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Bis(4-nitrophenyl) sulfide is a chemical compound that is typically presented as a yellow, crystalline solid. It belongs to the category of organosulfur and aromatic organic compounds, primarily composed of sulfur and nitrophenyl groups. This substance is particularly notable for its unusually strong electron-donating ability, which makes it useful in a variety of scientific and industrial applications. Additionally, it exhibits sulfide and nitro functionality which contributes to its reactivity or lack thereof under different conditions. It should be handled with care due to potential hazards associated with its reactive nature.

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  • 1223-31-0 Structure
  • Basic information

    1. Product Name: BIS(4-NITROPHENYL) SULFIDE
    2. Synonyms: 1,1’-thiobis[4-nitro-benzen;1-Nitro-4-[(4-nitrophenyl)sulfanyl]benzene;4,4’-Dinitrdiphenylsulphide;4,4'-Dinitrodiphenylsulphide;Benzene, 1,1'-thiobis[4-nitro-;p,p'-Dinitrodiphenyl sulfide;p-Nitrophenyl sulfide;p-Nitrophenylsulfide
    3. CAS NO:1223-31-0
    4. Molecular Formula: C12H8N2O4S
    5. Molecular Weight: 276.27
    6. EINECS: 214-950-0
    7. Product Categories: Diphenyl Sulfides (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research
    8. Mol File: 1223-31-0.mol
  • Chemical Properties

    1. Melting Point: 160°C
    2. Boiling Point: 487.4 °C at 760 mmHg
    3. Flash Point: 248.6 °C
    4. Appearance: White crystalline power
    5. Density: 1.4634 (rough estimate)
    6. Vapor Pressure: 3.54E-09mmHg at 25°C
    7. Refractive Index: 1.6930 (estimate)
    8. Storage Temp.: N/A
    9. Solubility: soluble in Acetone
    10. CAS DataBase Reference: BIS(4-NITROPHENYL) SULFIDE(CAS DataBase Reference)
    11. NIST Chemistry Reference: BIS(4-NITROPHENYL) SULFIDE(1223-31-0)
    12. EPA Substance Registry System: BIS(4-NITROPHENYL) SULFIDE(1223-31-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: 23/24/25-36/37/38
    3. Safety Statements: 26-36/37/39
    4. RIDADR: 2811
    5. WGK Germany:
    6. RTECS: WQ2150000
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 1223-31-0(Hazardous Substances Data)

1223-31-0 Usage

Uses

Used in Chemical Research:
Bis(4-nitrophenyl) sulfide is used as a reagent in chemical research for its strong electron-donating ability, which aids in various chemical reactions and synthesis processes.
Used in Pharmaceutical Industry:
Bis(4-nitrophenyl) sulfide is used as an intermediate in the synthesis of pharmaceutical compounds, leveraging its unique chemical properties to facilitate the production of drugs with desired therapeutic effects.
Used in Material Science:
Bis(4-nitrophenyl) sulfide is used as a component in the development of new materials, such as organic electronic devices, where its electron-donating properties can enhance the performance of these materials.
Used in Environmental Applications:
Bis(4-nitrophenyl) sulfide is used in environmental remediation processes, where its reactivity can be harnessed to detoxify or break down harmful substances in the environment.
Used in Analytical Chemistry:
Bis(4-nitrophenyl) sulfide is used as an analytical standard or reference material in various analytical techniques, such as spectroscopy and chromatography, to ensure accurate measurements and comparisons.

Check Digit Verification of cas no

The CAS Registry Mumber 1223-31-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,2 and 3 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1223-31:
(6*1)+(5*2)+(4*2)+(3*3)+(2*3)+(1*1)=40
40 % 10 = 0
So 1223-31-0 is a valid CAS Registry Number.
InChI:InChI=1/C12H8N2O4S/c15-13(16)9-1-5-11(6-2-9)19-12-7-3-10(4-8-12)14(17)18/h1-8H

1223-31-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Bis(4-nitrophenyl) Sulfide

1.2 Other means of identification

Product number -
Other names Benzene, 1,1‘-thiobis[4-nitro-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1223-31-0 SDS

