1579-80-2

Usage

Uses

Used in Pharmaceutical Industry:
(3,3,3-TRIFLUOROPROPYL)BENZENE is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure and reactivity contribute to the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, (3,3,3-TRIFLUOROPROPYL)BENZENE is utilized as a building block in the production of agrochemicals. Its incorporation into these compounds can enhance their effectiveness in pest control and crop protection.
Used in Specialty Chemicals Production:
(3,3,3-TRIFLUOROPROPYL)BENZENE is employed as a key intermediate in the synthesis of specialty chemicals, which are used in various applications such as coatings, adhesives, and sealants. Its unique properties allow for the creation of high-performance materials with specific characteristics.
Used as a Solvent:
(3,3,3-TRIFLUOROPROPYL)BENZENE is used as a solvent in various chemical processes. Its ability to dissolve a wide range of substances makes it a valuable component in the production of various industrial materials.
Used in Polymer Production:
As a chemical intermediate, (3,3,3-TRIFLUOROPROPYL)BENZENE plays a crucial role in the synthesis of polymers. Its incorporation into polymer structures can impart specific properties, such as enhanced stability or improved performance in various applications.
Safety Precautions:
Due to its highly flammable nature and potential hazards, proper safety measures should be taken when handling and storing (3,3,3-TRIFLUOROPROPYL)BENZENE. This includes using appropriate personal protective equipment, ensuring proper ventilation, and following established safety protocols to minimize risks.

InChI:InChI=1/C9H9F3/c10-9(11,12)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2

Synthetic route

styrene (292638-84-7) + iodotrifluoromethane (2314-97-8) → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
With 4-sulfanylphenol In ethanol; 1,2-dichloro-ethane at 23℃; for 18h; Schlenk technique; Microwave irradiation;	79%

3-Chloro-1,1,1-trifluoro-3-phenylpropane (126488-91-3) → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
With potassium hydroxide at 50℃;	62%

(2-phenylethyl)boronic acid (34420-17-2) + (trifluoromethyl)trimethylsilane (81290-20-2) → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
With potassium fluoride; copper(l) iodide; silver tetrafluoroborate; 3,4,7,8-Tetramethyl-o-phenanthrolin; silver fluoride In N,N-dimethyl-formamide at 80℃; for 24h; Glovebox; Inert atmosphere;	62%

1,1,1-trifluoropropylene (677-21-4) + benzene (71-43-2) → (3,3,3-trifluoropropyl)benzene (1579-80-2) + 1,4-bis(3,3,3-trifluoropropyl)benzene (86382-01-6) + bis(3,3,3-trifluoropropyl)benzene (96256-35-8)

Conditions	Yield
With hydrogen fluoride; boron trifluoride for 4.5h; Ambient temperature;	A 59% B n/a C n/a
With hydrogen fluoride; boron trifluoride for 4.5h; Ambient temperature;

2,2-dichloro-3,3,3-trifluoro-1-phenylpropyl methanesulfonate (107686-45-3) → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
With tetramethlyammonium chloride In methanol 11 F/mol, Pb cathode;	51%

2,2-dichloro-3,3,3-trifluoro-1-phenylpropyl methanesulfonate (107686-45-3) → (3,3,3-trifluoropropyl)benzene (1579-80-2) + (E)-3,3,3-trifluoro-1-phenylpropene (705-89-5, 74031-42-8, 74031-46-2)

Conditions	Yield
With tetramethlyammonium chloride In methanol 6.5 F/mol, Pb cathode;	A 19% B 50%

1,1,1-trifluoropropylene (677-21-4) + benzene (71-43-2) → (3,3,3-trifluoropropyl)benzene (1579-80-2) + 1,1-difluoroindane (96256-33-6) + 1,4-bis(3,3,3-trifluoropropyl)benzene (86382-01-6) + bis(3,3,3-trifluoropropyl)benzene (96256-35-8) + tris-(3,3,3-trifluoropropyl)benzene

Conditions	Yield
With hydrogen fluoride; boron trifluoride at 100℃; for 40h; Product distribution; other catalysts, other benzene derivatives;	A 35% B 8% C n/a D n/a E n/a

1,1,1-trifluoro-3-iodopropane (460-37-7) + phenylmagnesium chloride (100-59-4) → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at 20℃; Inert atmosphere; Glovebox;	22%
copper(l) iodide In tetrahydrofuran Ambient temperature;	74 % Spectr.

