456-48-4

Basic information

• Product Name: 3-Fluorobenzaldehyde
• Synonyms: 3-fluoro-benzaldehyd;Benzaldehyde, 3-fluoro-;Benzaldehyde, m-fluoro-;meta-Fluorobenzaldehyde;M-FLUOROBENZALDEHYDE;LABOTEST-BB LT00932056;AKOS BBS-00003262;3'-FLUORO-BENZALDEHYDE
• CAS NO: 456-48-4
• Molecular Formula: C₇H₅FO
• Molecular Weight: 124.11
• EINECS: 207-266-9
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Fluorobenzene;Adehydes, Acetals & Ketones;Fluorine Compounds;Aldehydes;C7;Carbonyl Compounds;Aryl Fluorinated Building Blocks;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Fluorinated Building Blocks;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks
• Mol File: 456-48-4.mol
• Article Data: 144

Chemical Properties

• Melting Point: 173 C
• Boiling Point: 66-68 °C20 mm Hg(lit.)
• Flash Point: 134 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.17 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.28mmHg at 25°C
• Refractive Index: n20/D 1.518(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, Methanol
• Sensitive: Air Sensitive
• BRN: 970178
• CAS DataBase Reference: 3-Fluorobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluorobenzaldehyde(456-48-4)
• EPA Substance Registry System: 3-Fluorobenzaldehyde(456-48-4)

Safety Data

• Hazard Codes: Xi,F
• Statements: 37/38-36/37/38
• Safety Statements: 24/25-37/39-26-36/37/39-27
• RIDADR: UN 1989 3/PG 3
• WGK Germany: 3
• TSCA: T
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 456-48-4(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellow liquid

Uses

3-Fluorobenzaldehyde is a monofluorinated aromatic aldehyde with potential antimicrobial activity. 3-Fluorobenzaldehyde showed inhibitory effects on the activity of mushroom tyrosinase.

InChI:InChI=1/C7H5FO/c8-7-3-1-2-6(4-7)5-9/h1-5H

Synthetic route

3-fluoro-benzenemethanol (456-47-3) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With tert.-butylhydroperoxide; zircornium(IV) n-propoxide In dichloromethane at 20℃; for 5h; molecular sieves;	98%
With ammonium nitrate; hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In water; acetonitrile at 60℃; for 6h; Green chemistry;	95%
With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(I) triflate; 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole In acetonitrile at 25℃; for 1.5h; Catalytic behavior; chemoselective reaction;	95%

1-dichloromethyl-3-fluoro-benzene (402-64-2) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With dimethyl sulfoxide at 100℃; for 10h;	93%
With dimethyl amine at 60℃; for 1h;	80%
With calcium carbonate

3-fluorostyrene (350-51-6) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen In 1,2-dichloro-ethane at 70℃; under 760.051 Torr; for 6h; Green chemistry; chemoselective reaction;	93%
With tetrafluoroboric acid; iodobenzene; 3-chloro-benzenecarboperoxoic acid In water; toluene at 35℃;	71 %Spectr.

1-(dibromomethyl)-3-fluorobenzene (455-34-5) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With dimethyl sulfoxide at 120℃; for 12h;	92%
With N,N-dimethyl-formamide at 120℃; for 7h;	90%

1-(dibromomethyl)-3-fluorobenzene (455-34-5) + dimethyl sulfoxide (67-68-5) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
at 100 - 120℃; for 10 - 12h;	92%

carbon monoxide (201230-82-2) + 1-Fluoro-3-iodobenzene (1121-86-4) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With triethylsilane; palladium diacetate; sodium hydrogencarbonate; sodium carbonate at 20℃; under 760.051 Torr; for 48h;	92%
With rhodium(III) chloride trihydrate; hydrogen; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 90℃; under 7500.75 Torr; for 12h; Autoclave;	82%

(3-fluorophenyl)acetic acid (331-25-9) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With 1H-imidazole; C17H16ClMnN2O2; tetrabutylammonium periodite In chloroform at 20℃; for 0.333333h;	91%
With potassium 12-tungstocobaltate(III) In water; acetonitrile for 0.3h; Microwave irradiation;	90%
With oxygen; copper diacetate In dimethyl sulfoxide at 120℃; for 18h; Sealed tube;	65%
With 1H-imidazole; [bis(acetoxy)iodo]benzene; Co(AAOPD) In acetonitrile at 20℃;

m-fluorobenzyl chloride (456-42-8) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With water; sodium hydroxide at 20℃; for 0.0833333h; Microwave irradiation;	87%
With (NH4)4[ZnMo6O18(OH)6]; oxygen In water; acetonitrile at 60℃; under 760.051 Torr; for 12h;	84%
With 4Na(1+)*6H(1+)*NiMo6O24(10-)=Na4H6NiMo6O24; oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 12h; Irradiation;	81%
With ethanol; carbon dioxide; hexamethylenetetramine

