7205-98-3

Basic information

• Product Name: CHLOROMETHYL PHENYL SULFONE
• Synonyms: PHENYL CHLOROMETHYL SULFONE;CHLOROMETHYL PHENYL SULFONE;[(CHLOROMETHYL)SULFONYL]BENZENE;[(chloromethyl)sulphonyl]benzene;chloromethyl phenyl sulphone;(Phenylsulfonyl)chloromethane;Phenylsulfonylmethyl chloride;Ai3-09778
• CAS NO: 7205-98-3
• Molecular Formula: C₇H₇ClO₂S
• Molecular Weight: 190.65
• EINECS: 230-581-8
• Product Categories: Organic Building Blocks;Sulfones;Sulfur Compounds
• Mol File: 7205-98-3.mol

Chemical Properties

• Melting Point: 51-53 °C(lit.)
• Boiling Point: 130 °C / 1mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.336 g/cm³
• Vapor Pressure: 0.000197mmHg at 25°C
• Refractive Index: 1.544
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• BRN: 2046644
• CAS DataBase Reference: CHLOROMETHYL PHENYL SULFONE(CAS DataBase Reference)
• NIST Chemistry Reference: CHLOROMETHYL PHENYL SULFONE(7205-98-3)
• EPA Substance Registry System: CHLOROMETHYL PHENYL SULFONE(7205-98-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 21
• Hazardous Substances Data: 7205-98-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Chloromethyl Phenyl Sulfone is used as a reactive intermediate for various chemical synthesis processes. Its unique chemical reactivity, due to the presence of sulfur and the ability to form stable compounds, makes it a valuable component in the creation of new molecules and materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Chloromethyl Phenyl Sulfone is used as a precursor molecule for the development of new drugs. Its potential role in drug synthesis could lead to the discovery of novel therapeutic agents with improved efficacy and safety profiles.
Used in Material Science:
Chloromethyl Phenyl Sulfone is used as a building block in the development of advanced materials. Its chemical properties may contribute to the creation of materials with unique characteristics, such as enhanced stability, reactivity, or selectivity, which could be beneficial in various applications, including electronics, energy storage, and environmental protection.
Used in Industrial Applications:
In industrial settings, Chloromethyl Phenyl Sulfone may be employed in the production of specialty chemicals, agrochemicals, or other industrial products. Its versatility as a reactive intermediate allows for its use in a wide range of applications, provided that appropriate safety measures are taken to mitigate potential health risks associated with its use.

InChI:InChI=1/C7H7ClO2S/c8-6-11(9,10)7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 64-17-5 ethanol 
• 75-09-2 dichloromethane 
• 873-55-2 sodium benzenesulfonate 
• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 
• 565446-69-7 N-[3-(4-benzenesulfonyl-5-oxy-furazan-3-yloxy)-propyl]-N'-benzoyl-N''-[3-(1-trityl-1H-imidazol-4-yl)-propyl]-guanidine 
• 38009-92-6 2-chloro-1-phenyl-2-(phenylsulfonyl)ethanone 
• 74-97-5 chlorobromomethane 
• 515-42-4 sodium phenylsulfonate 
• 3112-85-4 methylphenylsulfonate 
• 100-68-5 methyl-phenyl-thioether 
• 108-98-5 thiophenol 
• 3406-03-9 2-(phenylsulfonyl)acetophenone 
• 195371-23-4 p-Tolyl-chlorbrommethyl-sulfon 

