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456-22-4

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456-22-4 Usage

Description

4-Fluorobenzoic acid is used as an intermediate in organic synthesis. For instance, it is used to synthesize N-cuccinimidyl 4-[18F]-fluorobenzoate, which is used for the 18F labeling of antibodies. It has been used in high resolution charge density study.

Reference

AG. Vaidyanathan, M. R. Zalutsky, Improved Synthesis of N-Succinimidyl 4-[18F]Fluorobenzoate and Its Application to the Labeling of a Monoclonal Antibody Fragment, Bioconjuate Chemistry, 1994, vol. 5, pp. 352-356

Chemical Properties

white to light yellow crystal powder

Uses

4-Fluorobenzoic acid has been used in high resolution charge density study.

Definition

ChEBI: A fluorobenzoic acid carrying a fluoro substituent at position 4.

Purification Methods

Crystallise the acid from 50% aqueous EtOH, then purify it by zone melting or vacuum sublimation at 130-140o. [Beilstein 9 H 333, 9 III 1327, 9 IV 953.]

Check Digit Verification of cas no

The CAS Registry Mumber 456-22-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,5 and 6 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 456-22:
(5*4)+(4*5)+(3*6)+(2*2)+(1*2)=64
64 % 10 = 4
So 456-22-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H5FO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)

456-22-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Detail
  • TCI America

  • (F0112)  4-Fluorobenzoic Acid  >98.0%(GC)(T)

  • 456-22-4

  • 25g

  • 330.00CNY

  • Detail
  • Alfa Aesar

  • (A14129)  4-Fluorobenzoic acid, 98%   

  • 456-22-4

  • 25g

  • 313.0CNY

  • Detail
  • Alfa Aesar

  • (A14129)  4-Fluorobenzoic acid, 98%   

  • 456-22-4

  • 100g

  • 990.0CNY

  • Detail
  • Alfa Aesar

  • (A14129)  4-Fluorobenzoic acid, 98%   

  • 456-22-4

  • 500g

  • 4269.0CNY

  • Detail

456-22-4Synthetic route

p-fluorotoluene
352-32-9

p-fluorotoluene

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With hydrogen bromide; dihydrogen peroxide at 50℃; for 9h; Temperature; UV-irradiation;96.8%
With oxygen; Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Green chemistry;96%
With hydrogen bromide In water95.2%
1,2-bis(4-fluorophenyl)-2-hydroxyethan-1-one
53458-16-5

1,2-bis(4-fluorophenyl)-2-hydroxyethan-1-one

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With oxygen; sodium hydride In tetrahydrofuran; mineral oil at 25℃; under 760.051 Torr; for 0.5h;74%
With diphenyl diselenide; dihydrogen peroxide In water; acetonitrile at 20℃; for 24h;72%
Stage #1: 1,2-bis(4-fluorophenyl)-2-hydroxyethan-1-one With potassium cyanide; carbon dioxide In N,N-dimethyl-formamide at 12℃; under 760.051 Torr; for 1h;
Stage #2: With titanium(IV)isopropoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 40℃; for 18h; Reagent/catalyst;
10 %Spectr.
carbon dioxide
124-38-9

carbon dioxide

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide Ambient temperature; electrochemically;94%
Stage #1: 1-Bromo-4-fluorobenzene With bromobenzene; trifluoroacetic acid; cobalt(II) bromide; zinc dibromide; zinc In acetonitrile Inert atmosphere;
Stage #2: carbon dioxide With palladium diacetate; tricyclohexylphosphine In tetrahydrofuran; acetonitrile at 0℃; under 760.051 Torr; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate; acetonitrile
94%
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 2-(diphenylphosphino)-2’(3-(dimethylamino)-3-oxopropyl)-6’-(3-(icosyloxy)-3-oxopropyl)biphenyl; water; palladium diacetate; N-ethyl-N,N-diisopropylamine In toluene under 760.051 Torr; for 16h; Inert atmosphere; Schlenk technique; Irradiation;88%
carbon dioxide
124-38-9

carbon dioxide

2-(4-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane
225916-39-2

2-(4-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With (1,3-bis(2,6-diisopropyl-4-(morpholinomethyl)phenyl)imidazolidin-2-ylidene)copper(I) bromide; potassium tert-butylate In tetrahydrofuran under 760.051 Torr; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Reflux; Green chemistry;96%
Stage #1: carbon dioxide; 2-(4-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane With [Ni(N,N'-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene)(allyl)Cl]; potassium tert-butylate In toluene at 100℃; under 760.051 Torr; for 15h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride In water; ethyl acetate; toluene at 20℃;
96%
With potassium tert-butylate; copper(l) chloride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 70℃; under 760.051 Torr; for 24h;89%
4-fluorobenzylic alcohol
459-56-3

