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N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline
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Name

N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline

 EINECS 615-134-0
CAS No. 70627-52-0 Density 1.07 g/cm3
PSA 21.59000 LogP 5.15530
Solubility N/A Melting Point 136-138 °C
Formula C20H16FNO Boiling Point 455.2 °C at 760 mmHg
Molecular Weight 305.352 Flash Point 229.1 °C
Transport Information N/A Appearance light yellow flaky crystal
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 70627-52-0 (N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline) Hazard Symbols N/A
Synonyms

4-Benzyloxybenzylidene4-fluoroaniline;N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline;

Article Data 8

N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline Synthetic route

4397-53-9

p-benzyloxybenzaldehyde

371-40-4

4-fluoroaniline

70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

Conditions
ConditionsYield
In isopropyl alcohol at 40℃;95%
In toluene Reflux; Large scale;93.6%
In toluene for 48h; Heating;75%
With magnesium sulfate In dichloromethane at 20℃; for 2h;
100-39-0

benzyl bromide

123-08-0

4-hydroxy-benzaldehyde

371-40-4

4-fluoroaniline

70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

Conditions
ConditionsYield
Stage #1: benzyl bromide; 4-hydroxy-benzaldehyde With potassium carbonate at 20℃; for 12h;
Stage #2: 4-fluoroaniline In acetone for 4h; Reflux;		92%
Stage #1: 4-hydroxy-benzaldehyde With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 20℃; for 0.25h;
Stage #2: benzyl bromide In dichloromethane; water at 25 - 30℃; for 1.5h;
Stage #3: 4-fluoroaniline In isopropyl alcohol at 20 - 60℃; for 2.5h;
Reaxys ID: 30143016

Reaxys ID: 30143016

99395-88-7

(S)-4-phenyl-2-oxazolidinone

A

Reaxys ID: 30143012

Reaxys ID: 30143012

B

70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

123-08-0

4-hydroxy-benzaldehyde

70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 20 °C
2: isopropyl alcohol / 40 °C
View Scheme
100-44-7

benzyl chloride

70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 20 °C
2: isopropyl alcohol / 40 °C
View Scheme
3382-63-6

N-(4-hydroxybenzylidene)-4-fluorobenzenamine

100-44-7

benzyl chloride

70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;20.3 g
70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

1185883-39-9

C40H36F2N2O5

Conditions
ConditionsYield
Stage #1: 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -5℃; for 2h; Inert atmosphere;
Stage #2: With titanium tetrachloride In dichloromethane at -30℃; for 2h; Inert atmosphere;		94%
75-77-4

chloro-trimethyl-silane

70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

189028-95-3

(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

C43H44F2N2O5Si

Conditions
ConditionsYield
Stage #1: chloro-trimethyl-silane; 4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 5℃; Inert atmosphere;
Stage #2: With titanium tetrachloride In dichloromethane at -5 - 5℃; for 1h;		93%
942485-56-5

(S)-3-{4-[2-(4-fluorophenyl)dioxolan-2-yl]butanoyl}-4-phenyl-oxazolidin-2-one

70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

Conditions
ConditionsYield
With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride In toluene at 60℃;88.94%
70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

415960-63-3

N-(4-(benzyloxy)benzyl)-4-fluoroaniline

Conditions
ConditionsYield
With 4-Fluorothiophenol In toluene for 8h; Sealed tube; Irradiation;85%

N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline Specification

The n-(4-(Benzyloxy)benzylidene)-4-fluoroaniline, with the CAS register number 70627-52-0, has other names as 4-benzyloxybenzylidene-(4-fluoro)aniline; 4-(4-benzyloxybenzylidene)fluoroaniline; n-(4-(benzyloxy)benzylidene)-4-fluorobenzenamine; 4-fluoro-n-[[4-(phenylmethoxy)phenyl]methylene]benzenamine; n-(4-(benzyloxy)benzylidene)-4-fluoroaniline.

The physical characteristics could be summarized as: (1)ACD/LogP: 4.97; (2)#Hbondacceptors: 2; (3)#FreelyRotatingBonds: 5; (4)PolarSurfaceArea: 21.59; (5)IndexofRefraction: 1.558; (6)MolarRefractivity: 91.38cm3; (7)MolarVolume: 283cm3; (8)Polarizability: 36.22 ×10-24 cm3; (9)SurfaceTension: 37.6dyne/cm; (10)Density: 1.07g/cm3; (11)FlashPoint: 229.1°C; (12)EnthalpyofVaporization: 68.75kJ/mol; (13)BoilingPoint: 455.2°Cat760mmHg; (14)VapourPressure: 4.83E-08mmHgat25°C.

This is a kind of light yellow flaky crystal. As to its raw materials, they are including etanol, ethyl acetate, n,n-dimethylformamide, potassium carbonate, sodium sulfate, potassium iodide, benzyl bromide, petroleum ether, p-hydroxybenzaldehyde, 4-fluoroaniline. When store it, it should be kept sealing in low temperature. As to its usage, it is widely applied in many way, mainly in pharmaceutics, such as being used in the synthesis of cardiovascular drugs Ezetimibe.

In addition, you could refer to the following data information to get the molecular structure:
(1)SMILES:Fc3ccc(\N=C\c2ccc(OCc1ccccc1)cc2)cc3
(2)InChI:InChI=1/C20H16FNO/c21-18-8-10-19(11-9-18)22-14-16-6-12-20(13-7-16)23-15-17-4-2-1-3-5-17/h1-14H,15H2/b22-14+
(3)InChIKey:IWNBEFDVKWCBFY-HYARGMPZBF

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