34452-56-7

Basic information

• Product Name: P-TOLYL 2-(TRIMETHYLSILYL)ETHYNYL!
• Synonyms: P-TOLYL 2-(TRIMETHYLSILYL)ETHYNYL!;1-(p-Toluenesulfonyl)-2-(trimethylsilyl)acetylene, 2-(Trimethylsilyl)ethynyl p-tolyl sulfone
• CAS NO: 34452-56-7
• Molecular Formula: C₁₂H₁₆O₂SSi
• Molecular Weight: 252.408
• Product Categories: Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfones;Sulfur Compounds
• Mol File: 34452-56-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 80-83 °C(lit.)
• Boiling Point: 330°C at 760 mmHg
• Flash Point: 153.4°C
• Appearance: /
• Density: 1.085g/cm³
• Vapor Pressure: 0.000328mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: 2-8°C
• BRN: 2650368
• CAS DataBase Reference: P-TOLYL 2-(TRIMETHYLSILYL)ETHYNYL!(CAS DataBase Reference)
• NIST Chemistry Reference: P-TOLYL 2-(TRIMETHYLSILYL)ETHYNYL!(34452-56-7)
• EPA Substance Registry System: P-TOLYL 2-(TRIMETHYLSILYL)ETHYNYL!(34452-56-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 21
• Hazardous Substances Data: 34452-56-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H16O2SSi/c1-11-5-7-12(8-6-11)15(13,14)9-10-16(2,3)4/h5-8H,1-4H3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 1066-54-2 trimethylsilylacetylene 
• 68819-94-3 p-tolyl benzeneselenosulfonate 
• 86409-87-2 (E)-1-(phenylseleno)-1-(trimethylsilyl)-2-(p-tolylsulfonyl)ethene 

Downstream Products

• 107696-97-9 3,3-dimethyl-4-(p-tolylsulfonyl)-5-(trimethylsilyl)-3H-pyrazole 
• 110355-39-0 3,3-dimethyl-4-(p-tolylsulfonyl)-5-(trimethylsilyl)-3H-pyrazole 
• 75612-62-3 Trimethyl-[3-(toluene-4-sulfonyl)-bicyclo[2.2.1]hepta-2,5-dien-2-yl]-silane 
• 745017-96-3 p-tolylsulfonylethyne dicobalthexacarbonyl complex 
• 1416851-42-7 C₁₅H₂₃NSi 
• 1122594-14-2 1-(4-bromophenyl)-3-(trimethylsilyl)prop-2-yn-1-ol 
• 596092-44-3 2,2-Dimethyl-propionic acid (E)-(R)-1-{(4S,5S)-5-[1-hydroxy-3-(toluene-4-sulfonyl)-prop-2-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-penta-2,4-dienyl ester 
• 596092-42-1 2,2-Dimethyl-propionic acid (E)-(S)-1-{(4S,5S)-5-[1-hydroxy-3-(toluene-4-sulfonyl)-prop-2-ynyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-penta-2,4-dienyl ester 

Relevant articles and documents

Covalent Adaptable Networks with Tunable Exchange Rates Based on Reversible Thiol–yne Cross-Linking

The design of covalent adaptable networks (CANs) relies on the ability to trigger the rearrangement of bonds within a polymer network. Simple activated alkynes are now used as versatile reversible cross-linkers for thiols. The click-like thiol–yne cross-linking reaction readily enables network synthesis from polythiols through a double Michael addition with a reversible and tunable second addition step. The resulting thioacetal cross-linking moieties are robust but dynamic linkages. A series of different activated alkynes have been synthesized and systematically probed for their ability to produce dynamic thioacetal linkages, both in kinetic studies of small molecule models, as well as in stress relaxation and creep measurements on thiol–yne-based CANs. The results are further rationalized by DFT calculations, showing that the bond exchange rates can be significantly influenced by the choice of the activated alkyne cross-linker.

Synthesis of a fluorine-18 labeled derivative of epibatidine for in vivo nicotinic acetylcholine receptor PET imaging

Epibatidine (exo-2-(2'-chloro-5'-pyridyl)-7-azabicyclo[2.2.1]heptane), a natural compound isolated from the skin of the Ecuadorian poison frog Epipedobates tricolor, is the most potent nicotinic acetylcholine receptor (nAChR) agonist reported to date. In order to visualize and quantify in vivo these receptors in human brain using Positron Emission Tomography (PET), [18F]norchlorofluoroepibatidine (exo-2-(2'-[18F]fluoro-5'-pyridyl)-7-azabicyclo[2.2.1]heptane), a fluorine-18 (t(1/2): 110min) radiolabeled derivative of epibatidine has been designed. The corresponding 2'-bromo-, 2'-iodo- and 2'-nitro exo-2-(5'-pyridyl)-7-azabicyclo[2.2.1]heptane analogues as labeling precursors, as well as norchlorofluoroepibatidine as a reference compound have been synthesized by reductive, stereoselective, palladium-catalyzed Heck-type coupling between an N-Boc protected azanorbornene and the corresponding halopyridine. [18F]Norchlorofluoroepibatidine has been radiolabeled with fluorine-18 by nucleophilic aromatic substitution from the corresponding Boc-protected halo- and nitro precursors using [18F]FK-K222 complex in DMSO by conventional heating (at 150-180°C for 10min) or microwave activations (at 100 Watt, for 1 to 2.5min), followed by TFA-removal of the protective group. Typically, using the microwave activation procedure, 60-80mCi (2.22-2.96 GBq) of pure [18F]norchlorofluoroepibatidine could be obtained in less than 2h (110-115min) from the bromo labeling precursor, with specific radioactivities of 1.5-2.5Ci/μmol (55.5-92.5GBq/μmol) calculated for End of Bombardment. The preliminary PET experiments in baboon (Papio papio) with [18F]norchlorofluoroepibatidine show a high uptake and a rapid accumulation of the radiotracer into the brain within 30min. In the thalamus, a nAChR rich area, uptake of radioactivity reached a maximum at 40min (10% I.D./100mL tissue). The ratio of radioactivity thalamus/cerebellum (the latter being a nAChR poor area) was 2 at 40min and increased with time, up to 4.3 at 160min. Its specific regiodistribution and its high ratio of specific-to-nonspecific binding confirm the ideal profile of [18F]norchlorofluoroepibatidine as a suitable radioligand for PET imaging of nAChRs in the brain. Copyright (C) 1999 Elsevier Science Ltd.

A simplified method for the preparation of ethynyl P-tolyl sulfone and ethynyl phenyl sulfone

Silica gel mediated desilylation of aryl 2-(trimethylsilyl)ethynyl sulfones was found to greatly simplify the synthesis of the acetylenic sulfones, ethynyl p-tolyl sulfone 1 and ethynyl phenyl sulfone 2. Each were easily prepared in good yield and high purity on a multigram scale from bis(trimethylsilyl)acetylene 3.