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462-06-6 Usage

Chemical Description

Different sources of media describe the Chemical Description of 462-06-6 differently. You can refer to the following data:
1. Fluorobenzene is an organic compound with a fluorine atom attached to a benzene ring.
2. Fluorobenzene and azodicarboxylate are reactants used in the control experiments to gain insight into the mechanism.

Description

Fluorobenzene is a colourless, highly flammable liquid, stable and incompatible with oxidising agents. It is not compatible with oxidising agents such as perchlorates, peroxides, permanganates, chlorates, nitrates, chlorine, bromine and fluorine, ammonium nitrate, chromic acid, halogens, and nitric acid. It is used as an insecticide and as a reagent for plastic and resin polymers.

Chemical Properties

Different sources of media describe the Chemical Properties of 462-06-6 differently. You can refer to the following data:
1. colourless liquid
2. Fluorobenzene is a colorless liquid.

Uses

Different sources of media describe the Uses of 462-06-6 differently. You can refer to the following data:
1. Fluorobenzene is used as a reagent for plastic or resin polymers. It acts as a solvent for highly reactive species. On fluorination of fluorobenzene it gives 1,2-difluorobenzene. It is also used as a material in making medicine.
2. Insecticide and larvicide intermediate, identification reagent for plastic or resin polymers.

Definition

ChEBI: The simplest member of the class of monofluorobenzenes that is benzene carrying a single fluoro substituent.

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 452, 1984 DOI: 10.1021/ja00314a050The Journal of Organic Chemistry, 30, p. 3170, 1965 DOI: 10.1021/jo01020a073

General Description

A clear, colorless liquid with a characteristic aromatic odor. About the same density as water. Flash point 5°F. Vapors heavier than air. May irritate the skin, eyes, and mucous membranes. Used as an insecticide, larvacide and as a reagent for plastic or resin polymers.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

Incompatible with strong oxidizing agents.

Health Hazard

Irritating to skin, eyes and mucous membranes. Repeated exposure of skin may cause dermatitis due to defatting action. Chronic inhalation of vapors or mist may result to damage to lungs, liver and kidneys. Acute vapor exposures can cause symptoms ranging from coughing to transient anesthesia and central nervous system depression.

Flammability and Explosibility

Highlyflammable

Safety Profile

: Mddly toxic by ingestion and inhalation. A very dangerous fire hazard when exposed to heat, flame, or oxidizers. To fight fire, use water spray, mist, foam, dry chemical, CO2. When heated to decomposition it emits toxic fumes of F-

Potential Exposure

Fluorobenzene is used as an insecti cide and as a reagent for plastic or resin polymers.

Shipping

UN2387 Fluorobenzene, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

Dry fluorobenzene for several days with P2O5, then fractionally distil it. [Beilstein 5 H 198, 5 IV 632.]

Incompatibilities

Vapor may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, perox ides, permanganates, perchlorates, chlorine, bromine, fluo rine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Check Digit Verification of cas no

The CAS Registry Mumber 462-06-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,6 and 2 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 462-06:
(5*4)+(4*6)+(3*2)+(2*0)+(1*6)=56
56 % 10 = 6
So 462-06-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H5F/c7-6-4-2-1-3-5-6/h1-5H

462-06-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (F0034)  Fluorobenzene  >99.0%(GC)

  • 462-06-6

  • 25g

  • 135.00CNY

  • Detail
  • TCI America

  • (F0034)  Fluorobenzene  >99.0%(GC)

  • 462-06-6

  • 100g

  • 345.00CNY

  • Detail
  • TCI America

  • (F0034)  Fluorobenzene  >99.0%(GC)

  • 462-06-6

  • 500g

  • 730.00CNY

  • Detail
  • Alfa Aesar

  • (A14384)  Fluorobenzene, 99%   

  • 462-06-6

  • 250g

  • 422.0CNY

  • Detail
  • Alfa Aesar

  • (A14384)  Fluorobenzene, 99%   

  • 462-06-6

  • 1000g

  • 1389.0CNY

  • Detail
  • Sigma-Aldrich

  • (51411)  Fluorobenzene  analytical standard

  • 462-06-6

  • 51411-5ML-F

  • 590.85CNY

  • Detail

462-06-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name monofluorobenzene

