7499-66-3

Basic information

• Product Name: 2-Amino-6-bromonaphthalene
• Synonyms: 6-BroMo-2-naphthalenaMine;NSC 407685;6-broMo-2-aMinonaphthalene;6-Bromo-2-naphthylamine, 6-Bromonaphthalen-2-amine;2-Amino-6-bromophthalene;2-Amino-6-bromonaphthalene;6-Bromonaphthalen-2-ylamine;2-Naphthalenamine, 6-bromo-
• CAS NO: 7499-66-3
• Molecular Formula: C₁₀H₈BrN
• Molecular Weight: 222.08122
• EINECS: 1308068-626-2
• Product Categories: Amines;Aromatics
• Mol File: 7499-66-3.mol

Chemical Properties

• Melting Point: 128 °C
• Boiling Point: 364.4 °C at 760 mmHg
• Flash Point: 174.2 °C
• Appearance: /
• Density: 1.563 g/cm³
• Vapor Pressure: 1.69E-05mmHg at 25°C
• Refractive Index: 1.718
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 3.66±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-6-bromonaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-bromonaphthalene(7499-66-3)
• EPA Substance Registry System: 2-Amino-6-bromonaphthalene(7499-66-3)

Safety Data

• Hazardous Substances Data: 7499-66-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Amino-6-bromonaphthalene is used as a key intermediate in the synthesis of various organic compounds, particularly in the preparation of alkylsulphanylnaphthalenes. Its presence allows for the formation of new chemical bonds and the creation of a diverse range of molecules with different properties and applications.
Used in the Synthesis of Naphthylisothiocyanates:
In the field of liquid crystals and mesomorphic materials, 2-Amino-6-bromonaphthalene is utilized as a starting material for the synthesis of novel naphthylisothiocyanates. These compounds exhibit unique mesomorphic properties, which make them valuable for the development of advanced materials with potential applications in display technologies and other industries.
Used in Pharmaceutical and Chemical Research:
Due to its distinctive structure, 2-Amino-6-bromonaphthalene can be employed as a building block in the design and synthesis of new pharmaceutical agents or chemical probes. Its reactivity and the presence of both bromine and amino functional groups make it a promising candidate for the development of bioactive molecules with potential therapeutic applications.

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

Upstream product

• 15231-91-1 6-bromo-naphthalen-2-ol 
• 7664-41-7 ammonia 
• 13720-04-2 1,6-dibromonaphthalen-2-amine 
• 10034-85-2 hydrogen iodide 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 330803-80-0 6-bromo-naphthalene-2-carbonyl azide 
• 4133-35-1 6-bromo-2-tetralone 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 133277-09-5 6-bromo-2-oximino-1,2,3,4-tetrahydronaphthalene 
• 71590-31-3 6-bromo-2-aminonaphthalene hydrochloride 
• 869114-68-1 6-bromo-2-N-tert-butoxycarbonylaminonaphthalene 
• 91-59-8 naphthalen-2-ylamine 
• 3230-35-1 6-nitro-2-naphthylamine 

Downstream Products

• 71590-32-4 N-(6-bromo-[2]naphthyl)-acetamide 
• 5043-03-8 6?bromo?N,N?dimethylnaphthalen?2?amine 
• 324-41-4 2-bromo-6-fluoronaphthalene 
• 90134-00-2 1-(3-sulfonatopropyl)-4-<β-<2-(di-n-butylamino)-6-naphthyl>vinyl>pyridinium betaine 
• 5043-05-0 6-(N,N-dimethylamino)-2-naphthoic acid 
• 305835-80-7 6-(methylamino)-2-bromonaphthalene 
• 590417-29-1 (6-aminonaphthalen-2-yl) boronic acid 
• 590417-33-7 2-bromo-6-sulfamoylaminonaphthalene 
• 129667-70-5 6-amino-2-naphthalenecarbonitrile 
• 1132940-88-5 N-[6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)naphthalen-2-yl]methanesulfonamide 
• 3989-47-7 N-(naphthalen-2-yl)methanesulfonamide 
• 1132935-63-7 N-(6-(3-(tert-butyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl)methanesulfonamide 
• 1423686-08-1 C₂₉H₂₄N₂O₅ 
• 1423694-06-7 C₃₀H₂₆N₂O₅ 

Relevant articles and documents

Concise synthesis of 12a-methyl-11-aryl-1,2-dihydrobenzo[f]pyrrolo[1,2-a]quinolin-3(12aH)-ones as racemic 14-azaestrogen analogs

A concise method for the synthesis of 14-azasteroid analogs with angular methyl group at C-13 of the steroidal nucleus has been reported in this paper. We have developed an interesting cascade reaction of arylacetylenes and N-(naphthalen-2-yl)pent-4-ynamides under gold (III)-catalysis to produce novel tetracyclic 12a-methyl-11-aryl-1,2-dihydrobenzo[f]pyrrolo[1,2-a]quinolin-3(12aH)-ones which may be viewed as 14-azaestrogen analogs.

Organic electroluminescent compounds and organic electroluminescent device using the same

The present invention relates to an organic electroluminescent compound applied to a hole transfer material, which is characterized by being presented by chemical formula 1-1 and chemical formula 1-2. The organic electroluminescent compound according to the present invention can manufacture an organic electroluminescent device having improved light emitting efficiency and life properties, when applied to a hole transfer layer of the organic electroluminescent device.