(3,3,3-trifluoroprop-1-enyl)benzene (74031-42-8, 74031-46-2, 705-89-5) → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
With methanol In acetonitrile at 20℃; for 24h; UV-irradiation; Inert atmosphere;	8%

pentafluoroethyl phenyl ketone (394-52-5) → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
With hydrogenchloride; acetic acid; zinc

1,1,1-trifluoropropylene (677-21-4) + benzene (71-43-2) → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
With aluminum oxide at 100℃; for 0.5h; var. activated Al2O3; Yield given;

1,1,1-trifluoropropylene (677-21-4) + benzene (71-43-2) → (3,3,3-trifluoropropyl)benzene (1579-80-2) + 1,1-Difluoro-3-phenyl-1-propene (4980-68-1)

Conditions	Yield
With aluminum oxide; chlorotrifluoromethane at 100℃; for 0.5h; var. activated Al2O3; Yield given. Yields of byproduct given;
With aluminum chlorofluoride under 1500.15 Torr; regioselective reaction;

3-bromo-1,1,1-trifluoropropane (460-32-2) + phenylmagnesium chloride (100-59-4) → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
copper(l) iodide In tetrahydrofuran at 50℃; for 16h;	98 % Spectr.

1-(α,α-dichloro-β,β,β-trifluoroethyl)benzylalcohol (103654-96-2, 121591-61-5, 121591-67-1) → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / NEt3 / CH2Cl2 2: 51 percent / Me4NCl / methanol / 11 F/mol, Pb cathode View Scheme
Multi-step reaction with 2 steps 1: 96 percent / NEt3 / CH2Cl2 2: 19 percent / Me4NCl / methanol / 6.5 F/mol, Pb cathode View Scheme

benzaldehyde (100-52-7) → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / SiClMe3, Et4NOTs / dimethylformamide / 10 mF, Pt cathode, carbon anode 2: 96 percent / NEt3 / CH2Cl2 3: 51 percent / Me4NCl / methanol / 11 F/mol, Pb cathode View Scheme
Multi-step reaction with 3 steps 1: 87 percent / SiClMe3, Et4NOTs / dimethylformamide / 10 mF, Pt cathode, carbon anode 2: 96 percent / NEt3 / CH2Cl2 3: 19 percent / Me4NCl / methanol / 6.5 F/mol, Pb cathode View Scheme

(Z)-1-phenyl-3,3,3-trifluoroprop-1-en-2-yl trifluoromethanesulfonate → (3,3,3-trifluoropropyl)benzene (1579-80-2) + (E)-3,3,3-trifluoro-1-phenylpropene (705-89-5, 74031-42-8, 74031-46-2)

Conditions	Yield
With triethylsilane; palladium diacetate In N,N-dimethyl-formamide at 25℃; for 0.5h; Reagent/catalyst; Inert atmosphere;	A 49 %Spectr. B 51 %Spectr.

bromobenzene (108-86-1) → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium diacetate; copper(II) oxide; potassium carbonate / 1-methyl-pyrrolidin-2-one / 15 h / 130 °C / Inert atmosphere 2: methanol / acetonitrile / 24 h / 20 °C / UV-irradiation; Inert atmosphere View Scheme

Togni's reagent (887144-97-0) + 3-Phenylpropionic acid (501-52-0) → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
With 3,4,7,8-Tetramethyl-o-phenanthrolin; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; water; copper dichloride In ethyl acetate at 20℃; for 12h; Inert atmosphere; Irradiation; Sealed tube;	77 %Spectr.

styrene (292638-84-7) + S-(trifluoromethyl)thianthrenium triflate → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
With caesium carbonate; Benzene-1,2-dithiol In 2-methyl-propan-1-ol at 0℃; for 0.5h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Glovebox;

styrene (292638-84-7) + S-(trifluoromethyl)thianthrenium tetrafluoroborate → (3,3,3-trifluoropropyl)benzene (1579-80-2)

Conditions	Yield
With caesium carbonate; Benzene-1,2-dithiol In 2-methyl-propan-1-ol at 0℃; for 2.5h;	92 %Spectr.

