1442-06-4

Usage

Uses

Used in Pharmaceutical Industry:
4-(METHYLTHIO)BENZOYL CHLORIDE 95 is used as a key intermediate for the synthesis of various pharmaceuticals due to its reactivity as an acylating agent. It aids in the production of drugs by introducing the benzoyl moiety to other organic compounds, which is crucial for the development of new medicinal agents.
Used in Agrochemical Industry:
In the agrochemical industry, 4-(METHYLTHIO)BENZOYL CHLORIDE 95 is utilized as a building block in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural chemicals that enhance crop protection and productivity.
Used in Dye Industry:
4-(METHYLTHIO)BENZOYL CHLORIDE 95 is used as an intermediate in the production of dyes, where its reactivity allows for the creation of a variety of colorants used in different applications, such as textiles, plastics, and printing inks.
Used in Fine Chemicals Industry:
4-(METHYLTHIO)BENZOYL CHLORIDE 95 is employed as a versatile intermediate in the synthesis of fine chemicals, which are high-purity, specialty chemicals used in various applications, including research, pharmaceuticals, and other industries that require high-quality, specific chemical compounds.
Used in Organic Synthesis:
4-(METHYLTHIO)BENZOYL CHLORIDE 95 is used as a building block in organic synthesis, where its ability to introduce the benzoyl moiety to other organic compounds is essential for creating a wide range of chemical products with diverse applications.

InChI:InChI=1/C8H7ClOS/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3

Upstream product

• 13205-48-6 4-(methylthio)benzoic acid 
• 35371-03-0 4-iodothioanisole 
• 122-04-3 4-nitro-benzoyl chloride 
• 100-20-9 terephthaloyl chloride 
• 141-75-3 butyryl chloride 

Downstream Products

• 90005-49-5 4-(methylthio)benzamide 
• 83167-14-0 4-(4-Methylsulfanyl-benzoyl)-1,3-dihydro-imidazol-2-one 
• 103608-34-0 (2-Methyl-1H-indol-3-yl)-(4-methylsulfanyl-phenyl)-methanone 
• 77671-31-9 enoximone 
• 83167-15-1 1,3-dihydro-4-ethyl-5-[4-(methylthio)benzoyl]-2H-imidazol-2-one 
• 83167-16-2 4-(4-Methylsulfanyl-benzoyl)-5-propyl-1,3-dihydro-imidazol-2-one 
• 65935-84-4 4-Methylsulfanyl-thiobenzoic acid S-p-tolyl ester 
• 53551-23-8 N-methyl-4-(methylthio)benzamide 
• 54118-72-8 (4-methylthiophenyl)(4-methoxyphenyl)methanone 
• 329076-60-0 ethyl 2-(4-fluorophenyl)-2-((4-methylthio)benzoyl)acetic acid ethyl ester 
• 1043931-21-0 C₁₄H₁₃NO₃S₂ 
• 63084-99-1 bis(4-(methylthio)phenyl)methanone 
• 23405-48-3 4-methylthiobenzophenone 
• 1257513-87-3 5-hydroxy-4'-methylthioflavone 

Relevant academic research and scientific papers

Direct Synthesis of Enamides via Electrophilic Activation of Amides

A novel, one-step N-dehydrogenation of amides to enamides is reported. This reaction employs the unlikely combination of LiHMDS and triflic anhydride, which serves as both the electrophilic activator and the oxidant, and is characterized by its simple setup and broad substrate scope. The synthetic utility of the formed enamides was readily demonstrated in a range of downstream transformations.

Cu-Catalyzed C-H Alkenylation of Benzoic Acid and Acrylic Acid Derivatives with Vinyl Boronates

An efficient Cu-catalyzed C-H alkenylation with acyclic and cyclic vinyl boronates was realized for the first time under mild conditions. The scope of the vinyl borons and the compatibility with functional groups including heterocycles are superior than Pd-catalyzed C-H coupling with vinyl borons, providing a reliable access to multisubstituted alkenes and dienes. Subsequent hydrogenation of the product from the internal vinyl borons will lead to installation of secondary alkyls.

