68359-57-9

Basic information

• Product Name: 4-Fluoro-3-phenoxybenzaldehyde
• Synonyms: M-PHENOXY-P-FLUOROBENZALDEHYDE;2-FLUORO-5-FORMYLDIPHENYL ETHER;3-(phenoxy)-4-fluoro-benzaldehyde;4-FLUORO-3-PHENOXYBENZALDEHYDE;4-Fluoro-3-phenoxybenzaldehyde 98%;4-Fluoro-3-phenoxybenzaldehyde98%;4-Fluro-3- Phenoxy-Benzaldehyde;Benzaldehyde,4-fluoro-3-phenoxy-
• CAS NO: 68359-57-9
• Molecular Formula: C₁₃H₉FO₂
• Molecular Weight: 216.21
• EINECS: 269-856-2
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;C10 to C21;Carbonyl Compounds
• Mol File: 68359-57-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 310
• Flash Point: >230 °F
• Appearance: Colorless/Liquid
• Density: 1.2091 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000327mmHg at 25°C
• Refractive Index: n20/D 1.5830(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-Fluoro-3-phenoxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluoro-3-phenoxybenzaldehyde(68359-57-9)
• EPA Substance Registry System: 4-Fluoro-3-phenoxybenzaldehyde(68359-57-9)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-51/53
• Safety Statements: 61
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 2
• TSCA: Yes
• HazardClass: 9
• Hazardous Substances Data: 68359-57-9(Hazardous Substances Data)

Usage

Description

4-Fluoro-3-phenoxybenzaldehyde is an organic compound characterized by the presence of a fluorine atom at the 4-position and a phenoxy group at the 3-position on a benzene ring. It features an aldehyde functional group, which makes it a versatile intermediate in organic synthesis.
Used in Polymer Industry:
4-Fluoro-3-phenoxybenzaldehyde is used as a reactant for the preparation of ring-disubstituted propyl cyano(phenyl)propenoates. These compounds are then utilized as copolymers with styrene, contributing to the development of new materials with enhanced properties, such as improved thermal stability, mechanical strength, and chemical resistance. The incorporation of 4-fluoro-3-phenoxybenzaldehyde into these copolymers can also lead to unique optical and electronic characteristics, making them suitable for various applications in the polymer industry.

InChI:InChI=1/C13H9FO2/c14-12-7-6-10(9-15)8-13(12)16-11-4-2-1-3-5-11/h1-9H

Synthetic route

cyfluthrin (68359-37-5) → 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid (55701-05-8)

Conditions	Yield
With sodium hydroxide In methanol for 2h; Heating;

4-fluoro-3-phenoxybenzyl bromide (68359-55-7) + 1-Nitropropane (108-03-2) → 4-fluoro-3-phenoxybenzaldehyde (68359-57-9)

Conditions	Yield
In ethanol

4-fluoro-3-phenoxy-benzaldehyde ethyleneacetal (77771-05-2) → 4-fluoro-3-phenoxybenzaldehyde (68359-57-9)

Conditions	Yield
With hydrogenchloride In ethanol; water; toluene

cis-α-cyano-3-phenoxy-4-fluoro-benzyl 2,2-dimethyl-3-(2-chloro-vinyl)cyclopropanecarboxylate → 3-Methylbutenoic acid (541-47-9) + 3-(2-chloro-vinyl)-2,2-dimethylcyclopropanecarboxylic acid (60310-82-9) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + C8H11ClO + 2-(4-fluoro-3-phenoxyphenyl)-2-hydroxyethanenitrile (76783-44-3) + 4-fluoro-3-phenoxy benzoic acid (77279-89-1)

Conditions	Yield
In hexane for 17h; UV-irradiation;

4-fluoro-3-phenoxybenzaldehyde (68359-57-9) → 4-fluoro-3-phenoxy benzoic acid (77279-89-1)

