5332-25-2

Basic information

• Product Name: 6-Bromoquinoline
• Synonyms: 6-Bromo-1-azanaphthalene;6-Bromoquinoline,97%;6-Br-quinoline;6-BROMOQUINOLINE;TIMTEC-BB SBB001559;6-bromo-quinolin;Quinoline, 6-bromo-;6-BROMOQUINOLINE 95+%
• CAS NO: 5332-25-2
• Molecular Formula: C₉H₆BrN
• Molecular Weight: 208.05
• EINECS: 206-363-3
• Product Categories: blocks;Bromides;Quinolines;Halides;Quinolines, Isoquinolines & Quinoxalines;Quinoline&Isoquinoline;Miscellaneous;Quinoline Derivertives;Aromatics Compounds;Haloquinolines;quinoline;Aromatics;Heterocycles;Quinolines, Isoquinolines & Quinoxalines;Boronic Acid;Heterocyclic Compounds;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;QuinolinesHeterocyclic Building Blocks
• Mol File: 5332-25-2.mol

Chemical Properties

• Melting Point: 19°C
• Boiling Point: 116 °C / 6mmHg
• Flash Point: 19 °C
• Appearance: Light Yellow Colour Liquid
• Density: 1.55
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.663
• Storage Temp.: Refrigerator
• Solubility: Soluble in acetone, acetonitrile, dichloromethane, ethyl acetate
• PKA: 4.18±0.10(Predicted)
• CAS DataBase Reference: 6-Bromoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromoquinoline(5332-25-2)
• EPA Substance Registry System: 6-Bromoquinoline(5332-25-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-37/38-22-20/21/22
• Safety Statements: 26-37/39-39-36
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 5332-25-2(Hazardous Substances Data)

Usage

Uses

Used in Fine Chemicals Industry:
6-Bromoquinoline is used as a fine chemical intermediate for the synthesis of a wide range of organic compounds. Its reactivity and structural features make it a versatile component in the development of new molecules with specific properties and applications.
Used in Pharmaceutical Industry:
6-Bromoquinoline is utilized as a pharmaceutical intermediate in the development of various drugs. Its unique structure and functional groups allow for the creation of novel therapeutic agents with potential applications in the treatment of different diseases and medical conditions.
Used as a Coupling Reagent:
In addition to its roles as an intermediate in the fine chemicals and pharmaceutical industries, 6-Bromoquinoline is also employed as a coupling reagent in chemical reactions. Its ability to facilitate the formation of new chemical bonds between molecules makes it a valuable tool in the synthesis of complex organic compounds and pharmaceuticals.

Bromoquinoline

There are seven positional isomers of bromoquinoline and their main properties are listed below:

Application and synthetic method

3-bromo-quinoline is reacted with mixed acid for generating 3-bromo-5-nitro-quinoline, which heats together with potassium permanganate for being oxidation into 5-bromo-2, 3-pyridine dicarboxylic acid. 6-bromo-quinoline is heated together with nitric acid to generate 6-bromo-8-nitro quinolone with further reaction with potassium permanganate for being oxidized to 2, 3-pyridinedicarboxylic acid. 2-bromo-quinolien can be synthesized through the reaction between 2-hydroxy quinoline and phosphorus pentabromide. Quinoline perbromide is heated at 180 °C for generating 3-bromo-quinoline. From the heating between 4-hydroxy quinoline and phosphorus pentabromide, or from the diazotization reaction via 4-aminoquinoline to generate 4-bromo-quinoline; 5-bromo-quinoline is synthesize by the heating reaction between m-bromo-aniline, glycerol, m-bromo nitrobenzene and concentrated sulfuric acid, or from the diazotization reaction of 5-aminoquinoline. 6-bromo-quinoline can be synthesized from the heating of bromoaniline, glycerol, concentrated sulfuric acid, and p-bromo-nitrobenzene. 7-bromo-quinoline can be synthesized from the diazotization reaction of 7-aminoquinoline. 8-bromo-quinoline can be synthesized from the heating reaction of o-bromo-aniline, glycerol, concentrated sulfuric acid and o-bromo nitrobenzene. application: as organic synthesis reagents. The above information is edited by the lookchem of Dai Xiongfeng.

