1996-23-2

Usage

Uses

Used in Organic Synthesis:
Tetrafluorobenzene-1,2-diol is used as a building block in organic synthesis for the preparation of various other compounds. Its unique structure with fluorine and hydroxyl groups allows for the creation of a wide range of chemical entities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Tetrafluorobenzene-1,2-diol is utilized as a reagent in the production of fluorinated organic compounds. The presence of fluorine atoms in the molecule can enhance the pharmacological properties of the resulting compounds, such as their lipophilicity, metabolic stability, and bioavailability.
Used in Agrochemical Industry:
Tetrafluorobenzene-1,2-diol is also employed in the agrochemical industry for the synthesis of various agrochemicals. The incorporation of fluorine atoms can improve the performance and selectivity of these compounds, making them more effective in agricultural applications.
Used as a Precursor for Fluorinated Materials:
Tetrafluorobenzene-1,2-diol serves as a precursor for the synthesis of fluorinated materials. These materials have unique properties, such as high thermal stability, chemical resistance, and non-stick characteristics, which make them suitable for various applications, including coatings, lubricants, and specialty polymers.

InChI:InChI=1/C6H2F4O2/c7-1-2(8)4(10)6(12)5(11)3(1)9/h11-12H

Synthetic route

pyridine (110-86-1) + Hexafluorobenzene (392-56-3) + ethanol (64-17-5) + potassium hydroxide → 2,3,4,5,6-pentafluorophenol (771-61-9) + ethoxy pentafluorobenzene (776-39-6) + 3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) + 1,4,5,6-Tetrafluor-2,3-diethoxy-benzol (16250-99-0)

tetrahydrofuran (109-99-9) + tetrafluoro-1,2-benzoquinone (1423-12-7) → 2,3,4,5-tetrafluoro-6-((tetrahydrofuran-2-yl)oxy)phenol (1374518-12-3) + 3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2)

Conditions	Yield
for 0.5h; Irradiation;

diethyl ether (60-29-7) + tetrafluoro-1,2-benzoquinone (1423-12-7) → 2-(1-ethoxyethoxy)-3,4,5,6-tetrafluorophenol (1374518-16-7) + 3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2)

Conditions	Yield
for 0.5h; Irradiation;

3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) + pentafluorophenylboronic acid (1582-24-7) → 2-(pentafluorophenyl)-tetrafluoro-1,3,2-benzodioxaborole (365458-36-2)

Conditions	Yield
In toluene byproducts: water; mixt. heated to reflux; water removed by azeotropic distillation; after 4 h solvent evapd. under reduced pressure; residue sublimed at 110°C/0.1 mm Hg;	87%
In toluene under N2; C6F4(OH)2 and C6F5B(OH)2 in toluene heated to reflux for 12 h using Dean-Stark apparatus; volatiles removed under reduced pressure; sublimed at 80°C; takenup in pentane; filtered; cryst. at -35°C; elem. anal.;	42%
In toluene byproducts: H2O; (Ar or under vac.); mixed in toluene; heated to reflux; water removed byazeotropic distillation; after 4 h, solvent evapd. under reduced pressu re; sublimed at 110°C;

C37H42N2O3Ru + 3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → C37H38F4N2O3Ru

Conditions	Yield
In tetrahydrofuran at 22℃; for 0.5h; Inert atmosphere;	80%

tetrahydrofuran (109-99-9) + tetraacetatodiruthenium chloride + 3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) + sodium hydroxide (1310-73-2) → [Na3(Ru2(tetrafluorocatecholato)4)]*2tetrahydrofuran*2H2O

Conditions	Yield
In tetrahydrofuran byproducts: NaOCOCH3, NaCl, H2O; (N2); stirring a suspn. of ruthenium complex, ligand, NaOH in THF for 1 d at room temp.; drying in vac., extn. with THF, slow diffusion of hexane; elem. anal.;	72%

tripropyl arsenite (15606-91-4) + 3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → 2-oxabis(4,5,6,7-tetrafluorobenzo-1,3,2-dioxaarsole)

Conditions	Yield
at 150 - 160℃; for 2h;	64.8%

chromium chloride hexahydrate + 3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) + triethylamine (121-44-8) → (triethylammonium)3[Cr(perfluorocatecholato)3]

Conditions	Yield
In methanol for 12h; Inert atmosphere; Schlenk technique;	60%

3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) + diethylamine (109-89-7) → C12AsF8O4(1-)*C4H11N*H(1+)

Conditions	Yield
With arsenic trichloride In diethyl ether for 2h; Ambient temperature;	59%

tetrachlorosilane (10026-04-7, 53609-55-5) + 3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → bis(perfluorocatecholato)silane

Conditions	Yield
In acetonitrile at 0 - 25℃; for 20h;	53%

3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) + lithium tetramethanolatoborate (6867-35-2) → lithium bis[3,4,5,6-tetrafluoro-1,2-benzenediolato(2-)-O,O'] borate

Conditions	Yield
In acetonitrile (Ar); heating (50°C); crystn. (5°C, 3 d), recrystn. (benzene/MeCN), washing (benzene);	30.8%

3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) + 2,4-difluorophenylboronic acid (144025-03-6) → 2-(2,4-difluorophenyl)-tetrafluoro-1,3,2-benzodioxaborole (365458-35-1)

Conditions	Yield
In toluene byproducts: H2O; (Ar or under vac.); mixed in toluene; heated to reflux; water removed byazeotropic distillation; after 4 h, solvent evapd. under reduced pressu re; sublimed at 125°C;

3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) + 2-(trifluoromethyl)phenylboronic acid (1423-27-4) → 2-(2-trifluoromethyl phenyl)-tetrafluoro-1,3,2-benzodioxaborole (365458-37-3)

