4664-57-7

Usage

Uses

1. Used in Pharmaceutical Industry:
t-Butyl Tosylate was used as an intermediate in the synthesis of sulfonamides and sulfonic esters, which are important classes of compounds with various applications in the pharmaceutical industry.
2. Used in Chemical Industry:
In the chemical industry, t-Butyl Tosylate was utilized in the production of various organic compounds, particularly those involving indium metal-catalyzed reactions.

Synthetic route

p-toluenesulfonyl chloride (98-59-9) + tert-butyl alcohol (75-65-0) → tert-butyl 4-methylbenzenesulfonate (4664-57-7)

Conditions	Yield
With aluminum dodecatungstophosphate at 20℃; for 0.25h;	80%
indium In N,N-dimethyl-formamide at 120℃; for 12h;	79%
With potassium carbonate In acetonitrile at 50℃;

4-methylbenzenediazonium tetrafluoroborate (459-44-9) + tert-butyl alcohol (75-65-0) → tert-butyl 4-methylbenzenesulfonate (4664-57-7)

Conditions	Yield
With 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate; trifluoroacetic acid; copper(ll) bromide In dichloromethane at 20℃; for 12h;	12 mg

(15β,16α)-16-hydroxy-15-(hydroxymethyl)beyeran-18-oic acid (882175-40-8) + tert-butyl 4-methylbenzenesulfonate (4664-57-7) → t-butyl ent-15α-hydroxymethyl-16β-hydroxybeyeran-19-oate (1143506-01-7)

Conditions	Yield
With potassium carbonate In acetonitrile	94%

tert-butyl 4-methylbenzenesulfonate (4664-57-7) → bis(tert-butyl) diselenide (34172-61-7) + 1,3-di-tert-butyl triselenide

Conditions	Yield
With selenium; potassium hydroxide In water at 60℃; for 0.5h; Green chemistry;	A 10% B 89%

tert-butyl 4-methylbenzenesulfonate (4664-57-7) → di-tert-butyl disulfide (110-06-5) + di-tert-butyl trisulfide (4253-90-1)

Conditions	Yield
With sulfur; potassium hydroxide In water at 60℃; for 0.5h; Green chemistry;	A 10% B 86%

tert-butyl 4-methylbenzenesulfonate (4664-57-7) → di-tert-butyl trisulfide (4253-90-1)

Conditions	Yield
With potassium 5-methyl-1,3,4-oxadiazole-2-thiolate In water at 40℃; for 1.5h;	85%

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 75-65-0 tert-butyl alcohol 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 

Downstream Products

• 110-06-5 di-tert-butyl disulfide 
• 4253-90-1 di-tert-butyl trisulfide 

Relevant academic research and scientific papers

Copper-Catalyzed Multicomponent Reaction of DABCO·(SO2)2, Alcohols, and Aryl Diazoniums for the Synthesis of Sulfonic Esters

A Cu-catalyzed multicomponent cascade reaction of DABCO·(SO2)2 (DABSO), alcohol, and aryl diazonium tetrafluoroborate was developed which afforded sulfonic esters in moderate to good chemical yields. In this reaction, the SO2 surrogate DABSO was used for the first time in the synthesis of sulfonic aliphatic esters. This multicomponent reaction was carried out under mild conditions and tolerated a wide range of substrates, which provides a new and efficient strategy for the synthesis of sulfonic esters.

Stereoselective synthesis of bioactive isosteviol derivatives as α-glucosidase inhibitors

Considerable interest has been attracted in isosteviol and its derivatives because of their large variety of pharmacological activities. In this project, a series of novel compounds containing hydroxyl, hydroxymethyl group and heteroatom-containing frameworks fused with isosteviol structure were synthesized and evaluated as α-glucosidase inhibitors, aimed at clarifying the structure-activity correlation. The results indicated that these isosteviol derivatives were capable of inhibiting in vitro α-glucosidase with moderate to good activities. Among them, indole derivative 15b exhibited the highest activities and thus may be exploitable as a lead compound for the development of potent α-glucosidase inhibitors.

Mild and efficient indium metal catalyzed synthesis of sulfonamides and sulfonic esters

A facile and efficient method for synthesizing sulfonamides was developed using a catalytic amount of indium metal. A wide range of sulfonamides were synthesized in excellent yields using the new process. The method showed a generality for substrates including less nucleophilic and sterically hindered anilines, and it is also applicable for preparing sulfonic esters from sulfonyl chlorides and alcohols. Georg Thieme Verlag Stuttgart.

Solvent-free and selective tosylation of alcohols and phenols with p-toluenesulfonyl chloride by heteropolyacids as highly efficient catalysts

Tosylation of some alcohols and phenols has been directly carried out with p-toluenesulfonyl chloride using heterodoxy acids (H3PW 12O40, H3PMo12O40, A 3PW12O40, and AlPMo12O40) as catalysts in the absence of solvent. We found that heteropoly acids AlPW12O40 and AlPMo 12O40 were effective catalysts for the tosylation of alcohols and phenols. In the case of aliphatic alcohols, secondary alcohols undergo tosylation chemoselectively in the presence of primary hydroxyl groups. This new method consistently has the advantage of excellent yields and short reaction time.