1223-31-0Relevant articles and documents

Magnetically recoverable ferromagnetic 3D hierarchical core-shell Fe3O4@NiO/Co3O4 microspheres as an efficient and ligand-free catalyst for C–S bond formation in poly (ethylene glycol)

Vatandoust Namanloo, Ahad,Akhlaghinia, Batool,Mohammadinezhad, Arezou

, p. 446 - 461 (2020)

A simple and efficient protocol for the synthesis of diaryl thioethers from the reaction of thiourea with a wide variety of aryl halides, including aryl iodides, aryl bromides and aryl chlorides in the presence of 3D hierarchical core-shell Fe3O4@NiO/Co3O4 microspheres has been described. This reaction enables the one-pot synthesis of diaryl thioethers in good to high yields using a non-toxic and magnetically separable catalyst in PEG-400 as an eco-friendly, safe, inexpensive and thermally stable solvent. Magnetic separation and reusability of catalyst for eight times without any significant loss of activity, the use of a commercially available, eco-friendly, cheap and chemically stable sulfur transfer agent and solvent, operational simplicity, environmentally benign, easier work-up procedure and cost efficiency make this method a promising candidate for potential applications in some organic reactions. The catalytic activity of Fe3O4@NiO/Co3O4 as a novel and inexpensive catalyst was investigated in the C-S cross coupling reaction.

Synthesis of sulfides via reaction of aryl/alkyl halides with S8 as a sulfur-transfer reagent catalyzed by Fe3O4-magnetic-nanoparticles-supported L-Histidine-Ni(II)

Azadi, Gouhar,Taherinia, Zahra,Naghipour, Ali,Ghorbani-Choghamarani, Arash

, p. 303 - 313 (2017)

One-pot synthesis of symmetrical diaryl/alkyl sulfides in high yields from the reaction between aryl/alkyl halides and S8 can be carried out in a short period, using Fe3O4@SiO2@His@Ni(II) as a reusable catalyst. The present approach offers the advantages of a clean reaction, simple methodology and high efficiency, and avoids the use of a toxic catalyst.

Infrared spectroscopy of bis(4-nitrophenyl) disulfide grown on a Pb layer

McCluskey,Grover,Zhuravlev

, p. 1138 - 1139 (2002)

Crystal whiskers of bis(4-nitrophenyl) disulfide have been grown on a 100-nm thick Pb film from a supersaturated solution of p-nitrothiophenol. The whiskers preferentially grow on Pb but not on Si, In, or Ag. The crystals were characterized by electron microscopy and infrared spectroscopy. The optimized structure of the molecule was determined by ab initio calculations.

A novel heterogeneous nanocatalyst: 2-Methoxy-1-phenylethanone functionalized MCM-41 supported Cu(II) complex for C-S coupling of aryl halides with thiourea

Hajipour, Abdol R.,Fakhari, Farzaneh,Nabi Bidhendi, Gholamreza

, (2018)

An environmentally friendly copper-based catalyst supported on 2-Methoxy-1-phenylethanone functionalized MCM-41 was prepared and characterized by FT-IR, FE-SEM, TEM, XRD, EDX, BET and ICP techniques. The catalyst was applied for the C?S cross-coupling reaction of aryl halides with thiourea. Corresponding products were produced in good yields in aerobic conditions. The catalyst could be recovered and recycled for several times.

An efficient and recyclable catalytic system for carbon–sulfur coupling reaction and synthesis of 5-substituted 1H-tetrazoles

Ghorbani-Choghamarani, Arash,Moradi, Zahra,Azadi, Gouhar

, p. 237 - 251 (2018)

In this research paper, efficient and economical protocols for the synthesis of symmetrical sulfides and 5-substituted 1H-tetrazoles have been reported using Fe3O4@SBTU@Ni(II) as a heterogeneous and recoverable nanocatalyst. The noticeable features of this catalytic system are: operational simplicity, environmentally benign, easier work-up procedure, green and efficient synthetic entry to excellent yield of products in a high reusability and applicability to various starting materials and, therefore, cost efficiency.

Thiol-free route to diaryl sulfides by Cu catalyzed coupling of sodium thiosulfate with aryl halides

Nowrouzi, Najmeh,Abbasi, Mohammad,Latifi, Hadis

, p. 1550 - 1554 (2016)

A method for the synthesis of diaryl sulfides from aryl halides in polyethylene glycol was reported. Inodorous Na2S2O3·5H2O, which is readily available as a stable salt, is an effective source of sulfur in the presence of CuI as catalyst.

