96606-37-0

Basic information

• Product Name: 2,4,6-Trifluorobenzonitrile
• Synonyms: 2,4,6-Ditrfluorobenzonitrile;2,4,6-TRIFLUOROBENZONITRILE,99%;2,4,6-TRIFLUOROBENZONITRILE;2,4,6-Trifluorobenzonitrile 98%;2,4,6-Trifluorobenzonitrile98%
• CAS NO: 96606-37-0
• Molecular Formula: C₇H₂F₃N
• Molecular Weight: 157.09
• EINECS: -0
• Product Categories: Aromatic Nitriles;Fluorobenzene;Nitrile;Aromatics Compounds;Aromatics;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds;Fluorobenzene Series
• Mol File: 96606-37-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 57-61 °C
• Boiling Point: 92 °C
• Flash Point: 92°C
• Appearance: White/Solid
• Density: 1.2465 (estimate)
• Vapor Pressure: 0.0733mmHg at 25°C
• Refractive Index: 1.413
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• BRN: 5512504
• CAS DataBase Reference: 2,4,6-Trifluorobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Trifluorobenzonitrile(96606-37-0)
• EPA Substance Registry System: 2,4,6-Trifluorobenzonitrile(96606-37-0)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-36-36/37-9
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 96606-37-0(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

2,4,6-Trifluorobenzonitrile (cas# 96606-37-0) is a compound useful in organic synthesis.

InChI:InChI=1/C11H8F6O2/c1-2-19-9(18)6-3-7(10(12,13)14)5-8(4-6)11(15,16)17/h3-5H,2H2,1H3

Synthetic route

C26H17AuF3N2P → 2,4,6-trifluorobenzonitrile (96606-37-0)

Conditions	Yield
In 1,4-dioxane at 100℃; for 3h; Kinetics; Inert atmosphere; Schlenk technique; Sealed tube;	98%

2,4,6-trifluoro-3,5-dichlorobenzonitrile (31881-89-7) → 2,4,6-trifluorobenzonitrile (96606-37-0)

Conditions	Yield
With formic acid; zinc In water at 75℃; Solvent;	85%
With hydrogenchloride; acetic acid; zinc In water at 90 - 105℃; for 6h; Reagent/catalyst; Temperature;	79.8%
With palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine In ethyl acetate at 90℃; under 3750.38 Torr; for 12h; Solvent; Temperature; Reagent/catalyst; Autoclave;
With palladium 10% on activated carbon; hydrogen; triethylamine In ethyl acetate at 60 - 65℃; under 7500.75 - 9000.9 Torr; for 8h; Solvent; Temperature; Autoclave;

3-chloro-2,4,6-trifluorobenzonitrile → 2,4,6-trifluorobenzonitrile (96606-37-0)

Conditions	Yield
With acetic acid; zinc In water at 70℃; for 3h;	60%

2,4,6-trifluorobenzamide (82019-50-9) → 2,4,6-trifluorobenzonitrile (96606-37-0)

Conditions	Yield
With phosphorus pentoxide at 200 - 250℃; for 1.25h;	55%

pentachlorobenzonitrile (20925-85-3) → 2,4,6-trifluorobenzonitrile (96606-37-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium fluoride / sulfolane / 3 h / 130 - 140 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 90 °C / 3750.38 Torr / Autoclave View Scheme
Multi-step reaction with 2 steps 1: 1,3-dimethyl-2-imidazolidinone; potassium fluoride; cetyltrimethylammonium chloride / 3 h / 150 - 160 °C 2: palladium 10% on activated carbon; hydrogen; triethylamine / ethyl acetate / 8 h / 60 - 65 °C / 7500.75 - 9000.9 Torr / Autoclave View Scheme
Multi-step reaction with 2 steps 1: potassium fluoride; 18-crown-6 ether / sulfolane / 4 h / 125 - 135 °C / Inert atmosphere 2: zinc; hydrogenchloride; acetic acid / water / 6 h / 90 - 105 °C View Scheme

2,4,6-trifluorophenyl(triphenylphosphine)gold(I) → 2,4,6-trifluorobenzonitrile (96606-37-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: Hexafluorobenzene; benzene / 3 h / 80 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: dichloromethane / 4 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube 3: 1,4-dioxane / 3 h / 100 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme

trans-diacetato(2,4,6-trifluorophenyl)(triphenylphosphine)gold(III) → 2,4,6-trifluorobenzonitrile (96606-37-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 4 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: 1,4-dioxane / 3 h / 100 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme

