705-31-7

Basic information

• Product Name: 4'-TRIFLUOROMETHYLPHENYL ACETYLENE
• Synonyms: 4-ETHYNYL-ALPHA,ALPHA,ALPHA-TRIFLUOROTOLUENE;4-(TRIFLUOROMETHYL)PHENYLACETYLENE;4'-TRIFLUOROMETHYLPHENYL ACETYLENE;1-ETHYNYL-4-(TRIFLUOROMETHYL)BENZENE;4-ethynyl-trifluorotoluene-;4-ethynyl trifluorotoluene(4-(trifluoromethyl)phenylacetylene);4-(Trifluoromethyl)phenylacetylene 99%;4-(Trifluoromethyl)phenylacetylene99%
• CAS NO: 705-31-7
• Molecular Formula: C₉H₅F₃
• Molecular Weight: 170.13
• Product Categories: Alkynyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 705-31-7.mol

Chemical Properties

• Boiling Point: 78-80 °C2 mm Hg(lit.)
• Flash Point: 69 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.043 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.945mmHg at 25°C
• Refractive Index: n20/D 1.4650(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 4'-TRIFLUOROMETHYLPHENYL ACETYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-TRIFLUOROMETHYLPHENYL ACETYLENE(705-31-7)
• EPA Substance Registry System: 4'-TRIFLUOROMETHYLPHENYL ACETYLENE(705-31-7)

Safety Data

• Hazard Codes: F,Xi,F+
• Statements: 11
• Safety Statements: 16-26-36-45
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: Ⅱ
• Hazardous Substances Data: 705-31-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4'-TRIFLUOROMETHYLPHENYL ACETYLENE is used as a synthetic intermediate for the preparation of a variety of complex organic molecules. Its unique structure allows for the formation of multiple types of chemical bonds, facilitating the synthesis of a wide range of compounds with diverse applications.
Used in Pharmaceutical Industry:
4'-TRIFLUOROMETHYLPHENYL ACETYLENE is used as a key component in the synthesis of pharmaceutical compounds. Its unique structure can be incorporated into drug molecules to impart specific biological activities, potentially leading to the development of new therapeutic agents.
Used in Material Science:
4'-TRIFLUOROMETHYLPHENYL ACETYLENE is used as a building block for the development of advanced materials with unique properties. Its incorporation into polymers, for example, can lead to materials with enhanced thermal stability, electrical conductivity, or other desirable characteristics.
Specific Applications:
1. In the synthesis of 6,13-bis(4-trifluoromethylphenylethynyl)pentacene, 4'-TRIFLUOROMETHYLPHENYL ACETYLENE serves as a crucial component, contributing to the formation of a conjugated system that may exhibit unique electronic and optical properties.
2. It is used in the preparation of 1,2-dialkynylimidazoles, which can be further functionalized to create a variety of heterocycles with potential applications in medicinal chemistry and materials science.
3. 4'-TRIFLUOROMETHYLPHENYL ACETYLENE is also utilized in the synthesis of trans-[Co(cyclam)(p-CCC6H4CF3)2]OTf complex, where it acts as a ligand to the cobalt center, potentially leading to the development of new coordination compounds with interesting catalytic or magnetic properties.
4. Lastly, 4'-TRIFLUOROMETHYLPHENYL ACETYLENE is employed in the synthesis of spiroazetidinimine-2-oxindoles, which are structurally intriguing molecules with potential applications in various fields, including pharmaceuticals and materials science.

InChI:InChI=1/C9H5F3/c1-2-7-3-5-8(6-4-7)9(10,11)12/h1,3-6H

Upstream product

• 89619-12-5 1-(1,2-dibromoethyl)-4-(trifluoromethyl)benzene 
• 118527-34-7 1-(2,2-Dichloro-1-fluoro-vinyl)-4-trifluoromethyl-benzene 
• 1059140-27-0 1-(2-bromovinyl)-4-(trifluoromethyl)benzene 
• 67-56-1 methanol 
• 164171-90-8 1-(4-trifluoromethylphenyl)cyclobutene 
• 455-13-0 4-Iodobenzotrifluoride 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 98-08-8 α,α,α-trifluorotoluene 
• 4298-52-6 2-ethynyl-thiophene 
• 40230-95-3 1-(4-trifluoromethylphenyl)-2-trimethylsilylethyne 
• 173546-21-9 3-(4-trifluoromethylphenyl)prop-2-yn-1-ol 
• 131356-53-1 1-(2,2-dibromovinyl)-4-(trifluoromethyl)benzeney 
• 2062-26-2 3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid 

Downstream Products

• 121721-27-5 2-acetyl-2-(p-trifluoromethylphenyletynyl)-3,4-dihydronaphtalen-1(2H)-one 
• 121721-33-3 1-nitro-1-(p-trifluoromethylphenylethynyl)cyclohexane 
• 99256-89-0 [2-(3,4-Dimethoxy-phenyl)-ethyl]-{2-[5-methoxy-2-(4-trifluoromethyl-phenylethynyl)-phenyl]-1-methyl-ethyl}-methyl-amine 
• 151361-96-5 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[2,4-dioxo-5-(4-trifluoromethyl-phenylethynyl)-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 
• 121721-18-4 ethyl 2-oxo-1-(p-trifluoromethylphenyletynyl)cyclopentanecarboxylate 
• 79756-87-9 1-(prop-1-ynyl)-4-trifluoromethylbenzene 
• 2062-26-2 3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid 
• 313343-92-9 (E)-1-chloro-4-(4'-trifluoromethylphenyl)-1-buten-3-yne 
• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 
• 7386-61-0 (E)-3-(4-(trifluoromethyl)phenyl)but- 2-enoic acid 

Relevant articles and documents

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.

