoline;Quinazoline, 4-chloro-2-Methyl-
• CAS NO: 6484-24-8
• Molecular Formula: C₉H₇ClN₂
• Molecular Weight: 178.61828
• Mol File: 6484-24-8.mol
• Article Data: 28

Chemical Properties

• Melting Point: 86-88 °C
• Boiling Point: 211.2 °C at 760 mmHg
• Flash Point: 101.3 °C
• Appearance: /
• Density: 1.292 g/cm³
• Vapor Pressure: 0.269mmHg at 25°C
• Refractive Index: 1.643
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 1.28±0.30(Predicted)
• CAS DataBase Reference: 4-chloro-2-methylquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-2-methylquinazoline(6484-24-8)
• EPA Substance Registry System: 4-chloro-2-methylquinazoline(6484-24-8)

Safety Data

• Hazardous Substances Data: 6484-24-8(Hazardous Substances Data)

Usage

General Description

4-chloro-2-methylquinazoline is an organic compound with the chemical formula C9H7ClN2. It is a chlorinated quinazoline derivative that is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 4-chloro-2-methylquinazoline is a white crystalline solid that is sparingly soluble in water. It is mainly used in the production of diverse chemical products, including dyes, pigments, and pharmaceuticals. Additionally, it has potential applications in chemical research and development, as well as in the manufacturing of specialty chemicals. The compound's unique chemical structure and properties make it valuable in various industrial and research settings.

InChI:InChI=1/C9H7ClN2/c1-6-11-8-5-3-2-4-7(8)9(10)12-6/h2-5H,1H3

Upstream product

• 1769-24-0 2-methyl-4-quinazolone 
• 1769-24-0 4-hydroxy-2-methylquinazoline 
• 28144-70-9 anthranilic acid amide 
• 118-92-3 anthranilic acid 

Downstream Products

• 101290-94-2 (2-methylquinazolin-4-yl)(phenyl)methanone 
• 827031-30-1 N-(2-fluoro-4-methoxyphenyl)-2-methylquinazolin-4-amine 
• 827031-11-8 N-(3-fluoro-4-methoxyphenyl)-2-methylquinazolin-4-amine 
• 677748-57-1 N-(4-methoxyphenyl)-2-methylquinazolin-4-amine 
• 610255-68-0 N-(4-ethoxyphenyl)-2-methylquinazolin-4-amine 
• 898282-73-0 N-(3,4-dimethoxyphenyl)-2-methylquinazolin-4-amine 
• 827031-13-0 N-(4-ethylphenyl)-2-methylquinazolin-4-amine 
• 1427059-59-3 2-Methyl-4-(2-phenylethynyl)quinazoline 

Relevant articles and documents

Efficient N-arylation of 4-chloroquinazolines en route to novel 4-anilinoquinazolines as potential anticancer agents

Microwave-mediated N-arylation of 4-chloroquinazolines in THF/H2O rapidly and efficiently afforded a library of novel 6-halo-2- phenyl-substituted 4-anilinoquinazolines. The methodology was compatible with numerous ortho-, meta-, and para-substituted N-methylanilines as well as substituted anilines and furnished the corresponding 4-anilinoquinazolines in good yields. Preliminary screening of the synthesized compounds against tumor cells (HCT-116 and T98G) showed promising antiproliferative properties.

Design, synthesis, and anticancer activities of sodium quinazolin-4-diselenide compounds

Substituted 4-chloroquinazoline reacted with sodium diselenide to give novel sodium quinazoline-4-diselenide compounds. The reaction provides an efficient and facile approach to the synthesis of sodium quinazoline-4-diselenide compounds. Structures of title compounds were confirmed by IR, 1H NMR, 13C NMR, and elemental analysis. MTT assay was adopted to show anticancer activities of the compounds. Compounds 5a and 5h showed good activities against cancer-cell lines MDA-MB-435, MDA-MB-231, A549, SiHa, and HeLa. In addition, 5a exhibited quite good anticancer effects on relative above cell lines with 10μM concentration compared with oxaliplatin and gefitinib of the commercial anticancer drugs.

Synthesis, docking and biological evaluation of 2,4-disubstituted quinazolines with multi-target activities as anti-cancer and antimicrobial agents

A series of 2,4-disubstituted quinazoline derivatives was designed and synthesized as multi-target therapeutic agents that may act as anti-cancer and antimicrobial agents. The target compounds were evaluated for primary anti-cancer activity followed by EGFR inhibition assay for most potent compounds. Compounds 6 and 8c exhibited good EGFR inhibition activity with IC50 values of 0.201 and 0.405 μM, respectively, in comparison to lapatinib as a reference with IC50 value of 0.115 μM. Docking study of the synthesized compounds into the binding site of EGFR tyrosine kinase was performed to compare the binding mode of these compounds to the known EGFR inhibitor, lapatinib. Moreover, antimicrobial activity, cytotoxity and hemolytic analysis were estimated according to CO-ADD (The Community for Antimicrobial Drug Discovery) procedures. Compounds 4 and 5c possessed potent antifungal activity with minimum inhibitory concentration (MIC) values of 8 and 4 μg/mL against C. albicans and C. neoformance, respectively, compared to fluconazole as a reference drug with MIC values of 0.125 and 8 μg/mL against same fungi.