2298-07-9

Basic information

• Product Name: 4-Bromo-1-naphthylamine
• Synonyms: 4-BROMO-1-NAPHTHALENYLAMINE;4-Bromo-1-naphtylamine;4-Bromonaphthalene-1-amine;4-bromonaphthalen-1-amine;1-Amino-4-bromonaphthalene,4-Bromo-1-naphthylamine;1-Amino-4-bromonaphthalene ,98%;(4-Bromonaphthalen-1-yl)amine;1-Naphthylamine,4-bromo-
• CAS NO: 2298-07-9
• Molecular Formula: C₁₀H₈BrN
• Molecular Weight: 222.08
• EINECS: 218-944-9
• Product Categories: Amines and Anilines;Halides;Anilines, Aromatic Amines and Nitro Compounds;Building Blocks;C10;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Amines;blocks;Bromides
• Mol File: 2298-07-9.mol

Chemical Properties

• Melting Point: 102-103 °C(lit.)
• Boiling Point: 338.4 °C at 760 mmHg
• Flash Point: 158.5 °C
• Appearance: /
• Density: 1.563 g/cm³
• Vapor Pressure: 9.84E-05mmHg at 25°C
• Refractive Index: 1.718
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 2.93±0.10(Predicted)
• CAS DataBase Reference: 4-Bromo-1-naphthylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-1-naphthylamine(2298-07-9)
• EPA Substance Registry System: 4-Bromo-1-naphthylamine(2298-07-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 2298-07-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-Bromo-1-naphthylamine is used as a reagent for the catalytic asymmetric ring opening of meso-epoxides with aromatic amines in water. This application takes advantage of its reactivity to facilitate the formation of new compounds with enhanced selectivity and enantiomeric purity, which is crucial in the production of pharmaceuticals and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Bromo-1-naphthylamine is used as a key intermediate in the synthesis of 4-quinolones and quinolone heterocycles. These synthesized compounds have broad-spectrum antimicrobial properties and are widely used as antibiotics, particularly for treating bacterial infections. The versatility of 4-Bromo-1-naphthylamine in synthesis makes it a valuable component in the development of new drugs and therapeutic agents.
Used in Research and Development:
Due to its unique chemical structure and reactivity, 4-Bromo-1-naphthylamine is also utilized in research and development settings. It serves as a starting material or a building block for creating novel organic compounds with potential applications in various fields, including materials science, agrochemicals, and advanced materials for electronics and energy storage.

InChI:InChI=1/C10H8BrN/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H,12H2

Upstream product

• 84-86-6 4-amino-1-naphthalenesufonic acid 
• 91394-66-0 1-(acetylamino)-4-bromonaphthalene 
• 103859-95-6 N-(4-bromo-[1]naphthyl)-formamide 
• 90151-49-8 2-bromo-5,5-dimethyl-2-nitro-cyclohexane-1,3-dione 
• 134-32-7 1-amino-naphthalene 
• 6330-51-4 1-naphthylformamide 
• 4236-05-9 4-bromo-1-nitronaphthalene 

Downstream Products

• 83-53-4 1,4-dibromonaphthalene 
• 90-11-9 1-Bromonaphthalene 
• 571-57-3 4-bromo-1-naphthol 
• 63279-58-3 1-iodo-4-bromo-naphthalene 
• 4236-05-9 4-bromo-1-nitronaphthalene 
• 500699-70-7 N-(4-bromo-[1]naphthyl)-benzenesulfonamide 
• 30727-61-8 6-Bromobenzo(h)quinoline 
• 59557-93-6 4-bromo-1-(N,N-dimethylamino)naphthalene 
• 168169-11-7 4-bromo-N-(tert-butoxycarbonyl)-1-naphthylamine 
• 134-32-7 1-amino-naphthalene 
• 850650-46-3 1-(4-bromo-naphthalen-1-yl)-piperazine 
• 294852-03-2 1-Amino-4-[3-(morpholin-4-yl)phenyl]naphthalene 
• 945537-27-9 C₂₁H₂₂N₂O 

Relevant articles and documents

Direct cyanation of picolinamides using K4[Fe(CN)6] as the cyanide source

The efficient, simple, and environment-friendly route of direct cyanation of picolinamides has been developed with nontoxic K4[Fe(CN)6] as the cyanide source through Pdcatalyzed C-H bond activation. A series of N-(naphthalene-1- yl)picolinamide derivatives were successfully transformed to the corresponding cyanation products. The cyanation mechanism has also been speculated.

Electrochemical C-H Halogenations of Enaminones and Electron-Rich Arenes with Sodium Halide (NaX) as Halogen Source for the Synthesis of 3-Halochromones and Haloarenes

Without employing an external oxidant, the simple synthesis of 3-halochromones and various halogenated electron-rich arenes has been realized with electrode oxidation by employing the simplest sodium halide (NaX, X = Cl, Br, I) as halogen source. This electrochemical method is advantageous for the simple and mild room temperature operation, environmental friendliness as well as broad substrate scope in both C-H bond donor and halogen source components.