A simple, efficient and recyclable catalytic system for carbon-sulfur coupling of aryl halides with thioacetamide

Cai, Mingzhong,Yao, Ruiya,Chen, Lin,Zhao, Hong

, p. 349 - 354 (2014)

The carbon-sulfur coupling reaction of aryl halides with thioacetamide using an MCM-41-immobilized bidentate nitrogen copper(I) complex [MCM-41-2N-CuI] as an efficient heterogeneous catalyst is described. Developed catalytic system is found to be effective for the coupling reaction of aryl halides with thioacetamide providing moderate to high yield of diaryl sulfides. This heterogeneous copper catalyst exhibits higher activity than CuI and can be recovered by a simple filtration of the reaction solution and reused for at least 10 consecutive trials without any decreases in activity.

A simple and green synthesis of diaryl sulfides catalyzed by an MCM-41-immobilized copper(I) complex in neat water

Cai, Mingzhong,Xiao, Ruian,Yan, Tao,Zhao, Hong

, p. 55 - 60 (2014)

The heterogeneous carbon-sulfur bond formation reaction of aryl iodides with potassium thiocyanate was achieved in neat water at 130 C by using 5 mol% MCM-41-immobilized bidentate nitrogen/CuCl complex [MCM-41-2N-CuCl] as catalyst and Cs2CO3 as base, yielding a variety of diaryl sulfides in moderate to high yields. This heterogeneous copper catalyst can be easily prepared by a simple two-step procedure from commercially available and cheap reagents and recovered by a simple filtration and reused for 10 cycles without loss of catalytic activity.

CuI anchored onto mesoporous SBA-16 functionalized by aminated 3-glycidyloxypropyltrimethoxysilane with thiosemicarbazide (SBA-16/GPTMS-TSC-CuI): A heterogeneous mesostructured catalyst for: S -arylation reaction under solvent-free conditions

Ghodsinia, Sara S.E.,Akhlaghinia, Batool

, p. 3029 - 3049 (2019)

Herein, we report the novel synthesis of CuI anchored onto a cage-like mesoporous material (SBA-16), which was successfully functionalized by aminated 3-glycidyloxypropyltrimethoxysilane with thiosemicarbazide (SBA-16/GPTMS-TSC-CuI) into an efficient and highly recyclable heterogeneous catalyst. The as-synthesized mesostructured catalyst (SBA-16/GPTMS-TSC-CuI) was comprehensively characterized by different techniques, namely, FT-IR, FIR, SAXRD, XRD, XPS, BET, TEM, FE-SEM, EDX, EDX mapping, TGA, ICP-OES, and CHNS analyses. SBA-16 with a unique "super-cage" structure efficiently controlled the formation of dispersed organic and metal species in the mesoporous channels. These confined nanoparticles with a narrow particle size distribution (3-7 nm) exhibited excellent catalytic activity in the S-arylation reaction without necessitating the use of toxic solvents and/or expensive metal catalysts. Interestingly, the mesoporous catalyst was extremely stable under the reaction conditions and could be easily separated by a simple filtration process and reused for at least seven recycle runs (without any appreciable loss in catalytic activity). Due to the inimitable structure of the abovementioned mesostructured catalyst, the C-S coupling products of aryl halides with S8/thiourea under solvent-free conditions were obtained in good to excellent yields in remarkably reduced reaction times in comparison to those reported in earlier studies.

Preparation and Characterization of Ni-Modified Graphene Oxide Complex as an Efficient Catalyst for the Synthesis of Sulfides via Reaction of Arylhalides with S8 or Thiourea

Ghafouri-Nejad, Raziyeh,Hajjami, Maryam,Nejat, Razieh

, (2018)

In this work, complex of Ni-modified graphene oxide was prepared and characterized using FT-IR spectroscopy, SEM, XRD, TGA and ICP-OES techniques. This compound used as an efficient and recoverable catalyst for the C–S coupling reaction using sulfur-transfer reagents (S8 or thiourea). The catalyst was easily separated using a simple filtration and reusable without significant loss of their catalytic efficiency.

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