455-38-9

Basic information

• Product Name: 3-Fluorobenzoic acid
• Synonyms: 3-Fluorobenzoic acid, 99% 25GR;NSC 10320;NSC 176125;Fluorobenzoic aci;Between acid;Inter-fluoro-benzoic acid;3-Fluorobenzoic acid≥ 99% (GC);3-Fluorobenzonicacid
• CAS NO: 455-38-9
• Molecular Formula: C₇H₅FO₂
• Molecular Weight: 140.11
• EINECS: 207-248-0
• Product Categories: Aryl Fluorinated Building Blocks;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Fluorinated Building Blocks;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;Fluorine series;carboxylic acid| alkyl Fluorine;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;BenzoicAcidDerivative;Benzoic acid;Fluorobenzene;Acids & Esters;Fluorine Compounds;C7;Carbonyl Compounds;Carboxylic Acids;Aromatics;Miscellaneous Reagents
• Mol File: 455-38-9.mol
• Article Data: 100

Chemical Properties

• Melting Point: 122-124 °C(lit.)
• Boiling Point: 226.1°C (rough estimate)
• Flash Point: 105.7 °C
• Appearance: White to light yellow/Powder
• Density: 1.474
• Vapor Pressure: 0.0109mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: 1.5g/l
• PKA: 3.86(at 25℃)
• Water Solubility: Very soluble in water.
• BRN: 1906920
• CAS DataBase Reference: 3-Fluorobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluorobenzoic acid(455-38-9)
• EPA Substance Registry System: 3-Fluorobenzoic acid(455-38-9)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-36/37/38
• Safety Statements: 22-28-24/25-37/39-26-36
• WGK Germany: 1
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 455-38-9(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

3-Fluorobenzoic Acid (cas# 455-38-9) is a compound useful in organic synthesis.

Definition

ChEBI: A fluorobenzoic acid that is benzoic acid substituted by a fluoro group at position 3.

InChI:InChI=1/C7H5FO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,(H,9,10)/p-1

Synthetic route

3-Fluorobenzaldehyde (456-48-4) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With potassium ferrate(VI) In neat (no solvent) for 2h; Milling;	98.9%
With oxygen; copper(II) acetate monohydrate; cobalt(II) diacetate tetrahydrate In water at 70℃; under 760.051 Torr; for 12h;	98%
With oxygen; Langlois reagent In acetonitrile at 25℃; under 760.051 Torr; for 12h; Irradiation; Green chemistry;	95%

m-Fluorotoluene (352-70-5) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With oxygen; pyridinium chlorochromate In water at 120℃; under 45004.5 Torr; for 2h;	95%
With copper(l) iodide; oxygen; nitric acid at 160℃; under 11251.1 - 18751.9 Torr; for 4.7h; Autoclave;	84.7%
With cerium(III) chloride; 1,1,1-trichloroethanol; oxygen In acetonitrile at 60℃; Irradiation;	83%

meta-aminobenzoic acid (99-05-8) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With pyridine hydrogenfluoride; sodium nitrite 1.) O deg C, 20 min, 2.) 80 deg C, 1 h;	95%
With hydrogen fluoride; sodium nitrite
Ueberfuehrung in die Diazoaminoverbindung und Zersetzung mit rauchender Fluorwasserstoffsaeure;
With pyridine; hydrogen fluoride; sodium nitrite 1.) room temperature, 2.) 0 deg C, 3.) 80 deg C; Yield given. Multistep reaction;
Stage #1: meta-aminobenzoic acid With sodium nitrite at 70℃; for 1.5h; Schiemann Aromatic Fluorination; Stage #2: With hydrogen fluoride; boric acid Stage #3: In toluene at 110℃;

3-fluoro-benzenemethanol (456-47-3) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With dichloro(1,5-cyclooctadiene)ruthenium(II); C30H30N3P2(1+)*Cl(1-); potassium hydroxide In toluene at 120℃; for 24h; Inert atmosphere; Schlenk technique;	94%
With lithium hydroxide monohydrate; oxygen In water at 25℃; for 12h;	93%
With picoline; tert.-butylhydroperoxide; chlorophyllin coppered trisodium salt In water at 80℃; for 15h; Temperature; chemoselective reaction;	93%

