16499-61-9

Basic information

• Product Name: 4-CHLORO-6-FLUOROQUINAZOLINE
• Synonyms: 4-CHLORO-6-FLUOROQUINAZOLINE
• CAS NO: 16499-61-9
• Molecular Formula: C₈H₄ClFN₂
• Molecular Weight: 182.58
• Product Categories: pharmacetical;CHIRAL CHEMICALS
• Mol File: 16499-61-9.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 284.881 °C at 760 mmHg
• Flash Point: 126.092 °C
• Appearance: /
• Density: 1.447 g/cm³
• Vapor Pressure: 0.00498mmHg at 25°C
• Refractive Index: 1.634
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 0.17±0.30(Predicted)
• CAS DataBase Reference: 4-CHLORO-6-FLUOROQUINAZOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-6-FLUOROQUINAZOLINE(16499-61-9)
• EPA Substance Registry System: 4-CHLORO-6-FLUOROQUINAZOLINE(16499-61-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• HazardClass: IRRITANT
• Hazardous Substances Data: 16499-61-9(Hazardous Substances Data)

Usage

General Description

4-Chloro-6-Fluoroquinazoline, also referred to by its CAS number 20410-64-0, is a chemical compound with a molecular formula of C8H3ClFN3. While the specific description can change based on the compound's structure and functional groups, in basic terms, 4-Chloro-6-Fluoroquinazoline can be described as an organic compound with a quinazoline backbone, which consists of two fused six-membered rings, one aromatic and one containing two nitrogen atoms, and has a chlorine atom substituted at the 4th position and a fluorine atom substituted at the 6th position. Its applications are typically in the field of pharmaceuticals, often used as an intermediate in drug development or synthesis for the production of various drugs. Detailed information, including its physical and chemical properties or safety data, should be referenced from a dedicated chemical database or a Material Safety Data Sheet (MSDS).

InChI:InChI=1/C8H4ClFN2/c9-8-6-3-5(10)1-2-7(6)11-4-12-8/h1-4H

Upstream product

• 446-08-2 2-amino-5-fluorobenzoic acid 
• 16499-56-2 6-fluoroquinazolin-4-ol 
• 319-24-4 2-amino-5-fluoro-benzoic acid methyl ester 
• 63069-49-8 2-amino-5-fluorobenzamide 
• 16499-56-2 6-fluoro-3,4-dihydroquinazolin-4-one 

Downstream Products

• 1262888-20-9 N-(4-chlorobenzyl)-6-fluoroquinazoline-4-amine 
• 1262888-22-1 C₁₆H₁₃F₂N₃ 
• 1380650-78-1 methyl 4-(((6-fluoroquinazolin-4-yl)amino)methyl)benzoate 

Relevant articles and documents

Drug-like property optimization: Discovery of orally bioavailable quinazoline-based multi-targeted kinase inhibitors

In an effort to develop new cancer therapeutics, we have reported clinical candidate BPR1K871 (1) as a potent anticancer compound in MOLM-13 and MV4-11 leukemia models, as well as in colorectal and pancreatic animal models. As BPR1K871 lacks oral bioavailability, we continued searching for orally bioavailable analogs through drug-like property optimization. We optimized both the physicochemical properties (PCP) as well as in vitro rat liver microsomal stability of 1, with concomitant monitoring of aurora kinase enzyme inhibition as well as cellular anti-proliferative activity in HCT-116 cell line. Structural modification at the 6- and 7-position of quinazoline core of 1 led to the identification of 34 as an orally bioavailable (F% = 54) multi-kinase inhibitor, which exhibits potent anti-proliferative activity against various cancer cell lines. Quinazoline 34 is selected as a promising oral lead candidate for further preclinical evaluation.

Synthesis, in vitro antibacterial and antifungal evaluation of novel 1,3,4-oxadiazole thioether derivatives bearing the 6-fluoroquinazolinylpiperidinyl moiety

A series of structurally novel 1,3,4-oxadiazole thioether derivatives (6a–6z) containing a 6-fluoroquinazolinylpiperidinyl moiety were designed and synthesized using pharmacophore hybrid approach, and their structures were fully characterized by 1H NMR, 13C NMR and HRMS spectra. Among them, the structure of compound 6d was further corroborated via single-crystal X-ray diffraction analysis. In vitro antibacterial bioassays showed that compounds 6a, 6g, 6u and 6v possessed EC50 values of 30.4, 30.6, 27.5 and 26.0 μg/mL against phytopathogenic bacterium Xanthomonas oryzae pv. oryzae, respectively, which were significantly superior to that of commercially-available bactericide Bismerthiazol (85.1 μg/mL). Moreover, in vitro antifungal bioassays indicated that seven compounds demonstrated broad-spectrum fungicidal acitivties against six types of phytopathogenic fungi at 50 μg/mL. The present work showed the potential of 1,3,4-oxadiazole thioether derivatives carrying a 6-fluoroquinazolinylpiperidinyl moiety as effective antimicrobial agents for crop protection, deserving further investigations in the future.

Design, Synthesis, Crystal Structure, and Antimicrobial Evaluation of 6-Fluoroquinazolinylpiperidinyl-Containing 1,2,4-Triazole Mannich Base Derivatives against Phytopathogenic Bacteria and Fungi

A total of 20 1,2,4-triazole Mannich base derivatives bearing the 6-fluoroquinazolinylpiperidinyl moiety were designed, synthesized, and evaluated as antimicrobial agents against phytopathogenic bacteria and fungi according to the molecular hybridization strategy. Of note, the structure of target compound 4h was clearly confirmed through single-crystal X-ray diffraction analysis. The turbidimetric assays indicated that some compounds exhibited excellent antibacterial efficacies in vitro against Xanthomonas oryzae pv. oryzae (Xoo). For example, compounds 4c, 4f, 4j, and 7j had EC50 values of 23.6, 18.8, 23.4, and 24.3 μg/mL, respectively, which were far superior to that of agrobactericide bismerthiazol (EC50 = 92.4 μg/mL). In particular, compound 4f demonstrated a potent anti-Xoo activity approximately five times more active than that of bismerthiazol. Moreover, in vivo assays showed the excellent protective and curative activities of compound 4f against rice bacterial blight, having the potential as an alternative bactericide for controlling Xoo. The structure-activity relationship analysis showed a good pesticide-likeness concerning compound 4f, following Tice's criteria. The anti-Xoo mechanism of compound 4f was preliminarily explored by scanning electron microscopy measurements in living bacteria. Finally, several compounds also exhibited good antifungal activities in vitro against Gibberella zeae at 50 μg/mL. In short, the presented work showed the potential of 6-fluoroquinazolinylpiperidinyl-containing 1,2,4-triazole Mannich base derivatives as effective bactericides for controlling Xoo.