16064-14-5

Basic information

• Product Name: 6-Chloro-4-hydroxyquinazoline
• Synonyms: 6-chloro-4(3h)-quinazolinon;6-CHLOROQUINAZOLIN-4(3H)-ONE;6-CHLOROQUINAZOLIN-4-OL;6-CHLORO-4-HYDROXYQUINAZOLINE;6-CHLORO-3H-QUINAZOLIN-4-ONE;6-CHLORO-4-QUINAZOLINONE;6-CHLORO-4-QUINAZOLONE;6-Chloroquinazolin-4-ol, 6-Chloro-4-hydroxyquinazoline
• CAS NO: 16064-14-5
• Molecular Formula: C₈H₅ClN₂O
• Molecular Weight: 180.59
• Product Categories: blocks;Heterocycles;Quinolines
• Mol File: 16064-14-5.mol
• Article Data: 58

Chemical Properties

• Melting Point: 263-265 °C
• Boiling Point: 128.9°C (rough estimate)
• Flash Point: 169.166 °C
• Appearance: /
• Density: 1.4300 (rough estimate)
• Vapor Pressure: 2.99E-05mmHg at 25°C
• Refractive Index: 1.5430 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.93±0.20(Predicted)
• CAS DataBase Reference: 6-Chloro-4-hydroxyquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-4-hydroxyquinazoline(16064-14-5)
• EPA Substance Registry System: 6-Chloro-4-hydroxyquinazoline(16064-14-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 16064-14-5(Hazardous Substances Data)

Usage

General Description

6-Chloro-4-hydroxyquinazoline is a chemical compound with the molecular formula C8H5ClN2O. It is a synthetic intermediate used in the production of pharmaceuticals and agrochemicals. The compound is a derivative of quinazoline, which is a heterocyclic compound with a bicyclic structure containing a benzene ring fused to a pyrimidine ring. 6-Chloro-4-hydroxyquinazoline is known for its ability to inhibit the growth of bacteria and has potential applications in the development of new antibiotics. It is also used as a building block in organic synthesis for the preparation of various bioactive compounds. The compound is typically handled and stored in accordance with standard laboratory procedures for handling organic chemicals.

InChI:InChI=1/C8H5ClN2O/c9-5-1-2-7-6(3-5)8(12)11-4-10-7/h1-4H,(H,10,11,12)

Upstream product

• 491-36-1 4-Hydroxyquinazoline 
• 3473-63-0 formamidine acetic acid 
• 5202-85-7 2-Amino-5-chlorobenzamide 
• 635-21-2 5-chloroanthranilic acid 
• 20353-93-9 [3-(dimethylamino)-2-azaprop-2-en-1-ylidene]-dimethylammonium chloride 
• 64-18-6 formic acid 
• 5922-60-1 2-amino-5-chlorobenzonitrile 
• 5202-89-1 4-chlorobenzenesulfonyl chloride 
• 77287-34-4 formamide 
• 149-73-5 trimethyl orthoformate 
• 6313-33-3 formamidine hydrochloride 
• 2516-95-2 5-chloro-2-nitrobenzoic acid 
• 6628-86-0 5-chloro-2-nitrobenzaldehyde 
• 7782-50-5 chlorine 

Downstream Products

• 7253-22-7 4,6-dichloroquinazoline 
• 24585-93-1 3-benzyl-6-chloroquinazolin-4(3H)-one 

Relevant articles and documents

Substituted isoquinolines and quinazolines as potential antiinflammatory agents. Synthesis and biological evaluation of inhibitors of tumor necrosis factor α

A series of isoquinolin-1-ones and quinazolin-4-ones and related derivatives were prepared and evaluated for their ability to inhibit tumor necrosis factor α (TNFα) production in human peripheral blood monocytes stimulated with bacterial lipopolysaccharide (LPS). In an effort to optimize the TNFα inhibitory activity, a homologous series of N-alkanoic acid esters was prepared. Several electrophilic and nucleophilic substitutions were also carried out. Alkanoic acid esters of four carbons were found to be optimum for activity in both the isoquinoline and quinazoline series. Ring substituents such as fluoro, bromo, nitro, acetyl, and aminomethyl on the isoquinoline ring resulted in a significant loss of activity. Likewise, similar groups on the quinazoline ring also reduced inhibitory activity. However, the 6- and 7-aminoquinazoline derivatives, 75 and 76, were potent inhibitors, with IC50 values in the TNFα in vitro assay of approximately 5 μM for each. An in vivo mouse model of pulmonary inflammation was then used to evaluate promising candidate compounds identified in the primary in vitro assay. Compound 75 was selected for further study in this inhalation model, and was found to reduce the level of TNFα in brochoalveolar lavage fluid of LPS-treated mice by about 50% that of control mice. Thus, compounds such as 75, which can effectively inhibit proinflammatory cytokines such as TNFα in clinically relevant animal models of inflammation and fibrosis, may have potential as new antiinflammatory agents. Finally, a quinazoline derivative suitable to serve as a photoaffinity radiolabeled compound was prepared to help identify the putative cellular target(s) for these TNFα inhibitors.

