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

Chemical Properties

Clear colorless to yellow liquid

Uses

Different sources of media describe the Uses of 459-57-4 differently. You can refer to the following data:
1. 4-Fluorobenzaldehyde is a fluorinated benzaldehyde with inhibitory activity of mushroom tyrosinase. 4-Fluorobenzaldehyde is commonly used as a synthetic intermediate in the preparation of pharmaceutic al compounds.
2. Usually used in the preparation of pyrazolopyridine UR-13756.
3. 4-Fluorobenzaldehyde is used in the preparation of pyrazolopyridine derivative, which finds application as mitogen-activated protein kinase (MAPK) inhibitor. It also serves as a synthetic intermediate in the preparation of pharmaceutical compounds.

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

• 352-32-9 p-fluorotoluene 
• 363-02-0 4,4’-difluorobenzophenone oxime 
• 71-43-2 benzene 
• 67935-39-1 α-chloro-p-fluorobenzyl acetate 
• 462-06-6 fluorobenzene 
• 201230-82-2 carbon monoxide 
• 127598-79-2 N-(2-cyanoethyl) N-(4-fluorobenzyl)-4-methylaniline 
• 140-75-0 para-fluorobenzylamine 
• 459-46-1 4-Fluorobenzyl bromide 
• 32222-45-0 4-fluoromandelic acid 
• 405-99-2 para-fluorostyrene 
• 2826-22-4 4-fluorobenzylidenemalononitrile 
• 19962-26-6 1-fluoro-4-(phenoxymethyl)benzene 
• 100-97-0 hexamethylenetetramine 

Downstream Products

• 395-12-0 (2E,6E)-2,6-bis(4-fluorobenzylidene)cyclohexanone 
• 459-32-5 (E)-4-fluorocinnamic acid 
• 6578-86-5 2-(4-fluorobenzalamino)-5-phenyl-1,3,4-thiadiazole 
• 65791-52-8 5-(4-fluoro-benzylidene)-3,3'-(3-oxa-pentane-1,5-diyl)-bis-thiazolidine-2,4-dione 
• 62642-56-2 2r-(4-fluoro-phenyl)-5t-methoxy-3-(toluene-4-sulfonyl)-oxazolidine 
• 67962-19-0 trans-1-(4'-fluorophenyl)-4,4-dimethyl-1-penten-3-one 
• 67319-30-6 9-benzyl-5-ethyl-2-(4-fluoro-phenyl)-1,3-dioxa-9-aza-spiro[5.5]undecane 
• 5153-69-5 4-fluoro-β-nitrostyrene 
• 706-08-1 trans-1-(4-fluorophenyl)-2-nitro-ethene 
• 97579-25-4 2-cyano-3-(4-fluorophenyl)prop-2-enethioamide 
• 13499-58-6 Aethyl--phosphinsaeure-butylester 
• 3796-36-9 2-(4-fluoro-phenyl)-5,6-dihydro-4H-[1,3]oxazine 
• 1983-25-1 1-<4-Fluor-phenyl>-2-trifluormethylsulfonyl-ethylen 
• 70618-85-8 C₁₄H₁₁ClFN₃S 

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