1835-65-0

Usage

Chemical Properties

White powder

Uses

Tetrafluorophthalonitrile was used in the synthesis of dichloro-subphthalocyanine dimers.

General Description

Tetrafluorophthalonitrile reacts with:copper, copper (I) chloride or copper (II) chloride to yield copper (II) hexadecafluorophthalocyaninepotassium salt of 2-hydroxyhexafluoro-2-propylbenzene to yield 2-phenyl-2-(3,4-dicyano- trifluorophenoxy) hexafluoropropanedipotassium salt of 1,3-bis(2-hdroxyhexafluoro-2- propyl) benzene to yield fluorinated phthalonitrile resins

InChI:InChI=1/C8F4N2/c9-5-3(1-13)4(2-14)6(10)8(12)7(5)11

Synthetic route

tetrachlorophthalonitrile (1953-99-7) → 3-chloro-4,5,6-trifluoro phthalonitrile + Tetrafluorophthalonitrile (1835-65-0)

Conditions	Yield
With potassium fluoride In benzonitrile at 260℃; for 18h;	A 18.3% B 75.8%

sulfolane (126-33-0) + tetrachlorophthalonitrile (1953-99-7) → Tetrafluorophthalonitrile (1835-65-0)

Conditions	Yield
With potassium fluoride In water	74%

potassium fluoride + tetrachlorophthalonitrile (1953-99-7) → Tetrafluorophthalonitrile (1835-65-0)

Conditions	Yield
In dimethyl sulfoxide heating to 130-160°C, 0.5-1 h;	70%
In dimethyl sulfoxide heating to 130-160°C, 0.5-1 h;	70%

1,2-dibromo-3,4,5,6-tetrafluorobenzene (827-08-7) + copper(I) cyanide (544-92-3) → Tetrafluorophthalonitrile (1835-65-0)

Conditions	Yield
at 160 - 170℃;

tetrachlorophthalonitrile (1953-99-7) → benzoyl fluoride (455-32-3) + Tetrafluorophthalonitrile (1835-65-0)

Conditions	Yield
With sodium hydroxide at 270℃; for 16h;

1,2-dibromo-3,4,5,6-tetrafluorobenzene (827-08-7) + copper(l) cyanide → Tetrafluorophthalonitrile (1835-65-0)

tetrachlorophthalonitrile (1953-99-7) → Tetrafluorophthalonitrile (1835-65-0)

Conditions	Yield
With potassium fluoride In N,N-dimethyl-formamide at 110℃; for 7h; Temperature; Concentration;

Tetrafluorophthalonitrile (1835-65-0) → 4-Methoxy-3,5,6-trifluorphthalonitril (34251-54-2)

Conditions	Yield
With potassium hydroxide In methanol at -5 to 0°C;	98%
With KOH In methanol at -5 to 0°C;	98%

Tetrafluorophthalonitrile (1835-65-0) → 4-amino-3,5,6-trifluoro-1,2-phenylene dicyanide (25693-94-1)

Conditions	Yield
With ammonium hydroxide	98%
With NH4OH	98%
With ammonium hydroxide In 1,4-dioxane for 2h; Reflux;	81%

Tetrafluorophthalonitrile (1835-65-0) + Ethyl protocatechuate (3943-89-3) → C26H16N2O8

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 3h;	98%

Tetrafluorophthalonitrile (1835-65-0) + 4-hydroxy-2,7-naphthalenedisulfonic acid disodium salt (20349-39-7) → 3FNS-1 (1174937-70-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere;	97%

Tetrafluorophthalonitrile (1835-65-0) + 1,2-benzenedithiole (17534-15-5) → benzo[5,6][1,4]dithiino[2,3-a]thianthrene-6,7-dicarbonitrile

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere; Schlenk technique;	97%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Temperature;	94%

2,3,5,6-tetrafluoro-1,4-benzenediol (771-63-1) + Tetrafluorophthalonitrile (1835-65-0) → 1,4-bis(3,4-dicyano-2,5,6-trifluorophenoxy)tetrafluorobenzene

Conditions	Yield
With potassium fluoride In 4-methyl-2-pentanone at 50 - 80℃; for 5.25h;	96%

2,2,2-trifluoroethanol (75-89-8) + Tetrafluorophthalonitrile (1835-65-0) → 3,4,5,6-tetrakis-(2',2',2'-trifluoroethoxy)phthalonitrile (187093-60-3)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃;	95%
With potassium carbonate In N,N-dimethyl-formamide for 12h; Ambient temperature;	94%
With potassium carbonate In N,N-dimethyl-formamide for 4h; Ambient temperature;	92%

Tetrafluorophthalonitrile (1835-65-0) → 3,4-dicyano-2,5,6-trifluoromethyldiphenylamine (25566-74-9)

Conditions	Yield
With aniline In ethanol in 80 % C2H5OH;	94%
With C6H5NH2 In ethanol in 80 % C2H5OH;	94%
With aniline In further solvent(s) 10 min boiling in N-methyl-2-pyrrolidone;	61%
With C6H5NH2 In further solvent(s) 10 min boiling in N-methyl-2-pyrrolidone;	61%
Multi-step reaction with 2 steps 1: aniline / petroleum ether View Scheme

