459-57-4

Basic information

• Product Name: 4-Fluorobenzaldehyde
• Synonyms: 4-fluoro-benzaldehyd;Benzaldehyde, p-fluoro-;PFAD;PFBA;P-FLUOROBENZALDEHYDE;PARA FLUOROBENZALDEHYDE;FLUOROBENZALDEHYDE(4-);LABOTEST-BB LT00930357
• CAS NO: 459-57-4
• Molecular Formula: C₇H₅FO
• Molecular Weight: 124.11
• EINECS: 207-293-6
• Product Categories: Fluoro-Aromatics;Benzaldehyde;Fluorobenzene;Adehydes, Acetals & Ketones;Fluorine Compounds;Atorvastatin Calcium;Pharmaceutical Intermediate;Aldehydes;C7;Carbonyl Compounds
• Mol File: 459-57-4.mol
• Article Data: 409

Chemical Properties

• Melting Point: −10 °C(lit.)
• Boiling Point: 181 °C758 mm Hg(lit.)
• Flash Point: 134 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.157 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.51mmHg at 25°C
• Refractive Index: n20/D 1.521(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, Methanol
• Water Solubility: IMMISCIBLE
• Sensitive: Air Sensitive
• Stability: Air Sensitive
• BRN: 385857
• CAS DataBase Reference: 4-Fluorobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluorobenzaldehyde(459-57-4)
• EPA Substance Registry System: 4-Fluorobenzaldehyde(459-57-4)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/37/38
• Safety Statements: 26-36-37/39-36/37/39-27
• RIDADR: UN 1989 3/PG 3
• WGK Germany: 2
• F: 9-23
• TSCA: T
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 459-57-4(Hazardous Substances Data)

Usage

Description

4-Fluorobenzaldehyde is a fluorinated benzaldehyde that possesses inhibitory activity against mushroom tyrosinase, making it a valuable compound in various chemical and pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
4-Fluorobenzaldehyde is used as a synthetic intermediate for the preparation of pharmaceutical compounds, contributing to the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
4-Fluorobenzaldehyde is utilized in the preparation of pyrazolopyridine UR-13756, a compound with potential applications in various chemical processes.
Used in Biochemical Research:
4-Fluorobenzaldehyde is employed in the preparation of pyrazolopyridine derivatives, which serve as mitogen-activated protein kinase (MAPK) inhibitors. These inhibitors play a crucial role in studying and understanding cellular signaling pathways and have potential applications in the development of targeted therapies for various diseases.

InChI:InChI=1/C7H7FO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H3

Synthetic route

p-fluorotoluene (352-32-9) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With cerium(IV) triflate; water at 20℃; for 22h;	100%
With Xylaria polymorpha laccase; 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonate) diammonium salt In 1,4-dioxane at 20℃; for 1.83333h; pH=4.5; Green chemistry; Enzymatic reaction;	96%
With cobalt(II) acetate; acetic acid; potassium bromide at 120℃; under 15001.5 Torr; for 2.5h; Reagent/catalyst; Temperature; Pressure; Autoclave;	95%

4-fluorobenzylic alcohol (459-56-3) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With oxygen; perruthenate modified mesoporous silicate MCM-41 In toluene at 80℃; for 1h; Oxidation;	100%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; oxygen; copper(I) bromide dimethylsulfide complex In chlorobenzene at 90℃; for 6h;	100%
With iron(III) chloride; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; oxygen; sodium nitrite In 1,2-dichloro-ethane at 50℃; under 3000.3 Torr; for 5h; Autoclave;	99%