3-fluorobromobenzene (1073-06-9) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
Stage #1: 3-fluorobromobenzene With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at 0 - 5℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 1h; Further stages.;	81%

carbon dioxide (124-38-9) + 1-Fluoro-3-iodobenzene (1121-86-4) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With rhodium(III) iodide; hydrogen; acetic anhydride; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 24h; Autoclave;	80%

3-fluorobromobenzene (1073-06-9) + carbon dioxide (124-38-9) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With rhodium(III) iodide; dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); hydrogen; acetic anhydride; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 24h; Autoclave;	80%

(3-fluorophenyl)methanethiol (40096-23-9) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With dipotassium peroxodisulfate; tetrakis(pyridine)silver(II) peroxodisulfate; oxygen In N,N-dimethyl-formamide at 23℃; under 760.051 Torr; Irradiation;	78%

3-fluoro-benzenemethanol (456-47-3) + nitrobenzene (98-95-3) → N-[(3-fluorophenyl)methylidene]aniline (58606-65-8) + 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With α,α,α-trifluorotoluene; titanium(IV) oxide In dodecane under 750.075 Torr; for 3h; Darkness; Inert atmosphere; Irradiation;	A 72.67% B n/a

N-(benzylidene)-p-methylbenzenesulfonamide (51608-60-7) + C20H16F3NO (1418179-06-2) → C27H23F3N2O2S + 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With [Cp*Rh(CH3CN)3][SbF6]2 In tert-butyl alcohol at 90℃; for 3.5h; Schlenk technique; Inert atmosphere;	A 71% B n/a

1,2-bis(3-fluorophenyl)-1,2-ethanediol (24133-57-1) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With oxygen; cetyltrimethylammonim bromide In water at 20℃; under 760.051 Torr; for 5h; Irradiation; Green chemistry;	67%

2-(3-fluorophenyl)-2-hydroxyacetic acid (32222-47-2, 52923-24-7, 52950-14-8, 395-05-1) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With oxygen; copper diacetate In dimethyl sulfoxide at 120℃; for 10h; Sealed tube;	58%

3-fluorobenzoyl chloride (1711-07-5) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With hydrogen; quinoline; 5% palladium on barium sulfate; sulfur at 80 - 90℃; for 9.5h;	57%
With Pd-BaSO4; xylene

m-Fluorotoluene (352-70-5) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With sodium molybdate; dihydrogen peroxide; cobalt(II) acetate; acetic acid; sodium bromide at 140℃; for 0.5h; Temperature; Concentration;	56.1%
With oxygen In water at 150℃; under 30002.4 Torr; for 2h;	48%
With carbon disulfide; chromyl chloride Behandeln des Reaktionsprodukts mit kalter wss. SO2-Loesung;

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%

N-(2-cyanoethyl) N-(3-fluorobenzyl)-4-methylaniline (127598-78-1) → 3-(2-Dimethylaminomethyl-4-methyl-phenylamino)-propionitrile (118072-35-8) + N-(2-cyanoethyl) N-(3-fluorobenzyl)-2-amino-5-methylbenzaldehyde (127598-86-1) + 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With water; trichlorophosphate In N,N-dimethyl-formamide Vilsmeier reaction;	A 49% B 13% C 40%
With water; trichlorophosphate In N,N-dimethyl-formamide Vilsmeier reaction;	A n/a B 13% C 40%

acetic acid (64-19-7) + propionaldehyde (123-38-6) + (+/-)-1-(3'-fluorophenyl)but-3-en-1-ol (215320-36-8) → 4β-acetoxy-2β,6β-diethyl-tetrahydropyran + 4β-acetoxy-6β-ethyl-2β-(3'-fluorophenyl)-tetrahydropyran + 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With trimethylsilyl acetate; boron trifluoride diethyl etherate In cyclohexane at 20℃; for 3h; Prins cyclization;	A 9% B 46% C 9%

