2-AMINO-5-FLUOROBENZALDEHYDE Chemical Properties

Boiling point:

260℃

Density 

1.293

Flash point:

111℃

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

2-AMINO-5-FLUOROBENZALDEHYDE Usage And Synthesis

Uses

2-Amino-5-fluorobenzaldehyde is a building block used in various synthetic preparations. It was used as a reactant in the stereoselective preparation of aryltetrahydroquinolines via gold-phosphine catalyzed heterocyclization of aminobenzaldehyde with alkynes.

Synthesis

General procedure for the synthesis of 2-amino-5-fluorobenzaldehyde from (2-amino-5-fluorophenyl)methanol: Benzyl alcohol derivative (2-amino-5-fluorophenyl)methanol (1 eq.) was dissolved in dichloromethane (0.4 M). Manganese dioxide (2.1 eq.) was added and the reaction mixture was stirred at room temperature for 48 hours under argon protection. The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the manganese dioxide was removed by filtration and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using a solvent mixture of hexane and ethyl acetate as eluent to obtain the target product 2-amino-5-fluorobenzaldehyde.

References

[1] ChemistryOpen, 2015, vol. 4, # 2, p. 107 - 110
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 35, p. 10573 - 10576
[3] Angew. Chem., 2017, vol. 129, # 35, p. 10709 - 10712,4
[4] Synlett, 2017, vol. 28, # 14, p. 1724 - 1728
[5] Patent: US2010/331306, 2010, A1. Location in patent: Page/Page column 34

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