3-Fluoro-benzoic acid benzyl ester → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 60℃; for 3h; Inert atmosphere;	94%
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 50℃; for 5h; Inert atmosphere;	94%

3-fluoro(nitromethyl)benzene → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With water; tetra-(n-butyl)ammonium iodide at 80℃; for 15h; Reagent/catalyst;	91%
With zinc diacetate; water; tetra-(n-butyl)ammonium iodide at 80℃; for 24h;	90%
With tetra-(n-butyl)ammonium iodide; acetic acid In water at 80℃; for 15h; Reagent/catalyst;	84%

1-(3-fluorophenyl)ethane-1,2-diol (1041469-36-6) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With tert.-butylhydroperoxide; potassium tert-butylate In water at 80℃; for 8h;	87%

carbon dioxide (124-38-9) + 3-fluorophenyl sulfofluoridate → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With manganese; bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 20h; Schlenk technique; Inert atmosphere; Glovebox;	87%

3-fluorophthalic acid (1583-67-1) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With acetic acid; silver carbonate In dimethyl sulfoxide at 120℃; for 16h; regioselective reaction;	86%
With [Au(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)(O2CAd)] In toluene at 120℃; regioselective reaction;

methanol (67-56-1) + 3-fluorobromobenzene (1073-06-9) + carbon monoxide (201230-82-2) → 3-fluorobenzoic acid (455-38-9) + methyl 3-fluorobenzoate (455-68-5)

Conditions	Yield
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 7h; Irradiation;	A 8% B 85%

2,4-dimethylthiosemicarbazide (6621-75-6) + 3-fluorobenzoyl chloride (1711-07-5) → 3-fluorobenzoic acid (455-38-9) + 5-(3-fluorophenyl)-2,4-dihydro-2,4-dimethyl-3H-1,2,4-triazole-3-thione (110623-33-1)

Conditions	Yield
With sodium hydroxide In water; toluene at 50 - 84℃; for 1.75h; Kinetics; Temperature; Large scale;	A n/a B 85%

1-ethyl-3-fluorobenzene (696-39-9) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; oxygen; nitric acid at 90℃; under 1500.15 - 6000.6 Torr; for 30h; Autoclave; Green chemistry;	84.13%

1-ethynyl-3-fluoro-benzene (2561-17-3) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
Stage #1: 1-ethynyl-3-fluoro-benzene With tert.-butylhydroperoxide; iron(III) chloride hexahydrate; sodium hydroxide In water at 80℃; for 10h; Stage #2: With hydrogenchloride In water at 20℃;	83%
With hydroxylamine hydrochloride; iodine In dimethyl sulfoxide at 100℃; for 8h;	60%

1-Fluoro-3-iodobenzene (1121-86-4) + H2O*CHLiO2 → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With formic acid; 1,3-bis-(diphenylphosphino)propane; nickel(II) acetate tetrahydrate; acetic anhydride In tetrahydrofuran at 100℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;	81%

1-Fluoro-3-iodobenzene (1121-86-4) + lithium formate monohydrate (6108-23-2) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); formic acid; 1,3-bis-(diphenylphosphino)propane; acetic anhydride In tetrahydrofuran at 100℃; for 24h; Schlenk technique; Inert atmosphere;	81%

3-fluorobenzamide (455-37-8) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With niobium(V) oxide; water In neat (no solvent) for 24h; Reflux; Inert atmosphere;	80%
With hydrogenchloride In 1,4-dioxane at 90℃; for 3h; Rate constant;

2-(3-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane + carbon dioxide (124-38-9) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
Stage #1: 2-(3-fluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane; carbon dioxide 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℃;	78%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 3-Fluorobenzaldehyde (456-48-4) → 3-fluorobenzoic acid (455-38-9) + 3-(3-Fluorophenyl)acrylic acid ethyl ester (351-46-2)

