5120-72-9

Basic information

• Product Name: 1-CHLORO-4-(ETHYLTHIO)BENZENE
• Synonyms: 1-CHLORO-4-(ETHYLTHIO)BENZENE;4-Chlorophenyl ethyl sulphide~4-(Ethylthio)chlorobenzene;4-(Ethylthio)chlorobenzene;4-Chlorophenylethylsulfide;1-CHLORO-4-(ETHYLTHIO)BENZENE 98%;Ethyl 4-chlorophenyl sulfide;Ethyl(4-chlorophenyl) sulfide;p-Chlorophenylethyl sulfide
• CAS NO: 5120-72-9
• Molecular Formula: C₈H₉ClS
• Molecular Weight: 172.68
• Mol File: 5120-72-9.mol

Chemical Properties

• Boiling Point: 240.5°C at 760 mmHg
• Flash Point: 99.3°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 0.0586mmHg at 25°C
• Refractive Index: 1.574
• CAS DataBase Reference: 1-CHLORO-4-(ETHYLTHIO)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CHLORO-4-(ETHYLTHIO)BENZENE(5120-72-9)
• EPA Substance Registry System: 1-CHLORO-4-(ETHYLTHIO)BENZENE(5120-72-9)

Safety Data

• Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Safety Statements: S23:Do not inhale gas/fumes/vapour/spray.; S36/37:Wear suitable protective clothing and gloves.
• Hazardous Substances Data: 5120-72-9(Hazardous Substances Data)

Usage

Appearance

Colorless to pale yellow liquid

Odor

Distinct, sweet

Physical State

Liquid

Chemical Classification

Chlorinated derivative of thioanisole

Usage

Building block in organic synthesis

Applications

Intermediate in the production of pharmaceuticals, agrochemicals, and other organic compounds

Structural Features

Presence of both a chloro and an ethylthio group

Importance

Versatile reagent in various organic reactions

Field of Relevance

Organic chemistry

InChI:InChI=1/C8H9ClS/c1-2-10-8-5-3-7(9)4-6-8/h3-6H,2H2,1H3

Upstream product

• 106-39-8 bromochlorobenzene 
• 74-96-4 ethyl bromide 
• 14366-73-5 2-chloroethyl 4-chlorophenyl sulfide 
• 5755-58-8 p-chlorophenyl-3-hydroxypropyl-sulfide 
• 76542-10-4 S-(4-chlorophenyl) propanethioate 
• 75-03-6 ethyl iodide 
• 18803-44-6 sodium p-chlorothiophenolate 
• 51946-00-0 p-ClC₆H₄SGe(CH₃)3 
• 97-93-8 triethylaluminum 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 637-87-6 1-Chloro-4-iodobenzene 
• 75-08-1 ethanethiol 
• 140-89-6 potassium ethyl xanthogenate 

Downstream Products

• 101574-11-2 bis-(2-ethylsulfanyl-5-chloro-phenyl)-methane 
• 82961-58-8 4-ethoxyphenyl ethyl sulfide 
• 7205-69-8 ethyl (4-chloro)phenyl sulfoxide 
• 54583-13-0 1-chloroethyl 4-chlorophenyl sulfide 
• 74-85-1 ethene 
• 13343-26-5 phenyl p-chlorophenyl sulfide 
• 82961-62-4 4-Ethoxyphenyl ethyl sulphone 
• 43115-40-8 2-amino-4-(ethylsulfonyl)phenol 
• 74159-80-1 1-chloro-4-(ethylsulphonyl)-2-nitrobenzene 
• 84996-11-2 4-(ethylsulfonyl)-2-nitro-phenol 
• 7205-80-3 1-(ethylsulfonyl)-4-chlorobenzene 
• 128092-47-7 (-)-(S)-(4-chlorophenyl) ethyl sulfoxide 
• 144265-69-0 2-[1-(4-Chloro-phenylsulfanyl)-ethoxy]-benzaldehyde 
• 1026296-02-5 4-Chloro-1-[1-(4-chloro-phenylsulfanyl)-ethoxy]-2-methyl-benzene 

Relevant articles and documents

Quenching and Radical Formation in the Reaction of Photoexcited Benzophenone with Thiols and Thioethers (Sulfides). Nanosecond Flash Studies

Laser flash measurements have been made of rate constants and primary radical yields in the reactions of triplet benzophenone with aliphatic and aromatic thiols and with dialkyl and aryl sulfides.Reaction with n-pentylthiol in benzene leads mainly to quen

A mild and chemoselective CALB biocatalysed synthesis of sulfoxides exploiting the dual role of AcOEt as solvent and reagent

A mild, chemoselective and sustainable biocatalysed synthesis of sulfoxides has been developed exploiting CALB and using AcOEt with a dual role of more environmentally friendly reaction solvent and enzyme substrate. A series of sulfoxides, including the drug omeprazole, have been synthesised in high yields and with excellent E-factors.

