88-16-4

Basic information

• Product Name: 2-Chlorobenzotrifluoride
• Synonyms: CHLOROBENZOTRIFLUORIDE(O-);1-CHLORO-2-(TRIFLUOROMETHYL)BENZENE;2-CHLOROBENZOTRIFLUORIDE;2-CHLORO-ALPHA,ALPHA,ALPHA-TRIFLUOROTOLUENE;2-chloro(trifluoromethyl)benzene;2-CHLOROTRIFLUOROTOLUENE;1-(trifluoromethyl)-2-chlorobenzene;1-chloro-2-(trifluoromethyl)-benzen
• CAS NO: 88-16-4
• Molecular Formula: C₇H₄ClF₃
• Molecular Weight: 180.55
• EINECS: 201-805-1
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Chlorine Compounds;Fluorine Compounds
• Mol File: 88-16-4.mol
• Article Data: 25

Chemical Properties

• Melting Point: -7.4 °C
• Boiling Point: 152 °C(lit.)
• Flash Point: 138 °F
• Appearance: clear colourless to light yellow liquid
• Density: 1.379 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.456(lit.)
• Storage Temp.: Flammables area
• Explosive Limit: 1.7%(V)
• Water Solubility: <0.1 g/100 mL at 19.5℃
• Stability: Stable. Flammable. Incompatible with strong oxidizing agents, strong bases.
• BRN: 510993
• CAS DataBase Reference: 2-Chlorobenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chlorobenzotrifluoride(88-16-4)
• EPA Substance Registry System: 2-Chlorobenzotrifluoride(88-16-4)

Safety Data

• Hazard Codes: Xi,F,Xn,N
• Statements: 10-36/37/38-22
• Safety Statements: 26-36-36/37/39-16
• RIDADR: UN 2234 3/PG 3
• WGK Germany: 3
• RTECS: XS9141000
• TSCA: T
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 88-16-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear colourless to light yellow liquid

Uses

Dye intermediate, chemical intermediate, solvent, and dielectric fluid.

Purification Methods

Dry the trifluoride over CaSO4, and distil it at high reflux ratio through a silvered vacuum-jacketed glass column packed with one-eight inch glass helices [Potter & Saylor J Am Chem Soc 73 90 1951]. [Beilstein 5 H 302, 5 III 692, 5 IV 814.]

InChI:InChI=1/C7H4ClF3/c8-6-4-2-1-3-5(6)7(9,10)11/h1-4H

Synthetic route

2-iodochlorobenzene (615-41-8) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide at 60 - 70℃; for 6h;	84%

1,1'-dichloro-2,2'-difluoroethene (79-35-6) + o-trifluoromethylphenyl bromide (392-83-6) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4) + 1-(2,2-dichloro-1-fluoroethenyl)-2-(trifluoromethyl)benzene (88444-77-3)

Conditions	Yield
With n-butyllithium In diethyl ether for 1h; Heating;	A 3% B 77%

1-Chloro-2-(ethylsulfanyl-difluoro-methyl)-benzene (160911-81-9) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4) + 1-Chloro-2-(chloro-difluoro-methyl)-benzene (115345-92-1)

Conditions	Yield
With bromine trifluoride In trichlorofluoromethane at 0℃;	A 70% B 5%
With bromine trifluoride; trichlorofluoromethane at 0℃;	A 70% B 5%

2-Chloro-dithiobenzoic acid ethyl ester (160911-76-2) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
With bromine trifluoride In trichlorofluoromethane at 0℃; for 0.0333333h;	70%
Multi-step reaction with 2 steps 1: BrF3 / CCl3F / 0 °C 2: 70 percent / BrF3, CFCl3 / 0 °C View Scheme

2-iodochlorobenzene (615-41-8) + sodium 2,2,2-trifluoroacetate (2923-18-4) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
With potassium fluoride; potassium phosphate In water; N,N-dimethyl-formamide at 20℃; for 48h; Irradiation; Inert atmosphere;	63%
With 1-methyl-pyrrolidin-2-one; copper(l) iodide at 160℃; for 4h;	87 % Chromat.
With copper; silver(l) oxide In N,N-dimethyl-formamide at 130℃; for 15h; Inert atmosphere;	70 %Spectr.