Conditions	Yield
With dihydrogen peroxide; acetic acid In ethanol for 4h; Heating;	100%
With potassium permanganate In water for 2h; Heating;	65%
With dihydrogen peroxide; acetic acid at 60 - 80℃; for 2h;

4-fluoro-3-phenoxybenzaldehyde (68359-57-9) → 4-fluoro-3-phenoxyphenylmethanol (68359-53-5)

Conditions	Yield
With formic acid; C20H29ClIrN4(1+)*Cl(1-) In ethanol; water at 80℃; for 0.25h; chemoselective reaction;	98%
With sodium hydroxide In diethyl ether; water
With sodium hydroxide In diethyl ether; water
With sodium hydroxide In diethyl ether; water

potassium cyanide + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + C9H9Br2Cl2F3O → C23H18Br2ClF4NO2

Conditions	Yield
With tetrabutylammomium bromide In water; benzene at 15 - 20℃; for 10h;	95%

sodium cyanide (773837-37-9) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + cis-2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylic acid chloride → cis-α-cyano-4-fluoro-3-phenoxybenzyl-2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylate

Conditions	Yield
With triethylamine In water; toluene at 20℃; for 4h;	95%

potassium cyanide + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + (1R)-trans-2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylic acid chloride → (1R)-trans-α-cyano-4-fluoro-3-phenoxybenzyl-2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylate

Conditions	Yield
With pyridine In cyclohexane; water at 20℃; for 4h;	93%

Dibenzyl phosphite (17176-77-1) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) → dibenzyl α-hydroxy(4-fluoro-3-phenoxy)benzylphosphonate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 14h;	92%

4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + permethric acid chloride (52314-67-7) + sodium sulfate (7757-82-6) → 3'-phenoxy-4'-fluoro-benzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropane-carboxylate (68359-33-1)

Conditions	Yield
In water; ethyl acetate	91.5%

4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + 2-amino-N'-hydroxychroman-3-carboxamidine (1384471-91-3) → N-(4-fluoro-3-phenoxybenzylidene)-3-(5-(4-fluoro-3-phenoxyphenyl)-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2H-chromen-2-amine (1384471-90-2)

Conditions	Yield
for 0.0833333h; Irradiation;	91%

sodium cyanide (773837-37-9) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + cis/trans-2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylic acid chloride → cis/trans-α-cyano-4-fluoro-3-phenoxybenzyl-2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylate

Conditions	Yield
With pyridine In cyclohexane; water at 20℃; for 4h;	91%

pyridine-2,6-dicarbohydrazide (5112-36-7) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) → N'2,N’6-bis [(4-fluoro-3-phenoxyphenyl)methylidene]pyridine-2,6-dicarbohydrazide

Conditions	Yield
With acetic acid In ethanol Reflux;	89%

4-bromo-β-nitrostyrene (3156-37-4) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + β-naphthol (135-19-3) → C31H19BrFNO2

Conditions	Yield
With ammonium acetate; sodium hydroxide In water at 80℃; for 8h; Green chemistry;	87%

ethyl 4-[4-(methylthio)phenyl]-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (292871-44-4) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + chloroacetic acid (79-11-8) → CH3SC6H4C6HN2SOCH3CO2CH2CH3CHC6H3FOC6H5

Conditions	Yield
With sodium acetate; acetic anhydride; acetic acid for 3h; Heating;	84%

4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + toluene-4-sulfonic acid hydrazide (1576-35-8) → N'-[(4-fluoro-3-phenoxyphenyl)methylidene]-4-methylbenzenesulfonohydrazide

Conditions	Yield
In ethanol Reflux;	84%

4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + m-tyramine (588-05-6) → C21H18FNO2

Conditions	Yield
With acetic acid at 50℃; for 5h; Pictet-Spengler Synthesis; Molecular sieve; Inert atmosphere;	83%

tert-butyl diethylphosphonoacetate (27784-76-5) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) → tert-butyl (E)-3-(3'-phenoxy-4'-fluorophenyl)prop-2-enoate (1393363-56-8)

