705-28-2

Basic information

• Product Name: 3-ETHYNYL-ALPHA ALPHA ALPHA-TRIFLUORO&
• Synonyms: 3-Ethynylbenzotrifluoride, 1-Ethynyl-3-(trifluoromethyl)benzene;3-Ethynyl-alpha,alpha,alpha-trifluorotoluene 97%;3-ETHYNYL-ALPHA ALPHA ALPHA-TRIFLUORO&;3-Ethynylbenzotrifluoride;Toluene, m-ethenyl-alpha,alpha,alpha-trifluoro-;3-ethynyl-trifluorotoluene-;3-ethynyl trifluorotoluene(3-(trifluoromethyl)phenylacetylene);3-Ethynyl-a,a,a-trifluorotoluene
• CAS NO: 705-28-2
• Molecular Formula: C₉H₅F₃
• Molecular Weight: 170.1312096
• Product Categories: Organic Building Blocks;Alkynyl;Halogenated Hydrocarbons;Organic Building Blocks;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons
• Mol File: 705-28-2.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 146 °C(lit.)
• Flash Point: 95 °F
• Appearance: /
• Density: 1.178 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.76mmHg at 25°C
• Refractive Index: n20/D 1.464(lit.)
• CAS DataBase Reference: 3-ETHYNYL-ALPHA ALPHA ALPHA-TRIFLUORO&(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ETHYNYL-ALPHA ALPHA ALPHA-TRIFLUORO&(705-28-2)
• EPA Substance Registry System: 3-ETHYNYL-ALPHA ALPHA ALPHA-TRIFLUORO&(705-28-2)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20/21/22
• Safety Statements: 16-26-36-45
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 705-28-2(Hazardous Substances Data)

Usage

Description

3-Ethynyl-α,α,α-trifluorotoluene, also known as 3-(TRIFLUOROMETHYL)PHENYLACETYLENE, is a chemical compound that features a trifluoromethyl group attached to a toluene ring with an ethynyl (acetylene) functional group. 3-ETHYNYL-ALPHA ALPHA ALPHA-TRIFLUORO& is known for its unique properties and reactivity, making it a valuable research chemical.

Uses

Used in Research and Development:
3-Ethynyl-α,α,α-trifluorotoluene is used as a research chemical for the synthesis of various complex organic molecules and pharmaceutical intermediates. Its unique structure allows for a wide range of chemical reactions and modifications, making it a versatile building block in organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Ethynyl-α,α,α-trifluorotoluene is used as a key intermediate in the synthesis of several drug candidates. Its reactivity and structural features enable the development of novel therapeutic agents with potential applications in various medical fields.
Specific Applications:
1. Synthesis of 1-thioacetyl-4[3-trifluoromethyl-1-(ethynyl)phenyl]benzene:
3-Ethynyl-α,α,α-trifluorotoluene is used as a starting material for the synthesis of 1-thioacetyl-4[3-trifluoromethyl-1-(ethynyl)phenyl]benzene, a compound with potential applications in medicinal chemistry.
2. Synthesis of 4-[4-(3-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-1-yl]methylbenzoic acid:
3-ETHYNYL-ALPHA ALPHA ALPHA-TRIFLUORO& is utilized in the synthesis of 4-[4-(3-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-1-yl]methylbenzoic acid, which may have potential applications in drug development.
3. Synthesis of 4-4-[3-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-1-ylbenzoic acid:
3-Ethynyl-α,α,α-trifluorotoluene is also used in the synthesis of 4-4-[3-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-1-ylbenzoic acid, another compound with potential pharmaceutical applications.

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

Upstream product

• 40230-93-1 3-<(trimethylsilyl)ethynyl>benzotrifluoride 
• 401-06-9 β,β-dichloro-α-fluoro-3-trifluoromethyl-styrene 
• 79756-83-5 1-(1,2-Dibromo-ethyl)-3-trifluoromethyl-benzene 
• 30984-15-7 2-Brom-1-(3-trifluormethyl-phenyl)-aethylen 
• 67-56-1 methanol 
• 164171-91-9 1-(1-cyclobutenyl)-3-(trifluoromethyl)benzene 
• 164171-89-5 1-(3-(trifluoromethyl)phenyl)cyclobutan-1-ol 
• 114092-60-3 (Z)-β-bromo-3-trifluoromethylstyrene 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 402-24-4 3-(trifluoromethyl)styrene 
• 454-91-1 1-(3-trifluoromethylphenyl)ethanol 
• 98-08-8 α,α,α-trifluorotoluene 
• 349-76-8 3'-(trifluoromethyl)acetophenone 
• 402-26-6 3-(trifluoromethyl)phenylmagnesium bromide 

Downstream Products

• 65126-85-4 3-(3-(trifluoromethyl)phenyl)prop-2-yn-1-ol 
• 33675-48-8 1-(bromoethynyl)-3-(trifluoromethyl)benzene 
• 33675-55-7 1-(m-Trifluormethylphenyl)-2-iod-acetylen 
• 79756-86-8 1-(3-trifluoromethylphenyl)-prop-1-yne 
• 30984-15-7 2-Brom-1-(3-trifluormethyl-phenyl)-aethylen 
• 265661-05-0 4-[3-(trifluoromethyl)phenyl]-3-butyn-2-one 
• 851227-30-0 {4-[3-isopropyl-4-methoxymethoxy-5-(3-trifluoromethylphenylethynyl)benzyl]-3,5-dimethylphenoxy}acetic acid methyl ester 

Relevant articles and documents

1,2-Carbopentafluorophenylation of Alkynes: The Metallomimetic Pull-Push Reactivity of Tris(pentafluorophenyl)borane

We report the novel single-step 1,2-dicarbofunctionalization of an arylacetylene with an allylsilane and tris(pentafluorophenyl)borane [B(C6F5)3] involving C?C bond formation with C?H bond scission at the β-position to the silicon atom of an allylsilane and B→C migration of a C6F5 group. The 1,2-carbopentafluorophenylation occurs smoothly without the requirement for a catalyst or heating. Mechanistic studies suggest that the metallomimetic “pull-push” reactivity of B(C6F5)3 imparts consecutive electrophilic and nucleophilic characteristics to the benzylic carbon of the arylacetylene. Subsequent photochemical 6π-electrocyclization affords tetrafluoronaphthalenes, which are important in the pharmaceutical and materials sciences. Owing to the unique reactivity of B(C6F5)3, the 1,2-carbopentafluorophenylation using 2-substituted furan proceeded with ring opening, and the reaction using silyl enolates formed a C?C bond with C?O bond scission at the silyloxy-substituted carbon.

Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes

The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

Palladium-catalyzed tandem C-H functionalization/cyclization strategy for the synthesis of 5-hydroxybenzofuran derivatives

A palladium-catalyzed benzoquinone C-H functionalization/ cyclization strategy with terminal alkynes was employed for the synthesis of some biologically relevant 2, 3-disubstituted 5-hydroxybenzofuran derivatives. The benzoquinone acts as a reactant as well as an oxidant. During the process, an additional alkyne functionality can be introduced at the C3 position of the benzofuran. Base, ligand, and external oxidant are not required in this protocol.