5-Fluorosalicylaldehyde Chemical Properties

Melting point:

82-85 °C (lit.)

Boiling point:

56 °C / 1mmHg

Density 

1.350±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

8.18±0.18(Predicted)

form 

Powder or Flakes

color 

White to Orange to Green

Sensitive 

Air Sensitive

InChI

InChI=1S/C7H5FO2/c8-6-1-2-7(10)5(3-6)4-9/h1-4,10H

InChIKey

FDUBQNUDZOGOFE-UHFFFAOYSA-N

SMILES

C(=O)C1=CC(F)=CC=C1O

CAS DataBase Reference

347-54-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29130000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Fluorosalicylaldehyde Usage And Synthesis

Chemical Properties

White solid

Uses

5-Fluorosalicylaldehyde may be used to synthesize:

• managanese (III) complex [MnL^a(μ_1,3-N₃)]_n [H₂L^a = N,N′-bis(5-fluorosalicylidene)-1,2-diaminoethane]
• enantiopure 4-amino-6-fluoro-3-(hydroxymethyl)chromanes
• 4,4′-difluoro-2,2′-[(hydrazine-1,2-diylidene)bis(methanylylidene)]-diphenol
• N,N′-bis(5-fluoro-2-hydroxybenzylidene)ethylenediamine
• N,N′-(2-hydroxypropane-1,3-diyl)-bis(salicylaldimine (H₂L)

General Description

5-Fluorosalicylaldehyde can be synthesized from 4-fluorophenol.

Synthesis

The general procedure for the synthesis of 5-fluorosalicylaldehyde from 4-fluorophenol and trichloromethane is as follows: Step A: To a solution of water (400mL) containing NaOH (78g, 1950mmol) was added a mixture of 4-fluorophenol (50g, 446.43mmol) in water (200mL) and ethanol (150mL). After heating the mixture to 70°C, trichloromethane (110 mL) was slowly added dropwise through the addition funnel (approximately 2 hours to complete the drop) and the reaction mixture was continuously stirred at this temperature overnight (approximately 16 hours). Upon completion of the reaction, the mixture was cooled to room temperature and acidified with 3M HCl solution. Subsequently, the reaction mixture was partitioned between saturated saline and dichloromethane, the organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography (eluent: 3% ethyl acetate/hexane) to afford 13.6 g of 5-fluorosalicylaldehyde (22% yield, white solid).

References

[1] Journal of the American Chemical Society, 1998, vol. 120, # 33, p. 8340 - 8347
[2] Patent: WO2005/37763, 2005, A1. Location in patent: Page/Page column 126
[3] Patent: US2017/37038, 2017, A1. Location in patent: Paragraph 0372; 0373; 0374
[4] Journal of the American Chemical Society, 1946, vol. 68, p. 2502
[5] European Journal of Medicinal Chemistry, 1996, vol. 31, # 6, p. 449 - 460

5-Fluorosalicylaldehyde(347-54-6)Related Product Information

• 3-(Trifluoromethyl)benzaldehyde
• 3-Hydroxybenzaldehyde
• 2-(Trifluoromethyl)benzaldehyde
• Salicylaldehyde
• Benzaldehyde
• 4-Hydroxybenzaldehyde
• 5-Fluorosalicylic acid
• Fluorine
• 3',5'-DIFLUORO-2'-HYDROXYACETOPHENONE
• 6-Fluoro-4-chromanone
• 1-(5-Fluoro-2-hydroxyphenyl)-1-ethanone
• 4'-CHLORO-5-FLUORO-2-HYDROXYBENZOPHENONE
• 3-FLUOROSALICYLALDEHYDE,3-Fluorosalicylaldehyde,98%
• 6-FLUOROSALICYLALDEHYDE,6-Fluorosalicylaldehyde,97%
• 4-FLUOROSALICYLALDEHYDE (4-FLUORO-2-HYDROXYBENZALDEHYDE),4-FLUOROSALICYLALDEHYDE
• Formaldehyde
• 6-FLUORO-3-FORMYLCHROMONE
• 6-FLUORO-2-METHYL-4-CHROMANONE