InChI:InChI=1/C9H7NO/c11-8-4-3-7-2-1-5-10-9(7)6-8/h1-6,11H

Upstream product

• 56-81-5 glycerol 
• 106-40-1 4-bromo-aniline 
• 173089-80-0 quinolin-6-yl triflate 
• 104-55-2 3-phenyl-propenal 
• 6563-11-7 6-bromoquinoline-N-oxide 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 5467-74-3 4-Bromophenylboronic acid 
• 22190-35-8 6-bromo-1,2,3,4-tetrahydroquinoline 
• 1078160-86-7 4,6,8-tribromoquinoline 
• 190843-73-3 6,8-dibromo-1,2,3,4-tetrahydroquinoline 
• 333383-77-0 N-(4-bromo-phenyl)-4-methyl-N-(3-oxo-propyl)-benzenesulfonamide 
• 333383-76-9 N-(4-bromo-phenyl)-N-(3-oxo-propyl)-methanesulfonamide 
• 32857-48-0 N-(4-bromophenyl)-4-methylbenzenesulfonamide 
• 4284-50-8 N-(4-bromophenyl)methanesulfonamide 

Downstream Products

• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 683774-32-5 6-trimethylsilylethynylquinoline 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 22190-35-8 6-bromo-1,2,3,4-tetrahydroquinoline 
• 1381786-56-6 6-(4-Fluorophenyl)-2-(2-methyl-1-(1H-1,2,3-triazol-1-yl)propyl)quinoline 
• 1381787-05-8 C₁₉H₁₆FNO 
• 1381787-06-9 C₁₉H₁₈FNO 
• 1381787-07-0 C₂₆H₂₄FNO₃S 
• 1268250-77-6 2-[3,5-di(6-quinolyl)phenyl]-4,6-di-p-tolylpyrimidine 
• 77514-31-9 2,6-di-bromoquinoline 
• 1416440-23-7 6-bromo-3-iodoquinoline 

Relevant articles and documents

Synthesis, photophysical and electrochemical properties of aza-boron-diquinomethene complexes

A series of aza-boron-diquinomethene (aza-BODIQU) complexes with different aryl-substituents (B1-B6) were synthesized and characterized. Their photophysical properties were investigated systematically via spectroscopic and theoretical methods. All complexes exhibit strong 1π-π* absorption bands and intense fluorescent emission bands in the visible spectral region at room temperature. The fluorescence spectra in solution show the mirror image features of the S0→S1 absorption bands, which can be assigned to the 1π-π*/1ICT (intramolecular charge transfer) emitting states. Except for B6, all complexes exhibit high photoluminescence quantum yields (ΦPL = 0.47-0.93). The spectroscopic studies and theoretical calculations indicate that the photophysical properties of these aza-BODIQUs can be tuned by the appended aryl-substituents, which would be useful for rational design of boron-fluorine complexes with high emission quantum yield for organic light-emitting applications.

Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions

Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents

Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).

Metal–Organic Layers Hierarchically Integrate Three Synergistic Active Sites for Tandem Catalysis

We report the design of a bifunctional metal–organic layer (MOL), Hf12-Ru-Co, composed of [Ru(DBB)(bpy)2]2+ [DBB-Ru, DBB=4,4′-di(4-benzoato)-2,2′-bipyridine; bpy=2,2′-bipyridine] connecting ligand as a photosensitizer and Co(dmgH)2(PPA)Cl (PPA-Co, dmgH=dimethylglyoxime; PPA=4-pyridinepropionic acid) on the Hf12 secondary building unit (SBU) as a hydrogen-transfer catalyst. Hf12-Ru-Co efficiently catalyzed acceptorless dehydrogenation of indolines and tetrahydroquinolines to afford indoles and quinolones. We extended this strategy to prepare Hf12-Ru-Co-OTf MOL with a [Ru(DBB)(bpy)2]2+ photosensitizer and Hf12 SBU capped with triflate as strong Lewis acids and PPA-Co as a hydrogen transfer catalyst. With three synergistic active sites, Hf12-Ru-Co-OTf competently catalyzed dehydrogenative tandem transformations of indolines with alkenes or aldehydes to afford 3-alkylindoles and bisindolylmethanes with turnover numbers of up to 500 and 460, respectively, illustrating the potential use of MOLs in constructing novel multifunctional heterogeneous catalysts.

