10489-23-3

Usage

InChI:InChI=1/C15H22OS/c1-2-3-4-5-6-10-13-17-15(16)14-11-8-7-9-12-14/h7-9,11-12H,2-6,10,13H2,1H3

Upstream product

• 111-83-1 1-bromo-octane 
• 111-88-6 Octanethiol 
• 98-88-4 benzoyl chloride 
• 98-91-9 thiobenzoic acid 
• 111-66-0 oct-1-ene 
• 28170-13-0 thiobenzoic acid potassium salt 
• 111-85-3 n-chlorooctane 
• 959247-23-5 S-(2-methoxy)ethyl benzothioate 
• 822-27-5 dioctyl disulfide 
• 86763-31-7 S-octyl 4-methoxybenzothioate 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 93-97-0 benzoic acid anhydride 
• 7795-95-1 octane-1-sulfonyl chloride 

Downstream Products

• 822-27-5 dioctyl disulfide 
• 111-88-6 Octanethiol 
• 882-33-7 diphenyldisulfane 
• 6398-72-7 S-methoxycarbonylmethyl benzothioate 
• 382608-30-2 octyldisulfanyl-acetic acid methyl ester 
• 959247-23-5 S-(2-methoxy)ethyl benzothioate 
• 1020261-25-9 2-methoxyethyl octyl disulfide 
• 1020261-39-5 C₁₅H₃₁NO₂S₂ 
• 207554-43-6 S-(2-((tert-butoxycarbonyl)amino)ethyl) benzothioate 
• 884-09-3 phenyl thiobenzoate 
• 20129-24-2 phenyl n-octyl disulfide 
• 2005-08-5 4-chlorophenyl benzoate 

Relevant academic research and scientific papers

A Convenient Synthesis of Thioacetates and Thiobenzoates Using Silica-Gel Supported Potassium Thioacetate

A simple and efficient procedure has been developed for the synthesis of thioesters by a reaction of alkyl halides with silica-gel supported potassium thioacetate or thiobenzoate under mild conditions.

o-benzenedisulfonimide as a soft, efficient, and recyclable catalyst for the acylation of alcohols, phenols, and thiols under solvent-free conditions: Advantages and limitations

o-Benzenedisulfonimide turns out to be a highly efficient Bransted acid catalyst for the acylation of a number of alcohols, phenols, and thiols under a metal- and solvent-free procedure; reaction conditions are mild and yields very good. After the workup, the catalyst can be easily recovered and purified, ready to be reused, with economic and ecological advantages. Georg Thieme Verlag Stuttgart · New York.

Esterification or Thioesterification of Carboxylic Acids with Alcohols or Thiols Using Amphipathic Monolith-SO3H Resin

We have developed a method for the esterification of carboxylic acids with alcohols using amphipathic, monolithic-resin bearing sulfonic acid moieties as cation exchange functions (monolith-SO3H). Monolith-SO3H efficiently catalyzed the esterification of aromatic and aliphatic carboxylic acids with various primary and secondary alcohols (1.55.0 equiv) in toluene at 6080 °C without the need to remove water generated during the reaction. The amphipathic property of monolith-SO3H facilitates dehydration due to its capacity for water absorption. This reaction was also applicable to thioesterification, wherein the corresponding thioesters were obtained in excellent yield using only 2.0 equiv of thiol in toluene, although heating at 120 °C was required. Moreover, monolith-SO3H was separable from the reaction mixtures by simple filtration and reused for at least five runs without decreasing the catalytic activity.

Nickel-Catalyzed Thiocarbonylation of Arylboronic Acids with Sulfonyl Chlorides for the Synthesis of Thioesters

An interesting procedure for thioester synthesis via nickel-catalyzed thiocarbonylation of arylboronic acid with sulfonyl chlorides as the sulfur source has been explored. Using Mo(CO)6 as a solid CO surrogate and reductant, a broad range of thioesters were obtained in moderate to good yields with good functional group tolerance.

One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea

An efficient and odourless procedure for a one-pot synthesis of thioesters by the reaction of benzoic anhydrides, thiourea and various organic halides (primary, allylic, and benzylic) or structurally diverse, electron-deficient alkenes (ketones, esters, and nitriles) in the presence of Et3 N has been developed. In this method, thiobenzoic acids were in situ generated from the reaction of thiourea with benzoic anhydrides, which were subjected to conjugate addition with electron-deficient alkenes or a nucleophilic displacement reaction with alkyl halides.

Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatom acceptors

A rhodium complex catalyzed the equilibrium acyl transfer reaction between acid fluorides and thioesters. In the presence of fluoride or thiolate acceptors, the reaction could be shifted to either product. RhH(PPh 3)4-dppe catalyzed the reaction of acid fluorides and diorgano disulfides in the presence of triphenylphosphine giving thioesters, which was accompanied by triphenylphosphine difluoride. The same complex catalyzed the reaction of aryl thioesters and hexafluorobenzene giving acid fluorides, which was accompanied by 1,4-di(arylthio)-2,3,5,6- tetrafluorobenzenes.

Palladium-catalyzed thiocarbonylation of iodoarenes with thiols in phosphonium salt ionic liquids

(Chemical Equation Presented) Trihexyl(tetradecyl)phosphonium hexafluorophosphate, a phosphonium salt ionic liquid (PSIL) is a particularly effective general reaction media for the Pd-catalyzed carbonylation reaction of iodoarenes and thiols to form thioesters. Recycling of the ionic liquid containing active Pd-catalyst was also demonstrated.

Rhodium-catalyzed alkylthio exchange reaction of thioester and disulfide

The Wilkinson complex RhCl(PPh3)3 catalyzes equilibrating alkylthio exchange reaction of thioesters with disulfides. The treatment of a thioester and a dialkyl disulfide in refluxing diethyl ketone in the presence of RhCl(PPh3)3 (2.5 mol %) for 1.5 h gave an alkylthio exchanged thioester. The reaction of S-methyl ester was conducted shifting the equilibrium by removing volatile dimethyl disulfide.

Mild, powerful, and robust methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively

We developed two efficient practical methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively. The present mild and robust reaction was performed by two separate methods both by combining cheap and readily available amines, N-methylimidazole, and N,N,N′,N′-tetramethylethylenediamine (TMEDA). Method A uses catalytic N-methylimidazole and TMEDA with an equimolar amount of K2CO3, whereas Method B uses equimolar amounts of N-methylimidazole and TMEDA. The salient features are as follows. (i) With regard to reactivity, Method B was superior to Method A for esterification and thioesterification, whereas cost-effective Method A was superior to Method B for amide formation. (ii) Amide formation proceeded smoothly between acid chlorides and less nucleophilic and stereocongested amines such as 2,6-dichloroaniline. (iii) This protocol was applied to the successful synthesis of two agrochemicals, bromobutide and carpropamid.