4-Chlorophenyl phenyl sulfone

Base Information

• Chemical Name: 4-Chlorophenyl phenyl sulfone
• CAS No.: 80-00-2
• Deprecated CAS: 8012-45-1
• Molecular Formula: C12H9ClO2S
• Molecular Weight: 252.721
• Hs Code.: 2904909090
• European Community (EC) Number: 201-242-1
• NSC Number: 404335
• UNII: 7NVM546U2M
• DSSTox Substance ID: DTXSID9042259
• Nikkaji Number: J3.850D
• Wikidata: Q27268626
• NCI Thesaurus Code: C185138
• ChEMBL ID: CHEMBL3188889
• Mol file: 80-00-2.mol

Synonyms:Sulfone;Sulfones

Chemical Property of 4-Chlorophenyl phenyl sulfone

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 2.48E-06mmHg at 25°C
• Melting Point: 90-94 °C(lit.)
• Refractive Index: 1.602
• Boiling Point: 402.8 °C at 760 mmHg
• Flash Point: 197.4 °C
• PSA: 42.52000
• Density: 1.331 g/cm³
• LogP: 4.25360
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: acetone: soluble74.4 g/100ml at 20°C(lit.)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 252.0011784
• Heavy Atom Count: 16
• Complexity: 306

Purity/Quality:

97% ^*data from raw suppliers

4-Chlorophenyl Phenyl Sulfone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Organochlorine Pesticides
• Canonical SMILES: C1=CC=C(C=C1)S(=O)(=O)C2=CC=C(C=C2)Cl
• Uses: Sulfenone is an impurity of Dapson (D193250), an antibacterial used in the treatment of dermatitis herpetiformis. Acaricide. 4-Chlorophenyl Phenyl Sulfone is an impurity of Dapson (D193250), an antibacterial used in the treatment of dermatitis herpetiformis.

Technology Process of 4-Chlorophenyl phenyl sulfone

There total 61 articles about 4-Chlorophenyl phenyl sulfone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

1-Chloro-4-iodobenzene (637-87-6) + sodium benzenesulfonate (873-55-2) → 4-Chlorophenyl phenyl sulfone (80-00-2,8012-45-1)

Guidance literature:

With C₁₁H₂₀O₄*2C₁₈H₃₇NO₅; copper(I) bromide; In water; at 100 ℃; for 12h;

DOI:10.1016/j.molliq.2021.117464

Reference yield: 96.0%

bis(4-chlorophenyl)iodonium triflate + sodium benzenesulfonate (873-55-2) → 4-Chlorophenyl phenyl sulfone (80-00-2,8012-45-1)

Guidance literature:

In N,N-dimethyl-formamide; at 90 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1021/ol303248h

Reference yield: 92.0%

iodobenzene (591-50-4) + sodium p-chlorobenzenesulphinate (14752-66-0) → 4-Chlorophenyl phenyl sulfone (80-00-2,8012-45-1)

Guidance literature:

With caesium carbonate; In dimethyl sulfoxide; at 110 ℃; for 24h; Green chemistry;

DOI:10.1039/C8NJ02677G

upstream raw materials:

phenyl p-chlorophenyl sulfide

methyl p-chlorobenzenesulphonate

4-chlorobenzenesulfonyl chloride

benzene

Downstream raw materials:

(4-chloro-3-nitro-phenyl)-(3-nitro-phenyl)-sulfone

p-hydroxyphenyl p-tolyl sulfone

3-(4-chlorophenylsulfonyl)-1-nitrobenzene

4'-Phenylsulfonyl-3,5-di-tert-butyl-<1,1'-biphenyl>-4-ol

Refernces

On the development of a nucleophilic methylthiolation methodology

10.1039/d0ob01149e

The study presents a novel nucleophilic methylthiolation methodology that enables the incorporation of the CH3S- group into activated carbons through either conjugate additions or substitutions reactions. The researchers utilized a range of chemicals, including chalcones, acyl ester derivatives, Morita-Baylis-Hillman acetates, and methylthiomethyl esters as the primary substrates and reagents. Methanethiol, traditionally used for methylthiolation, was replaced with these novel reagents due to its flammability and toxicity. The study aimed to develop a safer, low-cost, transition-metal-free method that exhibits good group tolerance and yields moderate to excellent results. Key chemicals involved in the reaction mechanism include potassium trichloroacetate, acetic acid, and camphorsulfonic acid (CSA) as an organocatalyst. The reaction products were further utilized to synthesize sulfoxides and sulfones, demonstrating the synthetic utility of the methodology. The study also involved theoretical calculations using Density Functional Theory to investigate the reaction mechanism, confirming the role of sulfurane and sulfonium ylide as key intermediates and the importance of a Pummerer rearrangement in the formation of the reagent.