Visible light mediated selective oxidation of alcohols and oxidative dehydrogenation of N-heterocycles using scalable and reusable La-doped NiWO4nanoparticles

Visible light-mediated selective and efficient oxidation of various primary/secondary benzyl alcohols to aldehydes/ketones and oxidative dehydrogenation (ODH) of partially saturated heterocycles using a scalable and reusable heterogeneous photoredox catalyst in aqueous medium are described. A systematic study led to a selective synthesis of aldehydes under an argon atmosphere while the ODH of partially saturated heterocycles under an oxygen atmosphere resulted in very good to excellent yields. The methodology is atom economical and exhibits excellent tolerance towards various functional groups, and broad substrate scope. Furthermore, a one-pot procedure was developed for the sequential oxidation of benzyl alcohols and heteroaryl carbinols followed by the Pictet-Spengler cyclization and then aromatization to obtain the β-carbolines in high isolated yields. This methodology was found to be suitable for scale up and reusability. To the best of our knowledge, this is the first report on the oxidation of structurally diverse aryl carbinols and ODH of partially saturated N-heterocycles using a recyclable and heterogeneous photoredox catalyst under environmentally friendly conditions.

Monomeric vanadium oxide: A very efficient species for promoting aerobic oxidative dehydrogenation of N-heterocycles

Monomeric active species are very interesting in heterogeneous catalysis. In this work, we proposed a method to prepare VOx-NbOy@C catalysts, which involve the one-pot hydrothermal synthesis of inorganic/organic hybrid materials containing V/Nb followed by thermal treatment under a reducing atmosphere. The prepared catalysts were characterized using different techniques, such as high-angle annular dark-field scanning transmission electron microscopy and X-ray absorption fine structure spectroscopy. It was shown that monomeric VOx species were dispersed homogeneously in the catalysts. The VOx-NbOy@C catalysts displayed high performance in the aerobic oxidative dehydrogenation of N-heterocycles to aromatic heterocycles. It was demonstrated that the selectivity of reaction over the catalyst with a very small amount of V (0.07 wt%) was much higher than that over the NbOy@C, and the catalyst also exhibited excellent stability in the reaction. The detailed study indicated that monomeric VO2 species were the most effective for promoting the reaction. This journal is

Highly Ordered Mesoporous Cobalt Oxide as Heterogeneous Catalyst for Aerobic Oxidative Aromatization of N-Heterocycles

N-heterocycles are key structures for many pharmaceutical intermediates. The synthesis of such units normally is conducted under homogeneous catalytic conditions. Among all methods, aerobic oxidative aromatization is one of the most effective. However, in homogeneous conditions, catalysts are difficult to be recycled. Herein, we report a heterogeneous catalytic strategy with a mesoporous cobalt oxide as catalyst. The developed protocol shows a broad applicability for the synthesis of N-heterocycles (32 examples, up to 99 % yield), and the catalyst presents high turnover numbers (7.41) in the absence of any additives. Such a heterogenous approach can be easily scaled up. Furthermore, the catalyst can be recycled by simply filtration and be reused for at least six times without obvious deactivation. Comparative studies reveal that the high surface area of mesoporous cobalt oxide plays an important role on the catalytic reactivity. The outstanding recycling capacity makes the catalyst industrially practical and sustainable for the synthesis of diverse N-heterocycles.

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Superacid-promoted synthesis of quinoline derivatives

A series of vinylogous imines have been prepared from anilines and cinnamaldehydes. These substrates react in superacidic media to provide quinolines and related compounds. A mechanism for the conversion is proposed which involves the cyclization of dicationic superelectrophilic intermediates. Aromatization of the quinoline ring is thought to occur by superacid-promoted elimination of benzene.

Reusable, homogeneous water soluble photoredox catalyzed oxidative dehydrogenation of N-heterocycles in a biphasic system: Application to the synthesis of biologically active natural products

Herein, a simple and efficient method for the oxidative dehydrogenation (ODH) of tetrahydro-β-carbolines, indolines and tetrahydro-(iso)quinolines is described using a reusable, homogeneous cobalt-phthalocyanine photoredox catalyst in a biphasic medium. A biphasic system offers an advantage of easy separation of the product and an efficient reusability of the homogeneous photoredox catalyst. Also, the current system significantly helps to overcome the solubility issue of the substrate and catalyst at room temperature. Its potential applications to organic transformations are demonstrated by the synthesis of various biologically active N-heterocycles such as indoles, (iso)quinolines and β-carbolines and natural products such as eudistomin U, norharmane, and harmane and precursors to perlolyrine and flazin. Without isolation and purification, the catalyst solution can be reused up to 5 times with almost comparable reactivity. Furthermore, the efficiency of the reaction was demonstrated on a gram scale. To the best of our knowledge, this is the first report on ODH reactions using a non noble, reusable and homogeneous cobalt photoredox catalyst under environmentally friendly conditions.