Conditions	Yield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester; 3-Fluorobenzaldehyde With potassium carbonate for 6h; Horner-Wadsworth-Emmons olefination; Neat (no solvent); high-speed ball milling; Stage #2: With Oxone for 12h; Neat (no solvent); high-speed ball milling; optical yield given as %de; diastereoselective reaction;	A n/a B 77%

carbon dioxide (124-38-9) + 3-fluorophenol (372-20-3) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
Stage #1: 3-fluorophenol With fluorosulfonyl fluoride; sodium hydride In N,N-dimethyl-formamide for 0.5h; Stage #2: carbon dioxide With manganese; bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 20h; Schlenk technique; Inert atmosphere; Glovebox;	73%

carbon dioxide (124-38-9) + 3-chlorofluorobenzene (625-98-9) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
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;	71%
Stage #1: 3-chlorofluorobenzene 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;	60%

1-(3-fluorophenyl)cyclohexanol (1496-35-1) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With iron(III) chloride; cerium(III) chloride; tetrabutyl-ammonium chloride; oxygen In acetonitrile at 20℃; under 760.051 Torr; for 24h; Schlenk technique; Irradiation;	71%

1-(3-fluorophenyl)ethanone (455-36-7) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With copper(l) iodide; hydroxylamine hydrochloride; oxygen In dimethyl sulfoxide at 100℃; for 10h;	65%
With hydroxylamine hydrochloride; iodine In dimethyl sulfoxide at 100℃; for 5h;	64%
With sodium hydroxide; potassium chloride; potassium hexacyanoferrate(III) In methanol; water at 30℃; Kinetics; further temperature;

3-fluorobromobenzene (1073-06-9) + carbon dioxide (124-38-9) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With manganese; 2.9-dimethyl-1,10-phenanthroline; lithium acetate; cobalt(II) bromide In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique;	64%

4-bromo-2-chloro-5-fluorobenzoic acid (177480-81-8) → 3-fluorobenzoic acid (455-38-9) + 2-chloro-5-fluoro-benzoic acid (2252-50-8)

Conditions	Yield
With triethanolamine; C33H21IrN3O9S3(3-) In water for 6h; Alkaline conditions; Inert atmosphere; Irradiation;	A 60% B n/a

3-fluoro-benzenemethanol (456-47-3) → 3-fluorobenzoic acid (455-38-9) + 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With picoline; tert.-butylhydroperoxide; chlorophyllin coppered trisodium salt In water at 60℃; for 12h; Temperature; chemoselective reaction;	A 35% B 56%

carbon dioxide (124-38-9) + 1-Fluoro-3-iodobenzene (1121-86-4) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; diethylzinc In N,N-dimethyl acetamide at 70℃; under 760.051 Torr;	55%
Stage #1: 1-Fluoro-3-iodobenzene With copper In tetrahydrofuran at 25℃; for 0.5h; Stage #2: carbon dioxide In tetrahydrofuran for 24h;	31%
Stage #1: carbon dioxide; 1-Fluoro-3-iodobenzene With tert.-butyl lithium In pentane at -70℃; Inert atmosphere; Stage #2: With sulfuric acid; water In pentane at 20℃; Inert atmosphere;	17%

potassium cyanide + 4-Fluoronitrobenzene (350-46-9) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With ethanol In water at 85℃; for 50h; von Richter Aromatic Carboxylation; Ionic liquid;	52%

carbon dioxide (124-38-9) + 3-fluorophenyl 4-methylbenzenesulfonate (57606-64-1) → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With manganese; (2,2'-bipyridine)nickel(II) dibromide In N,N-dimethyl-formamide at 60℃; under 760.051 Torr;	51%

tris[2-perfluorohexylethyl]tin-3-benzoic acid → 3-fluorobenzoic acid (455-38-9)

Conditions	Yield
With fluorine In FC-72 at -85℃; for 0.583333h;	24%

3-fluorobromobenzene (1073-06-9) + carbon monoxide (201230-82-2) → 3-fluorobenzoic acid (455-38-9) + methyl 3-fluorobenzoate (455-68-5)

Conditions	Yield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 7h; Irradiation;	A 8% B 8%

3-fluorobenzoic acid (455-38-9) → 3-fluorobenzoyl chloride (1711-07-5)

Conditions	Yield
Stage #1: 3-fluorobenzoic acid With N,N-dimethyl-formamide In dichloromethane at 0℃; for 0.0833333h; Stage #2: With oxalyl dichloride In dichloromethane at 20℃; for 12h;	100%
With thionyl chloride Heating;	87%
With phosphorus pentachloride