2-bromo-1-chlorobenzene (694-80-4) + sodium 2,2,2-trifluoroacetate (2923-18-4) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
With potassium fluoride; potassium phosphate In water; N,N-dimethyl-formamide at 20℃; for 48h; Irradiation; Inert atmosphere;	39%

morpholine (110-91-8) + 2,4-dichloro-benzotrifluoride (320-60-5) → 4-(3-chloro-4-trifluoromethylphenyl)morpholine + 4-chlorobenzotrifluoride (98-56-6) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
With Adipic acid; N'-phenyloxalyl bishydrazide; copper diacetate; sodium acetate; cetyltrimethylammonim bromide; 2,5-hexanedione; potassium hydroxide In water at 110℃; for 3h; Inert atmosphere;	A 5% B n/a C n/a

2-chlorobenzotrichloride (2136-89-2) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
With hydrogen fluoride; antimonypentachloride
With antimony(III) fluoride
With hydrogen fluoride at 50℃; under 7500.75 Torr; for 1h; Autoclave;
With antimony (V)-fluoride chloride; phosphorus pentachloride; hydrogen fluoride
With hydrogen fluoride at 82℃; under 1500.15 - 13501.4 Torr; for 0.5h; Pressure; Temperature;

2-(trifluoromethyl)benzenamine (88-17-5) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuCl;

2,3,5-trichlorotrifluoromethylbenzene (61841-46-1) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
With Dichloromethylsilane at 240℃; (electron irradiation);

para-dichlorobenzene (106-46-7) → 4-chlorobenzotrifluoride (98-56-6) + 3-chlorotrifluoromethylbenzene (98-15-7) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) + 1,2,4-Trichlorobenzene (120-82-1)

Conditions	Yield
With α,α,α-trifluorotoluene; chlorine; iron(III) chloride In tetrachloromethane Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
With α,α,α-trifluorotoluene; chlorine; iron(III) chloride In tetrachloromethane Product distribution; Rate constant;

α,α,α-trifluorotoluene (98-08-8) → 4-chlorobenzotrifluoride (98-56-6) + 3-chlorotrifluoromethylbenzene (98-15-7) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
With chlorine; iron(III) chloride at 80℃; Product distribution;	A n/a B 40.0 % Chromat. C 3.9 % Chromat.

α,α,α-trifluorotoluene (98-08-8) → 4-chlorobenzotrifluoride (98-56-6) + 3-chlorotrifluoromethylbenzene (98-15-7) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) + 1,2,4-Trichlorobenzene (120-82-1)

Conditions	Yield
With para-dichlorobenzene; chlorine; iron(III) chloride In tetrachloromethane Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
With para-dichlorobenzene; chlorine; iron(III) chloride In tetrachloromethane Product distribution; Rate constant;

iodotrifluoromethane (2314-97-8) + chlorobenzene (108-90-7) → 4-chlorobenzotrifluoride (98-56-6) + 3-chlorotrifluoromethylbenzene (98-15-7) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
at 190℃; for 48h; Title compound not separated from byproducts;	A 23 % Chromat. B 25 % Chromat. C 52 % Chromat.

bis(trifluoroacetyl)peroxide (383-73-3) + chlorobenzene (108-90-7) → 4-chlorobenzotrifluoride (98-56-6) + 3-chlorotrifluoromethylbenzene (98-15-7) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane at 70℃; Yield given. Yields of byproduct given;

o-trifluoromethyl-α,α-dichlorotoluene (707-72-2) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
With chlorine Irradiation;

bis(trifluoromethyl)tellurium (55642-42-7) + chlorobenzene (108-90-7) → trifluoromethan (75-46-7) + bis(trifluoromethyl) ditelluride (1718-20-3) + 4-chlorobenzotrifluoride (98-56-6) + 3-chlorotrifluoromethylbenzene (98-15-7) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) + tellur

Conditions	Yield
for 168h; Product distribution; Irradiation;

bis(trifluoromethyl)tellurium (55642-42-7) + chlorobenzene (108-90-7) → trifluoromethan (75-46-7) + bis(trifluoromethyl) ditelluride (1718-20-3) + α,α,α-trifluorotoluene (98-08-8) + 4-chlorobenzotrifluoride (98-56-6) + 3-chlorotrifluoromethylbenzene (98-15-7) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) + tellur

Conditions	Yield
at 168℃; for 120h; Product distribution;

...Expand

2-chloro-thiobenzoic acid S-ethyl ester (32357-19-0) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 6H4P(S)S>2 2: BrF3 / CCl3F / 0 °C 3: 70 percent / BrF3, CFCl3 / 0 °C View Scheme

ortho-chlorobenzoic acid (118-91-2) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1) SO2Cl 2: 6H4P(S)S>2 3: BrF3 / CCl3F / 0 °C 4: 70 percent / BrF3, CFCl3 / 0 °C View Scheme