Downstream Products

• 131221-60-8 5-Benzenesulfonylmethyl-7-methoxy-4-nitro-benzo[1,2,5]oxadiazole 1-oxide 
• 131221-59-5 7-Benzenesulfonylmethyl-5-methoxy-4-nitro-benzo[1,2,5]oxadiazole 1-oxide 
• 87505-13-3 1a,1b,2,7b-tetrahydro-1,2-bis(phenylsulfonyl)-1H-azirino<1.2-a>cyclopropa<1.8>naphthyridine 
• 87505-10-0 1a,1b,2,7b-tetrahydro-1,2-bis(phenylsulfonyl)-1H-azirino<1.2-a>cyclopropa<1.5>naphthyridine 
• 130008-11-6 1,1a,1b,2-tetrahydro-1,2-bis(phenylsulfonyl)bisazirino<1,2-a:2',1'-c>quinoxaline 
• 87505-12-2 1a,1b,2,7b-tetrahydro-1,2-bis(phenylsulfonyl)-1H-azirino<1.2-a>cyclopropa<1.7>naphthyridine 
• 87505-11-1 1a,1b,2,7b-tetrahydro-1,2-bis(phenylsulfonyl)-1H-azirino<1.2-a>cyclopropa<1.6>naphthyridine 
• 89303-17-3 2-Benzenesulfonylmethyl-4-iodo-1-nitro-benzene 
• 110035-99-9 2-phenylsulfonylmethylquinoline 1-oxide 
• 129919-53-5 2-quinoxaline 
• 129919-50-2 1,1a-dihydro-1-(phenylsulfonyl)azirino<1.2-a>quinoxalin-2(3H)one 
• 129919-54-6 2--1,1a,2,3-tetrahydro-1-(phenylsulfonyl)azirino<1.2-a>quinoxaline 
• 89211-06-3 C₁₄H₁₆O₃S 
• 88912-78-1 4-nitro-3-(phenylsulfonylmethyl)pyridine 1-oxide 

Relevant articles and documents

Synthetic Studies on the Preparation of Alanyl Epoxysulfones as Cathepsin Cysteine Protease Electrophilic Traps

A Darzens reaction between tert-butoxycarbonyl alaninal and chloromethyl phenyl sulfone afforded chlorohydrins, which were converted into epoxysulfones by reaction with sodium tert-butoxide. Epoxysulfone 10 and chloroketone 14 derived from chlorohydrins by oxidation proved to be inhibitors of cathepsins H, S, and C as determined by competitive activity-based protein profiling.

Ni-Catalyzed Asymmetric Reductive Alkenylation of α-Chlorosulfones with Vinyl Bromides

A nickel-catalyzed enantioconvergent reductive cross-coupling of α-chlorosulfones with vinyl bromides is described here. This strategy enables the enantioselective construction of chiral allylic sulfones from simple α-chlorosulfones and vinyl bromides. The mild reaction conditions lead to excellent functional group compatibility, as evidenced by the broad substrate scope and tolerance of complex bioactive molecules. Our preliminary mechanistic study suggests that this enantioselective vinylation process operates through a radical intermediate.

Selectivity switch in the aerobic oxygenation of sulfides photocatalysed by visible-light-responsive decavanadate

Nanometre-sized metal oxides are promising species for the development of visible-light-responsive photocatalysts for the selective transformation of organic functional groups. In this article, we report that decavanadate ([V10O28]6-, V10) behaved as an efficient visible-light-responsive photocatalyst in the product-selective oxygenation of sulfides achieved using O2 (1 atm) as the green oxidant. In particular, we revealed that visible-light-responsive photocatalysis of V10 showed remarkable activity for the oxygenation of structurally diverse sulfides to form the corresponding sulfones using O2 in methyl ethyl ketone (MEK). Furthermore, by simply adding water to the reaction mixture, the product selectivity of sulfide oxygenation can be significantly switched toward the production of sulfoxides, without concomitant loss of photocatalytic activity. Based on experimental evidence, we inferred the following mechanistic steps for this photocatalytic system: the aerobic oxygenation of sulfides to form the corresponding sulfoxides initiated by a visible-light-induced photoredox reaction of V10. As for the formation of sulfones, MEK-derived peroxide species as the co-catalysts are probably involved in the oxygenation of sulfoxides to sulfones. The selectivity switch of the V10-photocatalysed reaction brought about by water addition is most likely achieved by suppressing the formation of MEK-derived peroxide species. This journal is

2,4-Disubstituted 5-Nitroimidazoles Potent against Clostridium difficile

Metronidazole is one of the first-line treatments for non-severe Clostridium difficile infections (CDI). However, resistance limits its use in cases of severe and complicated CDI. Structure–activity relationships previously described for the 5-nitroimidazole series have shown that functionalization at the 2- and 4-positions can impart better activity against parasites and anaerobic bacteria than metronidazole. Herein we report the synthesis of new 2,4-disubstituted 5-nitroimidazole compounds that show potent antibacterial activity against C. difficile. We used a vicarious nucleophilic substitution of hydrogen (VNS) reaction to introduce a phenylmethylsulfone at the 4-position and a unimolecular radical nucleophilic substitution (SRN1) reaction to introduce an ethylenic function at the 2-position of the 5-nitroimidazole scaffold.