2,4,6-trifluorobenzonitrile (96606-37-0) + N-(2-(trimethylsilyl)ethynyl)-N-(p-tosyl)pent-4-yn-1-amine → C24H25F3N2O2SSi (1379786-69-2)

Conditions	Yield
With μ1-carbonyl-η5-cyclopentadienyl-η2-dimethylfumaratecobalt In toluene at 110℃; for 15h; Inert atmosphere; regioselective reaction;	100%

4-Octyne (1942-45-6) + 2,4,6-trifluorobenzonitrile (96606-37-0) → (Z)-3-(2,4,6-trifluorophenyl)-2-propylhex-2-enenitrile (1453500-99-6)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); triphenylborane; bis[2-(diphenylphosphino)phenyl] ether at 100℃; for 8h; Inert atmosphere; chemoselective reaction;	98%

4-methylphenylthiotrimethylsilane (38325-59-6) + 2,4,6-trifluorobenzonitrile (96606-37-0) → 2,4,6-tris-p-tolylsufanylbenzonitrile

Conditions	Yield
With carbon dioxide; tetrabutylammomium bromide; cesium fluoride at 110℃; under 172517 Torr;	95%

2,4,6-trifluorobenzonitrile (96606-37-0) → (2,4,6-trifluorophenyl)methanamine (214759-21-4)

Conditions	Yield
With ammonia; hydrogen In isopropyl alcohol at 65 - 75℃; under 7500.75 Torr; Reagent/catalyst; Temperature;	94%
With hydrogen; triethylamine In toluene at 115 - 125℃; under 15001.5 Torr; for 4h; Pressure; Temperature; Solvent; Reagent/catalyst;	86.8%
With ammonia; hydrogen In methanol at 90℃; under 7500.75 Torr; for 8h; Temperature; Autoclave;	85%
With 5%-palladium/activated carbon; hydrogen; propionic acid at 10 - 15℃; under 9750.98 - 11251.1 Torr; for 5h; Pressure; Temperature; Autoclave;	39.3%
With palladium 10% on activated carbon; hydrogen; acetic acid at 90℃; under 7500.75 Torr; for 16h; Reagent/catalyst; Temperature;	6 g

(4-tert-butylphenoxy)trimethylsilane (25237-79-0) + 2,4,6-trifluorobenzonitrile (96606-37-0) → 2,4,6-tris(4-tert-butylphenoxy)benzonitrile (1085323-21-2)

Conditions	Yield
With carbon dioxide; tetrabutylammomium bromide; cesium fluoride at 110℃; under 172517 Torr;	90%

2,4,6-trifluorobenzonitrile (96606-37-0) + 3,6-di-methoxy-9H-carbazole → C49H38N4O6

Conditions	Yield
With potassium tert-butylate In dichloromethane; N,N-dimethyl-formamide for 6h; Inert atmosphere;	90%

C30H28N2 + 2,4,6-trifluorobenzonitrile (96606-37-0) → 2,4,6-tris(3-(6-(9H-carbazol-9-yl)hexyl)-9H-carbazol-9-yl)benzonitrile

Conditions	Yield
Stage #1: C30H28N2 With sodium hydride In N,N-dimethyl-formamide at 25℃; for 3h; Inert atmosphere; Stage #2: 2,4,6-trifluorobenzonitrile In N,N-dimethyl-formamide at 25℃; for 24h; Inert atmosphere;	90%

2,4,6-trifluorobenzonitrile (96606-37-0) → 2,4,6-trifluoro-3,5-di-deuterated benzonitrile

Conditions	Yield
With platinum(IV) oxide; water-d2 at 250℃; for 14h;	89%

2,4,6-trifluorobenzonitrile (96606-37-0) + 2-phenyl-1H-benzoimidazole (716-79-0) → 2,4,6-tris(2-phenyl-1H-benzo[d]imidazol-1-yl)benzonitrile

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 150℃; for 12h; Inert atmosphere;	88%
With potassium carbonate In dimethyl sulfoxide at 150℃; for 12h; Inert atmosphere;	88%