Biologically Active Heterocyclic Hybrids Based on Quinazolinone, Benzofuran and Imidazolium Moieties: Synthesis, Characterization, Cytotoxic and Antibacterial Evaluation

Cytotoxic and antimicrobial agents structurally based on quinazolinone, benzofuran and imidazole pharmacophores, have been designed and synthesized. Spectral (IR, 1H-NMR) and elemental analysis data established the structures of these novel 3-[1-(1-benzofuran-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)ethyl]-1-methyl-1H-imidazol-3-ium chloride hybrid derivatives. All the synthesized compounds were evaluated for in?vitro cytotoxicity and antimicrobial activities. Cytotoxic evaluation using MTT assay revealed that compounds 12c, 12g and 12i exhibited significant cytotoxicity with IC50 values 1, 1, and 0.57?μm on this cell line, respectively. Biological activity of the synthesized compounds as antibacterial agent were also evaluated against three Gram-negative (Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi), three Gram-positive (Staphylococcus aureus, Bacillus subtilis and Listeria monocitogenes) and one yeast-like fungi (Candida albicans) strains. All compounds 12a?–?12i showed slightly higher activity against Gram-positive bacteria than the Gram-negative one. Among the nine new compounds screened, 3-[1-(5-bromo-1-benzofuran-2-yl)-2-(6-chloro-4-oxoquinazolin-3(4H)-yl)ethyl]-1-methyl-1H-imidazol-3-ium chloride (12e) has pronounced higher antimicrobial activity against all tested strains. These results demonstrated potential importance of molecular hybridization in the development of new lead molecules with major cytotoxicity and antimicrobial activity.

Synthesis and antifungal bioactivities of 3-alkylquinazolin- 4-one derivatives

A simple, efficient, and general method has been developed for the synthesis of various 3-alkylquinazolin-4-one derivatives from quinazolin-4-one treated with alkyl bromides under phase transfer catalysis condition. The structures of the compounds were characterized by elemental analysis, IR, 1H-NMR and 13C-NMR spectra. Title compound 6-bromo-3-propylquinazolin-4-one (3h) was found to possess good antifungal activity.

Design, synthesis, and evaluation of novel (E)-N'-(3-allyl-2-hydroxy)benzylidene-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides as antitumor agents

In our continuing search for novel small-molecule anticancer agents, we designed and synthesized a series of novel (E)-N'-(3-allyl-2-hydroxy)benzylidene-2-(4-oxoquinazolin-3(4H)-yl)acetohydrazides (5), focusing on the modification of substitution in the quinazolin-4(3H)-one moiety. The biological evaluation showed that all 13 designed and synthesized compounds displayed significant cytotoxicity against three human cancer cell lines (SW620, colon cancer; PC-3, prostate cancer; NCI-H23, lung cancer). The most potent compound 5l displayed cytotoxicity up to 213-fold more potent than 5-fluorouracil and 87-fold more potent than PAC-1, the first procaspase-activating compound. Structure–activity relationship analysis revealed that substitution of either electron-withdrawing or electron-releasing groups at positions 6 or 7 on the quinazolin-4(3H)-4-one moiety increased the cytotoxicity of the compounds, but substitution at position 6 seemed to be more favorable. In the caspase activation assay, compound 5l was found to activate the caspase activity by 291% in comparison to PAC-1, which was used as a control. Further docking simulation also revealed that this compound may be a potent allosteric inhibitor of procaspase-3 through chelation of the inhibitory zinc ion. Physicochemical and ADMET calculations for 5l provided useful information of its suitable absorption profile and some toxicological effects that need further optimization to be developed as a promising anticancer agent.

Visible-Light Photosynthesis of CHF2/CClF2/CBrF2-Substituted Ring-fused Quinazolinones in Dimethyl Carbonate

With eco-friendly and sustainable CO2-derived dimethyl carbonate as the sole solvent, the visible-light-induced cascade radical reactions have been established as a green and efficient tool for constructing various CHF2/CClF2/CBrF2-substituted ring-fused quinazolinones.

Self-catalyzed phototandem perfluoroalkylation/cyclization of unactivated alkenes: Synthesis of perfluoroalkyl-substituted quinazolinones

A novel visible-light-induced radical tandem trifluoromethylation/cyclization of unactivated alkenes with sodium perfluoroalkanesulfinates (Rf = CF3, C3F7, C4F9, C6F13, C8F17) under air atmosphere has been developed. A range of quinazolinones containing unactivated alkene moiety and sodium perfluoroalkanesulfinates were compatible with this transformation, leading to a variety of perfluoroalkyl-substituted quinazoline alkaloids. Remarkably, the experiment can be carried out without any metal catalyst, strong oxidant, or external photosensitizer.