Aggregation induced emission-emissive stannoles in the solid state

The optoelectronic and structural properties of six stannoles are reported. All revealed extremely weak emission in solution at 295 K, but intensive fluorescence in the solid state with quantum yields (ΦF) of up to 11.1% in the crystal, and of up to 24.4% (ΦF) in the thin film.

Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids

A new palladium-catalyzed domino alkyne insertion/C-H activation/decarboxylation sequence has been developed, which provides an efficient approach for synthesizing a variety of functionalized phenanthrenes in moderate to good yields. The method shows broad substrate scope and good functional group tolerance by employing readily available materials, including aryl iodides, internal alkynes, and o-bromobenzoic acids, as three-component coupling partners.

Post synthetic exchange enables orthogonal click chemistry in a metal organic framework

Biphenyl-4,4′-dicarboxylic acid derivatives containing either azide or acetylene functional groups were inserted into UiO-67 metal organic frameworks (MOFs) via post synthetic linker exchange. Sequential and orthogonal click reactions could be performed o

Trimethylsilyl-Protected Alkynes as Selective Cross-Coupling Partners in Titanium-Catalyzed [2+2+1] Pyrrole Synthesis

Trimethylsilyl (TMS)-protected alkynes served as selective alkyne cross-coupling partners in titanium-catalyzed [2+2+1] pyrrole synthesis. Reactions of TMS-protected alkynes with internal alkynes and azobenzene under the catalysis of titanium imido comple

Intermolecular Desymmetrizing Gold-Catalyzed Yne–Yne Reaction of Push–Pull Diarylalkynes

Push–pull diaryl alkynes are dimerized in the presence of a cationic gold catalyst. The polarized structure of the applied starting materials enables the generation of a highly reactive vinyl cation intermediate in an intermolecular reaction. Trapping of the vinyl cation by a nucleophilic attack of the electron-poor aryl unit then leads to the selective formation of highly substituted naphthalenes in a single step and in complete atom economy.

A practical non-metal catalytic silicon of the amino protection of the new method (by machine translation)

The invention relates to a high efficiency, mild organic silicon reagent carbon silicon key fracture of the new method. The method of this reaction to the alkali is cheap and easy to obtain metal catalyst, in order to common commercial solvent as a reaction solvent and a hydrogen source, in the air and in the under mild conditions can be successfully catalytic trimethyl aryl silicon reagent or aryl alkyne base silicon reagent selectively generating carbon silicon key cracking hydrogenation reaction, the substrate universality is wide, functional group compatibility outstanding. The first innovative to realize the non-transition metal catalyzed carbon silicon key breaking reaction, also overcome the traditional method requires the use of greatly excessive inorganic alkali or an expensive metal catalyst to the limitation of the silicon of the amino protection, for the laboratory preparation and industry in the production of the organosilicon group deprotection provides a completely new strategy. (by machine translation)

Electron-density distribution tuning for enhanced thermal stability of luminescent gold complexes

Structure-property relationships of newly synthesized luminescent gold complexes were examined from the viewpoint of material applications. In particular, we investigated the effect of controlling the molecular electron-density distribution by introducing trifluoromethyl substituents into the complexes. The structures of the molecular aggregates were not affected by the trifluoromethyl substituents, as all the complexes formed antiparallel dimers in the crystal state. Moreover, we found that the trifluoromethyl substituents enhanced the thermal stability of the complexes without significantly changing the luminescence behaviour. Thus, while the thermal stability of these materials depends on the molecular structure, i.e. the molecular electron-density distribution, the luminescence behaviour mainly depends on the molecular aggregate structure. These results suggest that various material properties, e.g. luminescence colour and thermal stability, can be controlled independently by tuning the structures of molecules and molecular aggregates using trifluoromethyl substituents.

Copper-Catalyzed Hydrogen/Iodine Exchange in Terminal and 1-Iodoalkynes

Detailed kinetic profiles of the copper-catalyzed exchange between the acetylenic proton and iodide of terminal and 1-iodophenylacetylenes are reported. The electronic nature of the alkynes does not influence the equilibrium of the exchange (Keq/sub

Reaction discovery using acetylene gas as the chemical feedstock accelerated by the stop-flow micro-tubing reactor system

Acetylene gas has been applied as a feedstock under transition-metal catalysis and photo-redox conditions to produce important chemicals including terminal alkynes, fulvenes, and fluorinated styrene compounds. The reaction discovery process was accelerated through the use of stop-flow micro-tubing reactors. This reactor prototype was developed by joining elements from both continuous micro-flow and conventional batch reactors, which was convenient and effective for gas/liquid reaction screening. Notably, the developed transformations were either inefficient or unsuccessful in conventional batch reactors. Its success relies on the unique advantages provided by this stop-flow micro-tubing reactor system.