19387-54-3

Usage

Appearance

Yellow crystalline powder The compound has a yellow color and a crystalline structure in its solid form.

Uses

Rubber vulcanization accelerator, pesticide, dyes and pigments manufacturing It is commonly used in the production of tires, as a pesticide, and in the manufacturing of dyes and pigments.

Molecular weight

308.34 g/mol The mass of one mole of 2-[(4-nitrophenyl)thio]benzothiazole is 308.34 grams.

Melting point

155-158°C The compound transitions from a solid to a liquid state within this temperature range.

Toxicity

Ingestion or inhalation 2-[(4-nitrophenyl)thio]benzothiazole can be toxic if it is ingested or inhaled by humans or animals.

Skin and eye irritation

Upon contact The compound can cause irritation to the skin and eyes of those who come into contact with it.

Environmental hazards

Potential harm to aquatic life The chemical may have negative effects on the environment, particularly affecting aquatic organisms.

InChI:InChI=1/C13H8N2O2S2/c16-15(17)9-5-7-10(8-6-9)18-13-14-11-3-1-2-4-12(11)19-13/h1-8H

Upstream product

• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 13113-79-6 sodium 4-nitrobenzenethiolate 
• 100-00-5 4-chlorobenzonitrile 
• 2492-26-4 sodium 2-mercaptobenzothiazole 
• 7778-70-3 potassium 2-mercaptobenzothiazolate 
• 586-78-7 para-nitrophenyl bromide 
• 636-98-6 p-nitrobenzene iodide 
• 58654-89-0 triethylammonium o-bromophenyl dithiocarbamate salt 
• 1082738-80-4 triethylammonium o-iodophenyl dithiocarbamate salt 
• 149-30-4 2-Mercaptobenzothiazole 
• 350-46-9 4-Fluoronitrobenzene 
• 95-16-9 1,3-Benzothiazole 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 137-07-5 2-amino-benzenethiol 

Downstream Products

• 92017-54-4 2-<(4-nitrophenyl)sulfonyl>benzothiazole 

Relevant academic research and scientific papers

Highly active mesoionic chalcogenone zinc(II) derivatives for C-S cross-coupling reactions

The first mesoionic heavier chalcogenones, L1-L3 [L1 = 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-selone; L2 = 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-thione; L3 = 1-(benzyl)-2-3(methyl)-4-phenyltriazolin-5-selone], were isolated and characterised. Density functional theory was used to obtain insights into the σ donor and π accepting nature of mesoionic chalcogenones. Using these new ligands, a series of the first zinc(ii) mesoionic chalcogenone complexes were isolated. Three mono nuclear zinc(ii) chalcogenone complexes, [(L1)Zn(Cl)2(HOMe)] (1), [(L2)Zn(Cl)2(HOMe)] (3) and [(L2)Zn(Br)2(HOMe)] (4), and two dinuclear zinc complexes, [(L1)Zn(Br)(μ2-Br)]2 (2) and [(L3)Zn(Br)(μ2-Br)]2 (5), containing mesoionic thione and selone ligands were synthesized and characterised. These new complexes 1-5 represent the first structurally characterized mesoionic chalcogenone supported metal derivatives. Furthermore, all zinc complexes were characterized by thermogravimetric analysis and UV-vis spectroscopy. The solid-state structures of all zinc complexes were determined by single-crystal X-ray diffraction. The catalytic activities of the zinc(ii) complexes in thioetherification reactions were investigated without scrubbing of oxygen. The scope of the catalytic reactions was explored with a wide range of thiophenols and aryl halides. The diaryl thioethers were obtained in very good yield under mild conditions. The present protocol furnishes a synthetic route for the C-S cross-coupling of thiophenols and aryl halides without scrubbing oxygen and moisture.

Homoleptic and heteroleptic Zn(ii) selone catalysts for thioetherification of aryl halides without scrubbing oxygen

Five new mononuclear tetra-coordinated zinc(ii) selones, [Zn(L1)2Cl2] (1), [Zn(L1)2Br2] (2), [{Zn(L2)4}{BF4}2] (3), [{Zn(L2)4}{ClO4}2] (4), and [Zn(L2)2Br2] (5), have been isolated from a one-pot reaction between the corresponding zinc(ii) salt and selone ligand, 1-methyl 3-naphthylmethylimidazoline-2-selone (L1) or 1-isopropyl 3-methylimidazoline-2-selone (L2). All these complexes were characterized by CHN analysis, FT-IR, NMR studies, and single-crystal X-ray crystallography techniques. The Zn(ii) center in 1-5 exhibits a distorted tetrahedral geometry. Besides, 1-5 were employed as catalysts in the thioetherification of aryl halides. The first zinc(ii) catalyst-mediated thioetherification of aryl halides without scrubbing oxygen was demonstrated. Catalysts 1-5 are highly active towards the cross-coupling reaction between aryl halides and thiophenols. The catalytic ability of 1-5 was explored in THF, toluene, and CH3CN solvents with different bases such as K2CO3, Cs2CO3, and NaOtBu. Interestingly, the zinc(ii) center attached to two selone ligands is much more catalytically active than that attached to four selone ligands.

