21969-12-0

Basic information

• Product Name: 1-[(4-BROMOPHENYL)SULFANYL]-4-NITROBENZENE
• Synonyms: 4-BROMOPHENYL 4-NITROPHENYL SULFIDE;1-[(4-BROMOPHENYL)SULFANYL]-4-NITROBENZENE;(4-BroMophenyl)(4-nitrophenyl)sulfane
• CAS NO: 21969-12-0
• Molecular Formula: C₁₂H₈BrNO₂S
• Molecular Weight: 310.17
• Mol File: 21969-12-0.mol

Chemical Properties

• Boiling Point: 452.2°Cat760mmHg
• Flash Point: 227.3°C
• Appearance: /
• Density: 1.63g/cm³
• Vapor Pressure: 6.14E-08mmHg at 25°C
• Refractive Index: 1.701
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-[(4-BROMOPHENYL)SULFANYL]-4-NITROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(4-BROMOPHENYL)SULFANYL]-4-NITROBENZENE(21969-12-0)
• EPA Substance Registry System: 1-[(4-BROMOPHENYL)SULFANYL]-4-NITROBENZENE(21969-12-0)

Safety Data

• Hazardous Substances Data: 21969-12-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-[(4-BROMOPHENYL)SULFANYL]-4-NITROBENZENE is used as a key intermediate in organic synthesis for the production of a variety of substituted benzene derivatives. Its unique structure allows for further chemical reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Chemical Research:
In the field of chemical research, 1-[(4-BROMOPHENYL)SULFANYL]-4-NITROBENZENE serves as a model compound for studying the properties and reactions of nitrobenzene derivatives. It aids researchers in understanding the reactivity and behavior of similar compounds, contributing to the advancement of chemical knowledge.
Used in Pharmaceutical Industry:
1-[(4-BROMOPHENYL)SULFANYL]-4-NITROBENZENE is used as a building block in the development of pharmaceutical compounds. Its structural features make it a promising candidate for the creation of new drugs with potential therapeutic applications.
Used as a Precursor for Synthesis of Other Organic Compounds:
Due to its reactive functional groups, 1-[(4-BROMOPHENYL)SULFANYL]-4-NITROBENZENE is utilized as a precursor in the synthesis of other organic compounds. It can be further modified or transformed to produce a range of chemical products with diverse applications.

InChI:InChI=1/C12H8BrNO2S/c13-9-1-5-11(6-2-9)17-12-7-3-10(4-8-12)14(15)16/h1-8H

Upstream product

• 101-59-7 4-amino-4'-nitrodiphenyl sulfide 
• 106-53-6 para-bromobenzenethiol 
• 100-00-5 4-chlorobenzonitrile 
• 40973-69-1 4-bromo-benzenethiol; potassium salt 
• 636-98-6 p-nitrobenzene iodide 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 350-46-9 4-Fluoronitrobenzene 
• 5335-84-2 bis(4-bromophenyl)disulfide 
• 100-01-6 4-nitro-aniline 
• 5467-74-3 4-Bromophenylboronic acid 
• 1849-36-1 para-nitrobenzenethiol 
• 636-99-7 4-nitrophenylhydrazine hydrochloride 
• 586-76-5 4-Bromobenzoic acid 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 37750-33-7 (4-bromophenyl)(4-aminophenyl)thioether 
• 75124-91-3 1-bromo-4-((4-nitrophenyl)sulfonyl)benzene 
• 105583-13-9 4-bromo-4'-nitro-diphenyl sulphoxide 
• 7500-08-5 (4-iodophenyl)(4-nitrophenyl)thioether 
• 865179-25-5 1-(4-nitrophenylthio)-4-(4-bromophenylthio)benzene 
• 865179-27-7 I(C₆H₄S-4)2C₆H₄NO₂-4 
• 865179-29-9 ((4-nitrophenylthio)phenyl)((4-bromophenylthio)phenyl)thioether 
• 865179-30-2 C₂₄H₁₆INO₂S₃ 
• 865179-31-3 1-(4-nitrophenylthio)phenylthio-4-(4-bromophenylthio)phenylthio-benzene 
• 79995-57-6 acetic acid-[4-(4-bromo-phenylsulfanyl)-anilide] 
• 90309-21-0 acetic acid-[4-(4-bromo-benzenesulfinyl)-anilide] 
• 65082-45-3 1-(4-chlorophenylsulfonyl)-4-bromobenzene 
• 24535-57-7 1-bromo-4-(4-chlorophenylsulfanyl)-benzene 
• 875232-53-4 [4-(4-bromo-benzenesulfonyl)-phenyl]-[2]pyridyl-amine 

Relevant articles and documents

CuMoO4 Bimetallic Nanoparticles, An Efficient Catalyst for Room Temperature C?S Cross-Coupling of Thiols and Haloarenes

CuII catalyst is less efficient at room temperature for C?S cross-coupling. C?S cross-coupling by CuII catalyst at room temperature is not reported; however, doping of copper with molybdenum metal has been realized here to be more efficient for C?S cross-coupling in comparison to general CuII catalyst. The doped catalyst CuMoO4 nanoparticle is found to be more efficient than copper. The catalyst works under mild conditions without any ligand at room temperature and is recyclable and effective for a wide range of thiols and haloarenes (ArI, ArBr, ArF) from milligram to gram scale. The copper-based bimetallic catalyst is developed and recognized for C?S cross-coupling of haloarenes with alkyl and aryl thiols.