1.2 Other means of identification

Product number -
Other names Fluorobenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:462-06-6 SDS

462-06-6Synthetic route

4-fluorophenyl(m-carboran-9-yl)iodonium tetrafluoroborate
99506-39-5

4-fluorophenyl(m-carboran-9-yl)iodonium tetrafluoroborate

sodium chloride
7647-14-5

sodium chloride

A

fluorobenzene
462-06-6

fluorobenzene

B

9-iodo-m-carborane
17157-02-7

9-iodo-m-carborane

C

9-chloro-m-carborane
17819-85-1

9-chloro-m-carborane

D

4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

Conditions
ConditionsYield
In chloroform; water mixt. of aryl(m-carboran-9-yl)iodonium tetrafluoroborate, NaCl, water and chloroform was vigorously stirred under reflux at 56°C, 2-2.5 h; internal standard (chlorobenzene) added and org. layer was analysed by GLC;A 0%
B 0%
C 100%
D 100%
2-(trifluoromethyl)phenylacetic acid
3038-48-0

2-(trifluoromethyl)phenylacetic acid

2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
214360-58-4

2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

A

fluorobenzene
462-06-6

fluorobenzene

B

C15H10F4O2

C15H10F4O2

Conditions
ConditionsYield
With t-Boc-L-valine; 2,5-di-tert-butyl-p-benzoquinone; oxygen; potassium hydrogencarbonate In tert-Amyl alcohol at 90℃; under 2280.15 Torr; for 24h; Catalytic behavior;A n/a
B 99%
aniline
62-53-3

aniline

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
Stage #1: aniline With hydrogen fluoride at -10 - 0.5℃; Flow reactor; Large scale;
Stage #2: With nitrosylsulfuric acid at 0 - 10℃; Temperature; Flow reactor; Large scale;
98.9%
With pyridine; hydrogen fluoride; sodium nitrite Product distribution; changed molar ratio HF/Pyr, changed time and temperature, only HF; multistep reaction; 1.) 20 deg C, 30 min., 2.) 55 deg C, 1 h;95%
Stage #1: aniline With hydrogenchloride; fluoroboric acid; sodium nitrite In water at 25℃; for 0.00416667h; Balz-Schiemann Reaction;
Stage #2: at 125℃; for 0.0166667h; Balz-Schiemann Reaction;
92%
2-fluorobenzenediazonium tetrafluoroborate
446-46-8

2-fluorobenzenediazonium tetrafluoroborate

A

fluorobenzene
462-06-6

fluorobenzene

B

ortho-difluorobenzene
367-11-3

ortho-difluorobenzene

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; hydrogen fluoride at 12℃; for 1h; Decomposition; Fluoro-dediazoniation; Irradiation;A 0.2%
B 98.9%
With boron trifluoride diethyl etherate at 12℃; for 3h; Decomposition; Fluoro-dediazoniation; Irradiation;A 10.7%
B 84.6%
1-fluoro-3,5-dichlorobenzene
1435-46-7

1-fluoro-3,5-dichlorobenzene

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
With C60H48BP3Pd; potassium formate; [2.2.2]cryptande In tetrahydrofuran at 60℃; for 72h; Schlenk technique; Inert atmosphere;97%
o-fluorobromobenzene
1072-85-1