4-fluorobenzaldoxime (459-23-4) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With phosphoric acid In ethanol at 25℃; for 0.25h; Sonication; Green chemistry;	99%
With N,N'-dichlorophenobarbital In acetonitrile at 20℃; for 0.233333h;	96%
With water; Dess-Martin periodane In dichloromethane at 5℃; for 0.0333333h;	95%

para-fluorostyrene (405-99-2) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With sodium periodate; C53H44As2N2O3Ru In water; ethyl acetate; acetonitrile at 25℃; for 0.5h;	99%
With dihydrogen peroxide In water at 100℃; for 4h;	92%
With sodium periodate; C31H29Br2N3Ru*CH2Cl2 In water; ethyl acetate; acetonitrile at 25℃; for 0.5h; Inert atmosphere; Schlenk technique;	92%

p-fluorobenzyl acetate (502-00-1) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With methanol; potassium permanganate In ethyl acetate at 25℃; for 20h;	99%

para-fluorobenzylamine (140-75-0) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccasefrom Trametes versicolor; oxygen In water at 30℃; for 24h; pH=4.5; Enzymatic reaction;	97%
With sodium periodate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; acetic acid; trifluoroacetic acid In water; acetonitrile for 20h;	93%
With cercosporin; oxygen In methanol at 20℃; Schlenk technique; Irradiation; Green chemistry; chemoselective reaction;	87%

(4-fluorophenyl)methylene diacetate (64002-52-4) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With indium(III) bromide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 0.416667h;	97%
With bovine liver acetone powder In aq. phosphate buffer; acetone at 20℃; for 0.333333h; pH=7.4; Enzymatic reaction; chemoselective reaction;	97%
With sodium hydrogen sulfate; PEG-2000 at 70℃; for 0.416667h;	95%

4-fluorobenzylic alcohol (459-56-3) + di(p-tolyl) sulfoxide (1774-35-2) → di-(p-tolyl)sulfane (620-94-0) + 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With per-rhenic acid In toluene for 17h; Reflux;	A 97% B 90%

4-nitrobenzaldehdye (555-16-8) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.166667h; Inert atmosphere; Microwave irradiation;	95%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 10h; Inert atmosphere; Reflux; chemoselective reaction;	82.1 %Chromat.
Multi-step reaction with 2 steps 1: benzene-d6 / 23 °C / Inert atmosphere 2: benzene-d6 / 2 h / 60 °C View Scheme

4-hydroxy-benzaldehyde (123-08-0) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With 1,3-bis(2,6-diisopropylphenyl)-2,2-difluoro-2,3-dihydro-1h-imidazole; cesium fluoride In toluene at 80℃; for 3h; Product distribution / selectivity; Sealed vial;	95%
With 1,3-bis(2,6-diisopropylphenyl)-2,2-difluoro-2,3-dihydro-1h-imidazole; cesium fluoride In toluene at 23 - 80℃; for 3.5h; Inert atmosphere;	95 %Spectr.

4,4'-difluorodeoxybenzoin (366-68-7) + aniline (62-53-3) → 4-fluoro-N-phenylbenzamide (366-63-2) + 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With 1,10-Phenanthroline; copper(II) chloride dihydrate; oxygen In acetonitrile under 760.051 Torr; for 24h; Reflux;	A 95% B 96 %Chromat.

4-Fluorobenzoic acid (456-22-4) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With (CH3)2NCH2NpSiH2Ph at 110 - 140℃;	94%
With dipotassium hydrogenphosphate; fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane; dimethyl dicarbonate In acetonitrile at 20℃; for 6h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;	89%
With palladium(II) acetylacetonate; hydrogen; 2,2-dimethylpropanoic anhydride; dicyclohexylphenylphosphine In tetrahydrofuran at 80℃; under 3750.38 Torr; for 20h; Inert atmosphere;	80%

2-(4-fluorophenyl)-1,3-dithiolane (83521-64-6) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With 1,3,5-trichloro-2,4,6-triazine; dimethyl sulfoxide In dichloromethane at 20℃; for 3.5h;	93%

1-(dibromomethyl)-4-fluorobenzene (6425-24-7) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With dimethyl sulfoxide at 120℃; for 12h;	93%
With dimethyl amine at 60℃; for 0.166667h;	86%

