40230-91-9

Basic information

• Product Name: 2-(TRIMETHYLSILYLETHYNYL)ANISOLE 98
• Synonyms: 2-(TRIMETHYLSILYLETHYNYL)ANISOLE 98;3-(TRIMETHYLSILYLETHYNYL)ANISOLE, 98%;2-Methoxy-1-(trimethylsilylethynyl)benzene;[(2-Methoxyphenyl)ethynyl]trimethylsilane;(2-(2-methoxyphenyl)ethynyl)trimethylsilane
• CAS NO: 40230-91-9
• Molecular Formula: C₁₂H₁₆OSi
• Molecular Weight: 204.34034
• Mol File: 40230-91-9.mol
• Article Data: 47

Chemical Properties

• Boiling Point: 247-249 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.958 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5420(lit.)
• CAS DataBase Reference: 2-(TRIMETHYLSILYLETHYNYL)ANISOLE 98(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(TRIMETHYLSILYLETHYNYL)ANISOLE 98(40230-91-9)
• EPA Substance Registry System: 2-(TRIMETHYLSILYLETHYNYL)ANISOLE 98(40230-91-9)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 40230-91-9(Hazardous Substances Data)

Usage

Purity

98%

Usage

Reagent in chemical synthesis, building block in the synthesis of complex organic molecules, applications in organic and medicinal chemistry

Unique property

Electron-rich alkyne

Versatile synthetic building block

Yes (due to the trimethylsilylethynyl group)

Upstream product

• 578-57-4 2-bromoanisole 
• 1066-54-2 trimethylsilylacetylene 
• 6224-91-5 trimethyl(prop-1-ynyl)silane 
• 5293-78-7 2,2'-dimethoxytolane 
• 529-28-2 4-iodoanisol 
• 135-02-4 ortho-anisaldehyde 
• 75-77-4 chloro-trimethyl-silane 
• 90585-32-3 1,1-dibromo-2-(2-methoxyphenyl)ethene 

Downstream Products

• 130654-80-7 1-methoxy-2-(3,3,3-trifluoroprop-1-yn-1-yl)benzene 
• 41398-67-8 2-phenylethynylanisole 
• 7342-00-9 3-(2-methoxyphenyl)prop-2-ynoic acid 
• 1262482-66-5 C₁₄H₁₆O₃Si 
• 166757-00-2 <2-<2-(2-Methoxyphenyl)ethynyl>phenyl>methanol 

Relevant articles and documents

Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

Biomimetic carbene cascades enabled imine derivative migration from carbene -bearing thiocarbamates

Inspired by the body circulation of Omeprazole (irreversible proton pump inhibitor), we disclose the carbene-triggered cascades for the synthesis of 2-aminobenzofuran derivatives from N-sulfonyl-1,2,3-triazoles or benzothioazole-bearing thiocarbamates, which represents an unprecedented imine derivative migration process. Furthermore, the desulfurizing reagent-free Barton-Kellogg-type reactions starting from N-sulfonyl-1,2,3-triazoles have also been achieved for the first time, and elemental sulfur is confirmed as a byproduct during this transformation. Both experimental data and DFT calculations further thoroughly explained the unique reactivity.

B(C6F5)3-Catalyzed cyclization of alkynes: direct synthesis of 3-silyl heterocyclic compounds

An efficient one-pot strategy for easy access to 3-silyl heterocyclic compounds was developedviaa B(C6F5)3-catalyzed cycloaddition reaction ofo-(1-alkynyl)(thio)anisoles oro-(1-alkynyl)-N-methylaniline. In this reaction, benzenethiophene, benzofuran or indole skeletons could be constructed by an intermolecular cyclization with diphenylsilane. This protocol elicited moderate-to-good yields with metal-free reaction systems.