4-(6-(9H-carbazol-9-yl)hexyloxy)-9H-carbazole + 2,4,6-trifluorobenzonitrile (96606-37-0) → C97H83N7O3

Conditions	Yield
Stage #1: 4-(6-(9H-carbazol-9-yl)hexyloxy)-9H-carbazole With sodium hydride In tetrahydrofuran for 3.25h; Inert atmosphere; Stage #2: 2,4,6-trifluorobenzonitrile In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	88%
Stage #1: 4-(6-(9H-carbazol-9-yl)hexyloxy)-9H-carbazole With sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: 2,4,6-trifluorobenzonitrile In tetrahydrofuran for 12h;	64%

3-methoxycarbazole (18992-85-3) + 2,4,6-trifluorobenzonitrile (96606-37-0) → 2,4,6-tris(3-methoxy-9H-carbazol-9-yl)benzonitrile

Conditions	Yield
Stage #1: 3-methoxycarbazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,4,6-trifluorobenzonitrile In tetrahydrofuran at 20℃; for 12h;	88%

3-(6-(9H-carbazol-9-yl)hexyloxy)-9H-carbazole + 2,4,6-trifluorobenzonitrile (96606-37-0) → 2,4,6-tris(3-(6-(9H-carbazol-9-yl)hexyloxy)-9H-carbazol-9-yl)benzonitrile

Conditions	Yield
Stage #1: 3-(6-(9H-carbazol-9-yl)hexyloxy)-9H-carbazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,4,6-trifluorobenzonitrile In tetrahydrofuran at 20℃; for 12h;	86%

morpholine (110-91-8) + 2,4,6-trifluorobenzonitrile (96606-37-0) → 2,6-difluoro-4-morpholin-4-yl-benzonitrile (840481-30-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In methanol at 50℃; for 18h;	85%
With N-ethyl-N,N-diisopropylamine In methanol at 50℃; for 6h;	68%

N'-(3-hydroxyphenyl)-N,N-dimethyl-sulfamide (539807-29-9) + 2,4,6-trifluorobenzonitrile (96606-37-0) → N'-[3-(2-cyano-3,5-difluorophenoxy)phenyl]-N,N-dimethyl-sulfamide (1084333-31-2)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 48h;	84%

2,4,6-trifluorobenzonitrile (96606-37-0) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(4-cyano-2,5-difluorophenyl)piperazine-1-carboxylate

Conditions	Yield
With potassium carbonate at 90℃; for 24h; Inert atmosphere;	84%

(E)-but-2-enol (504-61-0) + 2,4,6-trifluorobenzonitrile (96606-37-0) → 2-((E)-but-2-enyloxy)-4,6-difluorobenzonitrile

Conditions	Yield
Stage #1: (E)-but-2-enol With sodium hydride In tetrahydrofuran; mineral oil for 0.166667h; Cooling with ice; Stage #2: 2,4,6-trifluorobenzonitrile In tetrahydrofuran; mineral oil at 20℃; for 4h; Cooling with ice;	80%

9H-carbazole (86-74-8) + 2,4,6-trifluorobenzonitrile (96606-37-0) → 2,4,6-tri(9H-carbazol-9-yl)benzonitrile

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 20 - 150℃; for 24h; Inert atmosphere;	80%
With potassium tert-butylate In N,N-dimethyl-formamide at 80℃;

1-(triisopropylsilyl)-1H-indole (123191-00-4) + 2,4,6-trifluorobenzonitrile (96606-37-0) → 2,4,6-trifluoro-3-(1-(triisopropylsilyl)-1H-indol-3-yl)benzonitrile

Conditions	Yield
With (triphenylphosphine)gold(I) chloride; 1-pivaloyloxy-1,2-benziodoxol-3(1H)-one; silver pivalate; dimethyl sulfoxide In 1,4-dioxane at 110℃; for 16h; Inert atmosphere; regioselective reaction;	78%

9-(6-((9H-carbazol-4-yl)oxy)hexyl)-4-((4-vinylbenzyl)oxy)-9H-carbazole + 2,4,6-trifluorobenzonitrile (96606-37-0) → C124H107N7O6