2-methylchlorobenzene (95-49-8) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 160 - 190 °C / Einleiten von Chlor 2: SbF3 View Scheme

2-nitrobenzotrifluoride (384-22-5) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium / Hydrogenation 2: Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuCl View Scheme

N-acetyl-3-trifluoromethylbenzenamine (351-36-0) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid; nitric acid / und Erwaermen des Reaktionsprodukts mit aethanol.Natronlauge 2: ethanol; concentrated H2SO4 / 0 - 10 °C / Erwaermen der Reaktionsloesung mit Kupferbronze 3: palladium / Hydrogenation 4: Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuCl View Scheme

4-nitro-3-(trifluoromethyl)benzeneamine (393-11-3) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol; concentrated H2SO4 / 0 - 10 °C / Erwaermen der Reaktionsloesung mit Kupferbronze 2: palladium / Hydrogenation 3: Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuCl View Scheme

o-dichloromethyltrichloromethylbenzene (2741-57-3) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: HF 2: Cl2 / Irradiation View Scheme

2-chlorobenzotrichloride (2136-89-2) → C7H4Cl3F (1258790-97-4) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) + 1-Chloro-2-(chloro-difluoro-methyl)-benzene (115345-92-1)

Conditions	Yield
With hydrogen fluoride; antimonypentachloride at 50℃; under 7500.75 Torr; for 1h; Autoclave;

2-chlorobenzotrichloride (2136-89-2) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4) + 1-Chloro-2-(chloro-difluoro-methyl)-benzene (115345-92-1)

Conditions	Yield
With hydrogen fluoride at 50℃; under 7500.75 Torr; for 1h; Autoclave;

2-iodochlorobenzene (615-41-8) + (1,10-phenanthroline)(trifluoromethyl)copper (I) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	89 %Spectr.

Acetanilid (103-84-4) → 1-chloro-2-(trifluoromethyl)benzene (88-16-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: palladium diacetate; copper diacetate; Trimethylacetic acid / 1,2-dichloro-ethane / 24 h / 110 °C / Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry 2.1: thionyl chloride / methanol / 1.5 h / 75 °C 3.1: sodium nitrite; hydrogenchloride / water / 0 - 5 °C 3.2: 3 h / 0 - 60 °C View Scheme
Multi-step reaction with 4 steps 1.1: toluene / 1 h / 120 °C / Sealed tube; Inert atmosphere 2.1: copper diacetate; Trimethylacetic acid / 1,2-dichloro-ethane / 12 h / 110 °C / Inert atmosphere; Schlenk technique; Sealed tube 3.1: thionyl chloride / methanol / 1.5 h / 75 °C 4.1: sodium nitrite; hydrogenchloride / water / 0 - 5 °C 4.2: 3 h / 0 - 60 °C View Scheme

1-chloro-2-(trifluoromethyl)benzene (88-16-4) + phenylacetylene (536-74-3) → 1-(phenylethynyl)-2-(trifluoromethyl)benzene (147344-86-3)

Conditions	Yield
With copper(l) iodide; potassium carbonate In ethanol; water at 90℃; for 5h; Sonogashira Cross-Coupling; Green chemistry;	100%
With potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In N,N-dimethyl-formamide at 140℃; for 20h; Sonogashira cross-coupling;	92%

methoxybenzene (100-66-3) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → (4-methoxyphenyl)-(2-chlorophenyl)-dichloromethane

Conditions	Yield
With aluminum (III) chloride In 1,2-dichloro-ethane at 0℃; for 3h;	100%

1H-imidazole (288-32-4) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 1-(2-trifluoromethylphenyl)-imidazole

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 7h;	97%

1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 4-chloro-3-(trifluoromethyl)nitrobenzene (777-37-7)

Conditions	Yield
With sulfuric acid; nitric acid at 25℃;	96.13%
With sulfuric acid; nitric acid at 20 - 45℃; for 4h;	91.3%
With sulfuric acid; nitric acid at 45℃; for 4h;	91.3%

1-chloro-2-(trifluoromethyl)benzene (88-16-4) + benzene (71-43-2) → 1-chloro-2-(dichloro(phenyl)methyl)benzene (3509-85-1)

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane at 0℃; for 3h;	96%

1-(4-fluorophenyl)propan-1-one (456-03-1) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → C16H12F4O