N-benzenesulfonyl-N'-(3-fluoro-benzoyl)-hydrazine (360-22-5) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With sodium carbonate; ethylene glycol

3-fluorobenzaldehyde-1,1-diacetate (1479-26-1) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With sulfuric acid In ethanol

(3-fluorophenyl)methanamine (100-82-3) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With N-chloro-succinimide In water at 24.9℃; Kinetics; Thermodynamic data; pH 10.6; ΔH(excit.), ΔS(excit.);
With N-bromoacetamide In water at 14.9 - 34.9℃; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.);

3-Fluorocinnamic acid (20595-30-6) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With oxalic acid; pyridinium chlorochromate In water at 35℃; Rate constant; Kinetics; Thermodynamic data; further temperatures, ΔH(act.), ΔS(act.);
With chloroamine-T; oxalic acid In water at 35℃; Rate constant; Kinetics; Thermodynamic data; furhter temperatures, ΔH(act.), ΔS(act.);

3-nitro-benzaldehyde (99-61-6) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With potassium fluoride; tetraphenylphosphonium bromide; Phthaloyl dichloride In sulfolane; toluene at 210℃; for 5h;	7 % Chromat.

benzaldehyde (100-52-7) → 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With fluorine In trichlorofluoromethane at -78℃; Product distribution; addition of BCl3;

4-{[1-(3-Fluoro-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid (108133-60-4) → 4-amino-benzoic acid (150-13-0) + 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With borate buffer; water In methanol at 25℃; Rate constant; Kinetics; Mechanism; ΔG(activ.), ΔH(activ.), ΔS(activ.);

C13H10FNO → Nitrosobenzene (586-96-9) + 3-Fluorobenzaldehyde (456-48-4)

Conditions	Yield
With perchloric acid; water; chloramine-B In N,N-dimethyl-formamide at 30℃; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.); var. temperature;
With perchloric acid; N-bromobenzenesulphonamide; acetic acid at 30℃; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.); other temp.;

1-amino-3-(dimethylamino)propane (109-55-7) + 3-Fluorobenzaldehyde (456-48-4) → N-(3-fluorobenzylidene)-N',N'-dimethyl-1,3-propanediamine

Conditions	Yield
In ethanol Heating;	100%
In benzene Heating;

methylamine (74-89-5) + 3-Fluorobenzaldehyde (456-48-4) → 1-(3-fluorophenyl)-N-methylmethanimine

Conditions	Yield
at 20℃; for 12h;	100%
at 80℃; for 1h;
at 20℃; for 1h;
In methanol; water at 20℃; for 0.333333h;
at 20℃; for 1h;

2,2-dimethoxyethylamine (22483-09-6) + 3-Fluorobenzaldehyde (456-48-4) → N-<(3-fluorophenyl)methylene>-2,2-dimethoxyethanamine (73261-94-6)

Conditions	Yield
In toluene for 1.5h; Heating;	100%
for 0.333333h; Heating;
In benzene Reflux;

trimethylsilyl cyanide (7677-24-9) + 3-Fluorobenzaldehyde (456-48-4) → 2-(3-fluorophenyl)-2-((trimethylsilyl)oxy)acetonitrile (100948-28-5, 82128-93-6)

Conditions	Yield
With triethylamine at 20℃; for 24h;	100%
With C32H39Br2MgN2(1-)*C16H32LiO4(1+) In chloroform-d1 at 20℃; for 1h; Inert atmosphere; Glovebox;	99%
With zinc(II) iodide at 5 - 20℃; for 0.333333h; Yield given;

3-Fluorobenzaldehyde (456-48-4) → 3-fluoro-benzenemethanol (456-47-3)

Conditions	Yield
With hydrogen; Et4N In 1,2-dimethoxyethane at 100℃; under 38000 Torr; for 13h;	100%
With triethylamine; isopropyl alcohol; lithium bromide at 20℃; for 48h; Meerwein-Ponndorf-Verley reaction;	98%
With Candida boidinii formate dehydrogenase; Geobacillus stearothermophilus ε‐deaminating L‐lysine dehydrogenase variant 24; nicotinamide adenine dinucleotide In aq. buffer at 30℃; for 24h; pH=7; Reagent/catalyst; Enzymatic reaction;	94%

(R)-2-amino-3-methylbutanol (4276-09-9) + 3-Fluorobenzaldehyde (456-48-4) → 2-[(3-fluoro-benzylidene)-amino]-3-methyl-butan-1-ol (860805-86-3)

