16116-80-6

Basic information

• Product Name: 4-((Trimethylsilyl)ethynyl)benzoic acid
• Synonyms: 4-((Trimethylsilyl)ethynyl)benzoic acid;4-[2-(Trimethylsilyl)ethynyl]benzoic acid
• CAS NO: 16116-80-6
• Molecular Formula: C₁₂H₁₄O₂Si
• Molecular Weight: 218.32386
• Product Categories: Carboxylic Acids;Phenyls & Phenyl-Het;Carboxylic Acids;Phenyls & Phenyl-Het
• Mol File: 16116-80-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 154-158°C
• Boiling Point: 299.3°Cat760mmHg
• Flash Point: 134.8°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 0.000537mmHg at 25°C
• Refractive Index: 1.536
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-((Trimethylsilyl)ethynyl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-((Trimethylsilyl)ethynyl)benzoic acid(16116-80-6)
• EPA Substance Registry System: 4-((Trimethylsilyl)ethynyl)benzoic acid(16116-80-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 16116-80-6(Hazardous Substances Data)

Usage

General Description

4-((Trimethylsilyl)ethynyl)benzoic acid is a chemical compound with a molecular formula C15H16O2Si. It is a derivative of benzoic acid with a trimethylsilyl group attached to the ethynyl carbon atom. 4-((Trimethylsilyl)ethynyl)benzoic acid is commonly used in organic synthesis as a versatile building block for the preparation of various functionalized benzoic acid derivatives. It also finds applications in materials science and pharmaceutical research. The presence of the trimethylsilyl group makes the compound stable and easily handled, making it a valuable reagent in chemical synthesis.

InChI:InChI=1/C12H14O2Si/c1-15(2,3)9-8-10-4-6-11(7-5-10)12(13)14/h4-7H,1-3H3,(H,13,14)

Upstream product

• 619-58-9 4-iodobenzoic acid 
• 1066-54-2 trimethylsilylacetylene 
• 619-44-3 methyl 4-iodobenzoate 

Downstream Products

• 10602-00-3 4-Ethynyl-benzoic acid 
• 949583-77-1 trans-4-(4-trimethylsilylethynylbenzoylamino)cyclohexanol 
• 949583-78-2 trans-4-(4-ethynylbenzoylamino)cyclohexanol 

Relevant articles and documents

4-[2-(Trimethylsilyl)ethynyl]benzoates: Synthesis and evaluation for mesomorphic properties of some novel calamitic molecules

A series of novel terminal trimethylsilylacetylene benzoate derivatives with various linking groups were synthesized using Friedel-Craft's O-acylation reaction. The chemical structures of the novel 4-[2-(trimethylsilyl)ethynyl]benzoates were confirmed by

Convenient and easy access to 2-hydroxycyclopent-2-enones from acylcyanohydrins

A convenient access to 2-hydroxycyclopentenones was designed from acylcyanohydrins, by using titanacyclopropane complexes as nucleophilic partners and an intramolecular aldol condensation in basic conditions. The development of a one-pot procedure allows a step- and atom-economic process, and the use of Grignard reagents other than ethylmagnesium bromide provided valuable 3,4-disubstituted 2-hydroxycyclopentenones. The utility of the hydroxy group was illustrated by further functionalization of the α-position using palladium-mediated cross-coupling reactions.

A sub-milligram-synthesis protocol for in vitro screening of HDAC11 inhibitors

This work demonstrated the high efficiency of a sub-milligram-synthesis based medicinal chemistry method. Totally 72 compounds, consisting a tri-substituted pyrrolidine core, were prepared. Around 0.1 mg of each compound was solid-phase synthesized. Based on the additive property of UV absorptions of unconjugated chromophores of a molecule, these compounds were quantified by UV measurement. A hit, whose IC50 value was 1.2 μM in HDAC11 inhibition assays, highlights the applicability of the approach reported here in future optimization works.