3-fluorobenzoic acid (455-38-9) + methyl 2-(4-(1H-pyrazol-1-yl)phenyl)-2-aminoacetate hydrochloride → methyl 2-(4-(1H-pyrazol-1-yl)phenyl)-2-(3-fluorobenzamido)-acetate

Conditions	Yield
With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2.25h;	100%

para-iodoanisole (696-62-8) + 3-fluorobenzoic acid (455-38-9) → 4'-fluoro-4,4''-dimethoxy-[1,1':3',1''-terphenyl]-2'-carboxylic acid

Conditions	Yield
With C30H54N6Ru(2+)*2BF4(1-); potassium perfluoro-tert-butoxide; potassium carbonate at 140℃; for 24h; Glovebox; Inert atmosphere;	99%

3-fluorobenzoic acid (455-38-9) + L-leucine ethyl ester hydrochloride (2743-40-0) → ethyl (3-fluorobenzoyl)-L-leucinate

Conditions	Yield
Stage #1: 3-fluorobenzoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; Stage #2: L-leucine ethyl ester hydrochloride In N,N-dimethyl-formamide at 0 - 20℃;	99%

3-fluorobenzoic acid (455-38-9) + benzylamine (100-46-9) → N-benzyl-3-fluorobenzamide (671-01-2)

Conditions	Yield
With borane-ammonia complex In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Reflux;	99%

3-fluorobenzoic acid (455-38-9) + 3-chlorodibenzo[b,d]bromol-5-ium methanesulfonate → 2'-bromo-4-chloro-[1,1'-biphenyl]-2-yl 3-fluorobenzoate

Conditions	Yield
With caesium carbonate In dichloromethane at 20℃; for 16h; Inert atmosphere; Schlenk technique;	99%

propan-1-ol (71-23-8) + 3-fluorobenzoic acid (455-38-9) → propyl 3-fluorobenzoate

Conditions	Yield
With sulfated zirconia at 130℃; for 1h; Catalytic behavior; Temperature; Time; Microwave irradiation;	98.5%

bis(dimethylphenylphosphine)tris(pentafluorothiophenolato)osmium(III) (120752-10-5, 214534-64-2) + 3-fluorobenzoic acid (455-38-9) → Os(SC6F5)2(FC6H4COO)(P(CH3)2C6H5)2

Conditions	Yield
In acetone (air); shaking (room temp., 48 h); solvent removal (vac.), washing (EtOH), crystn. (acetone-EtOH); elem. anal.;	98%

3-fluorobenzoic acid (455-38-9) + N-biphenyl-4-yl-3-oxo-3-piperazin-1-yl-propionamide hydrochloride (1187890-09-0) → N-biphenyl-4-yl-3-[4-(3-fluoro-benzoyl)-piperazin-1-yl]-3-oxo-propionamide (1187889-62-8)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 10 - 20℃;	98%

3-fluorobenzoic acid (455-38-9) + N-methoxy-2-(prop-1-en-2-yl)benzamide → (2-methoxy-1-methyl-3-oxoisoindolin-1-yl)methyl 3-fluorobenzoate

Conditions	Yield
With [2,2]bipyridinyl; oxygen; palladium diacetate In tetrahydrofuran at 60℃; under 760.051 Torr; for 12h; Schlenk technique; Molecular sieve;	98%

Cyclohexyl isocyanide (931-53-3) + 3-fluorobenzoic acid (455-38-9) + 4-[2,2-bis(trimethylsilyl)ethenyl]benzaldehyde (1268519-27-2) → (cyclohexylcarbamoyl)(4-(2,2-bis(trimethylsilyl)vinyl)phenyl)methyl 3-fluorobenzoate

Conditions	Yield
In water at 20℃; for 1.5h; Passerini Condensation;	98%

3-fluorobenzoic acid (455-38-9) → 5-fluoro-2-nitrobenzoic acid (320-98-9)

