18173-90-5

Basic information

• Product Name: 3-trimethylsilylpropane-1-sulfonic acid
• CAS NO: 18173-90-5
• Molecular Formula: C₆H₁₆O₃SSi
• Molecular Weight: 196.343
• Mol File: 18173-90-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.079g/cm³
• CAS DataBase Reference: 3-trimethylsilylpropane-1-sulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-trimethylsilylpropane-1-sulfonic acid(18173-90-5)
• EPA Substance Registry System: 3-trimethylsilylpropane-1-sulfonic acid(18173-90-5)

Safety Data

• Hazardous Substances Data: 18173-90-5(Hazardous Substances Data)

Usage

General Description

3-Trimethylsilylpropane-1-sulfonic acid is a synthetic organic compound with the chemical formula C7H18O3SSi. It is a strong acid and is commonly used as a catalyst in various organic reactions, including esterifications, acetalizations, and aldol condensations. It is also used as a reagent for the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds. 3-Trimethylsilylpropane-1-sulfonic acid is known for its high reactivity and stability, making it a valuable tool in organic synthesis. It is often utilized in research laboratories and chemical industries for its ability to facilitate complex chemical transformations.

Upstream product

• 2344-83-4 (3-chloropropyl)trimethylsilane 
• 13399-93-4 3-(trimethylsilyl)propane-1-thiol 

Relevant articles and documents

2-Thiabicyclohept-5-ene and Its S-Oxides and 3-Alkyl Derivatives: Sulfine and Sulfene Cyclopentadiene Diels-Alder Adducts. Conversion of the Cyclopentadiene-Sulfine Adducts into 2-Oxa-3-thiabicyclooct-7-enes, Novel Bicyclic Sultenes

Reaction of (trimethylsilyl)methanesulfonyl chloride (6a) or -sulfonic anhydride (6b) with cesium fluoride in the presence of cyclopentadiene affords 2-thiabicyclohept-5-ene 2,2-dioxide (4) by way of sulfene CH2=SO2.Similar reaction of (trimethylsilyl)methanesulfinyl chloride (7) gave unstable 2-thiabicyclohept-5-ene endo-2-oxide (3) via the intermediacy of sulfine CH2=SO.Compound 3 can be oxidized to 4 and reduced to 2-thiabicyclohept-5-ene (1) and the latter oxidized to the stable 2-thiabicyclohept-5-ene exo-2-oxide (2).Fluorodesilylation of 1-(trimethylsilyl)propanesulfonic anhydride (8) in the presence of cyclopentadiene gave a 77/23 ratio of endo/exo-3-ethyl-2-thiabicyclohept-5-ene 2,2-dioxide (9a/b) by way of propanethial S,S-dioxide.The structure of the major isomer 9a was established by an X-ray structure of the corresponding exo-epoxide 11a, formed from 9a by oxidation.Reaction of 4 with n-butyllithium followed by ethyl iodide gave a compound identical with minor isomer 9b.Reaction of propanethial S-oxide with cyclopentadiene gave unstable endo-3-ethyl-2-thiabicyclohept-5-ene endo-5-oxide (10a).The structure of 10a was established by oxidation to sulfone 9a, by reduction and reoxidation to a stable exo-5-oxide 10b, by its facile sigmatropic rearrangement to exo-4-ethyl-2-oxa-3-thiabicyclooct-7-ene (14c), and by NMR spectroscopic methods.Compound 14c was characterized by NMR spectroscopy and by its reactions.Oxidation of 14c gave the endo/exo-3-oxides 15c/15c' and the 3,3-dioxide 16c.Reaction of 14c with phenyllithium gave alcohol 17c, which was desulfurized and oxidized to 5-propyl-2-cyclopentenone or was oxidized at both carbon and sulfur to give (E)-5-propylidene-2-cyclopentenone 21c on gentle warming.Reaction of 14c with tert-butyl alcohol gave exo-6-tert-butoxy-exo-3-ethyl-syn-7-hydroxy-2-thiabicycloheptane (24), characterized by further oxidation to crystalline hydroxy sulfone 25 and keto sulfone 26.Mechanisms are proposed for the above series of reactions.