7205-90-5

Basic information

• Product Name: CHLOROMETHYL 4-CHLOROPHENYL SULFIDE
• Synonyms: CHLOROMETHYL 4-CHLOROPHENYL SULFIDE;(4-Chlorophenyl)thiomethyl chloride;(p-Chlorophenylthio)methyl chloride;1-chloro-4-(chloromethylthio)-benzen;1-Chloro-4-(chloromethylthio)benzene;1-Chloro-4-[(chloromethyl)sulfanyl]benzene;1-chloro-4-[(chloromethyl)thio]-benzen;Chloromethyl p-chlorophenyl sulfide
• CAS NO: 7205-90-5
• Molecular Formula: C₇H₆Cl₂S
• Molecular Weight: 193.09
• EINECS: 230-578-1
• Product Categories: Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds
• Mol File: 7205-90-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 21.5°C
• Boiling Point: 128-129 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.348 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0183mmHg at 25°C
• Refractive Index: n20/D 1.6065(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: CHLOROMETHYL 4-CHLOROPHENYL SULFIDE(CAS DataBase Reference)
• NIST Chemistry Reference: CHLOROMETHYL 4-CHLOROPHENYL SULFIDE(7205-90-5)
• EPA Substance Registry System: CHLOROMETHYL 4-CHLOROPHENYL SULFIDE(7205-90-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• RTECS: CZ0200000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 7205-90-5(Hazardous Substances Data)

Usage

Uses

Used in Solvolysis Studies:
Chloromethyl 4-chlorophenyl sulfide is used as a subject of study in the solvolysis of chloromethyl phenyl sulfide and its p-chloro-derivative. This process involves the reaction of the compound with a wide range of hydroxylic solvents, providing valuable insights into the reactivity and behavior of the compound under different conditions.
Used in Synthesis of (4-Chlorophenylthio) Methyl Acetate:
Chloromethyl 4-chlorophenyl sulfide serves as a starting reagent in the synthesis of (4-chlorophenylthio) methyl acetate. This derivative has potential applications in various chemical and pharmaceutical industries, making the synthesis process an important application of the parent compound.
Used as Alkylating Reagent in Microwave-Assisted Synthesis:
Chloromethyl 4-chlorophenyl sulfide is utilized as an alkylating reagent in the microwave-assisted synthesis of 2-amino-imidazo[1,2-a]pyridine derivatives. These derivatives have potential applications in the development of new drugs and pharmaceutical compounds, highlighting the importance of the alkylating reagent in this process.

InChI:InChI=1/C7H6Cl2S/c8-5-10-7-3-1-6(9)2-4-7/h1-4H,5H2

Upstream product

• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 74-97-5 chlorobromomethane 
• 106-54-7 p-Chlorothiophenol 
• 112474-70-1 <(4-chlorophenylthio)methyl>trimethylsilane 
• 50-00-0 formaldehyd 
• 744221-72-5 (4-chloro-phenylsulfanyl)-methanesulfonic acid 
• 13150-73-7 3-chlorophenyl methyl sulfoxide 
• 123-09-1 4-chlorophenyl methyl sulfide 

