10371-42-3

Basic information

• Product Name: Thiobenzoic acid S-(4-methylphenyl)
• Synonyms: 4-Methyl-1-(benzoylthio)benzene;S-(4-Methylphenyl)=benzenecarbothioate;Thiobenzoic acid S-(4-methylphenyl);Thiobenzoic acid S-p-tolyl ester;S-p-tolyl benzothioate
• CAS NO: 10371-42-3
• Molecular Formula: C₁₄H₁₂OS
• Molecular Weight: 228.3095
• Mol File: 10371-42-3.mol
• Article Data: 61

Chemical Properties

• Boiling Point: 336.7°Cat760mmHg
• Flash Point: 144°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 0.00011mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: Thiobenzoic acid S-(4-methylphenyl)(CAS DataBase Reference)
• NIST Chemistry Reference: Thiobenzoic acid S-(4-methylphenyl)(10371-42-3)
• EPA Substance Registry System: Thiobenzoic acid S-(4-methylphenyl)(10371-42-3)

Safety Data

• Hazardous Substances Data: 10371-42-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 68, 1983 DOI: 10.1055/s-1983-30228

InChI:InChI=1/C14H12OS/c1-11-7-9-13(10-8-11)16-14(15)12-5-3-2-4-6-12/h2-10H,1H3

Upstream product

• 98-88-4 benzoyl chloride 
• 106-45-6 para-thiocresol 
• 4124-41-8 p-toluenesulfonylanhydride 
• 65-85-0 benzoic acid 
• 203070-17-1 1-(Phenyl-phenylselanyl-p-tolylsulfanyl-methyl)-1H-benzotriazole 
• 7664-93-9 sulfuric acid 
• 201230-82-2 carbon monoxide 
• 108-88-3 toluene 
• 17671-92-0 subsituted benzenethiol 
• 154345-69-4 Triphenyl-[phenyl-(toluene-4-sulfinyl)-methylene]-λ⁵-phosphane 
• 2078-12-8 trimethylsilyl benzoate 
• 28170-13-0 thiobenzoic acid potassium salt 
• 6293-70-5 4,4'-dimethyldiphenyliodonium iodide 
• 624-31-7 4-tolyl iodide 

Downstream Products

• 1024-34-6 di(n-butyl) phenylphosphonate 
• 54441-76-8 benzyldi(p-tolyl)phosphine oxide 
• 18957-70-5 (phenyl)di(4-methylphenyl)phosphine oxide 
• 2959-74-2 benzyldiphenylphosphine oxide 
• 791-28-6 Triphenylphosphine oxide 
• 2129-79-5 Benzylphenylphosphinsaeureethylester 
• 1733-55-7 ethyl diphenylphosphinate 
• 4233-13-0 butyldiphenylphosphine oxide 
• 614-34-6 p-cresyl benzoate 
• 104128-50-9 (4-cyanophenyl)(4-methylphenyl)sulfide 

Relevant articles and documents

Copper-Mediated, Palladium-Catalyzed Coupling of Thiol Esters with Aliphatic Organoboron Reagents

Thiol esters and B-alkyl-9-BBN derivatives couple in the presence of a copper(I) carboxylate mediator and a palladium catalyst. In contrast to copper-mediated, palladium-catalyzed cross-couplings of thioorganics with boronic acids, the current coupling reaction of 9-BBN derivatives is facilitated by the addition of a base such as Cs2CO3. Under optimized conditions, a variety of thiol esters react with different B-alkyl-9-BBN derivatives giving ketones in moderate to excellent yields.

Methanesulfonic anhydride-promoted sustainable synthesis of thioesters from feedstock acids and thiols

Abstract: An unprecedented metal-, halogen- and solvent-free, MSAA-promoted S-carbonylation of thiols with feedstock acids has been developed. This new transformation provides an efficient and atom-economic strategy for the synthesis of thioesters in a single operation from readily available and inexpensive starting materials. The reaction avoids the use of expensive and hazardous coupling reagents, bases and generates water as the only by-product, thus making this chemical synthetic process more viable, environment-friendly and contributing towards sustainable chemistry. Graphic abstract: [Figure not available: see fulltext.].

Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters

We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.

Conversion of esters to thioesters under mild conditions

We report conversion of esters to thioestersviaselective C-O bond cleavage/weak C-S bond formation under transition-metal-free conditions. The method is notable for a general and practical transition-metal-free system, broad substrate scope and excellent functional group tolerance. The strategy was successfully deployed in late-stage thioesterification, site-selective cross-coupling/thioesterification/decarbonylation and easy-to-handle gram scale thioesterification. Selectivity and computational studies were performed to gain insight into the formation of weak C-S bonds by C-O bond cleavage, which contrasts with the traditional trend of nucleophilic additions to carboxylic acid derivatives.