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

Melting point:

136-138 ºC

Boiling point:

455.2±35.0 °C(Predicted)

Density 

1.07

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Acetonitrile (Slightly), Chlorofrom (Slightly), Methanol (Slightly, Sonicated)

form 

Solid

pka

3.71±0.50(Predicted)

color 

Very Dark Orange

InChI

InChI=1S/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

InChIKey

IWNBEFDVKWCBFY-UHFFFAOYSA-N

SMILES

C1(N=CC2=CC=C(OCC3=CC=CC=C3)C=C2)=CC=C(F)C=C1

CAS DataBase Reference

70627-52-0

Safety Information

HS Code 

2925.29.9000

N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline Usage And Synthesis

Uses

4-Benzyloxybenzylidene 4-Fluoroaniline is an intermediate in the synthesis of Linezolid (L466500).

Synthesis

General procedure for the synthesis of 4-benzylbenzylidene-(4-fluoro)aniline from 4-benzyloxybenzaldehyde and 4-fluorobenzenamine: 4-fluorobenzylidene-(4-fluoro)aniline (100 g, 1.1 eq.) was mixed with isopropanol (1730 ml, 10 V) and heated under mechanical stirring up to 40 °C, whereby a large amount of light yellow crystalline solid was gradually precipitated. Stirring was continued and the reaction was monitored until completion. The heating was stopped and the reaction was cooled naturally to room temperature with stirring. Extraction and filtration operations were carried out, and the filter cake was washed with cold isopropanol and dried to give the light yellow crystalline product SM 2 with a mass of 238 g, 95% yield and 99% purity.

References

[1] Patent: JP2016/147843, 2016, A. Location in patent: Paragraph 0016
[2] Patent: CN107793339, 2018, A. Location in patent: Paragraph 0021; 0023; 0031; 0038
[3] Pharmacy and Pharmacology Communications, 2000, vol. 6, # 1, p. 25 - 29
[4] Journal of Organic Chemistry, 2018,

N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline(70627-52-0)Related Product Information

• (3R,4S)-4-[4-(Benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
• Benzyloxyacetyl chloride
• 4-Fluoroaniline
• 3,3',5,5'-Tetramethylbenzidine dihydrochloride
• PHENYL VALERATE
• Phenetidine
• p-Anisidine
• 4-Methoxybenzyl alcohol
• N,N-Dimethylaniline
• 4-(Trifluoromethoxy)aniline
• Benzalacetone
• Methyltrimethoxysilane
• 4-Methoxybenzylchloride
• Phenylhydrazine
• 4-[[(4-Fluorophenyl)imino]methyl]-phenol
• 4,4'-Diphenylmethane diisocyanate
• Methylene Blue
• 5-(4-FLUOROPHENYL)VALERIC ACID