Conditions	Yield
With magnesium sulfate In dichloromethane at 0 - 20℃; for 16h;	100%
In dichloromethane at 0 - 20℃; for 16h; drying with MgSO4;	100%
With magnesium sulfate In dichloromethane at 0 - 20℃;

(R)-2-amino-3-methylbutanol (4276-09-9) + 3-Fluorobenzaldehyde (456-48-4) → C12H16FNO (562103-08-6)

Conditions	Yield
With magnesium sulfate In dichloromethane at 0 - 20℃; for 16h;	100%
With magnesium sulfate In dichloromethane at 0 - 20℃; for 16h;	100%
In dichloromethane

3-(2,3-dihydroxy-propylsulfanylmethyl)-N-[2-hydrazinocarbonyl-4,5-bis-(2-methoxy-ethoxy)-phenyl]-benzamide (773071-71-9) + 3-Fluorobenzaldehyde (456-48-4) → 3-(2,3-Dihydroxy-propylsulfanylmethyl)-N-[2-(3-fluorobenzylidene-hydrazinocarbonyl)-4,5-bis-(2-methoxy-ethoxy)-phenyl]-benzamide

Conditions	Yield
In toluene at 20℃; for 1h;	100%

carbon tetrabromide (558-13-4) + 3-Fluorobenzaldehyde (456-48-4) → 1-(2,2-Dibromo-vinyl)-3-fluoro-benzene (221148-37-4)

Conditions	Yield
With triphenylphosphine In dichloromethane	100%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0 - 10℃; for 1h; Stage #2: 3-Fluorobenzaldehyde In dichloromethane at 0℃; for 1h;	100%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0 - 10℃; for 1.05h; Stage #2: 3-Fluorobenzaldehyde In dichloromethane at 0℃; for 1h;	100%

cis, trans-1,3-dimethylaminocyclohexane (2579-20-6) + 3-Fluorobenzaldehyde (456-48-4) → C22H24F2N2 (1217527-05-3)

Conditions	Yield
In methanol at 20℃; Molecular sieve;	100%
In methanol at 20℃; Molecular sieve;

3-Fluorobenzaldehyde (456-48-4) → (E)-2-(3-fluorobenzylideneamino)-N-phenylbenzamide (1201652-24-5)

Conditions	Yield
	100%

tert-butyl 2,2-dideuterio-2-(diethoxyphosphoryl)ethanoate + 3-Fluorobenzaldehyde (456-48-4) → tert-butyl (E)-2-deuterio-3-(3'-fluorophenyl)propenoate (1332928-88-7)

Conditions	Yield
With water-d2; potassium carbonate at 50℃; for 30h; Horner-Wadsworth-Emmons olefination; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	100%

ethyl 2-(2-aminophenyl)indolizine-1-carboxylate + 3-Fluorobenzaldehyde (456-48-4) → ethyl 6-(3-fluorophenyl)indolizino[3,2-c]quinoline-12-carboxylate

Conditions	Yield
With iron(III) chloride In dichloromethane at 60℃; for 16h; Pictet-Spengler Synthesis;	100%

2-aminobenzanilide (4424-17-3) + 3-Fluorobenzaldehyde (456-48-4) → 2-(3-fluorobenzylideneamino)-N-phenylbenzamide

Conditions	Yield
In methanol	100%

(tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4) + 3-Fluorobenzaldehyde (456-48-4) → (E)-3-(3-fluorophenyl)acrylic acid tert-butyl ester (277745-38-7)

Conditions	Yield
In dichloromethane at 20℃; for 16h;	100%

3-amino-8-methoxy-2H-chromen-2-iminium chloride + 3-Fluorobenzaldehyde (456-48-4) → C17H13FN2O2

Conditions	Yield
In acetonitrile at 60℃; for 33h;	100%

o-hydroxyacetophenone (118-93-4) + 3-Fluorobenzaldehyde (456-48-4) → (2E)-3-(3-fluorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (1840-00-2)

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; Aldol Condensation;	99.2%
Stage #1: o-hydroxyacetophenone With potassium hydroxide In ethanol at 0℃; for 0.166667h; Claisen-Schmidt Condensation; Stage #2: 3-Fluorobenzaldehyde In ethanol at 0 - 20℃; for 8h; Claisen-Schmidt Condensation;	76%
With sodium hydroxide In ethanol; water at 20℃;	53%
With sodium hydroxide In ethanol; water at 20℃; for 24h;	32%
With sodium hydroxide In ethanol; water at 20℃;

malonic acid (141-82-2) + 3-Fluorobenzaldehyde (456-48-4) → 3-Fluorocinnamic acid (20595-30-6)