4-fluorobenzylic alcohol

A

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

B

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

Conditions
ConditionsYield
With peracetic acid; C24H29INO5 In acetic acid at 30℃; for 48h;A 67%
B 19%
With tert.-butylhydroperoxide In hexane; water at 50℃; for 9.5h;A 62%
B 22%
With sodium hypochlorite; sodium hydrogencarbonate for 4h; Yield given. Yields of byproduct given;
With [Rh(III)(OEP)(Cl)]/C; sodium hydroxide In water at 25℃; Electrochemical reaction; Inert atmosphere;
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; C40H32B2Cu2F10N8S2*2CH4O; potassium carbonate In water at 40℃; under 760.051 Torr; for 24h; Green chemistry;
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;99%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;99%
With tert.-butylnitrite; N-hydroxyphthalimide; oxygen In water at 60℃; under 760.051 Torr; for 48h; Schlenk technique;99%
4-Fluorobenzyl bromide
459-46-1

4-Fluorobenzyl bromide

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With sodium periodate; sulfuric acid In water at 95℃; for 12h;86%
With tert.-butylhydroperoxide at 100℃; for 5h;80%
With tert.-butylhydroperoxide In water at 80℃; for 12h; Green chemistry;
Multi-step reaction with 2 steps
1: silver(I) nitrite / diethyl ether / 5 h / 0 °C / Reflux
2: tetra-(n-butyl)ammonium iodide; zinc diacetate; water / 24 h / 80 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydride / tetrahydrofuran / 0.08 h / Inert atmosphere
1.2: 5 h / Inert atmosphere; Reflux
2.1: bis(acetylacetonate)oxovanadium; sodium acetate; methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen / 48 h / 120 °C
View Scheme
potassium monomethylcarbonate
14660-45-8

potassium monomethylcarbonate

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

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) In tetrahydrofuran at 70℃; for 16h; Inert atmosphere; Sealed tube;89%
methyl 4-flurobenzoate
403-33-8

methyl 4-flurobenzoate

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With iodine; aluminium In acetonitrile at 80℃; for 18h;98%
With high-silica Hβ-75 zeolite In water at 130℃; for 24h; Reagent/catalyst;75%
4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

carbon monoxide
201230-82-2

carbon monoxide

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With water; potassium carbonate In acetonitrile at 100℃; under 3750.38 Torr; for 0.0161111h;96%
With water; palladium diacetate; potassium carbonate at 20℃; under 760.051 Torr; for 5h;92%
With water; sodium carbonate; palladium diacetate at 20 - 165℃; under 10501.1 - 22502.3 Torr; for 0.333333h; microwave irradiation;77%
With 4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine; bis-triphenylphosphine-palladium(II) chloride; water; sodium carbonate In water at 100℃; under 7600.51 Torr; for 24h; Catalytic behavior; Autoclave;74%
1-(4-fluorophenyl)-2-[(4-methylphenyl)sulfonyl]-1-ethanone

1-(4-fluorophenyl)-2-[(4-methylphenyl)sulfonyl]-1-ethanone

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate; oxygen In acetonitrile at 20 - 50℃; for 4h;89%
4-fluorobenzylic alcohol
459-56-3

4-fluorobenzylic alcohol

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With sodium hypochlorite; sodium hydrogencarbonate for 1.33333h;100%
With diethylene glycol dimethyl ether at 70℃; for 0.5h; Sonication;97%
With oxygen at 120℃; for 10h; Green chemistry;95%
1-chloromethyl-4-fluorobenzene
352-11-4

1-chloromethyl-4-fluorobenzene

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With 4 Angstroem MS; methyl tri-n-octyl ammonium hydrogen sulfate; sodium tungstate at 90℃; for 10h;86%
With Oxone In water; acetonitrile for 12h; Reflux;85%
1-(4-fluorophenyl)ethanone
403-42-9

