5-FLUORO-2-METHOXYBENZALDEHYDE Chemical Properties

Melting point:

41-46 °C (lit.)

Boiling point:

118 °C / 14mmHg

Density 

1.192±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to lump

color 

White to Almost white

Sensitive 

Air Sensitive

CAS DataBase Reference

19415-51-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-36-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29130000

MSDS

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

5-FLUORO-2-METHOXYBENZALDEHYDE Usage And Synthesis

Chemical Properties

Pale yellow powder and lumps

Uses

5-Fluoro-2-methoxybenzaldehyde may be used in the synthesis of 5-(5-fluoro-2-methoxyphenyl)imidazolidine-2,4-dione.

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 3145, 1988 DOI: 10.1021/jo00249a004
Synthetic Communications, 19, p. 2001, 1989 DOI: 10.1080/00397918908052593

General Description

5-Fluoro-2-methoxybenzaldehyde is an aryl fluorinated building block.

Synthesis

Synthesis of compound 1.2. 2-Bromo-4-fluoroanisole (100 g, 487.75 mmol, 1.00 equiv) and THF (1.5 L) were added to a 3000 mL three-necked round-bottomed flask under nitrogen protection. With stirring at -78 °C, n-butyllithium (n-BuLi, 215.6 mL) was added slowly and dropwise. The reaction mixture was continued stirring at -78 °C for 1 hour. Subsequently, N,N-dimethylformamide (DMF, 71.54 g, 978.79 mmol, 2.01 eq.) was added slowly and dropwise at the same temperature. The reaction system was warmed up to room temperature and stirred for 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of 800 mL of aqueous ammonium chloride (NH4Cl aq.). The reaction mixture was extracted with 500 mL of ethyl acetate, the organic layers were combined and concentrated under reduced pressure. The crude product was purified by column chromatography to afford 65.7 g (87% yield) of 5-fluoro-2-methoxybenzaldehyde (1.2) as a light yellow solid.

References

[1] Patent: WO2017/91600, 2017, A1. Location in patent: Paragraph 0386-0387
[2] Patent: US2017/166584, 2017, A1. Location in patent: Paragraph 0418-0420
[3] Journal of Organic Chemistry, 2013, vol. 78, # 12, p. 5955 - 5963

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