o-fluorobromobenzene

A

fluorobenzene
462-06-6

fluorobenzene

B

2,2'-difluorobiphenyl
388-82-9

2,2'-difluorobiphenyl

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 2-pentanol at 100℃; for 18h; Inert atmosphere;A 95.5%
B 4.5%
With palladium; hydroquinone; potassium hydroxide In glycerol at 90℃; for 18h; chemoselective reaction;A n/a
B 71 %Chromat.
benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
With pyridine; hydrogen fluoride at 55℃; for 1h; Product distribution; Rate constant; Thermodynamic data; changed molar ratio HF/Pyr, temp. and time; energy/enthalpy of activation;95%
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; cesium fluoride In acetone at 30℃; Irradiation;37%
With sodium difluorohydrogenate; 1,2,4-Trichlorobenzene
benzene
71-43-2

benzene

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
With fluorine at 60℃; under 3750.38 Torr; Temperature;95%
With trifluorormethanesulfonic acid; Selectfluor In dichloromethane at 40℃; for 20h; Fluorination;83%
With Al2CuF8 at 500℃; Reagent/catalyst; Inert atmosphere;47%
4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
With formaldehyd; palladium diacetate; caesium carbonate In dimethyl sulfoxide at 80℃; for 12h;94%
With sodium tetrahydroborate; di-tert-butyl peroxide In N,N-dimethyl-formamide at 70℃; for 2h; Irradiation;82 % Chromat.
With hydrogenchloride; CuI*P(Et)3; naphthalen-1-yl-lithium 1.) THF, 25 deg C, 10 min; Yield given. Multistep reaction;
phenylthallium(III) bis(tetrafluoroborate)

phenylthallium(III) bis(tetrafluoroborate)

A

fluorobenzene
462-06-6

fluorobenzene

B

thallium(I) tetrafluoroborate
28625-02-7

thallium(I) tetrafluoroborate

Conditions
ConditionsYield
In solid byproducts: BF3; pyrolisis under Ar without solvent at 100-150°; TlBF4 identified by IR spectrum and comparison of m.p. with that of an authentic sample;A 51%
B 94%
o-fluoro-benzoic acid
445-29-4

o-fluoro-benzoic acid

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
With quinoline; copper(I) oxide; 1,10-Phenanthroline; tetradecane In 1-methyl-pyrrolidin-2-one at 170℃; for 6h; Reagent/catalyst; Inert atmosphere;91%
copper(I) oxide; 1,10-Phenanthroline In quinoline at 170℃; for 6h;75%
With [Rh(OH)(cod)]2; 1,3-bis-(diphenylphosphino)propane; water; sodium hydroxide In tetrahydrofuran at 150℃; for 24h; Inert atmosphere;8 %Chromat.
4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

carbon monoxide
201230-82-2

carbon monoxide

A

fluorobenzene
462-06-6

fluorobenzene

B

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

Conditions
ConditionsYield
With hydrogen; potassium carbonate In 1,4-dioxane at 120 - 140℃; under 30003 Torr; for 20h; Autoclave;A 7%
B 91%
4-fluorophenyl(m-carboran-9-yl)iodonium tetrafluoroborate
99506-39-5

4-fluorophenyl(m-carboran-9-yl)iodonium tetrafluoroborate

A

fluorobenzene
462-06-6

fluorobenzene

B

9-iodo-m-carborane
17157-02-7

9-iodo-m-carborane

C

9-hydroxy-1,7-dicarba-closo-dodecaborane
54360-42-8

9-hydroxy-1,7-dicarba-closo-dodecaborane

D

9-nitro-m-carbaborane
114992-96-0

9-nitro-m-carbaborane

E

4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

Conditions
ConditionsYield
With sodium nitrite In dichloromethane; water mixt. of NaNO2 and the boron contg. salt in a two phase system stirred vigorously at 40°C, 2.5h (accompanied by evolution of nitrogen oxides), further product: 4-F-C6H4NO2 (traces); organic layer sepd. from aq. layer, evapn. of CH2Cl2 in vac., residue sepd. by chromy. (silica gel, hexane (9-iodo-m-carbaborane); benzene-hexane 1:1 (9-nitro-m-carbaborane); ether (9-hydroxy-m-carbaborane);A 5%
B 8%
C 75%
D 8%
E 90%
phenyl(triphenyl-λ5-phosphanyl)gold