Downstream Products

• 786-19-6 carbophenothion 
• 22218-71-9 (4-chloro-phenylsulfanyl)-methyl thiocyanate 
• 92023-45-5 1-chloro-4-{[(phenylsulfanyl)methyl]sulfanyl}benzene 
• 5943-04-4 chloromethyl p-chlorophenyl sulfone 
• 35123-64-9 C₁₂H₁₇ClNOPS₃ 
• 35125-75-8 C₁₅H₂₃ClNOPS₃ 
• 53830-54-9 4-chlorophenyl benzyl sulfide 
• 2393-97-7 bis(4-chlorophenylthio)methane 
• 102618-23-5 iodomethyl 4-chlorophenyl sulfide 
• 143552-07-2 [(1R,2R,3S)-2-{3-[(1R,2R,3S)-2-Benzoyl-3-(4-chloro-benzenesulfonyl)-cyclopropyl]-phenyl}-3-(4-chloro-benzenesulfonyl)-cyclopropyl]-phenyl-methanone 
• 143517-32-2 [(1R,2R,3S)-2-{4-[(1R,2R,3S)-2-Benzoyl-3-(4-chloro-benzenesulfonyl)-cyclopropyl]-phenyl}-3-(4-chloro-benzenesulfonyl)-cyclopropyl]-phenyl-methanone 
• 143517-57-1 {4-[(1S,2R,3S)-2-(4-Chloro-benzenesulfonyl)-3-(4-methoxy-phenyl)-cyclopropanecarbonyl]-phenyl}-[(1S,2R,3S)-2-(4-chloro-benzenesulfonyl)-3-(4-methoxy-phenyl)-cyclopropyl]-methanone 
• 143552-11-8 {3-[(1S,2R,3S)-2-(4-Chloro-benzenesulfonyl)-3-(2,4-dimethoxy-phenyl)-cyclopropanecarbonyl]-phenyl}-[(1S,2R,3S)-2-(4-chloro-benzenesulfonyl)-3-(2,4-dimethoxy-phenyl)-cyclopropyl]-methanone 
• 143517-64-0 {6-[(1S,2R,3S)-2-(4-Chloro-benzenesulfonyl)-3-(2,4-dimethoxy-phenyl)-cyclopropanecarbonyl]-pyridin-2-yl}-[(1S,2R,3S)-2-(4-chloro-benzenesulfonyl)-3-(2,4-dimethoxy-phenyl)-cyclopropyl]-methanone 

Relevant articles and documents

Studies on the synthesis, stability and conformation of 2-sulfonyl-oxetane fragments

2-(Arylsulfonyl)oxetanes have been prepared as new structural motifs of interest for medicinal chemistry. These are designed to fit within fragment space and be suitable for screening in fragment based drug discovery, as well as being suitable for further elaboration or incorporation into drug-like compounds. The oxetane ring is constructed through an efficient C-C bond forming cyclisation which allows the incorporation of a wide range of aryl-sulfonyl groups. Furthermore, biaryl-containing compounds can be accessed through Suzuki-Miyaura coupling from halogenated derivatives. With a number of oxetane containing fragment compounds available, their pH stability was assessed, indicating good half-life values for mono-substituted aryl sulfonyl oxetanes across the pH range (1 to 10). Solubility and metabolic stability data is also reported. Finally, the conformation of the fragments is assessed computationally, providing an indication of possible binding orientations.

2-(Aryl-sulfonyl)oxetanes as designer 3-dimensional fragments for fragment screening: Synthesis and strategies for functionalisation

2-Sulfonyl-oxetanes have been prepared, affording non-planar structures with desirable physicochemical properties for fragment based drug discovery. The oxetane motif was formed by an intramolecular C-C bond formation. The fragments were further functionalised via organometallic intermediates at the intact oxetane and aromatic rings. the Partner Organisations 2014.

A simple and efficient synthesis of trihalomethyl and dihalonitromethyl aryl sulfones

A method for the preparation of aryl trihalomethyl sulfones - active biocidal agents - with identical or different halogens is presented. The synthesis is based on the reaction of aryl methyl, aryl halomethyl, or aryl nitromethyl sulfones with sodium hypohalite. The method is simple in implementation, does not necessarily require the use of organic solvents, and selectively affords the products in good to excellent yields. Notably, it allows the preparation of the hitherto unknown phenyl trihalomethyl sulfone with three different halogens: fluorine, chlorine, and bromine.

Evaluation of electrophilic activities of substituted nitroarenes in the VNS reaction with secondary and tertiary carbanions

Relative electrophilic activities of substituted nitroarenes in the vicarious nucleophilic substitution (VNS) reaction with carbanion of chloromethylp-chlorophenyl and bromomethyl phenyl sulfones, 1 and 2, were determined via competitive experiments. The results are in good agreement with relative activities determined earlier in the competitive experiments with carbanion of chloromethyl phenyl sulfone 3 confirming reliability of these data. On the other hand, analogous competitive experiments with tertiary carbanions of chloroform and 1-chloroethyl phenyl sulfone gave results much affected by steric effects thus the VNS reaction with these carbanions cannot be used for evaluation of electrophilic activities of nitroarenes.