Conditions	Yield
Stage #1: malonic acid; 3-Fluorobenzaldehyde With piperidine; pyridine Knoevenagel-Doebner reaction; Reflux; Stage #2: With hydrogenchloride In water Cooling with ice; optical yield given as %de;	99%
With piperidine In pyridine Heating;	80%
With ammonia Erhitzen des Reaktionsprodukts auf 180-190grad;

3-Fluorobenzaldehyde (456-48-4) → (rac)-1,2-bis(3-fluorophenyl)-2-hydroxyethan-1-one (66659-65-2)

Conditions	Yield
With 1,3-dimethylbenzimidazolium Iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran for 1h; Heating;	99%
With Thiamine hydrochloride; sodium hydroxide In ethanol at 55℃; for 16h; Schlenk technique; Inert atmosphere;	81%
With sodium cyanide In ethanol; water for 4h; Reflux;	68.4%

naltrexone Hydrochloride (16676-29-2) + 3-Fluorobenzaldehyde (456-48-4) → 7(E)-(3-fluorobenzylidene)naltrexone

Conditions	Yield
With piperidine In methanol at 120℃; Sealed tube;	99%
With sodium hydroxide for 24h; Ambient temperature;	76%

allyl iodid (556-56-9) + 3-Fluorobenzaldehyde (456-48-4) → (+/-)-1-(3'-fluorophenyl)but-3-en-1-ol (215320-36-8)

Conditions	Yield
With indium In water for 48h;	99%

acrylic acid methyl ester (292638-85-8) + 3-Fluorobenzaldehyde (456-48-4) → methyl 2-((3-fluorophenyl)(hydroxy)methyl)acrylate (784144-71-4)

Conditions	Yield
1,4-diaza-bicyclo[2.2.2]octane; tributyl(ethyl)phosphonium tosylate at 20℃; for 24h; Baylis-Hillman reaction;	99%
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 6h; Baylis-Hillman Reaction; Inert atmosphere;	98%
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 3h; Morita-Baylis-Hillman Alkylation; Inert atmosphere;	89%

phenylacetylene (536-74-3) + 3-Fluorobenzaldehyde (456-48-4) → 1-(3-fluorophenyl)-3-phenylprop-2-yn-1-ol

Conditions	Yield
Stage #1: With (1S,2S,5S)-4,6,6-trimethyl-2-[2-{(S)-6-phenylpyridin-2-yl}phenyl]bicyclo-[3.1.1]hept-3-en-2-ol; dimethyl zinc(II) In toluene at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: phenylacetylene In toluene at 20℃; for 0.75h; Inert atmosphere; Stage #3: 3-Fluorobenzaldehyde In toluene at 0℃; for 72h; Inert atmosphere;	99%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78 - 21℃; for 1h; Inert atmosphere; Stage #2: 3-Fluorobenzaldehyde In tetrahydrofuran; hexane at -78 - 21℃; for 1h; Inert atmosphere;	96%
Stage #1: phenylacetylene With dimethyl zinc(II) In toluene at 20℃; for 0.5h; Stage #2: 3-Fluorobenzaldehyde In toluene at 20℃; for 24h;	92%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 3-Fluorobenzaldehyde In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 3-Fluorobenzaldehyde In tetrahydrofuran at 20℃;

β-naphthol (135-19-3) + 3-Fluorobenzaldehyde (456-48-4) → 14-(3-fluorophenyl)-14H-dibenzo[a,j]xanthene (37096-98-3)

Conditions	Yield
With para-dodecylbenzenesulfonic acid at 125℃; under 5171.62 Torr; for 0.0666667h; Microwave irradiation; Neat (no solvent);	99%
With phospho sulphonic acid In neat (no solvent) at 110℃; for 0.75h; Green chemistry;	96%
With aminosulfonic acid for 0.0416667h; microwave irradiation;	95%

cyclohexanone (108-94-1) + 3-Fluorobenzaldehyde (456-48-4) → 2,6-bis(3-fluorobenzylidene)cyclohexanone (565416-89-9)