1-(4-fluorophenyl)ethanone

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
Stage #1: 1-(4-fluorophenyl)ethanone With tert.-butylhydroperoxide; sodium hydroxide; tungsten(VI) oxide In water at 80℃; for 8h;
Stage #2: With hydrogenchloride In water
93%
Stage #1: 1-(4-fluorophenyl)ethanone With iodine; dimethyl sulfoxide In chlorobenzene at 130℃; for 3h;
Stage #2: With tert.-butylhydroperoxide In chlorobenzene at 20 - 130℃; for 3h;
93%
With oxygen; manganese (II) acetate tetrahydrate; cobalt(II) diacetate tetrahydrate In acetic acid at 100℃; under 760.051 Torr; for 15h;88%
4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

carbon dioxide
124-38-9

carbon dioxide

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; diethylzinc In N,N-dimethyl acetamide at 70℃; under 760.051 Torr;60%
Stage #1: 4-fluoro-1-iodobenzene With copper In tetrahydrofuran at 25℃; for 0.5h;
Stage #2: carbon dioxide In tetrahydrofuran for 24h;
42%
4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

ethyl acetoacetate
141-97-9

ethyl acetoacetate

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;80%
carbon dioxide
124-38-9

carbon dioxide

4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium methanolate In N,N-dimethyl acetamide at 70℃; for 24h; Schlenk technique; Sealed tube;73%
carbon dioxide
124-38-9

carbon dioxide

C8H10FS(1+)*CF3O3S(1-)

C8H10FS(1+)*CF3O3S(1-)

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With 2.9-dimethyl-1,10-phenanthroline; neocuproine; zinc In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 16h;74%
carbon monoxide
201230-82-2

carbon monoxide

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

A

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

B

methyl 4-flurobenzoate
403-33-8

methyl 4-flurobenzoate

Conditions
ConditionsYield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 7h; Irradiation;A 8%
B 81.5%
1,2-bis(4-fluorophenyl)-1,2-ethanediol
24133-58-2

1,2-bis(4-fluorophenyl)-1,2-ethanediol

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With oxygen In dichloromethane at 20℃; under 760.051 Torr; for 12h; Irradiation;88%
Stage #1: 1,2-bis(4-fluorophenyl)-1,2-ethanediol With oxygen; sodium t-butanolate In tetrahydrofuran at 20℃; under 760.051 Torr; for 3h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=1; chemoselective reaction;
70%
para-fluorostyrene
405-99-2

para-fluorostyrene

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
Stage #1: para-fluorostyrene With tert.-butylhydroperoxide; iodine; sodium hydroxide In water at 105℃; for 16h; Sealed tube;
Stage #2: With hydrogenchloride In water
52%
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

A

4-fluorobenzylic alcohol
459-56-3

4-fluorobenzylic alcohol

B

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 25℃; for 3.5h; Cannizzaro Reaction;A n/a
B 86%
With potassium hydroxide
With barium dihydroxide; formaldehyd at 100 - 110℃; for 0.2h;A 88 % Chromat.
B 11 % Chromat.
Stage #1: 4-fluorobenzaldehyde In neat (no solvent) for 0.0333333h; Green chemistry;
Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 40℃; for 0.00416667h; Reagent/catalyst; Cannizzaro Reaction; Microwave irradiation; Green chemistry;
carbon monoxide
201230-82-2

carbon monoxide

1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With tetrabutylammomium bromide; dicobalt octacarbonyl In sodium hydroxide; benzene at 65℃; for 2h; Irradiation;97%
With dicobalt octacarbonyl; potassium carbonate; methyloxirane In methanol at 60℃; under 760 Torr; for 6h;89%
carbon dioxide
124-38-9

carbon dioxide

4-fluorophenyl trifluoromethanesulfonate
132993-23-8

4-fluorophenyl trifluoromethanesulfonate

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 90℃; electrochemical reaction;92%
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; palladium diacetate; caesium carbonate; N-ethyl-N,N-diisopropylamine; DavePhos In N,N-dimethyl acetamide at 20℃; for 36h; Irradiation; Green chemistry; chemoselective reaction;62%
With (2’,4’,6’-triisopropyl-[1,1’-biphenyl]-2-yl)-diphenylphosphine; bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate; tetrabutylammomium bromide; palladium diacetate; caesium carbonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 4h; Irradiation;
1-(4-Fluorophenyl)ethanol
403-41-8