Synthese et activite biologique de prodrogues de l'acide oxolinique

Synthesis and biological activities of oxolinic acid pro-drugs.Antiseptic phenols, anti-inflammatory acids and polyethyleneglycol moieties have been attached by labile bonds to oxolinic acid giving pro-drugs with anti-bacterial activities.Some of them are more soluble in water, exhibit a more sustained action in the time and give higher plasma and tissue concentrations compared with the free drug.

Desilylative Pummerer-like Rearrangement of α-Trimethylsilyl-substituted Sulphoxides and Sulphides: Formation of α-Acyloxy and α-Halogeno Sulphides

α-Trimethylsilyl-substituted sulphoxides and sulphides undergo rearrangement with loss of the silyl group when treated respectively with trifluoroacetic anhydride and with N-halogenosuccinimide in the presence of trifluoroacetic acid, giving α-acyloxy sulphides and α-halogeno sulphides.

Monomethylation of Aromatic Rings by Friedel-Crafts Reaction with Chloromethyl Sulfide

A novel method for the introduction of a methyl group into aromatic rings is described.Friedel-Crafts reactions of ethyl α-(chloromethylthio)acetate (3k) and α-chloromethylthio-γ-butyrolactone (3m) with an arene in the presence of stannic chloride gave ethyl α-(arylmethylthio)acetate (6) and α-arylmethylthio-γ-butyrolactone (7), respectively, which were easily converted to the corresponding methylated arene (8) by reductive desulfurization with Raney nickel or zinc dust-acetic acid.Keywords - monomethylation; ethyl α-(chloromethylthio)acetate Friedel-Crafts reaction; α-chloromethylthio-γ-butyrolactone Friedel-Crafts reaction; ethyl α-(arylmethylthio)acetate; α-arylmethylthio-γ-butyrolactone; methylated arene; reductive desulfurization; Raney nickel; zinc dust-acetic acid

SYNTHESIS AND CONFIGURATIONAL STUDIES OF ARYL CYCLOPROPYL SULFONES

The cycloaddition of arylthiocarbenes to styrene gave stereospecifically cis-1-(arylthio)-2-phenylcyclopropanes, which were subsequently oxidized to the corresponding sulfones.The cyclopropanation of α,β-unsaturated sulfones with dimethylsulfonium methylide yielded stereoselectively trans-1-(arylsulfonyl)-2-arylcyclopropanes.The configurational assignments of these compounds have been arrived at on the basis of IR and PMR spectral data.Chemical shifts for ring protons and other substituents reveal that all the substituents tend to cause protons cis to them to appear at higher fields than those trans to them.This has been used as a criterion to distinguish between cis and trans aryl cyclopropyl sulfones.

Reaction of Phosphinyl and Phosphinothioyl Disulfides with Diazomethane

Four kinds of 4-substituted phenyl diethoxyphosphinyl disulfide (substituents: H, CH3, C2H5, Cl) and phenyl diethoxyphosphinothioyl disulfide reacted readily with diazomethane.The phosphinyl disulfides produced diethyl (4-substituted phenylthio)methyl phosphorothionate and the isomer, diethyl S-(4-substituted phenylthio)methyl phosphorothiolate, as the main products, whereas the phosphinothioyl disulfide produced only diethyl S-(phenylthio)methyl phosphorodithioate.The possible mechanism involved is as follows: the S-S bond in (EtO)2P(X)-S-S-C6H4R (X=O or S) is cleaved by nucleophilic attack of diazomethane at the sulfur atom bonded to the phenyl group to produce and (+)N2CH2-S-C6H4R; the latter reacts with the former with loss of nitrogen; therefore, when X is O, two compounds, (EtO)2P(S)-O-CH2-S-C6H4R and (EtO)2P(O)-S-CH2-S-C6H4R, are produced, when X is S, only (EtO)2P(S)-S-CH2-S-C6H4R is obtained.