1-(dibromomethyl)-4-fluorobenzene (6425-24-7) + dimethyl sulfoxide (67-68-5) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
at 120℃; for 12h;	93%

4-fluoro-1-iodobenzene (352-34-1) + carbon monoxide (201230-82-2) → fluorobenzene (462-06-6) + 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With hydrogen; potassium carbonate In 1,4-dioxane at 120 - 140℃; under 30003 Torr; for 20h; Autoclave;	A 7% B 91%

1-chloromethyl-4-fluorobenzene (352-11-4) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With (NH4)4[ZnMo6O18(OH)6]; oxygen In water; acetonitrile at 60℃; under 760.051 Torr; for 12h;	90%
With water; sodium hydroxide at 20℃; for 0.0833333h; Microwave irradiation;	88%
With bismuth(III) nitrate; tetrabutyl ammonium fluoride at 100℃; for 4h;	87%

p-Fluorophenylacetic acid (405-50-5) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With 1H-imidazole; C17H16ClMnN2O2; tetrabutylammonium periodite In chloroform at 20℃; for 0.416667h;	90%
With potassium 12-tungstocobaltate(III) In water; acetonitrile for 0.3h; Microwave irradiation;	90%
With 1H-imidazole; [bis(acetoxy)iodo]benzene; Co(AAOPD) In acetonitrile at 20℃; for 5h;	89%

α,α-dimethoxy-4-fluorotoluene (32691-93-3) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
perchloric acid In methanol; water at 25 - 30℃; for 0.166667h;	90%
With water In methanol at 25 - 30℃; for 0.166667h;	90%

4-fluorobenzal chloride (456-19-9) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With dimethyl amine at 60℃; for 0.166667h;	89%
With sodium perchlorate; water In acetonitrile at 25℃; Kinetics;
Multi-step reaction with 2 steps 1: 94 percent / 14 h / 70 °C 2: H2O / Acid hydrolysis View Scheme

(±)-2-[(4-fluorobenzyl)oxy]tetrahydropyran (18539-44-1) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With 1-n-butylpyridinium tetrachloroferrate; pyridinium chlorochromate at 50℃; for 0.166667h;	89%
With trichloroisocyanuric acid In acetonitrile Reflux;

carbon monoxide (201230-82-2) + 1-Bromo-4-fluorobenzene (460-00-4) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium diacetate; propyl di-tert-butylphosphinite In toluene at 100℃; under 3750.38 Torr; for 20h; Inert atmosphere;	88%
With 4-methoxy-N'-tetramethylethylenediamine; hydrogen; catacxium A; palladium diacetate In toluene at 100℃; under 3750.3 Torr; for 16h;	89 % Chromat.
With N,N,N,N,-tetramethylethylenediamine; hydrogen; catacxium A; palladium diacetate In toluene at 100℃; under 3750.38 Torr; for 16h;	89 % Chromat.
With N,N,N,N,-tetramethylethylenediamine; C6H6*C48H78O2P2Pd; hydrogen In toluene at 20 - 100℃; under 3750.38 Torr; Inert atmosphere; Autoclave;	95 %Chromat.
With N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium diacetate; catacxium A In toluene at 120℃; under 9000.9 Torr; Flow reactor; Green chemistry;	86 %Chromat.

4-fluoro-1-iodobenzene (352-34-1) + carbon dioxide (124-38-9) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry;	88%
With rhodium(III) iodide; hydrogen; acetic anhydride; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 24h; Autoclave;	84%
With carbon supported Pd nanoparticles; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 80℃; under 7500.75 Torr; for 12h; Sealed tube; Green chemistry;	76%

4-fluoro-1-iodobenzene (352-34-1) + carbon monoxide (201230-82-2) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With rhodium(III) chloride trihydrate; hydrogen; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 90℃; under 7500.75 Torr; for 12h; Autoclave;	88%

carbon monoxide (201230-82-2) + 4-fluorophenyl fluorosulfate → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With pyridine; 1,3-bis-(diphenylphosphino)propane; hydrogen; palladium diacetate In dimethyl sulfoxide at 120℃; under 15001.5 Torr; for 0.716667h; Flow reactor;	87%

