3-Fluoro-2-hydroxybenzaldehyde Chemical Properties

Melting point:

68-70 °C(lit.)

Boiling point:

176.2±20.0 °C(Predicted)

Density 

1.350±0.06 g/cm3(Predicted)

storage temp. 

2-8°C, stored under nitrogen

Water Solubility 

Insoluble in water

pka

6.91±0.10(Predicted)

form 

Crystalline Powder

color 

White to light yellow

Sensitive 

Air Sensitive

BRN 

1932806

InChI

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

InChIKey

NWDHTEIVMDYWQJ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

394-50-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29124990

MSDS

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

3-Fluoro-2-hydroxybenzaldehyde Usage And Synthesis

Chemical Properties

White to light yellow crystalline powder

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 2502, 1946 DOI: 10.1021/ja01216a020

Synthesis

A hexane solution of n-butyllithium (17.07 mL, 1.42 M, 25.1 mmol) was slowly added dropwise to a stirred solution of 2-(2-bromo-5-methoxyphenyl)-1,3-dioxolane (5.00 g, 19.3 mmol) dissolved in dry tetrahydrofuran (60 mL) at -78°C. The reaction mixture was stirred continuously at -78 °C for 30 min before being quenched by the addition of iodomethane (2.40 mL, 38.6 mmol). After quenching, the solution was continued stirring at -78 °C for 20 min, followed by termination of the reaction with saturated aqueous ammonium chloride solution (60 mL). The organic phase was separated, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by fast column chromatography using hexane:ethyl acetate (10:1) as eluent to afford the light yellow oily target product 3-fluoro-2-hydroxybenzaldehyde (3.07 g, 82% yield). Thin layer chromatography showed an Rf value of 0.40 (Expanding agent: hexane:ethyl acetate, 10:1). The NMR hydrogen spectrum (300 MHz, CDCl3) data were as follows: δ 7.20-6.99 (2H, m, Ar-H), 6.75 (1H, dd, Ar-H), 5.92 (1H, s, CH), 4.20-4.01 (4H, m, 2 × CH2), 3.80 (3H, s, OCH3), 2.32 (3H, s, CH3) .

References

[1] Patent: WO2004/43903, 2004, A1. Location in patent: Page 31

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