ONIUM SALT, COMPOSITION, AND DEVICE MANUFACTURING METHOD USING THE SAME

PROBLEM TO BE SOLVED: To provide a photoacid generator for a chemically amplified resist simultaneously satisfying characteristics of sensitivity, resolution and pattern performance. SOLUTION: An onium salt is represented by one selected from general formulas (1) and (2). (R11 and R12 are each an alkyl group, alkenyl group, aryl group, or the like; R13 and R14 are each an alkyl group, hydroxy group, alkoxy group, or the like; R15 and R16 are each an alkyl group, alkenyl group, aryl group, or the like; L1 is a direct bond, alkylene group, alkenylene group, arylene group, or the like; L4 and L5 are each a direct bond, alkenylene group, alkynylene group, or carbonyl group; Y is an oxygen or sulfur atom; h and i are each an integer from 1 to 3; j is an integer from 0 to 4 if h is 1, from 0 to 6 if h is 2, and from 0 to 8 if h is 3; k is an integer from 0 to 5 if i is 1, from 0 to 7 if i is 2, and from 0 to 9 if i is 3; X- represents a monovalent counter anion; and R17 is an aryl group or heteroaryl group.) SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.

Preparation method of aromatic acyl chloride

The invention discloses a preparation method of aromatic acyl chloride. An aromatic acyl chloride compound is prepared through a reaction of aryl carboxylic acid and phosphorus trichloride. The preparation method of the aromatic acyl chloride has the advantages that the phosphorus trichloride is taken as a chloride reagent, the corresponding acyl chloride is synthesized from the aryl carboxylic acid, so that the production cost is low, the operation is simple, a by-product is low in toxicity, the environmental friendliness is achieved, the yield is high, and the method is conductive to industrial production.

Nickel-Catalyzed Decarbonylative Cyanation of Acyl Chlorides

Ni-catalyzed decarbonylative cyanation of acyl chlorides with trimethylsilyl cyanide has been achieved. This transformation is applicable to the synthesis of an array of nitrile compounds bearing a wide range of functional groups under neutral conditions. The step-by-step experimental studies revealed that the reaction sequences of the present catalytic reaction are oxidative addition, transmetalation, decarbonylation, and reductive elimination.

CoIII-Catalyzed Isonitrile Insertion/Acyl Group Migration Between C?H and N?H bonds of Arylamides

A general efficient and site-selective cobalt-catalyzed insertion of isonitrile into C?H and N?H bonds of arylamides through C?H bond activation and alcohol assisted intramolecular trans-amidation is demonstrated. This straightforward approach overcomes the limitation by the presence of strongly chelating groups. Isolation of CoIII-isonitrile complex B has been achieved for the first time to understand the reaction mechanism.

Functional Group Transposition: A Palladium-Catalyzed Metathesis of Ar-X σ-Bonds and Acid Chloride Synthesis

We describe the development of a new method to use palladium catalysis to form functionalized aromatics: via the metathesis of covalent σ-bonds between Ar-X fragments. This transformation demonstrates the dynamic nature of palladium-based oxidative addition/reductive elimination and offers a straightforward approach to incorporate reactive functional groups into aryl halides through exchange reactions. The reaction has been exploited to assemble acid chlorides without the use of high energy halogenating or toxic reagents and, instead, via the metathesis of aryl iodides with other acid chlorides.

Metathesis-active ligands enable a catalytic functional group metathesis between aroyl chlorides and aryl iodides

Current methods for functional group interconversion have, for the most part, relied on relatively strong driving forces which often require highly reactive reagents to generate irreversibly a desired product in high yield and selectivity. These approaches generally prevent the use of the same catalytic strategy to perform the reverse reaction. Here we describe a catalytic functional group metathesis approach to interconvert, under CO-free conditions, two synthetically important classes of electrophiles that are often employed in the preparation of pharmaceuticals and agrochemicals—aroyl chlorides (ArCOCl) and aryl iodides (ArI). Our reaction design relies on the implementation of a key reversible ligand C–P bond cleavage event, which enables a non-innocent, metathesis-active phosphine ligand to mediate a rapid aryl group transfer between the two different electrophiles. Beyond enabling a practical and safer approach to the interconversion of ArCOCl and ArI, this type of ligand non-innocence provides a blueprint for the development of a broad range of functional group metathesis reactions employing synthetically relevant aryl electrophiles.

C-F bond cleavage enabled redox-neutral [4+1] annulation via C-H bond activation

Using α,α-difluoromethylene alkyne as a nontraditional one-carbon reaction partner, a synthetically novel method for the construction of isoindolin-1-one derivatives via Rh(III)-catalyzed [4+1] annulation reaction is reported. The 2-fold C-F bond cleavage not only enables the generation of desired product under an overall oxidant-free condition but also results in a net migration of carbon-carbon triple bond. In addition, the present reaction protocol exhibits a tolerance of a wide spectrum of functional groups due to the mild reaction conditions employed.