(E)-2-(3-(4-fluorophenyl)allyl)benzaldehyde → 4-fluorobenzaldehyde (459-57-4) + 1-indene (95-13-6)

Conditions	Yield
With C25H19(1+)*BF4(1-) In dichloromethane at 20℃; for 1.5h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	A 86% B 22%

4-fluorobenzonitrile (1194-02-1) → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
Stage #1: 4-fluorobenzonitrile With diisobutylaluminium hydride In toluene at 0℃; for 0.00555556h; Flow reactor; Stage #2: With water; sodium L-tartrate In toluene at 0℃; chemoselective reaction;	85%
With lithium diisobutyl-iso-propoxyaluminium hydride In tetrahydrofuran; hexane at 20℃; for 1h;	99 %Chromat.
With lithium diisobutylmorpholinoaluminum hydride In tetrahydrofuran; hexane at 0℃; for 0.5h;	99 %Chromat.

2-(4-fluorophenyl)-1,3-oxathiolane → 4-fluorobenzaldehyde (459-57-4)

Conditions	Yield
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 1.5h;	85%
With eosin Y disodium salt In acetonitrile at 20℃; for 3h; Irradiation;	50%

4-fluorobenzaldehyde (459-57-4) → 4-fluoro-3-nitrobenzaldehyde (42564-51-2)

Conditions	Yield
With sulfuric acid; nitric acid	100%
With sulfuric acid; nitric acid at 20℃; for 3h;	99%
With sulfuric acid; nitric acid at -5 - 20℃; for 1h;	98%

morpholine (110-91-8) + 4-fluorobenzaldehyde (459-57-4) → (4-fluorophenyl)(morpholino)methane thione (73239-00-6)

Conditions	Yield
With sulfur In N,N-dimethyl-formamide at 110℃; for 2.5h;	100%
With sulfur In neat (no solvent) at 100℃; for 2h; Kindler Reaction; Green chemistry;	96%
With sulfur In dimethyl sulfoxide at 20℃; for 6h;	81%
With sulfur In N,N-dimethyl-formamide for 0.0333333h; Microwave irradiation;	80%
With toluene-4-sulfonic acid; sulfur at 60℃; for 4h;

4-fluorobenzaldehyde (459-57-4) + malononitrile (109-77-3) → 4-fluorobenzylidenemalononitrile (2826-22-4)

Conditions	Yield
With 1-(3-silica-supported propyl)-3-[(3-{[1-(3-silica-supported propyl)-4,5-dihydro-1H-imidazol-3-ium-3-yl]methyl}-2,4,6-trimethylphenyl)methyl]-4,5-dihydro-1H-imidazol-3-ium chloride at 100℃; for 4h; Knoevenagel condensation;	100%
With 2C9H3O6(3-)*2C27H18N6*3Ni(2+)*15H2O*5C2H6O In dichloromethane at 60℃; for 2h; Knoevenagel Condensation; Inert atmosphere;	100%
With N,N-dimethyl-N-hydroxyethylammonium acetate at 20℃; for 0.0333333h; Knoevenagel Condensation;	99%

acetic anhydride (108-24-7) + 4-fluorobenzaldehyde (459-57-4) → (4-fluorophenyl)methylene diacetate (64002-52-4)

Conditions	Yield
With titanium tetrachloride at 20℃; for 16h; screw-capped vial; Inert atmosphere; neat (no solvent);	100%
With indium(III) bromide at 20℃; for 0.333333h;	98%
With tetrafluoroboric acid at 20℃; for 0.0333333h;	98%

trimethylsilyl cyanide (7677-24-9) + 4-fluorobenzaldehyde (459-57-4) → 2-(4-fluorophenyl)-2-(trimethylsilyloxy)acetonitrile (82128-66-3)