Tetrafluorophthalonitrile (1835-65-0) + 9H-carbazole (86-74-8) → 1,2,3,4-tetrakis(carbazol-9-yl)-5,6-dicyanobenzene (1416881-51-0)

Conditions	Yield
Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran; mineral oil at 25℃; for 0.5h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In tetrahydrofuran; mineral oil at 25℃; Inert atmosphere;	94%
Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In tetrahydrofuran; mineral oil at 20℃; for 12h; Inert atmosphere;	91%
Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran; mineral oil at 26.84℃; for 0.5h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In tetrahydrofuran; mineral oil at 26.84℃; for 10h; Inert atmosphere;	38%
Stage #1: 9H-carbazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In N,N-dimethyl-formamide; mineral oil at 60℃; for 10h; Inert atmosphere;	28.5%
Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In tetrahydrofuran; mineral oil at 20℃; for 12h;

Tetrafluorophthalonitrile (1835-65-0) + C12(2)H9NO → C56(2)H32N6O4

Conditions	Yield
Stage #1: C12(2)H9NO With sodium t-butanolate In N,N-dimethyl-formamide for 3h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	94%

Tetrafluorophthalonitrile (1835-65-0) + C15(2)H15N → C68(2)H56N6

Conditions	Yield
Stage #1: C15(2)H15N With sodium t-butanolate In N,N-dimethyl-formamide for 3h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	94%

Tetrafluorophthalonitrile (1835-65-0) + boron tribromide (10294-33-4) → Br-F12(boron subphthalocyanine) (867153-85-3)

Conditions	Yield
In chlorobenzene W.M. Sharman, J.E. van Lier, J. Polrphyrins Phthalocyanines, 2005, 9, 651-659.;	93%

Tetrafluorophthalonitrile (1835-65-0) → Br-F12(boron subphthalocyanine) (867153-85-3)

Conditions	Yield
With boron tribromide In tetrahydrofuran; dichloromethane; chlorobenzene at 60℃; for 1h; Inert atmosphere;	93%

Tetrafluorophthalonitrile (1835-65-0) + benzene-1,2-diol (120-80-9) → C14H4F2N2O2

Conditions	Yield
With sodium hydride In acetonitrile at 20℃; for 0.166667h;	93%

2-thiophenethanol (5402-55-1) + Tetrafluorophthalonitrile (1835-65-0) → 4-{2-(2-thienyl)ethoxy}-3,5,6-trifluorophthalonitrile

Conditions	Yield
Stage #1: 2-thiophenethanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In tetrahydrofuran; mineral oil at -50 - 20℃; Reagent/catalyst; Temperature; Inert atmosphere;	93%

Tetrafluorophthalonitrile (1835-65-0) + C12(2)H9NS → C56(2)H32N6S4

Conditions	Yield
Stage #1: C12(2)H9NS With sodium t-butanolate In N,N-dimethyl-formamide for 3h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	93%

Tetrafluorophthalonitrile (1835-65-0) + C13(2)H12N2 → C60(2)H44N10

Conditions	Yield
Stage #1: C13(2)H12N2 With sodium t-butanolate In N,N-dimethyl-formamide for 3h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	93%

2,5-dichlorophenol (583-78-8) + Tetrafluorophthalonitrile (1835-65-0) → 4,5-bis(2,5-dichlorophenoxy)-3,6-difluorophthalonitrile (238074-06-1)

Conditions	Yield
With potassium fluoride In acetone at -5 - 0℃;	92.4%
With potassium fluoride In acetone at -1 - 20℃;	72.7%

C12(2)H9N + Tetrafluorophthalonitrile (1835-65-0) → C56H(2)H31N6

Conditions	Yield
Stage #1: C12(2)H9N With sodium t-butanolate In N,N-dimethyl-formamide for 3h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	92%

Tetrafluorophthalonitrile (1835-65-0) + (trimethylsilyl)diphenylphosphine (17154-34-6) → 3,6-difluoro-4,5-bis(diphenylphosphino)phthalonitrile

Conditions	Yield
In toluene for 6h; Inert atmosphere; Heating;	91%

Tetrafluorophthalonitrile (1835-65-0) → Anilin-Tetrafluorphthalonitril-1:1-Komplex (25579-63-9)

Conditions	Yield
With aniline In Petroleum ether at 100 to 120°C, 10 min;	90%
With aniline In petroleum ether at 100 to 120°C, 10 min;	90%
With aniline In Petroleum ether at 80 to 100°C, 10 min;
With aniline In petroleum ether at 80 to 100°C, 10 min;

Tetrafluorophthalonitrile (1835-65-0) + zinc(II) iodide → zinc hexadecafluorophthalocyanine (31396-84-6)

Conditions	Yield
1.5 h refluxing;	90%
1.5 h refluxing;	90%

Tetrafluorophthalonitrile (1835-65-0) + diphenylamine (122-39-4) → 3,4,5,6-tetrakis(diphenylamino)phthalonitrile