Conditions	Yield
Stage #1: tert-butyl diethylphosphonoacetate With methylmagnesium bromide In tetrahydrofuran; diethyl ether at 20℃; for 0.25h; Inert atmosphere; Stage #2: 4-fluoro-3-phenoxybenzaldehyde In tetrahydrofuran; diethyl ether for 15h; Horner-Wadsworth-Emmons olefination; Inert atmosphere; Reflux; optical yield given as %de; diastereoselective reaction;	82%

indole (120-72-9) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) → C29H21FN2O

Conditions	Yield
With sulfated anatase titania In neat (no solvent) at 20℃; for 0.5h; Green chemistry;	82%
With BiCl3-loaded montmorillonite K10 In neat (no solvent) at 20℃; for 0.666667h; Green chemistry;	82%

(2-nitroethenyl)benzene (102-96-5) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + formamide (77287-34-4, 77287-35-5, 60100-09-6) + malonic acid dimethyl ester (108-59-8) → 6-(4-fluoro-3-phenoxyphenyl)-5-nitro-4-phenylpiperidin-2-one

Conditions	Yield
Stage #1: (2-nitroethenyl)benzene; malonic acid dimethyl ester With sodium hydroxide In methanol at 0℃; for 0.75h; Stage #2: 4-fluoro-3-phenoxybenzaldehyde; formamide In methanol Reflux;	78%

4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carbohydrazide → (E)-2-(3-cyano-4-isobutoxyphenyl)-N’-(4-fluoro-3-phenoxybenzylidene)-4-methylthiazole-5-carbohydrazide

Conditions	Yield
With acetic acid In ethanol for 8h; Reflux;	72%

1,5-dioxaspiro[5.5]undecane-2,4-dione (1658-27-1) + (2-nitroethenyl)benzene (102-96-5) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) → 2-aza-1,3-di(4-fluoro-3-phenoxyphenyl)-4-nitro5-phenyl-8,15-dioxa-7,16-dioxodispiro[5,2,59,26]hexadecane

Conditions	Yield
Stage #1: 1,5-dioxaspiro[5.5]undecane-2,4-dione; (2-nitroethenyl)benzene With triethylamine In ethanol at 20℃; for 3h; Michael Addition; Stage #2: 4-fluoro-3-phenoxybenzaldehyde With ammonium acetate In ethanol at 45℃; for 20h; Mannich Aminomethylation;	71%

4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + ethyl acetoacetate (141-97-9) + malononitrile (109-77-3) → 6-amino-4-(4-fluoro-3-phenoxyphenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile

Conditions	Yield
With hydrazine hydrate; morpholine triflate In ethanol; water for 8h; Reflux; Green chemistry;	67%

4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + 5-amino-1-(2-hydroxy-2-phenylethyl)-1H-pyrazole-4-carbohydrazide → (E)-5-amino-1-(2-hydroxy-2-phenylethyl)-N’-(4-fluoro-3-phenoxybenzylidene)-1H-pyrazole-4-carbohydrazide

Conditions	Yield
In methanol; ethanol at 100℃; for 18h;	65%

1-methoxy-4-(2-nitro-vinyl)-benzene (3179-10-0) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + formamide (77287-34-4, 77287-35-5, 60100-09-6) + malonic acid dimethyl ester (108-59-8) → 6-(4-fluoro-3-phenoxyphenyl)-4-(4-methoxyphenyl)-5-nitropiperidin-2-one

Conditions	Yield
Stage #1: 1-methoxy-4-(2-nitro-vinyl)-benzene; malonic acid dimethyl ester With sodium hydroxide In methanol at 0℃; for 0.75h; Stage #2: 4-fluoro-3-phenoxybenzaldehyde; formamide In methanol Reflux;	63%

