1155-00-6

Basic information

• Product Name: Bis(2-nitrophenyl) disulfide
• Synonyms: Bis-(2-nitrophenyl)-disulfid;Disulfide, bis(2-nitrophenyl);Disulfide, bis(o-nitrophenyl);Disulfide,bis(2-nitrophenyl);o,o'-Dinitrodiphenyl disulfide;O-NITROPHENYLDISULFIDE;O,O'-DINITROPHENYL DISULFIDE;1-Nitro-2-[(2-nitrophenyl)disulfanyl]benzene
• CAS NO: 1155-00-6
• Molecular Formula: C₁₂H₈N₂O₄S₂
• Molecular Weight: 308.33
• EINECS: 214-581-5
• Mol File: 1155-00-6.mol
• Article Data: 58

Chemical Properties

• Melting Point: 194-197 °C(lit.)
• Boiling Point: 441.9 °C at 760 mmHg
• Flash Point: 221.1 °C
• Appearance: yellow to yellow-green crystalline powder
• Density: 1.62 g/cm3 (-123.16℃)
• Vapor Pressure: 1.36E-07mmHg at 25°C
• Refractive Index: 1.6510 (estimate)
• Storage Temp.: Store at +15°C to +25°C.
• BRN: 1016770
• CAS DataBase Reference: Bis(2-nitrophenyl) disulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(2-nitrophenyl) disulfide(1155-00-6)
• EPA Substance Registry System: Bis(2-nitrophenyl) disulfide(1155-00-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1155-00-6(Hazardous Substances Data)

Usage

Description

Bis(2-nitrophenyl) disulfide is a yellow to yellow-green crystalline powder that serves as a versatile building block in the synthesis of various pharmaceutical compounds and as a sensor for zinc ions in PVC membrane electrodes.

Uses

Used in Pharmaceutical Industry:
Bis(2-nitrophenyl) disulfide is used as a building block for the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and therapeutic agents.
Used in Analytical Chemistry:
Bis(2-nitrophenyl) disulfide is used as a sensor for zinc ions in PVC membrane electrodes, enabling the detection and measurement of zinc ion concentrations in different samples.
Used in Organic Synthesis:
Bis(2-nitrophenyl) disulfide is used in the preparation of a series of 4-Azaindole inhibitors of c-Met kinase, which are important in the development of targeted cancer therapies.
Used in Mechanochemical Processes:
Bis(2-nitrophenyl) disulfide undergoes mechanochemical grinding with bis(4-chlorophenyl)disulfide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene catalyst via metathesis reaction to yield non-symmetrical heterodimer 4-chlorophenyl-2′-nitrophenyl disulfide, demonstrating its utility in mechanochemical synthesis.

Purification Methods

Purify the disulfide by recrystallisation from glacial AcOH or from *C6H6 and the yellow needles are dried in an oven at 100o until the odour of the solvent is absent. It is sparingly soluble in EtOH and Me2CO. [Bogert & Stull Org Synth Coll Vol I 220 1941, Bauer & Cymerman J Chem Soc 3434 1949, Beilstein 6 IV 1672.]

InChI:InChI=1/C12H8N2O4S2/c15-13(16)9-5-1-3-7-11(9)19-20-12-8-4-2-6-10(12)14(17)18/h1-8H

Upstream product

• 7669-54-7 2-nitrobenzenesulfenyl chloride 
• 14608-72-1 N-(2-nitro-benzenesulfenyl)-glycine methyl ester 
• 64-19-7 acetic acid 
• 88-73-3 2-Chloronitrobenzene 
• 2769-30-4 2-nitrophenyl thiocyanate 
• 62-53-3 aniline 
• 528-29-0 1,2-Dinitrobenzene 
• 141-52-6 sodium ethanolate 
• 123-54-6 acetylacetone 
• 51-17-2 benzoimidazole 
• 22024-99-3 2-nitrobenzenesulfenyl bromide 
• 10400-19-8 3-pyridinecarbonyl chloride 
• 41601-49-4 bis(2-nitrobenzenesulfenyl)amine 
• 594-71-8 2-chloro-2-nitro-propane 

