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
• Article Data: 17

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

Description

4-Bromo-1-naphthylamine, also known as 1-Amino-4-bromonaphthalene, is a pale purple fibrous powder with unique chemical properties. It is a compound derived from naphthalene, with a bromine atom at the 4-position and an amine group at the 1-position. This structure endows it with specific reactivity and utility in various chemical processes.

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.

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.