1-(4-Fluorophenyl)ethanol

A

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

B

1-(4-fluorophenyl)ethanone
403-42-9

1-(4-fluorophenyl)ethanone

Conditions
ConditionsYield
Stage #1: 1-(4-Fluorophenyl)ethanol With oxygen; sodium hydride In tetrahydrofuran at 0 - 20℃; for 6h;
Stage #2: With hydrogenchloride In water
A 32%
B 64%
methyl 4-flurobenzoate
403-33-8

methyl 4-flurobenzoate

acetonitrile
75-05-8

acetonitrile

A

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

B

3-(4-fluorophenyl)-3-oxopropionitrile
4640-67-9

3-(4-fluorophenyl)-3-oxopropionitrile

Conditions
ConditionsYield
With sodium hydride In tert-butyl methyl ether; water at 90℃;A 17.5%
B 64%
N-(4-cyanophenyl)-4-fluorobenzamide
316142-60-6

N-(4-cyanophenyl)-4-fluorobenzamide

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride at 120℃; for 24h;98%
fluorobenzene
462-06-6

fluorobenzene

carbon dioxide
124-38-9

carbon dioxide

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
With aluminum tri-bromide; triisopropylsilyl chloride at 80℃; under 22502.3 Torr; for 48h; Autoclave;53%
With aluminium trichloride; aluminium at 40℃; under 42754.3 Torr; for 18h;47%
With triethylamine In acetonitrile at 20℃; under 760.051 Torr; for 24h; Irradiation;62 %Spectr.
carbon dioxide
124-38-9

carbon dioxide

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

1-Chloro-4-fluorobenzene

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide; 1-Chloro-4-fluorobenzene With manganese; bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; triphenylphosphine In 1,3-dimethyl-2-imidazolidinone at 25℃; under 760.051 Torr; for 20h;
Stage #2: With hydrogenchloride; water In diethyl ether at 20℃; for 0.166667h;
81%
With manganese; 2,9-dibutyl-4,7-dimethyl-1,10-phenanthroline; tetraethylammonium iodide; lithium acetate; cobalt(II) bromide In N,N-dimethyl acetamide at 100℃; under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique;62%
Stage #1: 1-Chloro-4-fluorobenzene With bis(cyclopentadienyl)titanium dichloride; butyl magnesium bromide In tetrahydrofuran at 40℃; for 6h; Inert atmosphere; Schlenk technique;
Stage #2: carbon dioxide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Schlenk technique;
59%
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 4h; Electrolysis;51%
4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

Conditions
ConditionsYield
100%
With pyridine hydrogenfluoride; sodium nitrite 1.) O deg C, 20 min, 2.) 100 deg C, 1 h;89%
With hydrogen fluoride; sodium nitrite

456-22-4Relevant articles and documents

Platinum nanoparticles supported on polymeric ionic liquid functionalized magnetic silica: effective and reusable heterogeneous catalysts for the selective oxidation of alcohols in water

Vessally, Esmail,Ghasemisarabbadeih, Mostafa,Ekhteyari, Zeynab,Hosseinzadeh-Khanmiri, Rahim,Ghorbani-Kalhor, Ebrahim,Ejlali, Ladan

, p. 106769 - 106777 (2016)

In this research, the syntheses of core-shell magnetic silica nanostructures, functionalized by a polymeric ionic liquid and immobilization of platinum nanoparticles, are described. Firstly, the magnetic silica nanoparticles were synthesized and modified using an amine-containing organosilane through a single-step process. The synthesized nanostructures were functionalized by the synthesis and polymerization of a pyridinium ionic liquid and a methyl methacrylate monomer, respectively, onto their surfaces. The platinum nanoparticles were immobilized on the functionalized nanoparticles. The obtained functionalized nanostructures have been used in the selective aerobic oxidation, in an aqueous medium, of primary and encumbered secondary aliphatic alcohols, and exhibit high activity at mild temperatures.