Downstream Products

• 4875-10-9 o-nitrothiophenol 
• 861571-71-3 1,2-bis-(2-nitro-phenylsulfanyl)-ethene 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 22024-99-3 2-nitrobenzenesulfenyl bromide 
• 20834-65-5 (2,4-dinitro-phenyl)-(2-nitro-phenyl)-sulfide 
• 2253-67-0 bis-(2,4-dinitro-phenyl)-sulfide 
• 3058-47-7 methyl 2-nitrophenyl sulfide 
• 22057-28-9 (2-nitro-phenylsulfanyl)-acetone 
• 20940-09-4 2-(2-nitro-phenylsulfanyl)-1-phenyl-ethanone 
• 80-82-0 2-nitrobenzenesulfonic acid 
• 24290-27-5 (2-nitro-phenylsulfanyl)-acetic acid ethyl ester 
• 1950-72-7 2-nitro-benzenesulfonyl bromide 
• 3292-42-0 2-aminobenzenethiol hydrochloride 
• 7669-54-7 2-nitrobenzenesulfenyl chloride 

Relevant articles and documents

Bromonitromethane, a Versatile Electrophile: Reactions with Thiolates

Thiolate ions react with bromonitromethane to give nitronate ion and, initially, sulphenyl bromide which reacts with further thiolate ion to give disulphide; when the disulphide bears an appropriately placed nitrile function, intramolecular attack by the nitronate ion at this function and subsequent intramolecular displacement of thiolate ion yields aminothiophenes.

Synthesis and structural study of 1-(N,N-diethylamino)-2,2-bis(2-nitrophenylthio)ethene

The synthesis, variable temperature NMR spectra, and crystal structures of two crystalline forms, 2a and 2b, of the enamine 1-(N,N-diethylamino)-2,2-bis(2-nitrophenylthio)ethene have been obtained. Both forms crystallize in the monoclinic space group P21/a. The two phases have similar molecular structures but possess different intermolecular C - H ... O hydrogen bonding interactions. Both forms exhibit disorder within the NEt2 fragment at 298 K: sufficient disorder persisted with 2a (orange needles) down to 100 K to make the geometric parameters pertaining to the enamine fragment unreliable. The disorder was effectively eliminated on cooling 2b down (red colored blocks) to 150 K. Cell dimensions for the 2a-phase are at 100 K: a = 11.1030(4) A, b = 15.1325(7) A, c = 12.4504(7) A, β = 114.606(3)°, while for the 2b-phase at 150 K, a = 15.5206(4) A, b = 7.6958(2) A, c = 15.7137(3) A, β = 92.580(7)°. The C - N bond length in the β-form at 150 K of 1.335(3) A indicates considerable double bond character: the rotational barrier of the C - N bond in CDCl3 was calculated to be 52.4 kJ mol-1.

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Palladium-Catalyzed Picolinamide-Directed Benzylic C(sp3)?H Chalcogenation with Diaryl Disulfides and Diphenyl Diselenide

The first palladium-catalyzed direct benzylic C(sp3)?H chalcogenation with diaryl disulfides and diphenyl diselenide has been established. The coupling reaction proceeds between the thioether radical and palladiumcycle intermediate. Picolinamide serves as an excellent directing group for the C?H activation of benzylic C(sp3)?H and can be easily removed. The current protocol exhibits a relatively broad substrate scope and high functional group compatibility. A mechanistic study indicates that palladium(IV) intermediate is probably formed during the course of the reaction. (Figure presented.).

Biocatalytic synthesis of diaryl disulphides and their bio-evaluation as potent inhibitors of drug-resistant Staphylococcus aureus

Staphylococcus aureus is a WHO Priority II pathogen for its capability to cause acute to chronic infections and to resist antibiotics, thus severely impacting healthcare systems worldwide. In this context, it is urgently desired to discover novel molecules to thwart the continuing emergence of antimicrobial resistance. Disulphide containing small molecules has gained prominence as antibacterials. As their conventional synthesis requires tedious synthetic procedure and sometimes toxic reagents, a green and environmentally benign protocol for their synthesis has been developed through which a series of molecules were obtained and evaluated for antibacterial activity against ESKAPE pathogen panel. The hit compound was tested for cytotoxicity against Vero cells to determine its selectivity index and time-kill kinetics was determined. The activity of hit was determined against a panel of S. aureus multi-drug resistant clinical isolates. Also, its ability to synergize with FDA approved drugs was tested as was its ability to reduce biofilm. We identified bis(2-bromophenyl) disulphide (2t) as possessing equipotent antimicrobial activity against S. aureus including MRSA and VRSA strains. Further, 2t exhibited a selectivity index of 25 with concentration-dependent bactericidal activity, synergized with all drugs tested and significantly reduced preformed biofilm. Taken together, 2t exhibits all properties to be positioned as novel scaffold for anti-staphylococcal therapy.