Controlled α-mono- and α,α-di-halogenation of alkyl sulfones using reagent-solvent halogen bonding

The direct and selective α-mono-bromination of alkyl sulfones was achieved through base-mediated electrophilic halogenation. The appropriate combination of solvent and electrophilic bromine source was found to be critical to control the nature of the products formed, where reagent-solvent halogen bonding is proposed to control the selectivity via alteration of the effective size of the electrophilic bromine source. Conversely, the α,α-di-brominated sulfones were selectively obtained in good yields following polyhalogenation followed by selective de-halogenation during workup. Both procedures can be applied on gram scale, and the mono-halogenation was successfully extended to the fully selective α-chlorination, α-iodination and α-fluorination of alkyl sulfones.

Sulfone compound (by machine translation)

[Problem] to safely and conveniently, highly selective, sulfide compound producing a sulfone compound. [Solution] pH is 9 - 12 under, water or water-insoluble solvent or an aromatic hydrocarbon-based solvent mixture, sodium hypochlorite is used as oxidizing agent, (1) (2) from the compound represented by the formula sulfide sulfone compound represented by the formula manufacturing method. (R1 And R2 Are each independently an alkyl, aryl, aralkyl, heteroaryl)[Drawing] no (by machine translation)

Lowering of 5-nitroimidazole's mutagenicity: Towards optimal antiparasitic pharmacophore

To improve the antiparasitic pharmacophore, 20 5-nitroimidazoles bearing an arylsulfonylmethyl group were prepared from commercial imidazoles. The antiparasitic activity of these molecules was assessed against Trichomonas vaginalis, the in vitro cytotoxicity was evaluated on human monocytes and the mutagenicity was determined by the Salmonella mutagenicity assay. All IC50 on T. vaginalis were below the one of metronidazole. The determination of the specificity indexes (SIs), defined as the ratios of the cytotoxic activity and the antitrichomonas activity, indicated that 11 derivatives had a SI over the one of metronidazole. Molecules, bearing an additional methyl group on the 2-position, showed a lower mutagenicity than metronidazole. Moreover, three derivatives were characterized by a low mutagenicity and an efficient antitrichomonas activity.

AMINOAZACYCLYL-3-SULFONYLINDAZOLES AS 5-HYDROXYTRYPTAMINE-6 LIGANDS

The present invention provides a compound of formula I and the use thereof in the therapeutic treatment of disorders related to or affected by the 5-HT6 receptor.

Chemoselective mono halogenation of β-keto-sulfones using potassium halide and hydrogen peroxide; synthesis of halomethyl sulfones and dihalomethyl sulfones

The synthesis of α-halo β-keto-sulfones using potassium halide and hydrogen peroxide as a chemoselective mono halogenation reagent and the synthesis of α,α-symmetrical and asymmetrical dihalo β-keto-sulfones and α-halo, α-alkyl and β-keto-sulfones is described. Base induced cleavage of α-halo β-keto-sulfones, α,α-dihalo β-keto-sulfones, and α-halo, α-alkyl β-keto-sulfones afforded the corresponding halomethyl sulfones, dihalomethyl sulfones and haloalkyl sulfones.

Rapid synthesis of new 5-nitroimidazoles as potential antibacterial drugs via VNS procedure

Original 4-arylsulfonylmethyl-5-nitroimidazoles were prepared by reacting four chloromethylaryl sulfones with 5-nitroimidazole derivatives via a vicarious nucleophilic substitution (VNS) of hydrogen reaction. Copyright Taylor & Francis Group, LLC.