4-[[(4-Fluorophenyl)imino]methyl]-phenol supplier

Name
4-[[(4-Fluorophenyl)imino]methyl]-phenol
EINECS 636-494-5
CAS No. 3382-63-6
Article Data23
CAS DataBase
Density 1.13 g/cm³
Solubility
Melting Point 179.0 to 183.0 °C
Formula C₁₃H₁₀FNO
Boiling Point 370.9 °C at 760 mmHg
Molecular Weight 215.227
Flash Point 178.1 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Phenol,p-[N-(p-fluorophenyl)formimidoyl]- (8CI);4-[(4-Fluorophenylimino)methyl]phenol;Phenol,4-[[(4-fluorophenyl)imino]methyl]-;
PSA 32.59000
LogP 3.28190

Synthetic route

: 123-08-0
4-hydroxy-benzaldehyde

: 371-40-4
4-fluoroaniline

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

Conditions

Conditions	Yield
In water at 20 - 85℃; for 5.5h; Large scale;	97.5%
In methanol at 20 - 30℃; Large scale;	90%
In isopropyl alcohol at 50℃; for 1h;	88%

: 163222-33-1
ezetemibe

A: 793673-93-5
(-)-6-(4-fluorophenyl)tetrahydro-2H-pyran-2-one

B: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

Conditions

Conditions	Yield
In water; acetonitrile UV-irradiation;

: 3296-02-4
p-azidofluorobenzene

: 6554-98-9
trans-4-Hydroxystilbene

A: 331-98-6, 83306-62-1, 83306-65-4
N-benzylidene-4-fluoroaniline

B: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

Conditions

Conditions	Yield
With iron(II) chloride In acetonitrile at 100℃; Sealed tube; Inert atmosphere;

...Expand

: 371-40-4
4-fluoroaniline

A: 331-98-6, 83306-62-1, 83306-65-4
N-benzylidene-4-fluoroaniline

B: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 - 5 °C / Inert atmosphere 1.2: 10 h / 20 °C / Inert atmosphere 2.1: iron(II) chloride / acetonitrile / 100 °C / Sealed tube; Inert atmosphere View Scheme

: 4-hydroxybenzenediazonium tetrafluoroborate

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate; palladium diacetate / 12 h / 20 °C / Inert atmosphere 2: iron(II) chloride / acetonitrile / 100 °C / Sealed tube; Inert atmosphere View Scheme

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 18162-48-6
tert-butyldimethylsilyl chloride

: 179411-51-9
N-(4-((tert-butyldimethylsilyl)oxy)benzylidene)-4-fluoroaniline

Conditions

Conditions	Yield
Stage #1: N-(4-hydroxybenzylidene)-4-fluorobenzenamine With dmap; triethylamine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 0 - 20℃; Inert atmosphere;	99%
With 1H-imidazole In N,N-dimethyl-formamide at 60℃; for 4h;	97.5%

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 75-36-5
acetyl chloride

: C15H12FNO2

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 5h;	98%

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 76-83-5
trityl chloride

: 1159183-26-2
N-(4-trityloxybenzylidene)-4-fluoroaniline

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 10 - 20℃; for 1.08333h;	97.8%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 10 - 20℃;
With N-ethyl-N,N-diisopropylamine In dichloromethane at 10 - 20℃;

: 75-77-4
chloro-trimethyl-silane

: 1076200-08-2
3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-2-oxazolidinone

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 858126-22-4
3-{2-[3-(fluorophenyl)-3-(trimethyl silyloxy)-propyl]-3-(4-fluoro phenyl amino)-3-(4-trimethyl silyloxy phenyl)-1-oxo-propyl}-4-(S)-phenyl oxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: 3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-2-oxazolidinone With dimethylsulfide borane complex; ascorbic acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane at -10 - 8℃; for 7.25h; Inert atmosphere; Large scale; Stage #2: With dihydrogen peroxide In methanol; dichloromethane at -5 - 20℃; for 0.5h; Inert atmosphere; Large scale; Stage #3: chloro-trimethyl-silane; N-(4-hydroxybenzylidene)-4-fluorobenzenamine Large scale; Further stages;	96.3%