Conditions	Yield
With sulfuric acid; nitric acid	97%
With sulfuric acid; nitric acid; phosphorus pentoxide at 0℃; for 3h;	95%
With sulfuric acid; nitric acid at 0 - 20℃; for 1h;	93%

dichloromethane (75-09-2) + 3-fluorobenzoic acid (455-38-9) → bis(3-fluorobenzoyloxy)methane

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 60℃; for 3h;	97%

3-fluorobenzoic acid (455-38-9) + (S)-methyl 2-(tert-butoxy)-2-(6-(p-tolyl)-4,7-bis(trifluoromethyl)isoindolin-5-yl)acetate → (S)-methyl 2-(tert-butoxy)-2-(2-(3-fluorobenzoyl)-6-(p-tolyl)-4,7-bis(trifluoromethyl)isoindolin-5-yl)acetate

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate for 1h;	97%

3-fluorobenzoic acid (455-38-9) + (2S)-ethyl 2-(tert-butoxy)-2-((M)-8-(8-fluoro-5-methylchroman-6-yl)-6,9-dimethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)acetate → (S)-ethyl 2-(tert-butoxy)-2-((M)-8-(8-fluoro-5-methylchroman-6-yl)-3-(3-fluorobenzoyl)-6,9-dimethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)acetate

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 20℃; for 1.16667h;	96%

3-fluorobenzoic acid (455-38-9) + N-isocyaniminotriphenylphosphorane (73789-56-7) + dimethylglyoxal (431-03-8) → 3-[5-(3-fluorophenyl)-1,3,4-oxadiazol-2-yl]-3-hydroxybutan-2-one (1278591-63-1)

Conditions	Yield
In water at 20 - 26℃; for 12h; Green chemistry;	95%
In dichloromethane at 20℃; for 12.25h; tandem Passerini/intramolecular aza-Wittig reaction;	90%

ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside (39483-51-7) + 3-fluorobenzoic acid (455-38-9) → ethyl 2,3,4-tri-O-benzyl-6-O-(3-fluorobenzoyl)-1-thio-α-D-glucopyranoside

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;	95%

1-methylindole (603-76-9) + 3-fluorobenzoic acid (455-38-9) → C25H19FN2O2

Conditions	Yield
With silver carbonate; palladium dichloride In dimethyl sulfoxide; N,N-dimethyl-formamide at 80℃; for 7h;	95%

3-fluorobenzoic acid (455-38-9) + 1-(2-methyl-6-amino-4-phenylquinolin-3-yl)ethanone → N‑(3‑acetyl‑2‑methyl‑4‑phenylquinolin‑6‑yl)‑3‑fluorobenzamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h;	95%

p-hydroxyphenethyl alcohol (501-94-0) + 3-fluorobenzoic acid (455-38-9) → 4-hydroxyphenethyl 3-fluorobenzoate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; Schlenk technique; Inert atmosphere;	95%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 24h;

3-fluorobenzoic acid (455-38-9) + dibenzo[b,d]bromol-5-ium methanesulfonate → 2'-bromo-[1,1'-biphenyl]-3-yl 3-fluorobenzoate

Conditions	Yield
With caesium carbonate In dichloromethane at 20℃; for 16h; Inert atmosphere; Schlenk technique;	95%

3-fluorobenzoic acid (455-38-9) + 22-(2-aminoethylsulfanyl)-22-deoxypleuromutilin → 22-(2-(3-fluorobenzoylamino)ethylsulfanyl)-22-deoxypleuromutilin

Conditions	Yield
With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; triethylamine In ethyl acetate at 70℃; for 1h;	94.15%

3-fluorobenzoic acid (455-38-9) + aniline (62-53-3) → 3-fluoro-N-phenylbenzamide (1629-09-0)

Conditions	Yield
With oxygen; lithium hydroxide In water at 20℃; for 14h; Sonication;	94%

3-fluorobenzoic acid (455-38-9) + 1-(3-fluoro-4-(piperazine-1-yl)phenyl)butane-1-one → 1-(3-fluoro-4-(4-(3-fluorobenzoyl)piperazine-1-yl)phenyl)butane-1-one

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 22h;	94%

1,2,3-Benzotriazole (95-14-7) + 3-fluorobenzoic acid (455-38-9) → 1-(3-fluorobenzoyl)benzotriazole (670231-03-5)