4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + 2-amino-4,6-di-tertbutylphenol (1643-39-6) → 2,4-di-tert-butyl-6-{[(4-fluoro-3-phenoxyphenyl)methylene]amino}phenol

Conditions	Yield
for 2h; Heating;	62%

1-methoxy-4-(2-nitro-vinyl)-benzene (3179-10-0) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + 1,3-cylohexanedione (504-02-9) → 2-(4-fluoro-3-phenoxybenzylideneamino)-3-(4-methoxyphenyl)benzofuran-4-ol

Conditions	Yield
With piperidine; ammonium acetate In N,N-dimethyl-formamide at 20℃; for 7h; Michael Addition; Reflux;	61%

4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + 3-(4-Ethoxyphenyl)-3-methyl-2-butanone (89765-17-3) → 1-(4-Fluoro-3-phenoxyphenyl)-4-(4-ethoxyphenyl)-4-methylpent-1-ene-3-one (89765-18-4)

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 6h; Condensation;	60%

4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + ethyltriphenylphosphonium bromide (1530-32-1) → (E)-1-fluoro-2-phenoxy-4-(prop-1-en-1-yl)benzene

Conditions	Yield
With potassium carbonate In 1,4-dioxane at 110℃;	56.8%

cycl-isopropylidene malonate (2033-24-1) + 1-methoxy-4-(2-nitro-vinyl)-benzene (3179-10-0) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) → 8-aza-7,9-di(4-fluoro-3-phenoxyphenyl)-11-(p-methoxyphenyl)-3,3-dimethyl-10-nitro-2,4-dioxa-1,5-dioxospiro[5,5]undecane

Conditions	Yield
Stage #1: cycl-isopropylidene malonate; 1-methoxy-4-(2-nitro-vinyl)-benzene With triethylamine In ethanol at 20℃; for 3h; Michael Addition; Stage #2: 4-fluoro-3-phenoxybenzaldehyde With ammonium acetate In ethanol at 45℃; for 20h; Mannich Aminomethylation;	55%

o-(chloromethyl)benzoic acid methyl ester (34040-62-5) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) → 3-(4-fluoro-3-phenoxyphenyl)-3,4-dihydroisocoumarin

Conditions	Yield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide at 20℃; for 16h; Glovebox; Inert atmosphere;	55%

(E)-1-methoxy-4-(2-nitrovinyl)benzene (3179-10-0, 5576-97-6) + 4-fluoro-3-phenoxybenzaldehyde (68359-57-9) + malonic acid dimethyl ester (108-59-8) → C26H23FN2O7

Conditions	Yield
Stage #1: (E)-1-methoxy-4-(2-nitrovinyl)benzene; malonic acid dimethyl ester With sodium hydroxide In methanol at 0℃; for 0.75h; Stage #2: 4-fluoro-3-phenoxybenzaldehyde With ammonium acetate In methanol at 20 - 85℃; for 40h;	53%

Upstream product

• 77771-05-2 4-fluoro-3-phenoxy-benzaldehyde ethyleneacetal 
• 68359-37-5 cyfluthrin 
• 68359-55-7 4-fluoro-3-phenoxybenzyl bromide 
• 108-03-2 1-Nitropropane 

Downstream Products

• 124865-31-2 Ethyl 2-(4-fluoro-3-phenoxy-benzylidene)-4-methyl-3-oxopentanoate 
• 1192002-32-6 4-fluoro-3-phenoxybenzaldehyde oxime 
• 1384471-90-2 N-(4-fluoro-3-phenoxybenzylidene)-3-(5-(4-fluoro-3-phenoxyphenyl)-1,2,4-oxadiazol-3-yl)-3,4-dihydro-2H-chromen-2-amine 
• 1093975-41-7 N-cyclohexyl-2-{4-[3-methoxy-4-(4-methylimidazol-1-yl)-phenyl]-1,2,3-triazol-1-yl}-N-phenylacetamide 

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