Two-Phase Electrochemical Generation of Aryldiazonium Salts: Application in Electrogenerated Copper-Catalyzed Sandmeyer Reactions

The electrochemical generation of aryldiazonium salts from nitroarenes in a two-phase system (ethyl acetate/water) was reported for the first time. Some compounds including azo, azosulfone, and arylazides were prepared in good yields with good purity. Cathodically generated aryldiazoniums and anodically produced copper(Ι) ions were used to perform Sandmeyer reactions. To improve the method, an H-type self-driving cell equipped with a Zn rod as an anode was introduced and used for two-phase aryldiazonium production.

Anionic Bismuth(III) chloride cluster with diselenide countercations: Application in C-S cross coupling reactions

The first weakly coordinating anion (WCA) with reactive p-block cation (rPBC) type of [(Bi4Cl16)4-{(LSeSeL)2+}2], L = 1,3-bis(2-benzhydryl-4,6-dimethylphenyl)-1H-imidazole-2(3H), ion pair is reported. The tetranuclear anionic bismuth(III) cluster shows a new type of ladder structure with two different types of Bi(III) coordination modes. In the solid state structure, the tetranuclear bismuth(III) cluster is sandwiched by two diselenide cations through hydrogen bonding interactions. Besides, this ion pair has been efficaciously employed as catalyst in C-S cross-coupling reactions under optimized reaction condition. This ion pair depicted a wide range of substrate scope with different thiols and aryl halides.

Copper(I)-Catalyzed Tandem One-Pot Synthesis of 2-Arylthiobenzothiazoles and 2-Arylthiobenzoxazoles in Water

An efficient tandem process for the preparation of 2-arylthiobenzothiazoles has been developed. By condensation of 2-aminobenzenethiol with tetramethylthiuram disulfide (TMTD), 2-mercaptobenzothiazoles was in situ generated, which susequently underwent coupling with iodobenzenes to give the desired 2-arylthiobenzothiazoles fluently in a one-pot manner. This method can also be used for the synthesis of 2-arylthiobenzoxazoles. Inexpensive metal catalyst and ligand, mild reaction temperature, and water as solvent make this protocol practically valuable and useful in organic synthesis.

Efficient C-S cross-coupling of thiols with aryl iodides catalyzed by Cu(OAc)2·H2O and 2,2′-biimidazole

The classical Ullmann C-S cross coupling reaction of aryl iodides with aromatic/alkyl thiols under catalysis of 15 mol% Cu(OAc)2· H2O and 15 mol% 2,2′-biimidazole works at 80°C in DMSO for 3 h to provide a variety of aryl sulfides in good to excellent yields. The classical Ullmann C-S cross coupling reaction of aryl iodides with aromatic/alkyl thiols under catalysis of 15 mol% Cu(OAc)2· H2O and 15 mol% 2,2′-biimidazole works at 80°C in DMSO for 3 h to provide a variety of aryl sulfides in good to excellent yields. Copyright

Synthesis of heteroaryl containing sulfides via enaminone ligand assisted, copper-catalyzed C-S coupling reactions of heteroaryl thiols and aryl halides

The C-S cross coupling reactions between electron deficient heteroaryl thiols and aryl halides have been smoothly performed to provide various heteroaryl containing sulfides in the presence of copper catalyst and enaminone ligand. the Partner Organisations 2014.

Copper oxide nanoparticle-catalyzed chalcogenation of the carbon-hydrogen bond in thiazoles: Synthesis of 2-(organochalcogen) thiazoles

We present (homepage: www.ufsm.br) herein the application of copper nanoparticles/dio-rganyl dichalcogenides to promote the synthesis of 2-(organochalcogen)thiazoles via direct carbon-hydro-gen bond activation in thiazoles. A systematic study of the catalytic system revealed that the presence and amount of base played an essential role in this reaction. The results revealed that electron-donating and electron-withdrawing substituents, in the aromat-ic ring bonded to the chalcogen atom of diorganyl di-chalcogenides, required one equiv. of base, while when neutral substituents were present two equiv. of base were needed to deliver the products in similar yields.

Substrate-promoted ligand-free CuI catalyzed S-arylation of 2-mercaptobenzothiazoles with aryl iodides in water

A green and efficient method has been developed for the cross-coupling of 2-mercaptobenzothiazoles with aryl iodides in water. The reactions proceeded smoothly under ligand-free conditions in the presence of TBAB to give the corresponding products in good yields. The protocol showed good tolerance toward a variety of functional groups. A substrate-promoted mechanism for this catalytic reaction has been proposed.

The [Cu]-catalyzed SNAR reactions: Direct amination of electron deficient aryl halides with sodium azide and the synthesis of arylthioethers under Cu(II) - Ascorbate redox system

A one pot [Cu]-promoted SNAr reaction of electron-deficient halobenzenes with sodium azide and the reduction of the intermediate aryl azides under the same Cu(II)-ascorbate redox conditions leading to anilines has been documented. Control experiments revealed that both ascorbate and proline play important role in the reaction path way. Further, the use of this catalytic Cu(II)-ascorbate redox system has been explored for the synthesis of arylthioethers.