Yield

Stage #1: 3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-2-oxazolidinone With dimethylsulfide borane complex; ascorbic acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In dichloromethane at -10 - 8℃; for 7.25h; Inert atmosphere; Large scale;
Stage #2: With dihydrogen peroxide In methanol; dichloromethane at -5 - 20℃; for 0.5h; Inert atmosphere; Large scale;
Stage #3: chloro-trimethyl-silane; N-(4-hydroxybenzylidene)-4-fluorobenzenamine Large scale; Further stages;

96.3%

...Expand

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 17341-93-4
2,2,2-Trichloroethyl chloroformate

: C16H11Cl3FNO3

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 5℃; for 6h;	95%

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 3282-30-2
pivaloyl chloride

: 1232148-23-0
2,2-dimethylpropionic acid 4-[(4-fluorophenylimino)methyl]phenyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane	93%

: 75-77-4
chloro-trimethyl-silane

: 870634-36-9
methyl 5S-5-(4-fluorophenyl)-5-hydroxyvalerate

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: (3R,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-(trimethylsilyloxy)propanyl)-4-(4-(trimethylsiloxy)phenyl)azetidinone

Conditions

Conditions	Yield
Stage #1: chloro-trimethyl-silane; methyl 5S-5-(4-fluorophenyl)-5-hydroxyvalerate; N-(4-hydroxybenzylidene)-4-fluorobenzenamine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -10 - 0℃; Inert atmosphere; Stage #2: With (R,R)-(+)-N-benzyl-3,4-bis(diphenylphosphino)pyrrolidine; lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -10 - 0℃; Inert atmosphere;	79%

...Expand

: 870634-36-9
methyl 5S-5-(4-fluorophenyl)-5-hydroxyvalerate

: 994-30-9
triethylsilyl chloride

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: C36H49F2NO3Si2

Conditions

Conditions	Yield
Stage #1: methyl 5S-5-(4-fluorophenyl)-5-hydroxyvalerate; triethylsilyl chloride; N-(4-hydroxybenzylidene)-4-fluorobenzenamine With tributyl-amine In 2-methyltetrahydrofuran at -10 - 0℃; Inert atmosphere; Stage #2: With (R,R)-(+)-N-benzyl-3,4-bis(diphenylphosphino)pyrrolidine; lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -10 - 0℃; Inert atmosphere;	78.3%

...Expand

: 870634-36-9
methyl 5S-5-(4-fluorophenyl)-5-hydroxyvalerate

: 995-25-5
chlorotripropylsilane

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: C42H61F2NO3Si2

Conditions

Conditions	Yield
Stage #1: methyl 5S-5-(4-fluorophenyl)-5-hydroxyvalerate; chlorotripropylsilane; N-(4-hydroxybenzylidene)-4-fluorobenzenamine With triethylamine In 2-methyltetrahydrofuran at -20 - -10℃; Inert atmosphere; Stage #2: With (R,R)-(+)-N-benzyl-3,4-bis(diphenylphosphino)pyrrolidine; lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -20 - -10℃; Inert atmosphere;	76.7%

...Expand

: 75-77-4
chloro-trimethyl-silane

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: C20H19ClFNO4

: C39H45ClF2N2O5Si2

Conditions

Conditions	Yield
Stage #1: chloro-trimethyl-silane; N-(4-hydroxybenzylidene)-4-fluorobenzenamine; C20H19ClFNO4 With N-ethyl-N,N-diisopropylamine for 1h; Stage #2: With titanium tetrachloride at -30 - -25℃; for 3h;	71%

...Expand

: 75-77-4
chloro-trimethyl-silane

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 272778-12-8
(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: chloro-trimethyl-silane; N-(4-hydroxybenzylidene)-4-fluorobenzenamine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - 0℃; Inert atmosphere; Stage #2: With titanium tetrachloride In dichloromethane at -30 - -25℃; Inert atmosphere;	66.6%
With triethylamine In dichloromethane at -20℃; Reagent/catalyst; Solvent;

