4-Formylphenoxyacetic acid

4-Formylphenoxyacetic acid Property

Melting point:

193-196 °C

Boiling point:

272.96°C (rough estimate)

Density 

1.2933 (rough estimate)

refractive index 

1.4500 (estimate)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in hot methanol within almost transparency.

form 

Crystalline Powder

pka

3.04±0.10(Predicted)

color 

Beige

Sensitive 

Air Sensitive

BRN 

779885

InChI

InChI=1S/C9H8O4/c10-5-7-1-3-8(4-2-7)13-6-9(11)12/h1-5H,6H2,(H,11,12)

InChIKey

OYNIIKHNXNPSAG-UHFFFAOYSA-N

SMILES

C(O)(=O)COC1=CC=C(C=O)C=C1

CAS DataBase Reference

22042-71-3(CAS DataBase Reference)

EPA Substance Registry System

Acetic acid, (4-formylphenoxy)- (22042-71-3)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29189900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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-Formylphenoxyacetic acid Chemical Properties,Usage,Production

Chemical Properties

BEIGE CRYSTALLINE POWDER

Uses

4-Formylphenoxyacetic acid is used as an organic chemical synthesis intermediate.

General Description

4-Formylphenoxyacetic acid is a formylphenoxyaliphatic acid that reacts with dimedone to form 1,8-dioxo-octahydroxanthenes. It participates in the synthesis of 4-substituted benzaldehyde derivatives and 4-carboxypheoxyacetic acid.

Synthesis

The general procedure for the synthesis of 2-(4-formylphenoxy)acetic acid from p-hydroxybenzaldehyde and bromoacetic acid was as follows: potassium carbonate (24.9 g, 180.0 mmol) was added to a solution of 4-hydroxybenzaldehyde (10.0 g, 82.0 mmol) in acetone (150 mL) and the reaction mixture was stirred for 15 min at 40 °C. Subsequently, bromoacetic acid (12.0 g, 86.0 mmol) was added slowly in batches and the reaction mixture was heated to reflux for 18 hours. After completion of the reaction, the reaction mixture was cooled and diluted by adding water (200 mL). The reaction mixture was extracted with ethyl acetate (2 x 200 mL) and after combining the organic phases, the aqueous layer was adjusted to pH 2 with 6N hydrochloric acid. the aqueous layer was again extracted with ethyl acetate (2 x 400 mL), the organic phases were combined and washed with water (200 mL), dried with anhydrous sodium sulfate and finally concentrated under vacuum. The residue was ground with isohexane to afford the target compound 2-(4-formylphenoxy)acetic acid (13.5 g, 91% yield) as a creamy white solid.1H NMR (d6-DMSO) δ: 13.12 (br s, 1H), 9.87 (s, 1H), 7.88-7.85 (m, 2H), 7.12-7.10 (m, 2H). 4.83 (s, 2H).

References

[1] Patent: WO2015/86509, 2015, A1. Location in patent: Page/Page column 92; 93
[2] Main Group Metal Chemistry, 2015, vol. 38, # 5-6, p. 157 - 164
[3] Patent: WO2004/89945, 2004, A1. Location in patent: Page 8
[4] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 230 - 239