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Sulfenone is an organic compound that serves as an impurity in Dapson (D193250), an antibacterial agent used for treating dermatitis herpetiformis. It is also known for its potential use as an acaricide.

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  • 80-00-2 Structure
  • Basic information

    1. Product Name: Sulfenone
    2. Synonyms: LABOTEST-BB LT00159657;1-CHLORO-4-(PHENYLSULFONYL)BENZENE;4-CHLORODIPHENYL SULFONE;4-CHLOROPHENYL PHENYL SULFONE;P-CHLOROPHENYL PHENYL SULFONE;SULFERONE;Sulfenone;SULPHENONE
    3. CAS NO:80-00-2
    4. Molecular Formula: C12H9ClO2S
    5. Molecular Weight: 252.72
    6. EINECS: 201-242-1
    7. Product Categories: Organic Building Blocks;Sulfones;Sulfur Compounds
    8. Mol File: 80-00-2.mol
  • Chemical Properties

    1. Melting Point: 90-94 °C(lit.)
    2. Boiling Point: 389 °C / 719mmHg
    3. Flash Point: 197.4 °C
    4. Appearance: solid
    5. Density: 1.3319 (estimate)
    6. Vapor Pressure: 2.48E-06mmHg at 25°C
    7. Refractive Index: 1.602
    8. Storage Temp.: -20°C Freezer, Under inert atmosphere
    9. Solubility: acetone: soluble74.4 g/100ml at 20°C(lit.)
    10. Stability: Stable. Incompatible with strong oxidizing agents.
    11. Merck: 14,8988
    12. CAS DataBase Reference: Sulfenone(CAS DataBase Reference)
    13. NIST Chemistry Reference: Sulfenone(80-00-2)
    14. EPA Substance Registry System: Sulfenone(80-00-2)
  • Safety Data

    1. Hazard Codes: Xn
    2. Statements: 20/21/22
    3. Safety Statements: 36
    4. WGK Germany: 3
    5. RTECS: WR5775000
    6. TSCA: Yes
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 80-00-2(Hazardous Substances Data)

80-00-2 Usage

Uses

Used in Pharmaceutical Industry:
Sulfenone is used as an impurity in Dapson (D193250) for the treatment of dermatitis herpetiformis, a chronic skin condition characterized by itchy blisters.
Used in Pest Control:
Sulfenone is used as an acaricide, which is a chemical agent designed to control or kill mites and ticks, helping to prevent infestations and the spread of diseases they may carry.
Used in Chemical Synthesis:
4-Chlorophenyl Phenyl Sulfone, an impurity of Dapson (D193250), is used in the synthesis of various chemical compounds, contributing to the development of new pharmaceuticals and other industrial applications.

Check Digit Verification of cas no

The CAS Registry Mumber 80-00-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 0 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 80-00:
(4*8)+(3*0)+(2*0)+(1*0)=32
32 % 10 = 2
So 80-00-2 is a valid CAS Registry Number.
InChI:InChI=1/C12H9ClO2S/c13-10-6-8-12(9-7-10)16(14,15)11-4-2-1-3-5-11/h1-9H

80-00-2 Well-known Company Product Price

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  • Aldrich

  • (194115)  4-Chlorophenylphenylsulfone  ≥97%

  • 80-00-2

  • 194115-100G

  • 4,359.42CNY

  • Detail

80-00-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Chlorophenyl Phenyl Sulfone

1.2 Other means of identification

Product number -
Other names Benzene, 1-chloro-4-(phenylsulfonyl)-

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:80-00-2 SDS

80-00-2Relevant articles and documents

Metal-free sulfonylation of arenes with: N -fluorobenzenesulfonimide via cleavage of S-N bonds: expeditious synthesis of diarylsulfones

Feng, Yueji,Tuo, Yanyan,Zhang, Xiaohui,Zheng, Qing-Zhong

supporting information, p. 768 - 772 (2022/02/03)