(3,3,3-trifluoropropyl)benzene (1579-80-2) + benzene (71-43-2) → 1,3-diphenylpropane (1081-75-0)

Conditions	Yield
With triethylsilane; triphenylmethyl closo-6,7,8,9,10,11-hexachloropentahydroundecacarborate In 1,2-dichloro-benzene at 25℃; for 48h; Friedel Crafts alkylation;

Upstream product

• 677-21-4 1,1,1-trifluoropropylene 
• 71-43-2 benzene 
• 460-37-7 1,1,1-trifluoro-3-iodopropane 
• 100-59-4 phenylmagnesium chloride 
• 460-32-2 3-bromo-1,1,1-trifluoropropane 
• 103654-96-2 1-(α,α-dichloro-β,β,β-trifluoroethyl)benzylalcohol 
• 100-52-7 benzaldehyde 
• 34420-17-2 (2-phenylethyl)boronic acid 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 100-42-5 styrene 
• 2314-97-8 iodotrifluoromethane 
• 108-86-1 bromobenzene 
• 74031-42-8 (3,3,3-trifluoroprop-1-enyl)benzene 
• 887144-97-0 Togni's reagent 

Downstream Products

• 1081-75-0 1,3-diphenylpropane 

Relevant academic research and scientific papers

REACTION OF 3,3,3-TRIFLUOROPROPENE WITH BENZENE OVER Al2O3 TREATED WITH CF3Cl

The reaction between 3,3,3-trifluoropropene and benzene in a vapor phase was carried out over various Al2O3.Trifluoropropylbenzene was obtained selectively when CF3Cl-treated Al2O3 was used as a catalyst.

Tailoring the Reactivity of the Langlois Reagent and Styrenes with Cyanoarenes Organophotocatalysts under Visible-Light

The selective one-step access to fluoroalkylated hexestrol derivatives, nonsteroidal estrogens, is achieved in good to excellent isolated yields under organophotoredox conditions by using the stable and easy to handle Langlois reagent. Furthermore, the ch

Starting from Styrene: A Unified Protocol for Hydrotrifluoromethylation of Diversified Alkenes

In contrast with unactivated alkenes, the corresponding hydrotrifluoromethylation of styrene has remained challenging due to the strong propensity of styrene for oligomerization and polymerization. On the basis of our newly developed trifluoromethylation reagent, TFSP, herein we present a general method for the hydrotrifluoromethylation of styrene under photoredox catalysis. The substrate scope was further extended to unactivated alkenes, acrylates, acrylamides, and vinyl-heteroatom-substituted alkenes. The tunability of this method was showcased via the relevant deprotonative trifluoromethylation and trifluoromethyltrifluoroethoxylation reactions.

Method for preparing fluoroalkane substituted compound by reducing halogenated fluoroalkane and olefin through metal elementary substance

The invention discloses a method for preparing a fluoroalkane substituted compound, which comprises the steps of taking a compound containing carbon-carbon double bonds and halogenated fluoroalkane as raw materials, taking a metal elementary substance as a reducing agent, taking a substance containing active protons as a hydrogen source, and carrying out an addition reaction to prepare a compound which is simultaneously substituted by hydrogen and fluoroalkyl, thereby obtaining the fluoroalkane substituted compound. According to the method, the metal elementary substance is used as the reducing agent for the first time, the compound containing active hydrogen is used as the hydrogen source, one hydrogen atom and one fluoroalkyl group are introduced to the two ends of olefin respectively, only one-step reaction is needed, the reaction process conditions are mild, the reaction raw materials are cheap and easy to obtain, the cost is low, and all reaction reagents are green and environmentally friendly; and the reaction substrate has strong applicability, can participate in the reaction as long as carbon-carbon double bonds exist in the structure, and is not influenced by the types of substituent groups on carbon atoms of the double bonds, and the yield of the product is good.