Conditions	Yield
With triethylamine at 20℃; for 24h;	100%
With C42H50Mg2N4 In benzene-d6 at 25℃; Glovebox; Inert atmosphere;	99%
at 100℃; for 6h; Glovebox;	99%

potassium cyanide (151-50-8) + aniline hydrochloride (142-04-1) + 4-fluorobenzaldehyde (459-57-4) → 2-(4-fluorophenyl)-2-(phenylamino) acetonitrile (124573-71-3)

Conditions	Yield
In ethanol; water 1.) 1 h cooling; 2.) 20 h room temperature;	100%

4-fluorobenzaldehyde (459-57-4) + 4-methoxy-aniline (104-94-9) → N-(4-fluorobenzylidene)-4-methoxyaniline (39769-08-9, 130632-07-4)

Conditions	Yield
In ethanol for 1h; Sonication;	100%
at 90 - 120℃; Irradiation;	98%
With magnesium sulfate In dichloromethane for 15h; Ambient temperature;	86%

4-fluorobenzaldehyde (459-57-4) + ethylamine (75-04-7) → (E)-N-(4-fluorobenzylidene)ethanamine (82605-86-5)

Conditions	Yield
With magnesium sulfate In dichloromethane; water at 24.84℃; for 4h;	100%
In diethyl ether for 2h;	74%

4-fluorobenzaldehyde (459-57-4) + N-butylamine (109-73-9) → (E)-N-(4-fluorobenzylidene)butan-1-amine

Conditions	Yield
In benzene at 80℃; for 2h;	100%
In neat (no solvent) at 60℃; for 0.0666667h; Microwave irradiation;	98%
In diethyl ether Ambient temperature;	87%

4-fluorobenzaldehyde (459-57-4) + ethyl 2-cyanoacetate (105-56-6) → ethyl (E)-2-cyano-3-(4-fluorophenyl)-2-propenoate (18861-57-9, 50737-52-5)

Conditions	Yield
With 1-(3-silica-supported propyl)-3-[(3-{[1-(3-silica-supported propyl)-4,5-dihydro-1H-imidazol-3-ium-3-yl]methyl}-2,4,6-trimethylphenyl)methyl]-4,5-dihydro-1H-imidazol-3-ium chloride at 130℃; for 2h; Knoevenagel condensation;	100%
With polyacrylonitrile fiber functionalized with N,N-dimethyl-1,3-propanediamine In ethanol for 1.5h; Knoevenagel condensation; Reflux;	99%
With N-(propylcarbamoyl)sulfamic acid bonded on silica at 100℃; for 0.25h;	97%

4-fluorobenzaldehyde (459-57-4) + acetone (67-64-1) → (E)-4-(4-fluorophenyl)but-3-en-2-one (65300-29-0)

Conditions	Yield
With sodium hydroxide In water at 65℃; for 2h;	100%
With sodium hydroxide In ethanol; water at 20℃; Claisen-Schmidt Condensation; Inert atmosphere;	98%
With sodium hydroxide In water at 4 - 20℃; for 2h; Claisen-Schmidt condensation; Inert atmosphere;	87%

4-fluorobenzaldehyde (459-57-4) + benzylamine (100-46-9) → N-(4-fluorophenylmethylene)-benzylamine (67907-60-2)

Conditions	Yield
for 6h; Molecular sieve; Reflux;	100%
With sodium sulfate In dichloromethane for 1h; Ambient temperature;	88.6%
With magnesium sulfate In dichloromethane Molecular sieve; Inert atmosphere;	58%

4-fluorobenzaldehyde (459-57-4) + 2-Methylacetophenone (577-16-2, 122382-54-1) → (E)-3-(4-fluorophenyl)-1-o-tolylprop-2-en-1-one