Conditions	Yield
Stage #1: diphenylamine With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In tetrahydrofuran; mineral oil at 20℃; for 12h; Inert atmosphere;	90%
Stage #1: diphenylamine With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Stage #2: Tetrafluorophthalonitrile In tetrahydrofuran; mineral oil at 20℃; for 12h;	81%

Tetrafluorophthalonitrile (1835-65-0) + C14(2)H13N → C64(2)H48N6

Conditions	Yield
Stage #1: C14(2)H13N With sodium t-butanolate In N,N-dimethyl-formamide for 3h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	90%

Tetrafluorophthalonitrile (1835-65-0) + C20(2)H25N → C88(2)H96N6

Conditions	Yield
Stage #1: C20(2)H25N With sodium t-butanolate In N,N-dimethyl-formamide for 3h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	90%

Tetrafluorophthalonitrile (1835-65-0) + C18(2)H21N → C80(2)H80N6

Conditions	Yield
Stage #1: C18(2)H21N With sodium t-butanolate In N,N-dimethyl-formamide for 3h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	90%

Tetrafluorophthalonitrile (1835-65-0) + C14(2)H13NO2 → C64(2)H48N6O8

Conditions	Yield
Stage #1: C14(2)H13NO2 With sodium t-butanolate In N,N-dimethyl-formamide for 3h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	90%

Tetrafluorophthalonitrile (1835-65-0) + C13(2)H9NO → C60(2)H32N6O4

Conditions	Yield
Stage #1: C13(2)H9NO With sodium t-butanolate In N,N-dimethyl-formamide for 3h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	90%

Tetrafluorophthalonitrile (1835-65-0) + C18(2)H14N2 → C80(2)H52N10

Conditions	Yield
Stage #1: C18(2)H14N2 With sodium t-butanolate In N,N-dimethyl-formamide for 3h; Inert atmosphere; Stage #2: Tetrafluorophthalonitrile In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	90%

Upstream product

• 827-08-7 1,2-dibromo-3,4,5,6-tetrafluorobenzene 
• 544-92-3 copper(I) cyanide 
• 1953-99-7 tetrachlorophthalonitrile 
• 126-33-0 sulfolane 
• 7789-23-3 potassium fluoride 

Downstream Products

• 652-03-9 3,4,5,6-tetrafluorophthalic acid 
• 438187-95-2 3,4,5,6-tetraneopentoxyphthalonitrile 
• 25693-94-1 4-amino-3,5,6-trifluoro-1,2-phenylene dicyanide 

Relevant academic research and scientific papers

Tetrafluoroisophthalonitrile production method

The present invention discloses a tetrafluoroisophthalonitrile production method which belongs to the technical field of fine chemical production, a tetrafluoroisophthalonitrile product is prepared from raw materials of tetrachlorophthalonitrile, anhydrous potassium fluoride and N, N dimethyl formamide in a molar ratio of tetrachlorophthalonitrile to anhydrous potassium fluoride to N, N dimethyl formamide of 1.0-1.1: 4.0-4.8: 20-25 by fluorination of the tetrachlorophthalonitrile, solid-liquid separation of reactants, drying and crushing. The production method has the advantages of simple process, high efficiency, low cost, short conversion time, no pollution, and high yield; and compared with a conventional method, the conversion temperature is low, due to the low conversion temperature, first, energy is saved, second, the making difficulty of a convertor is reduced, due to reduction of the conversion temperature, the yield of the end product tetrafluoroisophthalonitrile is improved to 90.0%, the content of the product can reach 99.0%; and the tetrafluoroisophthalonitrile product is an intermediate for synthesis of fluoroquinolone antibacterial drugs, polyimide materials and other functional materials, and is an important intermediate of pesticides of tefluthrin and transfluthrin.

METHOD FOR PRODUCING AROMATIC FLUOROCOMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing an aromatic fluorocompound, by which an corresponding aromatic fluorocompound (for example, pentafluorobenzonitrile) can be produced in a high yield by the halogen exchange reaction of an aromatic halogen compound (for example, pentachlorobenzonitrile) with a fluorinating agent (for example, potassium fluoride). SOLUTION: This method for producing the aromatic fluorocompound is characterized by supplying the aromatic halogen compound of raw material as particles having an average particle diameter of 20 to 200μm.

Method for production of organic fluorine compound

A method for the production of an aromatic fluorine compound is provided which is capable of preventing the occurrence of benzoic acid fluorides during the course of a halogenation exchange reaction or allowing removal of the benzoic acid fluorides formed at all. A method for the production of an organic fluorine compound is disclosed which comprises preventing the occurrence of acid fluorides of an aromatic compound during the production of the organic fluorine compound by the reaction of an organic chlorine or bromine compound with a fluorinating agent in benzonitrile as a solvent or allowing removal of the acid fluorides formed.

Process for tetrafluorobenzoic acid

An improved process for the preparation of 2,3,4,5-tetrafluorobenzoic acid is described which involves decarboxylation of tetrafluorophthalic acid in the presence of a base catalyst. Also described is an improved method for preparing tetrafluorophthalic acid and, in turn, a one-pot process for tetrafluorobenzoic acid using the combination of the two improvements.