Conditions	Yield
Stage #1: 9-(6-((9H-carbazol-4-yl)oxy)hexyl)-4-((4-vinylbenzyl)oxy)-9H-carbazole With sodium hydride In tetrahydrofuran for 0.5h; Stage #2: 2,4,6-trifluorobenzonitrile In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;	78%

(1,3-dimethylimidazol-2-ylidene)borane (1211417-77-4) + 2,4,6-trifluorobenzonitrile (96606-37-0) → (2-cyano-3,5-difluorophenyl)(1,3-dimethyl-1H-imidazol-3-ium-2-yl)dihydroborate

Conditions	Yield
With [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; sodium acetate; ethyl 2-sulfanylacetate In tetrahydrofuran at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation; regioselective reaction;	75%

TEMPOL (45985-24-8, 2226-96-2) + 2,4,6-trifluorobenzonitrile (96606-37-0) → C34H53N4O6 (1239967-19-1)

Conditions	Yield
Stage #1: TEMPOL With sodium amide In 1,3-dimethyl-2-imidazolidinone at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,4,6-trifluorobenzonitrile In 1,3-dimethyl-2-imidazolidinone at 0 - 50℃; Inert atmosphere;	73%

tert-butyl 3-hydroxyphenylcarbamate (19962-06-2) + 2,4,6-trifluorobenzonitrile (96606-37-0) → C18H16F2N2O3 (1084333-33-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃;	70%
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 17h;	70%
With sodium hydride In tetrahydrofuran at 0 - 20℃;	70%

N-(trifluoromethylsulfonyloxy)pyridinium trifluoromethanesulfonate (93743-67-0) + 2,4,6-trifluorobenzonitrile (96606-37-0) → 1-(3-cyano-2,4,6-trifluorophenyl)pyridin-1-ium trifluoromethanesulfonate

Conditions	Yield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate In acetonitrile for 1.5h; Sealed tube; Schlenk technique; Inert atmosphere; Irradiation;	68%

t-butoxycarbonylhydrazine (870-46-2) + 2,4,6-trifluorobenzonitrile (96606-37-0) → tert-butyl 2-(4-cyano-3,5-difluorophenyl)hydrazinecarboxylate (1073973-04-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃; for 120.16h;	61%

diguanidine carbonate (593-85-1) + 2,4,6-trifluorobenzonitrile (96606-37-0) + phenol (108-95-2) → 5,7-diphenoxy-2,4-quinazolinediamine

Conditions	Yield
Stage #1: 2,4,6-trifluorobenzonitrile; phenol With potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 0.166667h; Microwave irradiation; Stage #2: diguanidine carbonate In 1-methyl-pyrrolidin-2-one at 150℃; for 0.25h; Microwave irradiation;	61%

2,4,6-trifluorobenzonitrile (96606-37-0) → 2-amino-4,6-difluorobenzonitrile (190011-84-8) + 4-amino-2,6-difluorobenzonitrile

Conditions	Yield
With ammonia In ethanol at 35℃; for 18h;	A 60% B 37%
With ammonium hydroxide In water; acetonitrile at 20℃; for 72h;	A 47% B n/a
With ammonia In isopropyl alcohol at 45℃; for 16h;

dimethylbis(η5-pentamethylcyclopentadienyl)uranium (67605-92-9) + 2,4,6-trifluorobenzonitrile (96606-37-0) → [(C5(CH3)5)2U(NC(CH3)-2,4,6-F3-C6H2)2] (951238-97-4)

Conditions	Yield
In toluene under N2; soln. of nitrile (2 equiv.) in toluene added to soln. of U complex in toluene; mixt. stirred at room temp. for 12-15 h; volatiles removed (vac.); dissolved in pentane; filtered through Celite;solvent removed (vac.);	59%

Upstream product

• 82019-50-9 2,4,6-trifluorobenzamide 
• 31881-89-7 3,5-dichloro-2,4,6-trifluorobenzonitrile 
• 20925-85-3 pentachlorobenzonitrile 