Trifluoromethyl Thianthrenium Triflate: A Readily Available Trifluoromethylating Reagent with Formal CF3+, CF3?, and CF3-Reactivity

Here we report the synthesis and application of trifluoromethyl thianthrenium triflate (TT-CF3+OTf-) as a novel trifluoromethylating reagent, which is conveniently accessible in a single step from thianthrene and triflic anhydride. We demonstrate the use of TT-CF3+OTf- in electrophilic, radical, and nucleophilic trifluoromethylation reactions.

Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids

Herein we disclose an efficient method for the conversion of carboxylic acids to trifluoromethyl groups via the combination of photoredox and copper catalysis. This transformation tolerates a wide range of functionality including heterocycles, olefins, al

Photocatalytic alkene reduction by a B12-TiO2 hybrid catalyst coupled with C-F bond cleavage for: Gem -difluoroolefin synthesis

Photocatalytic syntheses of gem-difluoroolefins were performed using the B12-TiO2 hybrid catalyst during the CC bond reduction of α-trifluoromethyl styrenes with C-F bond cleavage at room temperature under nitrogen. The gem-difluoroolefins were used as synthetic precursors for fluorinated cyclopropanes.

Palladium-catalyzed geometrically selective hydrogenation of (Z)-trifluoromethyl alkenyl triflate: An efficient approach to (Z) or (E)-3,3,3-trifluoropropenyl derivatives

A Pd-catalyzed hydrogenation of (Z)-trifluoromethyl alkenyl triflate providing either (Z)- or (E)-3,3,3-trifluoropropenyl derivatives with excellent divergent geometric control in good yield is described. Catalyzed by Pd(OAc)2/PPh3, the reduction of (Z)-trifluoromethyl alkenyl triflates with HSiEt3 gave (E)-3,3,3-trifluoropropenyl derivatives, and while using HCOOH/Et3N as the reducing agent, the (Z)-isomers were obtained through an elimination/hydrogenation tandem pathway. Both transformations showed excellent geometrical selectivity.

Heterogeneous Catalytic Hydroarylation of Olefins at a Nanoscopic Aluminum Chlorofluoride

We report on hydroarylation reactions of arenes with olefins under very mild conditions catalyzed heterogeneously by aluminum chlorofluoride (ACF; AlClxF3?x, x≈0.05–0.25). The reactions of benzene and toluene with ethylene or propylene proceed with high conversions to afford various alkylated arenes. For cyclohexene and 1-hexene, the reactions require higher temperatures and the conversions are lower. ACF also catalyzes the hydroarylation of 1,3,5-trifluorobenzene and pentafluorobenzene with ethylene and propylene. The alkylations of arenes with non-fluorinated olefins resemble typical Friedel–Crafts chemistry to give rise to Markovnikov regioselectivity. The reaction of CF3CH=CH2 with benzene proceeds with anti-Markovnikov regioselectivity to give the fluorinated olefin PhCHCH=CF2 and the alkylation product PhCH2CH2CF3 as products of C?F and C?H activation.

Practical Photocatalytic Trifluoromethylation and Hydrotrifluoromethylation of Styrenes in Batch and Flow

Styrenes represent a challenging class of substrates for current radical trifluoromethylation and hydrotrifluoromethylation methods due to a myriad of potential side reactions. Herein, we describe the development of mild, selective and broadly applicable photocatalytic trifluoromethylation and hydrotrifluoromethylation protocols for these challenging substrates. The methods use fac-Ir(ppy)3, visible light and inexpensive CF3I and can be applied to a diverse set of vinylarene substrates. The use of continuous-flow photochemical reaction conditions allowed to reduce the reaction time and increase the reaction selectivity.