DIAMINE COMPOUND AND POLYIMIDE PRECURSOR AND POLYIMIDE FILM PREPARED BY USING SAME

The present invention can provide a polyimide precursor whose molecular weight is significantly increased by improving reactivity during polymerization by including a sulfonyl group and a novel diamine having asymmetry as a polymerization component. Accordingly, the present invention can provide a polyimide film having significantly improved mechanical and thermal properties while maintaining optical properties of a polyimide containing a sulfonyl group.COPYRIGHT KIPO 2020

Metal-Free Cercosporin-Photocatalyzed C-S Coupling for the Selective Synthesis of Aryl Sulfides under Mild Conditions

Aryl sulfides are important motifs of bioactive molecules, which are generally synthesized by transition metal-based coupling reactions under harsh conditions. Herein, we developed a new method that visible light along with cercosporin, produced by liquid fermentation and functioned as a cost-effective and environmentally friendly photocatalyst, prompted the selective synthesis of aryl sulfides through C–S coupling of thiols and diazonium salts under mild conditions. Furthermore, this method can also be performed with a great conversion by the direct use of cercosporin-containing fermentation supernatant as catalytic system without organic solvent extraction.

C-S coupling with nitro group as leaving group via simple inorganic salt catalysis

An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition-elimination mechanism.

Cu(I)-PNF, an organic-based nanocatalyst, catalyzed C-O and C-S cross-coupling reactions

Peptide nanofiber has been prepared via a self-assembly protocol and decorated with Cu(I) to prepare a nanostructural catalyst. The catalytic activity of this prepared nanomaterial (Cu(I)-PNF) was examined in C-O and C-S cross-coupling reactions. Compared with conventional copper-ligand catalytic systems, CuNP-PNF has unique advantages such as water solubility, high efficiency, and low cost, which makes it a highly efficient and beneficial catalyst to reuse in cross-coupling reactions.

Palladium-Catalyzed Oxidative Cross-Coupling of Arylhydrazines and Arenethiols with Molecular Oxygen as the Sole Oxidant

A highly efficient palladium-catalyzed oxidative cross-coupling of arylhydrazines and arenethiols with molecular oxygen as the sole oxidant to afford unsymmetrical diaryl sulfides has been developed. The only byproducts are nitrogen and water. A broad range of functional groups, even the reactive iodides, are tolerated and thus offer the opportunity for further functionalization.

A quick Chan-Lam C-N and C-S cross coupling at room temperature in the presence of square pyramidal [Cu(DMAP)4I]I as a catalyst

A rapid and efficient protocol for C-N and C-S cross coupling has been developed using a new square pyramidal copper complex, [Cu(DMAP)4I]I. The complex was successfully synthesized via a disproportionation reaction of CuI and DMAP in DMSO. The catalytic activity of the complex was found to be excellent for Chan-Lam coupling reaction between aryl boronic acid and amine, amide, azide or thiol. The reaction could be carried out in the presence of only 2 mol% of the copper catalyst in methanol at room temperature within a short time.

Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: An electrophile-nucleophile dual activation by [Omim]Br for the reaction

A facile aromatic nucleophilic substitution (SNAr) reaction in recyclable [Omim]Br under relatively mild conditions has been described. An electrophile-nucleophile dual activation by [Omim]Br is also discovered based on control experiments, 1H NMR and IR spectroscopies. This chemistry provides an efficient and metal-free approach for the generation of Caryl-X (XS, N, O) bonds, many of which are significant synthetic intermediates or drugs, making this methodology attractive to both synthetic and medicinal chemistry.

Synthesis of molecular chains: Application of cross-coupling and bromo by iodo exchange reactions

The synthesis of a series of molecular chains by use of C-S, C-N and C-Alkyne cross coupling, as well as bromo by iodo exchange reactions, has been reported. Two different types of chains R-C6H4-S-C6H4-CC-C6H4-NH-C6H4-Br, and R-C6H4-S-C6H4-NH-C6H4-CC-C6H4-Br (R=MeO, CN, NO2) could be obtained starting from the same thioether but applying different reaction sequences. Compounds R-C6H4-CC-C6H4-S-C6H4-NH-C6H4-Br were prepared from diaryl acetylenes after two bromo by iodo replacements alternated with a C-S and a C-N cross coupling.

Ascorbic Acid Promoted Metal-Free Synthesis of Aryl Sulfides with Anilines Nitrosated in Situ by tert -Butyl Nitrite

A mild, metal-free synthesis of aryl sulfides has been disclosed. Aryl diazonium ion was generated by the in situ nitrosation of aniline, and it was reduced by ascorbic acid (vitamin C) to form aryl radical, which underwent a thiolation with disulfide to yield aryl sulfide. The reaction proceeded smoothly without heating or irradiation. This strategy was also expanded to the synthesis of aryl selenides.