3-ALLYLSALICYLALDEHYDE Chemical Properties

Melting point:

45 °C

Boiling point:

248.88°C (rough estimate)

Density 

1.099 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.5645

Flash point:

224 °F

storage temp. 

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

solubility 

Soluble in chloroform.

pka

8.50±0.10(Predicted)

form 

Oil

color 

Light Yellow to Yellow

Sensitive 

Air Sensitive

InChI

InChI=1S/C10H10O2/c1-2-4-8-5-3-6-9(7-11)10(8)12/h2-3,5-7,12H,1,4H2

InChIKey

INLWEXRRMUMHKB-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

24019-66-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29124990

3-ALLYLSALICYLALDEHYDE Usage And Synthesis

Chemical Properties

Light Yellow Liquid

Uses

3-Allyl Salicylaldehyde is a synthetic intermediate for the sythesis of 3-aminoflavones. Flavonoids have been studied for their antiproliferative activity and in vitro cytotoxicity. Used in the prepar ation of oxazole derivatives. Used in the preparation of imidazole scaffold-based 2-substituted benzofurans for application against human tumor cell lines. Also a reagent in the synthesis of antioxida nt and antimicrobial novel chalcones.

Uses

3-Allylsalicylaldehyde is a synthetic intermediate for the synthesis of 3-aminoflavones. Flavonoids have been studied for their antiproliferative activity and in vitro cytotoxicity. It is used in the preparation of oxazole derivatives and also imidazole scaffold-based 2-substituted benzofurans for application against human tumor cell lines. It is a reagent in the synthesis of antioxidant and antimicrobial novel chalcones.

Synthesis

The general procedure for the synthesis of 3-allyl-2-hydroxybenzaldehyde from formaldehyde and 2-allylphenol was as follows: 13.5 g (0.1 mol) of 2-allylphenol and 100 mL of acetonitrile were added to a three-necked flask, and 6.5 g of paraformaldehyde, 22 g (0.39 mol) of anhydrous magnesium chloride, and 0.02 mol of triethylamine were added sequentially under stirring conditions. The reaction mixture was refluxed for 4 h. The reaction solution was poured into ice water and the pH was adjusted with aqueous hydrochloric acid to 5. It was extracted twice with ethyl acetate, the organic phases were combined and dried over anhydrous sodium sulfate. After concentration under reduced pressure, 11 g of solid product was obtained in 68% yield. Mass spectrometry analysis showed a molecular ion peak of 163 (M + 1).

References

[1] Patent: US2012/142921, 2012, A1. Location in patent: Page/Page column 13
[2] Patent: EP2468730, 2012, A1. Location in patent: Page/Page column 14
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 8, p. 1525 - 1532
[4] Organic Letters, 2012, vol. 14, # 12, p. 3226 - 3229

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