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

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

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 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 402-24-4 3-(trifluoromethyl)styrene 
• 98-08-8 α,α,α-trifluorotoluene 
• 454-91-1 1-(3-trifluoromethylphenyl)ethanol 
• 402-26-6 3-(trifluoromethyl)phenylmagnesium bromide 
• 893746-73-1 2-methyl-4-[3-(trifluoromethyl)phenyl]but-3-yn-2-ol 
• 401-81-0 m-trifluoromethylphenyl iodide 

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 
• 870010-39-2 1-(methoxymethoxy)-2-{[3-(trifluoromethyl)phenyl]ethynyl}benzene 

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.

Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines

Transition metal-catalyzed hydroalkynylation reactions are efficient transformations allowing the straightforward formation of functionalized alkynes. Therein, we disclose the cobalt-catalyzed hydroalkynylation of vinylaziridines giving rise to both linea

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.

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.

TRIAZOLONE COMPOUNDS AS mPGES-1 INHIBITORS

The present disclosure is directed to compounds of formula (I), and pharmaceutically acceptable salts thereof, as mPGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (mPGES-1) enzyme and are therefore useful in the treatment of pain and/or inflammation from a variety of diseases or conditions, such as asthma, osteoarthritis, rheumatoid arthritis, acute or chronic pain and neurodegenerative diseases.

Stereodivergent zinc-mediated three-component synthesis of tri- and tetrasubstituted alkenes

Zinc simple: The loading-dependent zinc-mediated addition of benzyl bromides to alkynes is the key step for the formation of vinyl bromides. In combination with a palladium-catalyzed Suzuki cross-coupling reaction with boronic acids, tri- and tetrasubstit

Fluorinated phenylethynyl-terminated imide oligomers with reduced melt viscosity and enhanced melt stability

Two novel fluorinated phenyethynyl-contained endcapping agents, 4-(3-trifluoromethyl-1-phenylethynyl)phthalic anhydride (3F-PEPA) and 4-(3,5-bistrifluoromethyl-1-phenylethynyl)phthalic anhydride (6F-PEPA) were synthesized, which were employed to synthesiz

One-pot desilylation/dimerization of terminal alkynes by ruthenium and acid-promoted (RAP) catalysis

The dimerization of terminal arylalkynes promoted by the (p-cymene)ruthenium dichloride dimer/acetic acid system {[RuCl 2(p-cymene)]2/AcOH} can be performed starting from the trimethylsilylethynyl derivatives (12 substrates), deprotected in situ, to afford 1,4-disubstituted 1-en-3-ynes with high regio- and (E)-stereoselectivity, at room temperature. The extension of this unprecedented two-reaction sequence to a diyne substrate affords a fluorene-based conjugated oligomer. The reaction mixture resulting from the desylilation-dimerization process dimerizes additional aliquots of phenylacetylene. The one-pot protocol results in shorter reaction times due to the presence of acetate salts which increase the concentration of active catalytic species, in which the acetate ligand acts as base toward the bound alkyne. The ruthenium source is transformed into a new trihapto-hexa-1,3-dien-5-yn-3-yl complex, formed by metal-assisted coupling of the enyne product and the terminal alkyne, and still maintaining catalytic activity. Selectivity, endurance, medium and functional group compatibility are the key features of the catalytic system obtained from the p-cymene ruthenium dimer under the one-pot conditions.

Two-stage sonogashira coupling method in the synthesis of auxin active acetylenes

A sequential Sonogashira coupling of a protected acetylene precursor with aryl halides (5) followed by pyrazolyl iodides (14) allows efficient access to the unsymmetrical aryl-heteroarylacetylene (8). Subsequent regioselective lithiation exchange followed by dimethyl oxalate quench produced readily vicinal ketoesters (9) which show auxin effects in a wide variety of plant species.