Mild and Selective Method of Bromination of Flavonoids

A new method was developed for the mild and selective bromination of simple aromatic compounds and flavonoids in good yields using α,β-dibromohydrocinnamic acid in the presence of a base. This procedure enables selective mono- or dibromination of compounds highly sensitive to oxidative or radical attack. New brominated derivatives of silymarin flavonolignans and related flavonoids were prepared. These brominated derivatives can be used as valuable synthetic intermediates in further synthesis.

Preparation method of high-purity 1,4-dibromonaphthalene

The invention relates to a preparation method of high-purity 1,4-dibromonaphthalene and belongs to the technical field of organic synthesis. The provided preparation method of high-purity 1,4-dibromonaphthalene aims to solve the problems that preparation methods of 1,4-dibromonaphthalene in the prior art are complicated, the reaction conditions are high, the product purity is low, the yield is low, and the product quality is unstable. The method comprises the four steps of a one-pot acetylation protection and selective bromination process, a hydrolysis deprotection process, a diazotization coupling reaction process and a recrystallization purification process to obtain high-purity 1,4-dibromonaphthalene. The provided preparation method has the advantages that the synthesis route is short,the reaction conditions are mild and easy to control, and the production cost is low. The organic synthesis reaction site is monotonous, the selectivity is high, the product purity is up to 99.0%, andthe total yield can reach 71.7%. Industrial production is easily realized, the need for large-scale production of 1,4-dibromonaphthalene can be effectively met, and the method has a broad applicationprospect.

Making endo-cyclizations favorable again: A conceptually new synthetic approach to benzotriazoles via azide group directed lithiation/cyclization of 2-azidoaryl bromides

Although benzotriazoles are important and ubiquitous, currently there is only one conceptual approach to their synthesis: bridging the two ortho-amino groups with an electrophilic nitrogen atom. Herein, we disclose a new practical alternative-the endo-cyclization of 2-azidoaryl lithiums obtained in situ from 2-azido-aryl bromides. The scope of the reaction is illustrated using twenty-four examples with a variety of alkyl, alkoxy, perfluoroalkyl, and halogen substituents. We found that the directing effect of the azide group allows selective metal-halogen exchange in aryl azides containing several bromine atoms. Furthermore, (2-bromophenyl)diazomethane undergoes similar cyclization to give an indazole. Thus, cyclizations of aryl lithiums containing an ortho-X = Y = Z group emerge as a new general approach for the synthesis of aromatic heterocycles. DFT computations suggested that the observed endo-selectivity applies to the anionic cyclizations of other functionalities that undergo "1,1-additions" (i.e., azides, diazo compounds, and isonitriles). In contrast, cyclizations with the heteroatomic functionalities that follow the "1,2-addition" pattern (cyanates, thiocyanates, isocyanates, isothiocyanates, and nitriles) prefer the exo-cyclization path. Hence, such reactions expand the current understanding of stereoelectronic factors in anionic cyclizations.

ANTICANCER COMPOUNDS

The present invention discloses compounds for inhibition of uncontrolled cell proliferation particularly in cancer stem cells. Particularly, the invention relates to compounds of Formula III to XIV for the treatment of cancer, such as breast and prostate cancer.

A facile, regioselective and controllable bromination of aromatic amines using a CuBr2/Oxone system

A combination of cupric bromide and Oxone serves as a facile, mild and effective reagent for the bromination of aromatic amines. Primary, secondary and tertiary aromatic amines are all suitable substrates. The reaction possesses high regioselectivity and functional group tolerance, and mono- and multi-brominated products can be obtained controllably in moderate to excellent yields. The Royal Society of Chemistry 2013.

Silica-supported quinolinium tribromide: A recoverable solid brominating reagent for regioselective monobromination of aromatic amines

Silica-supported quinolinium tribromide was synthesized and found to be an efficient, stable, and recoverable solid brominating reagent for the regioselective monobromination of aromatic amines. This protocol has advantages of high yield, mild condition and simple work-up procedure.

A convenient and selective method for the para-bromination of aromatic compounds with potassium bromide in the presence of poly(4-vinylpyridine)- supported peroxodisulfate in nonaqueous solution

A convenient and selective procedure for the para-bromination of aromatic compounds has been developed using potassium bromide in the presence of poly(4-vinylpyridine)-supported peroxodisulfate in nonaqueous solution.

LEWIS ACID CATALYZED HALOGENATION OF ACTIVATED CARBON ATOMS

A practical and efficient method for halogenation of activated carbon atoms using readily available /V-haloimides and a Lewis acid catalyst has been disclosed. This methodology is applicable to a range of compounds and any halogen atom can be directly introduced to the substrate. The mild reaction conditions, easy workup procedure and simple operation make this method valuable from both an environmental and preparative point of view.