phenyl(triphenyl-λ5-phosphanyl)gold

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
With Selectfluor chemoselective reaction;90%
perfluoro-
128812-96-4

perfluoro-

benzene
71-43-2

benzene

A

fluorobenzene
462-06-6

fluorobenzene

B

1,1,1-trifluoro-N-(perfluoropyridin-4-yl)methanesulfonamide
128812-95-3

1,1,1-trifluoro-N-(perfluoropyridin-4-yl)methanesulfonamide

Conditions
ConditionsYield
In chloroform-d1 at 60℃; for 0.166667h; sealed in vacuo;A 88%
B n/a
phenol
108-95-2

phenol

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
With 1,3-bis(2,6-diisopropylphenyl)-2,2-difluoro-2,3-dihydro-1h-imidazole; cesium fluoride In toluene at 80℃; for 18h; Product distribution / selectivity; Sealed vial;88%
With 1,3-bis(2,6-diisopropylphenyl)-2,2-difluoro-2,3-dihydro-1h-imidazole; cesium fluoride In toluene at 23 - 80℃; for 18.5h; Inert atmosphere;82 %Spectr.
Multi-step reaction with 2 steps
1: fluorosulfonyl fluoride; triethylamine / 1,4-dioxane / 24 h / 20 °C
2: tetramethylammonium fluoride / N,N-dimethyl-formamide / 24 h / 100 °C / Inert atmosphere; Glovebox; Sealed tube
View Scheme
(p-fluorophenyl)trimethylsilane
455-17-4

(p-fluorophenyl)trimethylsilane

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
With potassium trimethylsilonate In dimethyl sulfoxide at 60℃; under 760.051 Torr; for 5.5h; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube;88%
With potassium trimethylsilonate In dimethyl sulfoxide at 70℃; for 6h; Sealed tube; Schlenk technique;85 %Chromat.
benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

A

fluorobenzene
462-06-6

fluorobenzene

B

benzene
71-43-2

benzene

Conditions
ConditionsYield
With pyridine; hydrogen fluoride for 2h; Decomposition; Fluoro-dediazoniation; Irradiation;A 87.9%
B 0.4%
diphenyliodonium tetrafluoroborate

diphenyliodonium tetrafluoroborate

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
With potassium fluoride at 160 - 170℃; for 20h;85%
(2,4,6-trimethylphenyl)(phenyl)iodonium tetrafluoroborate

(2,4,6-trimethylphenyl)(phenyl)iodonium tetrafluoroborate

A

fluorobenzene
462-06-6

fluorobenzene

B

1-fluoro-2,4,6-trimethylbenzene
392-69-8

1-fluoro-2,4,6-trimethylbenzene

Conditions
ConditionsYield
With potassium fluoride; 18-crown-6 ether; copper(II) methanesulfonate In N,N-dimethyl-formamide at 60℃; for 18h; Reagent/catalyst; Time; Solvent;A 85%
B n/a
With potassium fluoride; 18-crown-6 ether; copper(II) bis(trifluoromethanesulfonate) In ethyl acetate at 60℃; for 18h; Reagent/catalyst; Solvent; Glovebox; Overall yield = 39 %Spectr.;
With tetrabutyl ammonium fluoride; copper(II) bis(trifluoromethanesulfonate) In N,N-dimethyl-formamide at 60℃; for 18h; Glovebox;
(2,4,6-trimethylphenyl)(phenyl)iodonium tetrafluoroborate