...Expand

: 75-77-4
chloro-trimethyl-silane

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: C39H46F2N2O5Si2

Conditions

Conditions	Yield
Stage #1: N-(4-hydroxybenzylidene)-4-fluorobenzenamine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - -5℃; Stage #2: chloro-trimethyl-silane In dichloromethane at -5℃; for 1.5h; Stage #3: With N,O-bis-(trimethylsilyl)-acetamide; titanium tetrachloride more than 3 stages;	65%

...Expand

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 107-30-2
chloromethyl methyl ether

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: C37H38F2N2O7

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -20 - -10℃; for 1h; Temperature; Reagent/catalyst;	64.5%

...Expand

: 75-77-4
chloro-trimethyl-silane

: 10416-59-8
N,O-bis-(trimethylsilyl)-acetamide

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

: 272778-12-8
(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: chloro-trimethyl-silane; N-(4-hydroxybenzylidene)-4-fluorobenzenamine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - -5℃; for 1h; Stage #2: With titanium tetrachloride In dichloromethane at -30℃; for 20h; Stage #3: N,O-bis-(trimethylsilyl)-acetamide	60%

...Expand

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 121-90-4
m-nitrobenzoic acid chloride

: C20H13FN2O4

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20 - 30℃; Large scale;	59%

: 1185883-41-3
(S)-3-(5-(4-fluorophenyl)-5,5-dimethoxypentanoyl)-4-phenyloxazolidin-2-one

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 501-53-1
benzyl chloroformate

: 1185883-42-4
C41H34F2N2O7

Conditions

Conditions	Yield
Stage #1: N-(4-hydroxybenzylidene)-4-fluorobenzenamine; benzyl chloroformate With N-ethyl-N,N-diisopropylamine In dichloromethane; toluene at 0 - 20℃; for 1.66667h; Stage #2: (S)-3-(5-(4-fluorophenyl)-5,5-dimethoxypentanoyl)-4-phenyloxazolidin-2-one With titanium(IV) trichloride isopropoxide In dichloromethane; toluene at -35 - -30℃; for 3.33333h;	51.76%

...Expand

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 57-11-4
stearic acid

: C31H44FNO2

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 6h;	45%

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 57-10-3
1-hexadecylcarboxylic acid

: C29H40FNO2

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 6h;	44%

: 143-07-7
lauric acid

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: C25H32FNO2

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 6h;	41%

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 544-63-8
n-tetradecanoic acid

: C27H36FNO2

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 6h;	41%

: 334-48-5
1-decanoic acid

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: C23H28FNO2

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 6h;	38%

: 5050-41-9
N-(2-chloroethyl)-pyrrolidine

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 4-fluorophenyl[4-(2-pyrrolidin-1-yl-ethoxy)benzylidene]amine

Conditions

Conditions	Yield
Stage #1: N-(4-hydroxybenzylidene)-4-fluorobenzenamine With potassium carbonate In acetone for 0.166667h; Inert atmosphere; Stage #2: N-(2-chloroethyl)-pyrrolidine In acetone Inert atmosphere; Reflux;	37%

: 3-[(5S)-5-(4-fluorophenyl)-5-hydroxy-1-oxopentyl]-4-phenyl-2-oxazolidinone

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: C39H47FN2O4Si2

Conditions

Conditions	Yield
Stage #1: 3-[(5S)-5-(4-fluorophenyl)-5-hydroxy-1-oxopentyl]-4-phenyl-2-oxazolidinone; N-(4-hydroxybenzylidene)-4-fluorobenzenamine With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine; titanium tetrachloride In n-heptane; toluene at -35 - -10℃; for 4.75h; Stage #2: With bistrimethylsilylacetamide In n-heptane; toluene for 0.5h; Heating / reflux;

: 942485-56-5
(S)-3-{4-[2-(4-fluorophenyl)dioxolan-2-yl]butanoyl}-4-phenyl-oxazolidin-2-one

