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

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

 EINECS 636-494-5
CAS No. 3382-63-6 Density 1.13 g/cm3
PSA 32.59000 LogP 3.28190
Solubility N/A 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 N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 3382-63-6 (4-[[(4-Fluorophenyl)imino]methyl]-phenol) Hazard Symbols N/A
Synonyms

Phenol,p-[N-(p-fluorophenyl)formimidoyl]- (8CI);4-[(4-Fluorophenylimino)methyl]phenol;Phenol,4-[[(4-fluorophenyl)imino]methyl]-;

Article Data 23

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

123-08-0

4-hydroxy-benzaldehyde

371-40-4

4-fluoroaniline

3382-63-6

N-(4-hydroxybenzylidene)-4-fluorobenzenamine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With iron(II) chloride In acetonitrile at 100℃; Sealed tube; Inert atmosphere;
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
3382-63-6

N-(4-hydroxybenzylidene)-4-fluorobenzenamine

17341-93-4

2,2,2-Trichloroethyl chloroformate

C16H11Cl3FNO3

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

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 .

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