A novel metal-free sulfonylation of arenes with N-fluorobenzenesulfonimide (NFSI) toward the synthesis of diarylsulfones has been developed. The reaction represents a rare example of sulfonylation reaction using NFSI as an efficient sulfonyl donor and the first example of acid-mediated sulfonylation of unactivated arenes with NFSI via selective cleavage of S-N bonds. This protocol provides a concise approach for the construction of pharmaceutically and biologically important diarylsulfones. Applications in the functionalization of natural products (e.g., β-estradiol) and in the synthesis of a key intermediate to an inhibitor of farnesyl-protein transferase, as well as in the gram-scale synthesis of the EPAC2 antagonist, are demonstrated. This journal is

Visible-Light-Mediated Late-Stage Sulfonylation of Boronic Acids via N-S Bond Activation of Sulfonamides

Du, Xian,Li, Yihui,Luo, Yong,Xu, Dejing,Xu, Xiaohong,Xue, Can,Yuan, Han,Zhen, Jingsong

, p. 1986 - 1991 (2022/02/07)

A visible-light-mediated late-stage arylation of N-S bonds in sulfonamides has been developed with using readily available imines as sulfonyl radical source. Diverse complex sulfones could be synthesized by prefunctionalizaiton and subsequent N-S bond ary

On the important transition of sugar-based surfactant as a microreactor for C-S coupling in water: From micelle to vesicle

Ge, Xin,Lei, Qiuyun,Liao, Xiong,Liu, Xuemin,Song, Weili,Wu, Lei,Wu, Siyuan,Zhou, Shaodong

, (2021/09/15)

A reversible, temperature-induced micelle-to-vesicle transition of a sugar-based pseudogemini surfactant (C11D12) was employed for copper-catalyzed C-S coupling in water. The phase behavior and morphology of the C11D12 aqueous solution were investigated by DLS and cryo-TEM. The aggregates undergo a series of transitions upon increasing the temperature: spherical micelles were initially transformed into large vesicles, but they eventually transformed into smaller vesicles. The vesicular catalytic protocol accommodates an excellent substrate scope with moderate to high yields. The mechanisms of temperature-induced aggregate transition and vesicular catalysis were elucidated by experimental results and DFT calculations. It was revealed that the charge layer of the vesicle grants stronger nucleophilicity to the PhSO2-Cu-D12Ga intermediate. Furthermore, the aqueous reaction medium can be recycled and reused several times after easily separating the precipitated product.

Interfacing sugar-based surfactant micelles and Cu nanoparticles: A nanoreactor for C-S coupling reactions in water

Ge, Xin,He, Xi,Liu, Xuemin,Qian, Chao,Song, Weili,Yang, Jinguo,Zhou, Shaodong

supporting information, p. 6322 - 6329 (2021/09/10)

A simple and sustainable synergistic catalytic protocol by interfacing nanomicelles and metal nanoparticles (MNPs) is reported for C-S coupling reactions in water. The sugar-based surfactant GluM was synthesized by introducing a PEG chain to stabilize MNPs and self-assembled to form nanomicelles. Cu2O nanoparticles were generated via in situ reduction of copper salt in an aqueous solution of the sugar-based surfactant. The nature of the interaction between nanomicelles and Cu2O nanoparticles was revealed by XPS, XRD, in situ IR, TEM, and 1H NMR. A broad substrate scope with moderate to excellent yields was documented and the recycling of the GluM/Cu aqueous mixture was surprising.

Sulfonylation of Bismuth Reagents with Sulfinates or SO2through BiIII/BiV Intermediates

Zhao, Fengqian,Wu, Xiao-Feng

supporting information, p. 2400 - 2404 (2021/07/28)

Studies to explore the catalytic activities of main-group elements are attractive. We report here our study of sulfonylation of bismuth reagents with sulfinates or SO2 surrogates. Under oxidative conditions, triarylbismuthines and sulfinates were transformed into diaryl sulfones. A transition-metal-like two-electron redox process at the Bi center was achieved in this reaction. Sulfur dioxide generated in situ can also replace sulfinates to deliver the corresponding symmetric diaryl sulfones. A rational mechanism for this reaction was also proposed that involves a Bi(III)-Bi(V) manifold.

