(4-FLUORO-PHENYL)-OXO-ACETALDEHYDE

(4-FLUORO-PHENYL)-OXO-ACETALDEHYDE Property

Melting point:

84-88℃

Boiling point:

115℃/35mm

Density 

1.241±0.06 g/cm3(Predicted)

RTECS 

CY1440000

solubility 

Chloroform, Methanol

form 

Solid

color 

White

Safety

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Toxicity

mouse,LD50,intraperitoneal,681mg/kg (681mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION,Journal of the Indian Chemical Society. Vol. 60, Pg. 369, 1983.

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.

(4-FLUORO-PHENYL)-OXO-ACETALDEHYDE Chemical Properties,Usage,Production

Chemical Properties

White Solid

Uses

4-Fluoro-α-oxo-benzeneacetaldehyde (cas# 403-32-7) is a compound useful in organic synthesis.

Synthesis

The general procedure for the synthesis of 4-fluorobenzoylformaldehyde from 4-fluoroacetophenone was as follows: selenium dioxide (6.70 g, 61.0 mmol) was added to a mixed solution of dioxane (100 mL) and water (3 mL) containing 4-fluoroacetophenone (8.43 g, 61.0 mmol). The resulting mixture was heated at 55 °C until selenium dioxide was completely dissolved. Subsequently, the reaction mixture was refluxed for 5 to 6 hours. After monitoring the completion of the reaction by thin layer chromatography (TLC), the mixture was filtered and the filtrate was concentrated under vacuum to obtain a viscous oily substance. Water (50 mL) was added to the oily substance and the resulting mixture was stirred for 12 hours. Afterwards, the solid formed was collected on a filter, washed with water (25 mL) and dried under vacuum to finally obtain 4-fluorophenylglyoxal (6.60 g, 85% yield).1H NMR (400 MHz, CDCl3) δ: 7.18 (m, 2H), 8.11 (d, 2H), no signal for aldehyde CHO was observed.

References

[1] Patent: WO2011/95625, 2011, A1. Location in patent: Page/Page column 94
[2] Tetrahedron Letters, 2017, vol. 58, # 7, p. 658 - 662
[3] Patent: WO2007/39821, 2007, A2. Location in patent: Page/Page column 16
[4] Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1651 - 1653
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 36, p. 10890 - 10894