Conditions	Yield
In toluene byproducts: H2O; (Ar or under vac.); mixed in toluene; heated to reflux; water removed byazeotropic distillation; after 4 h, solvent evapd. under reduced pressu re; sublimed at 110°C;

(2,5-di(trifluoromethyl)phenyl)boronic acid (196083-18-8) + 3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → 2,5-bis(trifluoromethyl)phenyl-tetrafluoro-1,3,2-benzodioxaborole (365458-38-4)

Conditions	Yield
In toluene byproducts: H2O; (Ar or under vac.); mixed in toluene; heated to reflux; water removed byazeotropic distillation; after 4 h, solvent evapd. under reduced pressu re; sublimed at 105-110°C;

3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) + 4-fluoroboronic acid (1765-93-1) → 2-(4-fluorophenyl)-tetrafluoro-1,3,2-benzodioxaborole (365458-34-0)

Conditions	Yield
In toluene byproducts: H2O; (Ar or under vac.); mixed in toluene; heated to reflux; water removed byazeotropic distillation; after 4 h, solvent evapd. under reduced pressu re; sublimed at 135°C;

3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → ethyl 4,5,6,7-tetrafluorobenzo[d]-1,3-dioxole-2-carboxylate (1353670-84-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / nitromethane / -30 °C 2: benzene / 8 h / Reflux View Scheme

3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → 2,3,4,5-tetrafluoro-6-(1-hexyl-1H-indol-3-yl)-6-hydroxycyclohexa-2,4-dienone (1353670-86-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / nitromethane / -30 °C 2: benzene / 0.17 h / 20 °C View Scheme

3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → 2,3,4,5-tetrafluoro-6-hydroxy-6-(1-methyl-1H-pyrrol-2-yl)-cyclohexa-2,4-dienone (1353670-90-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / nitromethane / -30 °C 2: chloroform-d1 / 0.03 h / 20 °C View Scheme

3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → C7H4F4O3 (1353670-93-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / nitromethane / -30 °C 2: chloroform-d1 / 0 °C View Scheme

3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → C8H7F3O4 (1353670-95-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid / nitromethane / -30 °C 2: chloroform-d1 / 0 °C 3: chloroform-d1 / 0 - 20 °C View Scheme

3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → C6F4O2*C12H18 (1353671-02-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / nitromethane / -30 °C 2: chloroform / 1 h View Scheme

3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → tetrafluoro-1,2-benzoquinone (1423-12-7)

Conditions	Yield
With nitric acid In nitromethane at -30℃;

C14H6Cl2F4N6O4 + 3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → C20H6F8N6O6 (1451257-93-4)

Conditions	Yield
With potassium carbonate In water; acetone for 3h; Solvent; Time; Reflux; Inert atmosphere;	1.36 g

C16H12Cl2F4N8O2 + 3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → C22H12F8N8O4 (1451257-94-5)

Conditions	Yield
With caesium carbonate In water; acetone for 40h; Reflux;	0.181 g

2,4-Dichloro-6-methoxy-1,3,5-triazine (3638-04-8) + 3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → C14H6Cl2F4N6O4

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 1h; Inert atmosphere;

2-dimethylamino-4,6-dichloro-1,3,5-triazine (2401-64-1) + 3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → C16H12Cl2F4N8O2

Conditions	Yield
With caesium carbonate In acetone at 30℃; for 8h; Inert atmosphere;

2-dimethylamino-4,6-dichloro-1,3,5-triazine (2401-64-1) + 3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) → C22H12F8N8O4 (1451257-94-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: caesium carbonate / acetone / 8 h / 30 °C / Inert atmosphere 2: caesium carbonate / acetone; water / 40 h / Reflux View Scheme

3,4,5,6-tetrafluorobenzene-1,2-diol (1996-23-2) + C36H63O3PRu → C34H45F4O3PRu

Conditions	Yield
In dichloromethane for 0.5h; Inert atmosphere;

Upstream product

• 110-86-1 pyridine 
• 392-56-3 Hexafluorobenzene 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 
• 1423-12-7 tetrafluoro-1,2-benzoquinone 
• 109-99-9 tetrahydrofuran 

Downstream Products

• 365458-36-2 2-(pentafluorophenyl)-tetrafluoro-1,3,2-benzodioxaborole 
• 365458-35-1 2-(2,4-difluorophenyl)-tetrafluoro-1,3,2-benzodioxaborole 
• 365458-37-3 2-(2-trifluoromethyl phenyl)-tetrafluoro-1,3,2-benzodioxaborole 
• 365458-38-4 2,5-bis(trifluoromethyl)phenyl-tetrafluoro-1,3,2-benzodioxaborole 
• 365458-34-0 2-(4-fluorophenyl)-tetrafluoro-1,3,2-benzodioxaborole 
• 1353670-86-6 2,3,4,5-tetrafluoro-6-(1-hexyl-1H-indol-3-yl)-6-hydroxycyclohexa-2,4-dienone 
• 1353670-90-2 2,3,4,5-tetrafluoro-6-hydroxy-6-(1-methyl-1H-pyrrol-2-yl)-cyclohexa-2,4-dienone 
• 1353670-93-5 C₇H₄F₄O₃ 
• 1353670-95-7 C₈H₇F₃O₄ 
• 1353671-02-9 C₆F₄O₂*C₁₂H₁₈ 
• 1423-12-7 tetrafluoro-1,2-benzoquinone 

Relevant academic research and scientific papers

Photochemistry of o-fluoranil

Initial exploration of the photochemical behavior of o-fluoranil has revealed dimer formation, cycloaddition to alkenes, and hydrogen abstraction from hydrocarbons, aldehydes, and ethers.