Enantioselective Construction of Axially Chiral Amino Sulfide Vinyl Arenes by Chiral Sulfide-Catalyzed Electrophilic Carbothiolation of Alkynes

The enantioselective construction of axially chiral compounds by electrophilic carbothiolation of alkynes is disclosed for the first time. This enantioselective transformation is enabled by the use of a Ts-protected bifunctional sulfide catalyst and Ms-protected ortho-alkynylaryl amines (Ts=tosyl; Ms=mesyl). Both electrophilic arylthiolating and electrophilic trifluoromethylthiolating reagents are suitable for this reaction. The obtained products of axially chiral vinyl–aryl amino sulfides can be easily converted into biaryl amino sulfides, biaryl amino sulfoxides, biaryl amines, vinyl–aryl amines, and other valuable difunctionalized compounds.

Discovery and Development of Metal-Catalyzed Coupling Reactions in the Synthesis of Dasabuvir, an HCV-Polymerase Inhibitor

Dasabuvir (1) is an HCV polymerase inhibitor which has been developed as a part of a three-component direct-acting antiviral combination therapy. During the course of the development of the synthetic route, two novel coupling reactions were developed. First, the copper-catalyzed coupling of uracil with aryl iodides, employing picolinamide 16 as the ligand, was discovered. Later, the palladium-catalyzed sulfonamidation of aryl nonaflate 33 was developed, promoted by electron-rich palladium complexes, including the novel phosphine ligand, VincePhos (50). This made possible a convergent, highly efficient synthesis of dasabuvir that significantly reduced the mutagenic impurity burden of the process.

6-bromo-2-aminonaphthalene preparation method

The invention provides a 6-bromo-2-aminonaphthalene preparation method. According to the present invention, the easily-available and inexpensive starting materials such as 2-aminonaphthalene, bromine,di-tert-butyl dicarbonate and the like are used; most of the intermediates are not required to be purified and directly enter the next step so as to substantially improve the consistency of the process; the high temperature and high pressure special reaction is not used so as to reduce the production risks; the yields of each reaction are high while the quality of the product meets the requirement; the amount of the three-waste is low so as to reduce the environmental protection pressure of the factory and meet the national conditions; and the product is refined by using the slat forming method so as to substantially improve the purity of the product.

A N, N - diaryl - 2 - bromo - 6 - naphthylamine synthetic method and its application

The invention discloses a synthetic method of N, N-diaryl-2-bromine-6-naphthylamine. The synthetic method comprises the step of carrying out C-N coupled reaction on halogenated arene and a 6-bromine-2-naphthylamine unit to obtain an N, N-diaryl-2-bromine-6-naphthylamine unit. The invention also discloses application of N, N-diaryl-2-bromine-6-naphthylamine, namely, N, N-diaryl-2-bromine-6-naphthylamine provided by the invention is adopted as the raw material to prepare an organic semiconductor material; compared with the conventional synthetic method, the synthetic method of N, N-diaryl-2-bromine-6-naphthylamine provided by the invention is simple in synthetic route and high in comprehensive yield; the organic semiconductor material which contains a diaryl naphthyl amine functional unit and is prepared from N, N-diaryl-2-bromine-6-naphthylamine provided by the invention is relatively high in hole mobility and thin film morphology stability.

Discovery of potent macrocyclic HCV NS5A inhibitors

HCV NS5A inhibitors have demonstrated impressive in vitro virologic profiles in HCV replicon assays and robust HCV RNA titer reduction in the clinic making them attractive components for inclusion in an all oral fixed-dose combination (FDC) regimen for the treatment of HCV infection. Merck's effort in this area identified MK-4882 and MK-8325 as early development leads. Herein, we describe the discovery of potent macrocyclic NS5A inhibitors bearing the MK-8325 or MK-4882 core structure.

Substituted benzoquinazolinones. Part 2: Synthesis of amino-, and sulfanyl-derivatives of benzo[f]- and benzo[h]quinazolinones

Amino- and sulfanyl-derivatives of benzoquinazolinones 16a-c, 20a-c and 21a-c were prepared under palladium-catalyzed Buchwald-Hartwig coupling reaction using bromobenzoquinazolinones 15, 19a, 19b and 1-substituted piperazines or mercaptans. The combination of Pd(OAc)2 with XantPhos proved to be the best for these conversions in the presence of KOt-Bu, in 1,4-dioxane as a solvent, at 90-100 °C. The 8-bromobenzo[f]quinazolin-1(2H)-one 15 was synthesized via condensation of the ethyl or tert-butyl 2-amino-8-bromonaphthalene-1-carboxylate 6, 10 with formamide, followed by reaction with 3,4-dimethoxybenzyl bromide. However, the 6-bromobenzo[h]quinazolin-4(3H)-ones 19a, 19b were prepared from ethyl 4-bromo-1-[(tert-butoxycarbonyl)amino]naphthalene-2-carboxylate (17). Biological screening of the potential cytotoxicity of compounds 16a, 20a, 20c on HT29 and HCT116 cell lines, has shown that compound 20a has a significant anticancer activity.

N-(1-HYDROXY-3-(PYRROLIDINYL)PROPAN-2-YL)PYRROLIDINE-3-CARBOXAMIDE DERIVATIVES AS GLUCOSYLCERAMIDE SYNTHASE INHIBITORS

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and compounds I for use to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).

Reduction of hydrazines to amines with aqueous solution of titanium(iii) trichloride

N-N bond cleavage in hydrazines is widely used in the preparation of amines and thus occupies a significant place in organic synthesis. In this paper, we report a new method for the reductive cleavage of N-N bonds in hydrazines by commercially available and cheap aqueous titanium(iii) trichloride. The reaction proceeds smoothly under a broad pH range from acidic to neutral and basic conditions to afford amines in good yields. This method is compatible with substrates containing functionalities such as C-C double bonds, benzyl-nitrogen bonds, benzyloxy and acyl groups. The Royal Society of Chemistry 2011.