(2,4,6-trimethylphenyl)(phenyl)iodonium tetrafluoroborate

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
With potassium fluoride; 18-crown-6 ether; copper(II) bis(trifluoromethanesulfonate) In N,N-dimethyl-formamide at 60℃; for 18h; Mechanism; Reagent/catalyst; Solvent; Time; Glovebox;85%
With tetrabutyl ammonium fluoride; copper(II) bis(trifluoromethanesulfonate) In N,N-dimethyl-formamide at 60℃; for 18h; Glovebox;29%
tris(4-fluorophenyl)cyanurate
54416-55-6

tris(4-fluorophenyl)cyanurate

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); sodium isopropylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 2-methyltetrahydrofuran at 80℃; for 12h; Green chemistry;85%
triethylsilane
617-86-7

triethylsilane

1-Chloro-4-fluorobenzene
352-33-0

1-Chloro-4-fluorobenzene

A

fluorobenzene
462-06-6

fluorobenzene

B

triethyl(4-fluorophenyl)silane

triethyl(4-fluorophenyl)silane

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl acetamide at 100℃; for 7h; Schlenk technique; Inert atmosphere;A 13%
B 85%
diphenyliodonium p-toluenesulfonate
6293-66-9

diphenyliodonium p-toluenesulfonate

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 8h; Heating;84%
Multi-step reaction with 3 steps
1: potassium iodide / water; acetonitrile
2: silver(l) oxide / water / 11 h / 0 - 20 °C
3: dimethylsulfoxide-d6 / 0.17 h / 100 °C
View Scheme
diphenylmercury(II)
587-85-9

diphenylmercury(II)

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
With hypofluorous acid trifluoromethyl ester In chloroform for 0.5h; Ambient temperature;83%
With sulfur tetrafluoride at -70 - -60℃; for 8h;58%
trimethylphenylsilane
768-32-1

trimethylphenylsilane

lead(IV) tetraacetate
546-67-8

lead(IV) tetraacetate

trifluoroborane diethyl ether
109-63-7

trifluoroborane diethyl ether

A

fluorobenzene
462-06-6

fluorobenzene

B

benzene
71-43-2

benzene

Conditions
ConditionsYield
Stirring of silane with a slurry of Pb(OAc)4 in excess of BF3*Et2O overnight at room temp.; GC anal.;A 83%
B 6%
4-fluorophenyl(m-carboran-9-yl)iodonium tetrafluoroborate
99506-39-5

4-fluorophenyl(m-carboran-9-yl)iodonium tetrafluoroborate

sodium fluoride

sodium fluoride

A

fluorobenzene
462-06-6

fluorobenzene

B

9-iodo-m-carborane
17157-02-7

9-iodo-m-carborane

C

9-fluoro-m-carborane
73050-37-0

9-fluoro-m-carborane

D

4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

Conditions
ConditionsYield
In chloroform; water mixt. of aryl(m-carboran-9-yl)iodonium tetrafluoroborate, NaF, water and chloroform was vigorously stirred under reflux at 56°C, 1.25 h; internal standard (chlorobenzene) added and org. layer was analysed by GLC;A 9%
B 2%
C 83%
D 82%
phenylboronic acid
98-80-6

phenylboronic acid

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
Stage #1: phenylboronic acid With sodium hydroxide In methanol at 23℃; for 0.25h; Inert atmosphere;
Stage #2: With silver trifluoromethanesulfonate In methanol at 0℃; for 0.5h; Inert atmosphere;
Stage #3: With Selectfluor In acetone at 23℃; for 1h; Inert atmosphere; Molecular sieve; regiospecific reaction;
82%
Stage #1: phenylboronic acid With sodium hydroxide In methanol at 23℃;
Stage #2: With silver trifluoromethanesulfonate In methanol at 0℃; for 0.5h;
Stage #3: With Selectfluor In acetone for 0.5h; Molecular sieve;
Stage #1: phenylboronic acid With sodium hydroxide In methanol at 23℃; for 0.25h;
Stage #2: With silver trifluoromethanesulfonate In methanol at 0℃; for 0.5h;
Stage #3: With Selectfluor In [(2)H6]acetone for 1h; Molecular sieve;
95 %Spectr.
C28H21N5O6PdS

C28H21N5O6PdS

fluorobenzene
462-06-6

fluorobenzene

Conditions
ConditionsYield
With Selectfluor In [(2)H6]acetone at 50℃; for 0.166667h; Product distribution / selectivity;82%
With Selectfluor In [(2)H6]acetone at 50℃; for 0.166667h; Product distribution / selectivity;47%

