17882-06-3

Basic information

• Product Name: TRIMETHYLSILYLBENZENESULFONATE
• Synonyms: TRIMETHYLSILYLBENZENESULFONATE;TRIMETHYLSILYLBENZENESULPHONATE;Trimethylsilanol benzenesulfonate
• CAS NO: 17882-06-3
• Molecular Formula: C₉H₁₄O₃SSi
• Molecular Weight: 230.36
• EINECS: 241-833-1
• Mol File: 17882-06-3.mol

Chemical Properties

• Boiling Point: 154-156 °C(lit.)
• Flash Point: 48 °F
• Appearance: /
• Density: 1.138 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.019mmHg at 25°C
• Refractive Index: n20/D 1.493(lit.)
• CAS DataBase Reference: TRIMETHYLSILYLBENZENESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLSILYLBENZENESULFONATE(17882-06-3)
• EPA Substance Registry System: TRIMETHYLSILYLBENZENESULFONATE(17882-06-3)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16
• RIDADR: UN 3272 3/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 17882-06-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Manufacturing:
Trimethylsilylbenzenesulfonate is used as a catalyst for various chemical reactions, including alkylation, esterification, and condensation processes. Its role in these reactions is to facilitate the formation of new chemical bonds, making it an essential component in the production of certain chemicals and materials.
Used in Organic Synthesis:
In the field of organic synthesis, trimethylsilylbenzenesulfonate is used as a protective group for certain functional groups. This application helps to increase the stability of the compound during the synthesis process and allows for the selective removal of the protective group when it is no longer needed, enabling further reactions to proceed.
Used in Research Applications:
Trimethylsilylbenzenesulfonate is also utilized in research settings, where its unique properties and reactivity are studied to gain insights into chemical behavior and to develop new methodologies for chemical synthesis and analysis. Its moderate toxicity and the need for stringent handling procedures make it a compound of interest for understanding the effects of such properties on chemical processes and safety protocols.

InChI:InChI=1/C9H14O3SSi/c1-14(2,3)12-13(10,11)9-7-5-4-6-8-9/h4-8H,1-3H3

Upstream product

• 18306-29-1 bis(trimethylsilyl)sulphate 
• 768-32-1 trimethylphenylsilane 
• 4353-77-9 chlorosulfonate de trimethylsilyle 
• 71-43-2 benzene 
• 81293-11-0 Benzolpyrosulfonsaeure-trimethylsilylester 
• 3385-94-2 hexamethyldisilathiane 
• 98-11-3 benzenesulfonic acid 
• 7446-11-9 sulfur trioxide 
• 14468-90-7 N-trimethylsilyl-pyrrolidin-2-one 
• 515-46-8 Ethyl benzenesulfonate 
• 3553-94-4 1-trimethylsilanyl-azepan-2-one 
• 7449-74-3 N-methyl-N-trimethylsilylacetamide 
• 10557-63-8 N-phenyl-N-trimethylsilylacetamide 
• 16029-98-4 trimethylsilyl iodide 

Downstream Products

• 18306-29-1 bis(trimethylsilyl)sulphate 
• 512-35-6 benzenesulfonic anhydride 
• 124663-81-6 C₁₃H₁₉NO₄SSi 
• 124663-83-8 C₁₄H₂₁NO₄SSi 
• 124663-84-9 C₁₅H₂₃NO₄SSi 
• 61657-37-2 tetrabutylammonium benzenesulfonate 
• 1054646-73-9 benzenesulfonyl 2,3,4,6-tetra-O-methyl-α-D-mannopyranoside 
• 1357445-28-3 [(C₅H₅)2Ti(OSO₂C₆H₅)(CF₃)] 

Relevant articles and documents

Trimethylsilyl directed aromatic sulfonation with sulfur trioxide- dioxane complex

A mild procedure for trimethylsilyl group directed sulfonation through ipso aromatic substitution has been developed using in situ generated sulfur trioxide-dioxane complex. The process is effective with electron rich aromatic rings, but fails in the case of aromatic rings substituted by groups such as a carboxylate. Aromatic heterocycles form sulfur trioxide complexes which deactivate them to substitution.

N-Alkylation of N-trimethylsilyl derivatives of lactams, amides, and imides with alkyl sulfonates

The reaction of N-trimethylsilyl derivatives of amides and imides with alkyl sulfonates on heating affords the corresponding N-alkyl derivatives and trimethylsilyl sulfonates.

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).