Conditions	Yield
With sodium ethanolate In ethanol	100%
With sodium ethanolate In ethanol for 16h; Ambient temperature;

4-fluorobenzaldehyde (459-57-4) → 4-fluorobenzylic alcohol (459-56-3)

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 1h;	100%
With C24H30Cl2NPRuS2; potassium tert-butylate; hydrogen In dichloromethane; toluene at 80℃; under 15001.5 Torr; for 5h; Autoclave;	100%
With C55H44O2P4Ru; hydrogen In toluene at 80℃; under 38002.6 Torr; for 18h; Glovebox; Autoclave;	99%

4-fluorobenzaldehyde (459-57-4) → di[1-hydroxy(4-fluorophenyl)methyl]peroxide (60008-54-0)

Conditions	Yield
With dihydrogen peroxide for 1h; Ambient temperature;	100%
With dihydrogen peroxide In water at 0 - 20℃;	98%

cyclohexanone (108-94-1) + 4-fluorobenzaldehyde (459-57-4) → 2-(4-fluorobenzylidene)cyclohexanone (117601-22-6)

Conditions	Yield
sodium hydroxide In water at 90 - 95℃; for 3h;	100%

4-fluorobenzaldehyde (459-57-4) + thiophenol (108-98-5) → 4-phenylsulfanyl-benzaldehyde (1208-88-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 4.5h; Substitution;	100%
Stage #1: thiophenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 4-fluorobenzaldehyde In N,N-dimethyl-formamide at 80℃; for 6h;	96%
With potassium carbonate In dimethyl sulfoxide for 1h; Reflux;	92%

isovanillin (621-59-0) + 4-fluorobenzaldehyde (459-57-4) → 3-(4-formylphenoxy)-4-methoxybenzaldehyde (2748-98-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 18h; Reflux;	100%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	89%
With potassium carbonate In N,N-dimethyl-formamide for 4h; Heating;	80%

diethylzinc (557-20-0) + 4-fluorobenzaldehyde (459-57-4) → (S)-1-(4-fluorophenyl)propanol

Conditions	Yield
(1S)-1-(9-piperidylfluoren-9-yl)ethanol In hexane; toluene at 0℃; for 4h; Addition;	100%
Stage #1: diethylzinc In toluene at 0℃; for 0.5h; Inert atmosphere; Stage #2: 4-fluorobenzaldehyde In toluene at 0℃; for 6h; Inert atmosphere; Stage #3: With ammonium chloride In water; toluene at 0℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	92%
Stage #1: diethylzinc With (Sa)-1-[2-diphenylhydroxymethyl-6-(trifluoromethyl)phenyl]-2-(1-pyrrolidinomethyl)-1H-pyrrole In hexane at 20℃; for 1h; Inert atmosphere; Stage #2: 4-fluorobenzaldehyde In hexane at 0℃; for 16h; Inert atmosphere; enantioselective reaction;	91%

hexamethylene imine (111-49-9) + 4-fluorobenzaldehyde (459-57-4) → 4-(hexamethylenimin-1-yl)benzaldehyde (50333-45-4)

Conditions	Yield
In acetonitrile for 16h; Heating / reflux;	100%
With potassium carbonate In dimethyl sulfoxide for 0.25h; ultrasound;	95%
With tetrabutylammomium bromide; potassium carbonate In dimethyl sulfoxide at 90℃; for 48h;	83%

4-fluorobenzaldehyde (459-57-4) → 1,2-bis(4-fluorophenyl)-1,2-ethanediol (24133-58-2)

Conditions	Yield
With (t-BuOK)3FeK; magnesium In tetrahydrofuran at 20℃; for 12h;	100%
With aluminium; potassium hydroxide In methanol at 0℃; for 1h; Inert atmosphere;	100%
With ZnIn2S4; triethylamine In water; acetonitrile for 0.5h; Sealed tube; Sonication; Irradiation; Inert atmosphere;	99%