462-06-6Relevant articles and documents

Fluoroaromatics from arylamines, a convenient one-pot conversion using nitrosonium tetrafluoroborate

Milner

, p. 73 - 82 (1992)

A simple, novel and extremely versatile procedure has been identified for the conversion of arylamines into the corresponding arylfluorides. The amine is treated with nitrosonium tetrafluoroborate in dichloromethane and the resulting diazonium tetrafluoroborate is heated, without isolation or drying, to give the fluoroaromatic, generally in good yield. The method is applicable even to arylamines bearing carboxyl and hydroxyl substituents which give poor yields of arylfluorides under Balz-Schiemann conditions.

Cleavage of Aryl-Tin Bonds with Elemental Fluorine: Rapid Synthesis of Fluorobenzene

Adam, Michael J.,Pate, Brian D.,Ruth, Thomas J.,Berry, Joffre M.,Hall, Laurance D.

, p. 733 (1981)

Fluorobenzene has been synthesized rapidly by treatment of aryltin derivatives with F2 in CFCl3 or CCl4 at -78 to 0 deg C.

DIRECT LIQUID-PHASE FLUORINATION OF AROMATIC COMPOUNDS. NEW ADVANCES IN ELECTROPHILIC FLUORINATION

Gambaretto, G. P.,Conte, L.,Fraccaro, C.,Napoli, M.

, p. 241 (1991)

-

Preparation of Fluoroarenes in One-Pot Diazotization and Fluoro-Dediazoniation of Aminoarenes Using HF or HF-Base. The Functions of Bases in the HF Solution

Fukuhara, Tsuyoshi,Sasaki, Satoshi,Yoneda, Norihiko,Suzuki, Akira

, p. 2058 - 2062 (1990)

In a one-pot diazotization of anilines followed by fluoro-dediazoniation in situ using HF or HF with bases (HF-Base) as a solvent, the diazotization stage has been found to play the most important part to yield fluoroarenes effectively.Diazotization of anilines was greatly influenced by the composition of the HF solution, and greatly enhanced by employing appropriate amounts of bases, such as pyridine.On the other hand, fluoro-dediazoniation of diazonium salts, once formed, took place very readily in HF or HF-Base to produce fluoroarenes in high yield, although such bases served to slow down the rate of decomposition of diazonium salts to some extent.

-

Feng,Mamula

, p. 507 (1958)

-

Speranza et al.

, p. 5583,5588 (1977)

Photochemical Sandmeyer-type Halogenation of Arenediazonium Salts

Belitz, Florian,Goo?en, Lukas J.,Manu Martínez, ángel,Schmid, Rochus,Sivendran, Nardana,Sowa Prendes, Daniel

, (2022/01/19)

Trihalide salts were found to efficiently promote photochemical dediazotizing halogenations of diazonium salts. In contrast to classical Sandmeyer reactions, no metal catalysts are required to achieve high yields and outstanding selectivities for halogena

Mechanistic studies into visible light-driven carboxylation of aryl halides/triflates by the combined use of palladium and photoredox catalysts

Caner, Joaquim,Iwasawa, Nobuharu,Martin, Ruben,Murata, Kei,Shimomaki, Katsuya,Toriumi, Naoyuki

supporting information, p. 1846 - 1853 (2021/08/13)

The reaction mechanism of palladium-catalyzed visible light-driven carboxylation of aryl halides and triflates with a photoredox catalyst was examined in detail. Experimental and theoretical studies indicated that the active species for photoredox- catalyzed reduction was cationic ArPd(II)+ species to generate nucleophilic ArPd(I) or its further reduced ArPd(0)- species, which reacted with CO2 to give carboxylic acids. Hydrodehalogenated compounds, main byproducts in this carboxylation, were thought to be generated by protonation of these reduced species.

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