3-Ethylbenzaldehyde Chemical Properties

Boiling point:

73 °C(Press: 5.5 Torr)

Density 

1.001±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

color 

Colourless

Stability:

Moisture Sensitive

LogP

2.701 (est)

Safety Information

HS Code 

2912290090

3-Ethylbenzaldehyde Usage And Synthesis

Description

3-Ethylbenzaldehyde is a natural compound that is found in the essential oils of plants such as Capsicum annuum and Cinnamomum zeylanicum.

Uses

3-Ethylbenzaldehyde has been used as a bioassay for the presence of fatty acids in laminar magnetic resonance spectroscopy (MRS) studies on cordata.

Biological Activity

3-Ethylbenzaldehyde has been shown to have antimicrobial activity against Gram-positive bacteria, including Staphylococcus aureus, and Mycobacterium tuberculosis.

Synthesis

General procedure for the synthesis of 3-ethylbenzaldehyde from m-bromobenzaldehyde and triethylboron: To a suspension containing m-bromobenzaldehyde (0.370 g, 2.00 mmol), Pd(dppf)Cl2 (14.6 mg, 20.0 μmol), and CsOAc (0.384 g, 2.00 mmol), protected by argon, triethylborane (1.00 M in THF, 2.00 mL, 2.00 mmol) and THF (3.0 mL). The mixture was heated to reflux and held for 6 hours. After completion of the reaction, it was cooled to room temperature, diluted with ether, washed sequentially with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel fast column chromatography to afford 3-ethylbenzaldehyde (0.123 g, 0.920 mmol, 46% yield) as a colorless oil.1H-NMR (CDCl3, 400 MHz) δ: 1.28 (t, J = 7.2 Hz, 3H, -CH3), 2.74 (q, J = 7.2 Hz, 2H, -CH2-), 7.42 -7.48 (m, 2H, Ar-H), 7.69-7.72 (m, 2H, Ar-H), 10.0 (s, 1H, -CHO); the data are consistent with those reported in the literature (Wang et al., 2009).

References

[1] Phytochemistry, 2013, vol. 96, p. 132 - 147
[2] Patent: WO2005/95326, 2005, A2. Location in patent: Page/Page column 114-115

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