4-fluorobenzaldehyde (459-57-4) + acrylic acid methyl ester (292638-85-8) → methyl 3-(4-fluorophenyl)-3-hydroxy-2-methylenepropanoate (353506-65-7)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 3.5h; Baylis-Hillman reaction; neat (no solvent);	100%
With 1,4-diaza-bicyclo[2.2.2]octane; 1-n-butyl-2,3-dimethylimidazolium hexafluorophosphate at 20℃; for 24h; Baylis-Hillman;	99%
With 1,4-diaza-bicyclo[2.2.2]octane In methanol at 0℃; for 48h; Baylis-Hillman reaction;	99%

4-fluorobenzaldehyde (459-57-4) → 4-fluorobenzaldoxime (459-23-4)

Conditions	Yield
With sodium hydroxide; hydroxylamine hydrochloride In ethanol for 3h;	100%
With hydroxylamine hydrochloride In tetrahydrofuran; etanol; water at 20℃; for 0.416667h;	100%
With hydroxylamine hydrochloride; sodium carbonate In ethanol at 20℃;	100%

4-fluorobenzaldehyde (459-57-4) → [(4-fluorophenyl)methylidene]hydrazine (401514-49-6)

Conditions	Yield
With hydrazine hydrate In ethanol for 1h; Reflux; Inert atmosphere;	100%
With hydrazine hydrate In methanol at 20℃; for 1h;	99%
With hydrazine hydrate In ethanol

4-fluorobenzaldehyde (459-57-4) + allyl alcohol (107-18-6) → 1-(4-fluorophenyl)-3-buten-1-ol (86718-78-7, 136185-86-9)

Conditions	Yield
With indium(III) chloride; indium; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 20℃; for 20h;	100%

4-fluorobenzaldehyde (459-57-4) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl 4-fluorocinnamate (136265-10-6, 352-03-4, 24393-50-8)

Conditions	Yield
In dichloromethane at 20 - 25℃; for 16h; Inert atmosphere;	100%
In dichloromethane at 20℃; for 16h;	98%
In dichloromethane at 20℃;	93%

4-fluorobenzaldehyde (459-57-4) + 2-(4-(3,4-dichlorophenyl)piperazino)-4-hydroxy-1,6-dihydro-6-oxopyridine-3-carboxylic acid ethyl ester (556039-75-9) → C43H41Cl4FN6O8

Conditions	Yield
With piperidine In ethanol for 3h; Heating;	100%

4-fluorobenzaldehyde (459-57-4) + thiophenol (108-98-5) → 1-((4-fluorophenyl)(phenylthio)methylthio)benzene (175235-76-4)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 120℃; for 15h; Inert atmosphere; Schlenk technique;	100%
In chloroform at 20℃;	77%
With boron trifluoride diethyl etherate In chloroform at 25℃; for 1h;	75%

Upstream product

• 462-06-6 fluorobenzene 
• 201230-82-2 carbon monoxide 
• 100-97-0 hexamethylenetetramine 
• 76-05-1 trifluoroacetic acid 
• 56464-70-1 2-amino-2-(4-fluorophenyl)acetonitrile 
• 32691-93-3 α,α-dimethoxy-4-fluorotoluene 
• 127598-66-7 N-(4-fluorobenzyl)-4-methylbenzeneamine 
• 1421745-30-3 Cp*Ir(CO)(Cl)(CH₂C₆H₄F) 
• 52881-64-8 2-(4-fluorophenyl)-3-phenyloxirane 
• 382642-97-9 2,3-di-(p-fluorophenyl)-oxirane 
• 366-68-7 4,4'-difluorodeoxybenzoin 
• 62-53-3 aniline 
• 4885-02-3 Dichloromethyl methyl ether 
• 502-00-1 p-fluorobenzyl acetate 

