1579-80-2

Basic information

• Product Name: (3,3,3-TRIFLUOROPROPYL)BENZENE
• Synonyms: (3,3,3-TRIFLUOROPROPYL)BENZENE;(3,3,3-Trifluoropropyl)benzene 97%;(3,3,3-Trifluoropropyl)benzene97%
• CAS NO: 1579-80-2
• Molecular Formula: C₉H₉F₃
• Molecular Weight: 174.16
• Mol File: 1579-80-2.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 155 °C
• Flash Point: 38.1 °C
• Appearance: /
• Density: 1.131
• Refractive Index: 1.437
• CAS DataBase Reference: (3,3,3-TRIFLUOROPROPYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: (3,3,3-TRIFLUOROPROPYL)BENZENE(1579-80-2)
• EPA Substance Registry System: (3,3,3-TRIFLUOROPROPYL)BENZENE(1579-80-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 1579-80-2(Hazardous Substances Data)

Usage

General Description

(3,3,3-Trifluoropropyl)benzene is a chemical compound with the molecular formula C9H9F3. It is a colorless liquid that is used as an intermediate in the production of various chemicals and materials. (3,3,3-TRIFLUOROPROPYL)BENZENE is often used as a building block in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals. It is also used as a solvent and a chemical intermediate in the production of polymers and other industrial materials. (3,3,3-Trifluoropropyl)benzene is a highly flammable and potentially hazardous chemical, and proper safety precautions should be taken when handling and storing this compound.

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

• 100-42-5 styrene 
• 2926-29-6 Langlois reagent 
• 75-63-8 Bromotrifluoromethane 
• 2648079-79-0 S-(trifluoromethyl)thianthrenium triflate 
• 887144-97-0 Togni's reagent 
• 501-52-0 3-Phenylpropionic acid 
• 74031-42-8 (3,3,3-trifluoroprop-1-enyl)benzene 
• 108-86-1 bromobenzene 
• 2314-97-8 iodotrifluoromethane 
• 34420-17-2 (2-phenylethyl)boronic acid 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 100-52-7 benzaldehyde 
• 103654-96-2 1-(α,α-dichloro-β,β,β-trifluoroethyl)benzylalcohol 
• 677-21-4 1,1,1-trifluoropropylene 

Downstream Products

• 1081-75-0 1,3-diphenylpropane 

Relevant articles and documents

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.

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.

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.