Conditions	Yield
With C41H50ClN3Pd; sodium t-butanolate In 1,4-dioxane at 100℃; for 4h; Reagent/catalyst; Inert atmosphere;	96%

styrene (292638-84-7) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → C15H11F3 (928030-90-4)

Conditions	Yield
With potassium carbonate In ethanol; water at 90℃; for 15h; Heck Reaction; Green chemistry;	95%

1-chloro-2-(trifluoromethyl)benzene (88-16-4) + L-prolinamide (7531-52-4) → (S)-N'-((2-trifluoromethyl)phenyl)prolinylamide (403478-68-2)

Conditions	Yield
With 4-diphenylphosphino-13-dicyclohexylphosphino-[2.2]paracyclophane; water; palladium diacetate; caesium carbonate In 1,4-dioxane at 125℃; for 24h; Buchwald-Hartwig coupling;	94%

1-chloro-2-(trifluoromethyl)benzene (88-16-4) + ethyl acrylate (140-88-5) → ethyl 2-trifluoromethylcinnamate (50620-98-9)

Conditions	Yield
With potassium carbonate In ethanol; water; N,N-dimethyl-formamide at 100℃; for 5h; Heck Reaction; Green chemistry;	94%

1-chloro-2-(trifluoromethyl)benzene (88-16-4) + chlorobenzene (108-90-7) → dichloro-(2-chloro-phenyl)-(4-chloro-phenyl)-methane

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane at 0℃; for 3h;	92%

1-chloro-2-(trifluoromethyl)benzene (88-16-4) + sodium thiomethoxide (5188-07-8) → 2-(methylthio)-1-(trifluoromethyl)benzene (322-58-7)

Conditions	Yield
With N,N-dimethyl-formamide at 40 - 50℃; for 20h;	92%

bromobenzene (108-86-1) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 2-chloro-4'-bromo-diphenyldichloromethane

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane at 0℃; for 3h;	91%

1-chloro-2-(trifluoromethyl)benzene (88-16-4) + phenylboronic acid (98-80-6) → 2-trifluoromethyl-biphenyl (362-59-4)

Conditions	Yield
With potassium carbonate; 2-(di-tert-butyl-phosphino)-1-phenyl-1H-pyrrole; palladium diacetate In toluene at 100℃; Suzuki coupling;	91%
With 1-(2,6-diisopropylphenyl)-3-(2-oxo-2-(2,4,6-tri-tert-butylphenylamino)ethyl)-1H-imidazol-3-ium bromide; palladium diacetate; sodium hydroxide In 1-methyl-pyrrolidin-2-one; dichloromethane; water at 130℃; for 12h; Suzuki coupling;	78%
With potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); Tedicyp In xylene at 130℃; for 20h; Suzuki reaction;	100 % Chromat.

magnesium (7439-95-4) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 2-trifluoromethylphenylmagnesium chloride (3796-19-8)

Conditions	Yield
With ethyl bromide; tert-butylmagnesium chloride In tetrahydrofuran at 35 - 50℃; for 3h; Product distribution / selectivity;	91%

5,5-dimethyl-1,3,2-dioxaborinane (668987-38-0) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 5,5-dimethyl-2-(2-(trifluoromethyl)phenyl)-1,3,2-dioxaborinane (95753-22-3)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); triethylamine; zinc In toluene at 100℃; for 4h; Inert atmosphere;	91%
With 1,1'-bis-(diphenylphosphino)ferrocene; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); triethylamine In toluene at 23 - 100℃; Inert atmosphere;	52%

1-chloro-2-(trifluoromethyl)benzene (88-16-4) → o-trifluoromethylbenzenethiol (13333-97-6)

Conditions	Yield
With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 110℃; for 20h; Inert atmosphere;	91%
With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 90℃; for 20h; Reagent/catalyst; Inert atmosphere;	91%

naphthalene (91-20-3) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 1-[Dichloro-(2-chloro-phenyl)-methyl]-naphthalene

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane at 0℃; for 3h;	90%

1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 2',4-dichloro-3-(trifluoromethyl)benzophenone (1313994-80-7)

Conditions	Yield
With trifluorormethanesulfonic acid Inert atmosphere; neat (no solvent);	90%

bis(1,5-cyclooctadiene)nickel (0) (1295-35-8) + N,N,N,N,-tetramethylethylenediamine (110-18-9) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → (TMEDA)Ni(Cl)(o-CF3Ph)