A Copper(I)-Catalyzed Sulfonylative Hiyama Cross-Coupling

Adenot, Aurélien,Anthore-Dalion, Lucile,Nicolas, Emmanuel,Berthet, Jean-Claude,Thuéry, Pierre,Cantat, Thibault

supporting information, p. 18047 - 18053 (2021/11/16)

An air-tolerant Cu-catalyzed sulfonylative Hiyama cross-coupling reaction enabling the formation of diaryl sulfones is described. Starting from aryl silanes, DABSO and aryliodides, the reaction tolerates a large variety of polar functional groups (amines, ketones, esters, aldehydes). Control experiments coupled with DFT calculations shed light on the mechanism, characterized by the formation of a Cu(I)-sulfinate intermediate via fast insertion of a SO2 molecule.

Method for synthesizing sulfone compounds under photocatalysis condition

-

Paragraph 0105-0109, (2021/03/31)

The invention belongs to the technical field of compound preparation, and particularly relates to a method for synthesizing sulfone compounds under a photocatalysis condition. Aromatic hydrazine and sulfinate are used as raw materials, and under the action of alkali and a solvent, a sulfone compound is generated through reaction under the condition of air or oxygen under the illumination of visible light. According to the method disclosed by the invention, aryl hydrazine is used as an arylation reagent, polyacid salt is used as a catalyst or an organic photosensitizer is used as a catalyst, and the sulfones compound can be efficiently synthesized by coupling with sulfinate under the condition of room temperature through visible light irradiation. The method has good substrate universalityand relatively mild reaction conditions, is not only a substitute for synthesizing sulfone compounds by coupling from simple substrates reported at present, but also broadens the new application of the polyacid salt in the field of photocatalysis.

Pd/NHC-catalyzed arylsulfonylation of boronic acids: A general and direct protocol to access diarylsulfones

Zhu, Haibo,Yang, Liu,Meng, Jia,Xie, Zongbo,Le, Zhang-Gao,Tu, Tao

supporting information, (2020/12/29)

For the first time, robust NHC-Pd complexes have been demonstrated as highly efficient catalysts in the direct arylsulfonylation of boronic acids. Remarkably, a broad number of diaryliodonium salts as powerful electrophilic arylation reagents are well compatible to form functional ortho-substituted diarylsulfones in satisfactory yields. Owing to the stronger σ-donor and weaker π-acceptor properties, the acenaphthoimidazolylidene ligands exhibit higher catalytic activities towards this challenging one-step arylsulfonylation reaction.

Micelle catalysis and extraction separation coupling method based on nonionic surfactant (by machine translation)

-

Paragraph 0057-0061, (2020/08/18)

The invention discloses a micelle catalysis and extraction separation coupling method based on a nonionic surfactant, and belongs to the technical field of chemical synthesis. M 202070 is used as a reaction medium, the Ullmann C-S coupling reaction is catalyzed, and the product is separated by directly heating to a cloud point after the reaction is completed. The method provided by the invention is mild in condition, convenient to operate, less in organic matter content in the reaction waste liquid, small in environmental pollution, green and environment-friendly; meanwhile, the yield of the aromatic sulfone can reach 75% or above, the extraction yield reaches 100%, and the method is suitable for industrial mass production. (by machine translation)

Selective oxidation of (hetero)sulfides with molecular oxygen under clean conditions

Liu, Kai-Jian,Deng, Ji-Hui,Yang, Jie,Gong, Shao-Feng,Lin, Ying-Wu,He, Jun-Yi,Cao, Zhong,He, Wei-Min

supporting information, p. 433 - 438 (2020/02/13)

The development of eco-friendly and switchable catalytic systems for the conversion of a sole raw-material into distinct high-value products is a particularly attractive concept and a daunting synthetic challenge. In the present work, the first example of efficient and selective oxidation of sulfides to sulfones and sulfoxides using molecular oxygen under clean conditions was established.

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