17872-98-9

Basic information

• Product Name: trimethylsilyl p-toluenesulphonate
• Synonyms: trimethylsilyl p-toluenesulphonate;Trimethylsilanol 4-methylbenzenesulfonate;Trimethylsilyl p-toluenesulfonate
• CAS NO: 17872-98-9
• Molecular Formula: C₁₀H₁₆O₃SSi
• Molecular Weight: 244.38274
• EINECS: 241-826-3
• Mol File: 17872-98-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 274°Cat760mmHg
• Flash Point: 119.5°C
• Appearance: /
• Density: 1.097g/cm³
• Vapor Pressure: 0.00929mmHg at 25°C
• Refractive Index: 1.491
• CAS DataBase Reference: trimethylsilyl p-toluenesulphonate(CAS DataBase Reference)
• NIST Chemistry Reference: trimethylsilyl p-toluenesulphonate(17872-98-9)
• EPA Substance Registry System: trimethylsilyl p-toluenesulphonate(17872-98-9)

Safety Data

• Hazardous Substances Data: 17872-98-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H16O3SSi/c1-9-5-7-10(8-6-9)14(11,12)13-15(2,3)4/h5-8H,1-4H3

Upstream product

• 4124-41-8 p-toluenesulfonylanhydride 
• 97730-09-1 trimethylsilyl tert-butylphenylphosphinate 
• 16029-98-4 trimethylsilyl iodide 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 
• 108-88-3 toluene 
• 4353-77-9 chlorosulfonate de trimethylsilyle 
• 31614-66-1 tributyl(p-tolyl)stannane 
• 18306-29-1 bis(trimethylsilyl)sulphate 
• 18306-68-8 diethyltrimethylsilyl phosphate 
• 953-91-3 cyclohexyl tosylate 

Downstream Products

• 98806-81-6 C₂₀H₁₉IO₆S₂ 
• 657-84-1 sodium tosylate 
• 245551-47-7 [(η(5)-C5Me5)TiF(μ-F)(μ-OSO2-p-C6H4CH3)]2 

Relevant articles and documents

Synthesis of Aromatic and Olefinic Sodium Sulfonates by Electrophilic Destannylation with Trimethylsilyl Chlorosulfonate

A mild and effective method for the preparation of a variety of aromatic, olefinic, and acetylenic sodium sulfonates is described.The reaction of trialkylaryl- (2a-k) and -heteroarylstannanes (4a-d), bis-(1-alkenyl)dibutylstannanes (6a-f), or trialkylakynylstannanes with trimethylsilyl chlorosulfonate (1) followed by hydrolysis with aqueous NaHCO3 provides the sodium sulfonates in an ipso-specific and in the case of vinylic stannanes stereospecific manner.A comparision of the reactivity of stannylated and silylated olefinic compounds 13 and 14 underlines the greater leaving ability of the stannyl moiety.The in situ preparation of the stannanes makes it possible to apply the synthetic method to natural products such as N-substituted apocodeine (17). - Key Words: Electrophilic aromatic substitution/ Electrophilic vinylic substitution/ Trialkylstannanes, application of/ Arylsulfonates, sodium salts of/ Vinylsulfonates, sodium salts of

Sulfosilylation of Aromatic Hydrocarbons by Trimethylsilyl Chlorosulfonate

Aromatic hydrocarbons 2 ,6 ,8 ,9 ,13 ,16 ,18 ,19 ,22 react with trimethylsilyl chlorosulfonate (1) to give trimethylsilyl arenesulfonates 5, 7, 11, 12, 15, 23 or sulfonic acids 17, 20, 21.If trimethylsilyl sulfonates are obtained, working up of the sulfonation mixtures is possible by distillation.By hydrohalogenolysis of trimethylsilyl sulfonates 5 at 0-5 deg C anhydrous sulfonic acids 3 result.The pathways to diphenylsulfone (25a) in the reaction of benzene (2a) with 1 were investigated.In this connection we succeeded in synthesizing benzenepyrosulfonic acid (28) and trimethylsilyl benzenepyrosulfonate (29).

Synthetic Application of Iodo- and Bromotrimethylsilane in Saccharide Chemistry

In simple model compounds an enhanced rate is observed in the reaction of iodotrimethylsilane with acetates and with cyclohexyl esters.Primary and secondary acetoxy-substituted saccharides show an exclusive formation of glycosyl iodides.Accordingly, pentaacetyl hexopyranoses and iodotrimethylsilane give in high yields the corresponding glycosyl iodides.Methyl glycosides can be transformed similarly, and with lactose octaacetate the formation of α-heptaacetyllactosyl iodide proceeds smoothly without rupture of the interglycosidic linkage.This procedure is particularly valuable for the synthesis of 2-deoxyglycosyl iodides.Corresponding reactions with bromotrimethylsilane are achieved in a similar way.By opening of epoxides with iodotrimethylsilane in the case of sterically fixed saccharide oxiranes the trans-diaxial, and with more flexible derivatives predominantly the trans-diequatorial iodohydrines are obtained.