Conditions	Yield
at 20℃; for 72h; Glovebox; Inert atmosphere;	90%

styrene (292638-84-7) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 2-styryl-α,α,α-trifluorotoluene (191867-92-2)

Conditions	Yield
With tetrabutylammomium bromide; sodium acetate; C84H60N12O8Pd4 at 140℃; for 6h; Heck Reaction; Inert atmosphere; Schlenk technique;	89%

1-chloro-2-(trifluoromethyl)benzene (88-16-4) + bis(pinacol)diborane (73183-34-3) → 2-[2-(trifluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1073339-21-5)

Conditions	Yield
With tris(trimethylphosphine)nickel(II) chloride; (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride In tetrahydrofuran at 100℃; for 12h; Inert atmosphere;	88%
With (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; dichlorobis(trimethylphosphine)nickel In tetrahydrofuran at 100℃; for 12h; Inert atmosphere; Sealed tube;	88%

tri(allyl)phenylsilane (2633-57-0) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 2-trifluoromethyl-biphenyl (362-59-4)

Conditions	Yield
Stage #1: triallyl(phenyl)silane With tetrabutyl ammonium fluoride In tetrahydrofuran; water at 20℃; for 1h; Stage #2: 1-chloro-2-(trifluoromethyl)benzene With XPhos; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran; water at 80℃; for 3h;	86%
Stage #1: triallyl(phenyl)silane With tetrabutyl ammonium fluoride In tetrahydrofuran; water at 20℃; for 1h; Stage #2: 1-chloro-2-(trifluoromethyl)benzene With XPhos; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran; water at 80℃; for 3h;	86%

furan (110-00-9) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 1,4-epoxy-1,4-dihydro-5-(trifluoromethyl)-naphthalene (853017-48-8)

Conditions	Yield
Stage #1: 1-chloro-2-(trifluoromethyl)benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: furan In tetrahydrofuran; hexane at 25℃;	86%
Stage #1: 1-chloro-2-(trifluoromethyl)benzene With n-butyllithium In tetrahydrofuran; hexane at -75℃; for 1h; Stage #2: furan In tetrahydrofuran; hexane at 25℃;	76%

pyrrolidine (123-75-1) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 1-(2-trifluoromethyl-phenyl)pyrrolidine (893086-73-2)

Conditions	Yield
With polymethylhydrosiloxane; sodium t-butanolate; bis(acetylacetonate)nickel(II) In 1,2-dimethoxyethane; toluene at 130℃; for 18h;	85%

acetic anhydride (108-24-7) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 1-(2-(trifluoromethyl)phenyl)ethan-1-one (17408-14-9)

Conditions	Yield
Stage #1: 1-chloro-2-(trifluoromethyl)benzene With ethyl bromide; ethylmagnesium bromide; magnesium; lithium chloride In tetrahydrofuran at 45 - 50℃; for 4h; Inert atmosphere; Stage #2: acetic anhydride In tetrahydrofuran at 20 - 30℃; for 2h; Reagent/catalyst; Inert atmosphere; Further stages;	82.7%
Stage #1: 1-chloro-2-(trifluoromethyl)benzene With ethylmagnesium bromide; magnesium; lithium chloride In tetrahydrofuran; ethyl bromide at 45 - 50℃; for 5h; Inert atmosphere; Stage #2: acetic anhydride In tetrahydrofuran; ethyl bromide; toluene at 20 - 30℃; for 2h; Inert atmosphere;	72.4%

1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 1-chloro-2-(tribromomethyl)benzene

Conditions	Yield
With aluminum tri-bromide; trimethylsilyl bromide at 80℃; Inert atmosphere;	82%
With carbon disulfide; aluminum tri-bromide

phenyl trimethylsiloxane (2996-92-1) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 2-trifluoromethyl-biphenyl (362-59-4)

Conditions	Yield
With tBu2P-N=P(iBuPCH2CH2)3N; tetrabutyl ammonium fluoride; palladium diacetate at 80℃; for 3h; Hiyama coupling; Inert atmosphere; Neat (no solvent);	82%

4-(trimethylsilyl)morpholine (13368-42-8) + 1-chloro-2-(trifluoromethyl)benzene (88-16-4) → 4-(3-(trifluoromethyl)-2-(trimethylsilyl)phenyl)morpholine

Conditions	Yield
With lithium di-1-admantylamide In diethyl ether; cyclohexane at 50℃; for 28h; Inert atmosphere;	81%