Downstream Products

• 1009034-66-5 5,7-difluoroquinazolin-4-amine 
• 1211514-57-6 C₇H₅F₂N₃ 
• 3939-09-1 2,4-difluorobenzonitrile 
• 28314-80-9 2,4,6-trifluorobenzoic acid 
• 190011-84-8 2-amino-4,6-difluorobenzonitrile 
• 1005460-15-0 2,4,6-trifluorobenzimidamide 
• 1226784-85-5 2-(3-ethanesulfonylamino-phenoxy)-4-fluoro-6-(2-fluoro-4-iodo-phenylamino)-benzamide 
• 1226784-86-6 4-fluoro-2-(2-fluoro-4-iodo-phenylamino)-6-[3-(propane-2-sulfonylamino)-phenoxy]-benzamide 
• 1084333-64-1 {2-cyano-3-[3-(3,3-dimethyl-ureido)-phenoxy]-5-fluoro-phenyl}-(2-fluoro-4-iodo-phenyl)-carbamic acid tert-butyl ester 
• 1084332-51-3 2-[3-[[(propylamino)sulfonyl]amino]phenoxy]-4-fluoro-6-[(2-fluoro-4-iodophenyl)amino]-benzamide 
• 1084332-06-8 {3-[2-carbamoyl-5-fluoro-3-(2-fluoro-4-iodo-phenylamino)-phenoxy]-phenyl}-carbamic acid tert-butyl ester 
• 1084332-07-9 2-[3-[[(dimethylamino)sulfonyl]amino]phenoxy]-4-fluoro-6-[(2-fluoro-4-iodophenyl)amino]-benzamide 
• 1084331-91-8 {3-[2-cyano-5-fluoro-3-(2-fluoro-4-iodo-phenylamino)-phenoxy]-phenyl}-carbamic acid tert-butyl ester 
• 1084332-48-8 4-fluoro-2-(2-fluoro-4-iodo-phenylamino)-6-(3-methanesulfonylamino-phenoxy)-benzamide 

Relevant articles and documents

PROCESS FOR PREPARATION OF 2,4,6-TRIFLUOROBENZOIC ACID

The present invention provides a process for the preparation of 2,4,6-trifluorobenzoic acid, having less than 0.05% of 2,6-difluorobenzoic acid and/or 2,4-difluorobenzoic acid impurities. The 2,4,6-trifluorobenzoic acid is crucial and an important raw material for preparing the photosensitizers, medicines and pesticides, and also finds applications in pharmaceutical and agrochemical industries.

Mechanistic Insights into C(sp2)?C(sp)N Reductive Elimination from Gold(III) Cyanide Complexes

A new family of phosphine-ligated dicyanoarylgold(III) complexes has been prepared and their reactivity towards reductive elimination has been studied in detail. Both, a highly positive entropy of activation and a primary 12/13C KIE suggest a late concerted transition state while Hammett analysis and DFT calculations indicate that the process is asynchronous. As a result, a distinct mechanism involving an asynchronous concerted reductive elimination for the overall C(sp2)?C(sp)N bond forming reaction is characterized herein, for the first time, complementing previous studies reported for C(sp3)?C(sp3), C(sp2)?C(sp2), and C(sp3)?C(sp2) bond formation processes taking place on gold(III) species.

Preparation method of 2,4,6-trifluorobenzylamine

The invention provides a preparation method of 2,4,6-trifluorobenzylamine. The preparation method comprises the following steps: S1, by taking pentachloro benzonitrile as a starting material, adding the pentachloro benzonitrile into anhydrous potassium fluoride for fluorination reaction in a first organic solvent, thus obtaining 3,5-dichloro-2,4,6-trifluoro-cyanophenyl; S2a, adding the 3,5-dichloro-2,4,6-trifluoro-cyanophenyl prepared in the step S1 into a second organic solvent, adding organic alkali, feeding hydrogen, and carrying out dehydrochlorination reaction under the action of a firstcatalyst, thus obtaining 2,4,6-trifluoro-cyanophenyl serving as an intermediate; S3, adding the 2,4,6-trifluoro-cyanophenyl prepared in the step S2a into a third organic solvent, adding acid, feedinghydrogen, and reducing the 2,4,6-trifluoro-cyanophenyl serving as the intermediate through a cyanogroup under the action of a second catalyst, thus obtaining 2,4,6-trifluorobenzylamine. By the adoption of the technical scheme, the preparation method has the advantages that steps of a synthesis route are simple and short, conditions are mild, operation is simple and convenient, the raw materials are low in cost and readily available, and the production cost is low; the catalysts and solvents can be recycled for use, so that pollution is reduced; the preparation method is environmentally friendly and suitable for industrial large-scale production.