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 954109-25-2
(S)-3-{(R)-2-[(S)-(4-fluorophenylamino)-(4-hydroxyphenyl)methyl]-4-[2-(4-fluorophenyl)-[1,3]-dioxolan-2-yl]butyryl}-4-phenyloxazolidin-2-one

Conditions

Conditions	Yield
Stage #1: (S)-3-{4-[2-(4-fluorophenyl)dioxolan-2-yl]butanoyl}-4-phenyl-oxazolidin-2-one; N-(4-hydroxybenzylidene)-4-fluorobenzenamine With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane at -10℃; for 1.5h; Stage #2: With titanium tetrachloride In dichloromethane at -15℃;

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 501-53-1
benzyl chloroformate

: 1159183-27-3
benzyl-[4-(4-fluorophenyliminomethyl)phenyl]-carbonate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane; toluene at 5 - 10℃;
With N-ethyl-N,N-diisopropylamine In dichloromethane; toluene at 5 - 10℃; for 1.08333h;

Reaxys ID: 19845321: Reaxys ID: 19845321

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

Reaxys ID: 19845322: Reaxys ID: 19845322

Reaxys ID: 19845323: Reaxys ID: 19845323

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: 189028-95-3
(4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one

Reaxys ID: 19845322: Reaxys ID: 19845322

Conditions

Conditions	Yield
With titanium tetrachloride; N-ethyl-N,N-diisopropylamine In dichloromethane

...Expand

: (S)-3-(5-(4-fluorophenyl)-5-(hydroxyimino)pentanoyl)-4-phenyloxazolidin-2-one

: 3382-63-6
N-(4-hydroxybenzylidene)-4-fluorobenzenamine

: C39H45F2N3O5Si2

Conditions

Conditions	Yield
Stage #1: (S)-3-(5-(4-fluorophenyl)-5-(hydroxyimino)pentanoyl)-4-phenyloxazolidin-2-one; N-(4-hydroxybenzylidene)-4-fluorobenzenamine With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - -5℃; Stage #2: titanium tetrachloride In dichloromethane at -30 - -25℃; for 3 - 6h;

4-[[(4-Fluorophenyl)imino]methyl]-phenol Chemical Properties

The Molecular Structure of 4-[[(4-Fluorophenyl)imino]methyl]-phenol (CAS NO.3382-63-6):

Empirical Formula: C₁₃H₁₀FNO
Molecular Weight: 215.223
IUPAC Name: 4-[(4-fluoroanilino)methylidene]cyclohexa-2,5-dien-1-one
Product Categories: Intermediate of ezetimibe
Nominal Mass: 215 Da
Average Mass: 215.223 Da
Monoisotopic Mass: 215.074642 Da
Index of Refraction: 1.558
Molar Refractivity: 61.135 cm³
Molar Volume: 189.753 cm³
Surface Tension: 38.376 dyne/cm
Density: 1.134 g/cm³
Flash Point: 178.131 °C
Enthalpy of Vaporization: 64.215 kJ/mol
Boiling Point: 370.927 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C

4-[[(4-Fluorophenyl)imino]methyl]-phenol Uses

4-[[(4-Fluorophenyl)imino]methyl]-phenol (CAS NO.3382-63-6) is used for synthesis of ezetimibe .

4-[[(4-Fluorophenyl)imino]methyl]-phenol Specification

4-[[(4-Fluorophenyl)imino]methyl]-phenol (CAS NO.3382-63-6) is also called as 4-(4-Hydroxybenzylidene) fluoro aniline ; 2-(4 ' -Hydrophenyl)-4-fluorobenyl imine ; Alpha-4-fluorophenylimino-p-cresol ; (E)-4-((4-fluorophenylimino)methyl)phenol ; 4-Fluoro-n-(hydroxyphenyl)methylene-benzenamine .

Product Name

4-[[(4-Fluorophenyl)imino]methyl]-phenol

Synthetic route

4-[[(4-Fluorophenyl)imino]methyl]-phenol Chemical Properties

4-[[(4-Fluorophenyl)imino]methyl]-phenol Uses

4-[[(4-Fluorophenyl)imino]methyl]-phenol Specification

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