Conditions	Yield
With sodium hydroxide In methanol at 20℃;	99%
With 1-methyl-3-(2-(sulfooxy)ethyl)-1H-imidazol-3-ium chloride at 20℃; for 2h;	91%
With potassium hydroxide In ethanol at 20℃; for 4h;	90.5%
With sodium hydroxide In ethanol at 5 - 20℃; Claisen Schmidt condensation;
With potassium hydroxide In ethanol at 20℃; Claisen-Schmidt Condensation;

cyclopentanone (120-92-3) + 3-Fluorobenzaldehyde (456-48-4) → 2,5-bis(3-fluorobenzylidene)cyclopentanone (892253-13-3)

Conditions	Yield
With sodium hydroxide In methanol at 20℃;	99%
With 1-methyl-3-(2-(sulfooxy)ethyl)-1H-imidazol-3-ium chloride at 20℃; for 2h;	91%
With sodium hydroxide In ethanol at 5 - 20℃; Claisen Schmidt condensation;

diethyl<<(p-chlorophenyl)sulfonyl>methyl>phosphonate (40137-12-0) + 3-Fluorobenzaldehyde (456-48-4) → (E)-1-(2-((4-chlorophenyl)sulfonyl)vinyl)-3-fluorobenzene (1554271-57-6)

Conditions	Yield
Stage #1: diethyl<<(p-chlorophenyl)sulfonyl>methyl>phosphonate With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Stage #2: 3-Fluorobenzaldehyde In tetrahydrofuran; cyclohexane at -78 - 20℃; for 1h;	99%

3-acetylcoumarin (3949-36-8) + malononitrile (109-77-3) + 3-Fluorobenzaldehyde (456-48-4) → 2-amino-6-(2-oxo-2H-chromen-3-yl)-4-(3-fluorophenyl)nicotinonitrile (1421234-48-1)

Conditions	Yield
With ammonium acetate In neat (no solvent) at 100℃; for 0.25h;	99%
With perchloric acid adsorbed on silica gel; ammonium acetate In neat (no solvent) at 60℃; for 1.2h; Green chemistry;	94%

2,5-dimethoxyaniline (102-56-7) + 3-Fluorobenzaldehyde (456-48-4) → 4-((4-amino-2,5-dimethoxyphenyl)(3-fluorophenyl)methyl)-2,5-dimethoxybenzenamine

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In nitromethane at 80℃; for 0.166667h; Microwave irradiation; Sealed tube; regioselective reaction;	99%

phenylhydrazine (100-63-0) + 3-Fluorobenzaldehyde (456-48-4) → 1-(3-fluorobenzylidene)-2-phenylhydrazine (351-24-6)

Conditions	Yield
In ethanol for 0.00833333h; Sonication;	99%
With Fe(+3)-montmorillonite K10

Upstream product

• 456-47-3 3-Fluorobenzyl alcohol 
• 4564-72-1 N-hexyl-N-[(Z)-[4-(hexyloxy)naphthalen-1-yl](imino)methyl]hexan-1-aminium chloride 
• 4564-71-0 4-butoxy-N,N-diheptylnaphthalene-1-carboximidamide hydrochloride (1:1) 
• 4564-68-5 Dispiro[5.1.5.3]hexadecan-14-one 
• 4564-64-1 propyl 2-oxo-1,2-dihydroquinoline-4-carboxylate 
• 456-46-2 3-(FluoroMethyl)aniline 
• 45644-21-1 2-Amino-6-chloropyridine 
• 456-44-0 3-Methylbenzyl fluoride 
• 4564-35-6 bis(1-methylethyl) 4-hydroxy-4-methyl-6-oxo-2-pyridin-2-ylcyclohexane-1,3-dicarboxylate 
• 45642-86-2 3-AMINO-1-METHYLPYRIDINIUM 
• 456-42-8 3-Fluorobenzyl chloride 
• 4564-21-0 1-(2-deoxy-3,5-di-O-propanoylpentofuranosyl)-5-fluoropyrimidine-2,4(1H,3H)-dione 
• 456-41-7 3-Fluorobenzyl bromide 
• 456396-56-8 3-(4-BROMO-5-METHYL-PYRAZOL-1-YL)-PROPIONIC ACID 

Downstream Products

• 81028-92-4 3-(3,5-DICHLOROPHENOXY)BENZALDEHYDE 
• 79124-76-8 3-(3,4-DICHLOROPHENOXY)BENZALDEHYDE 
• 90389-84-7 (3-FLUOROBENZYL)METHYLAMINE 
• 852227-92-0 3-(1H-PYRAZOL-1-YL)BENZALDEHYDE 

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