2-FLUORO-6-HYDROXYBENZALDEHYDE

2-FLUORO-6-HYDROXYBENZALDEHYDE Property

Melting point:

37-39°C

Boiling point:

201.3±20.0 °C(Predicted)

Density 

1.350±0.06 g/cm3(Predicted)

storage temp. 

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

form 

powder to lump

pka

7.18±0.10(Predicted)

color 

White to Yellow to Orange

Sensitive 

Air Sensitive

BRN 

1935289

InChI

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

InChIKey

FZIBGCDUHZBOLA-UHFFFAOYSA-N

SMILES

C(=O)C1=C(O)C=CC=C1F

CAS DataBase Reference

38226-10-7(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-36/37/39-27

Hazard Note 

Irritant

HS Code 

2912490090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

2-FLUORO-6-HYDROXYBENZALDEHYDE Chemical Properties,Usage,Production

Uses

2-FLUORO-6-HYDROXYBENZALDEHYDE is used in the preparation of aromatic compounds as human PAI-1 inhibitors.

Synthesis

Step 3: Synthesis of 2-fluoro-6-hydroxybenzaldehyde A solution of 2-fluoro-6-((tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde (6.5 g, 29.0 mmol) and p-toluenesulfonic acid (TsOH, 2 g, 11.6 mmol) in dichloromethane (DCM, 30 mL) was stirred for 5 hours at room temperature. After completion of the reaction, the mixture was diluted with dichloromethane (100 mL). The organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 100:1 to 20:1 gradient elution) to afford 2-fluoro-6-hydroxybenzaldehyde (3.0 g, 74% yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3): δ 11.49 (s, 1H), 10.29 (s, 1H), 7.46-7.52 (m, 1H), 6.79 (d, J = 8.8 Hz, 1H), 6.63-6.68 (m, 1H).

References

[1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 19, p. 2925 - 2929
[2] Patent: US2017/37038, 2017, A1. Location in patent: Paragraph 0096; 0378; 0382; 0383