Upstream product

• 79-35-6 1,1'-dichloro-2,2'-difluoroethene 
• 392-83-6 o-trifluoromethylphenyl bromide 
• 55642-42-7 bis(trifluoromethyl)tellurium 
• 108-90-7 chlorobenzene 
• 615-41-8 2-iodochlorobenzene 
• 13333-97-6 o-trifluoromethylbenzenethiol 
• 106-46-7 para-dichlorobenzene 
• 61841-46-1 2,3,5-trichlorotrifluoromethylbenzene 
• 88-17-5 2-(trifluoromethyl)benzenamine 
• 2136-89-2 2-chlorobenzotrichloride 
• 870195-94-1 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-chlorobenzene 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 694-80-4 2-bromo-1-chlorobenzene 

Downstream Products

• 39226-97-6 2-chloro-3-trifluoromethylbenzoic acid 
• 322-58-7 2-(methylthio)-1-(trifluoromethyl)benzene 
• 192139-23-4 2-[(1-methylethyl)thio]-1-(trifluoromethyl)benzene 
• 98-16-8 3-trifluoromethylaniline 
• 98-08-8 α,α,α-trifluorotoluene 
• 39974-35-1 2-chloro-1-nitro-3-(trifluoromethyl)benzene 
• 777-37-7 4-chloro-3-(trifluoromethyl)nitrobenzene 
• 95753-22-3 5,5-dimethyl-2-[2-(trifluoromethyl)phenyl]-1,3,2-dioxaborinane 
• 441072-21-5 2-(2-(trifluoromethyl)phenyl)pyridine 
• 1313994-80-7 2',4-dichloro-3-(trifluoromethyl)benzophenone 
• 5162-03-8 (2-chlorophenyl)(phenyl)methanone 
• 66774-02-5 o-chlorotriphenylmethanol 
• 1073339-21-5 4,4,5,5-tetramethyl-2-(2-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane 
• 21726-23-8 2-trifluoromethyl-4,4'-dinitrodiphenyl ether 

Relevant articles and documents

Chromoselective Synthesis of Sulfonyl Chlorides and Sulfonamides with Potassium Poly(heptazine imide) Photocatalyst

Among external stimuli used to promote a chemical reaction, photocatalysis possesses a unique one—light. Photons are traceless reagents that provide an exclusive opportunity to alter chemoselectivity of the photocatalytic reaction varying the color of incident light. This strategy may be implemented by using a sensitizer capable to activate a specific reaction pathway depending on the excitation light. Herein, we use potassium poly(heptazine imide) (K-PHI), a type of carbon nitride, to generate selectively three different products from S-arylthioacetates simply varying the excitation light and otherwise identical conditions. Namely, arylchlorides are produced under UV/purple, sulfonyl chlorides with blue/white, and diaryldisulfides at green to red light. A combination of the negatively charged polyanion, highly positive potential of the valence band, presence of intraband states, ability to sensitize singlet oxygen, and multi-electron transfer is shown to enable this chromoselective conversion of thioacetates.

Novel synthesis method of chlorobenzotrifluoride

The invention discloses a novel synthesis method of chlorobenzotrifluoride, wherein o-chlorotoluene is used as a raw material, copper chloride or cuprous chloride is used as a catalyst, and o-chlorobenzotrifluoride is synthesized through two steps of chlorination and fluorination. Compared with the method in the prior art, the method of the invention has the following characteristics that raw materials are subjected to heating dehydration treatment in the dehydration kettle, so that the chlorination side reactions are few, the product purity is high, the graded chlorination device does not need to be additionally arranged, the technological process is simple, and the operation is convenient. According to the chlorination process of the invention, the catalyst is added in batches to increase the efficiency of the catalyst, so that the by-product generated by thechlorination reaction and the emission of waste gas in the production are greatly reduced, and the emission of pollutants in the production process is reduced.

Cathodic C-H Trifluoromethylation of Arenes and Heteroarenes Enabled by an in Situ-Generated Triflyltriethylammonium Complex

While several trifluoromethylation reactions involving the electrochemical generation of CF3 radicals via anodic oxidation have been reported, the alternative cathodic, reductive radical generation has remained elusive. Herein, the first cathodic trifluoromethylation of arenes and heteroarenes is reported. The method is based on the electrochemical reduction of an unstable triflyltriethylammonium complex generated in situ from inexpensive triflyl chloride and triethylamine, which produces CF3 radicals that are trapped by the arenes on the cathode surface.