Production of Alkyl Aryl Sulfides from Aromatic Disulfides and Alkyl Carboxylates via a Disilathiane–Disulfide Interchange Reaction

The results of this study show that disilathiane is an effective mediator in the synthesis of alkyl aryl sulfides with disulfides and alkyl carboxylates. Mechanistic studies suggest that disilathiane promotes cleavage of the sulfur–sulfur bond of disulfides to generate thiosilane as a key intermediate. Diselenides were also applicable to this transformation to produce the corresponding selenides.

Copper-Catalyzed Three-Component Coupling Reaction of Aryl Iodides, a Disilathiane, and Alkyl Benzoates Leading to a One-Pot Synthesis of Alkyl Aryl Sulfides

A copper-catalyzed three-component coupling reaction of aryl iodides, hexamethyldisilathiane and alkyl benzoates leading to alkyl aryl sulfides has been demonstrated. A disilathiane acted as both a sulfur source and a promoter of the sulfidation, and the alkyl moiety of the alkyl benzoate was effectively introduced on one side of the sulfide. Moreover, we found that the protocol can be expanded to the preparation of ethyl phenyl selenide with diphenyl diselenide.

Transition-Metal-Free and Oxidant-Free Cross-Coupling of Arylhydrazines with Disulfides: Base-Promoted Synthesis of Unsymmetrical Aryl Sulfides

A novel synthesis of unsymmetrical aryl sulfides, which requires no transition metal catalyst and no oxidant, was developed. This base-promoted cross-coupling reaction proceeded using arylhydrazines and 1 equiv amount of disulfides under inert gas conditions to afford the unsymmetrical aryl sulfides in good yields.

A convergent route to geminal difluorosulfides and to functionalized difluorothiochromans, a new family of organofluorine compounds

The synthesis of the novel O-ethyl-S-(4-chlorophenylthio)difluoromethyl xanthate and its radical addition to various terminal alkenes are described. The geminal difluorosulfide adducts undergo closure onto the aromatic ring by further treatment with perox

Copper-catalyzed Ullmann coupling under ligand- and additive-free conditions. Part 2: S-Arylation of thiols with aryl iodides

S-Arylation of a wide variety of substituted aryl and aliphatic thiols with aryl halides catalyzed by copper iodide under mild ligand- and additive-free conditions (nBu4NBr, PhMe, NaOH, reflux, 22 h) is accomplished in good to excellent product yields (up to 96%).

5-Sulfonyl-benzimidazoles as selective CB2 agonists

A novel series of benzimidazole CB2-receptor agonists was synthesized and the structure-activity relationship explored. The results showed agonistic activities with an EC50 up to 0.5 nM and excellent selectivity (>4000-fold) over the CB1 receptor. The size of the substituent on the 2-position determined the level of agonism, ranging from inverse agonism to partial agonism to full agonism, which was more pronounced for the rat CB2 receptor. A wide variation of sulfonyl substituents at the benzimidazole 5-position was tolerated, which was used to optimize the drug-like properties. This resulted into lead compound 14j that can be used to investigate the potential of a selective, peripherically acting CB2 agonist. The in vitro profile of key compounds is displayed using pie bar charts (VlaaiVis).

Sulfite-promoted one-pot synthesis of sulfides by reaction of aryl disulfides with alkyl halides

A sodium dithionite, sodium thiosulfate and rongalite promoted one-pot synthesis of aryl alkyl sulfides at room temperature has been developed. The reactions of a range of disulfides with alkyl halides proceeded smoothly in the presence of rongalite. Possible reaction pathways are discussed and the effects of these sulfites on disulfides are investigated. The important features of this protocol are metal-free, strong-base-free, and mild reaction conditions, operational simplicity, short reaction times and high yields of products. Georg Thieme Verlag Stuttgart.

One-pot synthesis of sulfides by reaction of disulfides with alkyl halides in the presence of sodium dithionite

Sodium dithionite-promoted synthesis of unsymmetrical diorganyl sulfides by a reaction of diaryl disulfides with alkyl halides at r.t. has been developed. The advantages offered by this method are operational simplicity, a faster reaction, neutral and mild reaction conditions, and moderate to good yields of products.