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

Uses

4-Fluoro-3-phenoxybenzaldehyde is a reactant in the preparation of ring-disubstituted propyl cyano(phenyl)propenoates which are then used as copolymers with styrene.

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 
• 68359-55-7 4-fluoro-3-phenoxybenzyl bromide 
• 108-03-2 1-Nitropropane 
• 68359-37-5 cyfluthrin 

Downstream Products

• 143680-39-1 (R)-1-cyano-1-(4-fluoro-3-phenoxyphenyl)methyl acetate 
• 143680-40-4 (S)-(+)-1-cyano-1-(4-fluoro-3-phenoxyphenyl)methyl acetate 
• 89765-18-4 1-(4-Fluoro-3-phenoxyphenyl)-4-(4-ethoxyphenyl)-4-methylpent-1-ene-3-one 
• 77279-89-1 4-fluoro-3-phenoxy benzoic acid 
• 117252-08-1 4-fluoro-3-phenoxybenzoic acid methyl ester 
• 791615-40-2 4-fluoro-3-phenoxybenzoic acid hydrazide 
• 89764-44-3 1-[4-fluoro-3-phenoxy-phenyl]-4-[p-ethoxyphenyl]-4-methyl-pentane 

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