New benzothiazole based copper(II) hydrazone Schiff base complexes for selective and environmentally friendly oxidation of benzylic alcohols: The importance of the bimetallic species tuned by the choice of the counterion

Bocian, Aleksandra,Gorczyński, Adam,Marcinkowski, Damian,Witomska, Samanta,Kubicki, Maciej,Mech, Paulina,Bogunia, Ma?gorzata,Brzeski, Jakub,Makowski, Mariusz,Pawlu?, Piotr,Patroniak, Violetta

, (2020)

Green and sustainable chemistry approaches necessitate an ongoing investigation towards new, environmentally benign and selective catalysts. We have thus prepared a new benzothiazole-scaffolded hydrazone Schiff base ligand L and coordinated it with copper(II) ions leading to five different complexes, the form of which in the solid state is counterion-dependent. Nitrate, chloride and triflate anions lead to monometallic species, whereas utilization of sulfates and tetrafluoroborates is responsible for the formation of bimetallic assemblies. The catalytic efficiency of synthesized compounds was shown in Cu-TEMPO (2,2,6,6-tetramethyl-l-piperidinoxyl) aerobic oxidation of activated alcohols resulting in good to excellent conversions and 100% selectivity to form the corresponding aldehydes. Considering the experimental results and Density Functional Theory calculations we propose two most plausible reaction mechanisms that further corroborate the enhanced activity of bimetallic species. It appears that the tridentate character of the ligand sacrifices some of the overall catalytic efficiency for the selectivity of the process. Aqueous reaction medium, low catalyst loading, air as oxidant and exclusive oxidative selectivity render these CuII complexes promising candidates for further improvement.

Efficient synthesis of aromatic carboxylic acids from aryl ketones in ionic liquid

Jong, Chan Lee,Jang, Mi Lee

, p. 1071 - 1074 (2006)

Conversion of aryl ketones to the corresponding aromatic carboxylic acids has been achieved using sequential treatment of HDNIB and urea-hydrogen peroxide in [bmim]BF4 ionic liquid. Copyright Taylor & Francis Group, LLC.

Active-sodium-promoted reductive cleavage of halogenated benzoic acids

Azzena, Ugo,Dettori, Giovanna,Mocci, Sarah,Pisano, Luisa,Cerioni, Giovanni,Mocci, Francesca

, p. 9171 - 9174 (2010)

The outcome of the reaction between 1,2-diaryl-1,2-disodioethanes and halogenated benzoic acids strongly depends on the nature of both reaction partners. Indeed, whilst chloro-, bromo- and iodobenzoic acids are easily dehalogenated, the reductive cleavage of fluorobenzoic acids proceeds to a high extent only in the presence of the dianions endowed with more powerful reducing properties. Moreover, it was observed that ortho-substituted benzoic acids are more easily dehalogenated than the corresponding para or meta isomers. These observations allowed the development of reaction conditions for the exhaustive or regioselective cleavage of selected polyhalogenated benzoic acids.

Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process

Fu, Qiang,Liang, Fu-Shun,Lou, Da-Wei,Pan, Gao-Feng,Wang, Rui,Wu, Min,Xie, Kai-Jun

supporting information, p. 2020 - 2024 (2022/03/31)

A visible-light-promoted atomic substitution reaction for transforming thiocacids into carboxylic acids with dimethyl sulfoxide (DMSO) as the oxygen source has been developed, affording various alkyl and aryl carboxylic acids in over 90% yields. The atomic substitution process proceeds smoothly through the photochemical reactivity of the formed hydrogen-bonding adduct between thioacids and DMSO. A DMSO-involved proton-coupled electron transfer (PCET) and the simultaneous generation of thiyl and hydroxyl radicals are proposed to be key steps for realizing the transformation.

Milled Dry Ice as a C1 Source for the Carboxylation of Aryl Halides

O'Brien, Connor J.,Nicewicz, David A.

supporting information, p. 814 - 816 (2021/03/01)

The use of carbon dioxide as a C1 chemical feedstock remains an active field of research. Here we showcase the use of milled dry ice as a method to promote the availability of CO 2in a reaction solution, permitting practical synthesis of arylcarboxylic acids. Notably, the use of milled dry ice produces marked increases in yields relative to those obtained with gaseous CO 2, as previously reported in the literature.

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