Conditions	Yield
With thionyl chloride In dichloromethane for 2h; Inert atmosphere;	93%
With thionyl chloride In dichloromethane at 20℃;	80%

Upstream product

• 602-94-8 Pentafluorobenzoic acid 
• 1073-06-9 3-fluorobromobenzene 
• 201230-82-2 carbon monoxide 
• 455-86-7 3,4-Difluorobenzoic acid 
• 2358-29-4 2,3,6-trifluorobenzoic acid 
• 4519-39-5 2,3-difluorobenzoic acid 
• 1711-07-5 3-fluorobenzoyl chloride 
• 65-85-0 benzoic acid 
• 2561-17-3 1-ethynyl-3-fluoro-benzene 
• 451-02-5 ethyl 3-fluorobenzoate 
• 1041469-36-6 1-(3-fluorophenyl)ethane-1,2-diol 
• 456-47-3 3-fluoro-benzenemethanol 
• 1489-53-8 1,2,3-trifluorobenzene 
• 499-55-8 3-fluoro-benzoic acid hydrazide 

Downstream Products

• 348-34-5 2-(3-fluorophenyl)-5-nitro-1H-benzo[d]imidazole 
• 366-43-8 3-fluorobenzoic acid phenyl ester 
• 455-68-5 methyl 3-fluorobenzoate 
• 147696-86-4 4-amino-3'-fluorobenzophenone 
• 831-34-5 tert-butyl 3-fluorobenzoate 
• 161372-82-3 N-(4,6-dimethylpyridin-2-yl)-3-fluorobenzamide 
• 939027-70-0 C₁₇H₁₆FNO₂ 
• 369358-34-9 N'-((2RS,3R)-3-amino-5-(ethylsulfanyl)-2-hydroxypentanoyl)-3-fluorobenzohydrazide 
• 127919-30-6 ethyl 5-(3-fluorophenyl)-4-oxazolecarboxylate 
• 104941-39-1 4-fluorophenyl 3-fluorobenzoate 
• 226226-30-8 C₂₀H₂₁ClFN₃O₂ 

Relevant articles and documents

On the difference in the results of reductive defluorination of pentafluorobenzoic acid by sodium and zinc in liquid ammonia medium

Under the reduction of pentafluorobenzoic acid in liquid ammonia by sodium the deep defluorination with removal of three or more fluorine atoms has been observed, whereas with zinc only the product of para-defluorination has been obtained.

Meso-Carbazole substituted palladium porphyrins: Efficient catalysts for visible light induced oxidation of aldehydes

The A3B and A2B2 type porphyrins having N-butylcarbazole and p-cyanophenyl groups are synthesized and characterized. Their palladium complexes have also been prepared and utilized as catalysts for the photo-oxidation reactions of aromatic aldehydes in good yields. Pd(II)porphyrins displayed decent phosphorescence at a670 nm and were able to generate singlet oxygen upon light irradiation. The calculated singlet oxygen quantum yields for Pd(II)porphyrins were between 57% and 73%. The photo-catalytic application of Pd(II)porphyrins for aerobic oxidation of aromatic aldehydes is demonstrated.

Photo-induced deep aerobic oxidation of alkyl aromatics

Oxidation is a major chemical process to produce oxygenated chemicals in both nature and the chemical industry. Presently, the industrial manufacture of benzoic acids and benzene polycarboxylic acids (BPCAs) is mainly based on the deep oxidation of polyalkyl benzene, which is somewhat suffering from environmental and economical disadvantage due to the formation of ozone-depleting MeBr and corrosion hazards of production equipment. In this report, photo-induced deep aerobic oxidation of (poly)alkyl benzene to benzene (poly)carboxylic acids was developed. CeCl3 was proved to be an efficient HAT (hydrogen atom transfer) catalyst in the presence of alcohol as both hydrogen and electron shuttle. Dioxygen (O2) was found as a sole terminal oxidant. In most cases, pure products were easily isolated by simple filtration, implying large-scale implementation advantages. The reaction provides an ideal protocol to produce valuable fine chemicals from naturally abundant petroleum feedstocks. [Figure not available: see fulltext.].