163275-58-9

Basic information

• Product Name: 5-fluorobenzo[h]quinoline
• Synonyms: 5-Fluorobenzo(h)quinoline; 5-Fluorobenzo[h]quinoline; benzo[h]quinoline, 5-fluoro-
• CAS NO: 163275-58-9
• Molecular Formula: C₁₃H₈FN
• Molecular Weight: 197.2077
• Mol File: 163275-58-9.mol

Chemical Properties

• Boiling Point: 353.9°C at 760 mmHg
• Flash Point: 167.8°C
• Density: 1.271g/cm³
• Vapor Pressure: 7.09E-05mmHg at 25°C
• Refractive Index: 1.701
• CAS DataBase Reference: 5-fluorobenzo[h]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-fluorobenzo[h]quinoline(163275-58-9)
• EPA Substance Registry System: 5-fluorobenzo[h]quinoline(163275-58-9)

Safety Data

• Hazardous Substances Data: 163275-58-9(Hazardous Substances Data)

Upstream product

• 230-27-3 7,8-benzoquinoline 
• 854046-61-0 5-bromobenzo[h]quinoline 
• 854046-66-5 5-aminobenzo[h]quinoline 

Relevant articles and documents

Synthesis of 5-Substituted Benzo[h]quinoline Derivatives via Reactions Involving C(sp2)?Br Bond Activation

In view of literature reports, benzo[h]quinoline and its substituted analogues, due to their structural similarity to 2-phenylpyridine derivatives, appear to be very promising C,N-cyclometalating ligands for iridium-based Phosphorescent Organic Light Emitting Diode technology. 5-bromo-benzo[h]quinoline aroused our particular interest as a convenient precursor for further transformations, and was successfully functionalized in the course of transition metal-promoted exclusive C?C, C?O and C?N bond formation, yielding a series of 5-substituted benzo[h]quinoline derivatives with unique structures and properties. Some of the synthesized compounds seemed to be appropriate starting materials for subsequent transformations, and enabled the preparation of new benzo[h]quinoline-based materials, for instance those with fluorine or silsesquioxane groups, which have not been synthesized by the conventional Scraup protocol. In selected transformations, the assistance of microwave irradiation as a non-conventional energy carrier significantly improved efficiency, leading to the formation of desired products with yields of up to 99%. (Figure presented.).

Fluorinated benzo[h]quinolines and benzo[f]quinolines

Thirteen kinds of fluorinated derivatives of benzo[h]quinoline and benzo[f]qninoline were synthesized by means of the Schiemann reaction or Skraup reaction, or by an electrolytic method. The synthesized derivatives carry one or two fluorine atoms at the bay-region, the K-region, and/or on the pyridine moiety of the molecules. These compounds can be used as models to examine the effect upon genotoxicity of fluorine substitution at appropriate sites on aromatic rings. Physicochemical and spectroscopic data of the fluorinated derivatives are given.