Downstream Products

• 135950-61-7 (E)‐3‐(4‐fluorophenyl)‐1‐(thiophen‐2‐yl)prop‐2‐en‐1‐one 
• 459-32-5 4-fluorocinnamic acid 
• 90672-22-3 (4-Fluoro-phenyl)-(3-methyl-isothiazol-5-yl)-methanol 
• 90514-72-0 4-(1H-benzo[d]imidazol-1-yl)benzaldehyde 
• 71732-10-0 5-(4-fluorobenzylidene)-2,4,6(1H,3H,5H)-pyrimidinetrione 
• 130235-62-0 (4-Fluoro-phenyl)-(1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 
• 125772-83-0 (Z)-4-(4-fluorobenzylidene)-2-methyloxazol-5(4H)-one 
• 64002-52-4 (4-fluorophenyl)methylene diacetate 
• 137586-37-9 1-(1,3-Benzodioxol-4-yl)-3-(4-fluorophenyl)-2-propen-1-one 
• 74705-51-4 bis[4-(4'-fluorobenzylidenamino)phenyl]disulfide 
• 137096-58-3 2-benzyl-5-p-fluorobenzylidenecyclopentanone 
• 72739-46-9 3-[(E)-3-(4-Fluoro-phenyl)-acryloyl]-4-hydroxy-benzoic acid 
• 18511-62-1 4-fluorostyrene oxide 
• 126985-28-2 3-Cyano-4-(p-fluorophenyl)-6-hydroxy-6-phenyl-5-(1-pyridinio)-4,5-trans-1,4,5,6-tetrahydro-2-pyridinethiolate 

Relevant articles and documents

A porphyrin-conjugated TiO2/CoFe2O4nanostructure photocatalyst for the selective production of aldehydes under visible light

We investigated the photocatalytic performance of a magnetic nanohybrid of CoFe2O4 and TiO2 hetero-nanostructures (TiO2/CoFe2O4) conjugated with zinc tetrakis carboxyphenyl porphyrin (ZnTCPP) for controlled oxidation of alcohols to aldehydes under visible

Synthesis, characterization, crystal structure, and catalytic activity of an end-on azido-bridged polymeric copper(Ii) complex derived from 4-methyl-2- [(3-methylaminopropylimino)methyl]phenol

An end-on azido-bridged polymeric copper(II) complex, [CuL(μ1,1-N3)]n (HL D 4-methyl-2- [(3-methylaminopropylimino)methyl]phenol), was synthesized and characterized by elemental analysis, IR spectra, and single-crystal X-r

Cobalt(II) supported on ethylenediamine-functionalized nanocellulose as an efficient catalyst for room temperature aerobic oxidation of alcohols

Ethylenediamine-functionalized nanocellulose complexed with cobalt(II) was found to be a highly efficient heterogeneous catalyst for the room temperature aerobic oxidation of various types of primary and secondary benzylic alcohols into their correspondin

Controlled reduction of activated primary and secondary amides into aldehydes with diisobutylaluminum hydride

A practical method is disclosed for the reduction of activated primary and secondary amides into aldehydes using diisobutylaluminum hydride (DIBAL-H) in toluene. A wide range of aryl and alkyl N-Boc, N,N-diBoc and N-tosyl amides were converted into the corresponding aldehydes in good to excellent yields. Reduction susceptible functional groups such as nitro, cyano, alkene and alkyne groups were found to be stable. Broad substrate scope, functional group compatibility and quick conversions are the salient features of this methodology.

Selective oxidation of alkenes to carbonyls under mild conditions

Herein, a practical and sustainable method for the synthesis of aldehydes, ketones, and carboxylic acids from an inexpensive olefinic feedstock is described. This transformation features very sustainable and mild conditions and utilizes commercially available and inexpensive tetrahydrofuran as the additive, molecular oxygen as the sole oxidant and water as the solvent. A wide range of substituted alkenes were found to be compatible, providing the corresponding carbonyl compounds in moderate-to-good yields. The control experiments demonstrated that a radical mechanism is responsible for the oxidation reaction.