4-N-BUTOXYBENZALDEHYDE Chemical Properties

Melting point:

184 °C

Boiling point:

285 °C (lit.)

Density 

1.031 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.539(lit.)

Flash point:

>230 °F

storage temp. 

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

form 

Liquid

Specific Gravity

1.031

color 

Clear yellow to orang-red

InChI

InChI=1S/C11H14O2/c1-2-3-8-13-11-6-4-10(9-12)5-7-11/h4-7,9H,2-3,8H2,1H3

InChIKey

XHWMNHADTZZHGI-UHFFFAOYSA-N

SMILES

C1C=C(OCCCC)C=CC=1C=O

CAS DataBase Reference

5736-88-9(CAS DataBase Reference)

EPA Substance Registry System

Benzaldehyde, 4-butoxy- (5736-88-9)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29124990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-N-BUTOXYBENZALDEHYDE Usage And Synthesis

Chemical Properties

CLEAR YELLOW TO ORANG-RED LIQUID

Uses

4-Butoxybenzaldehyde has been used in the synthesis of:

• 6-amino-4-(4-butoxyphenyl)-3,5-dicyanopyridine-2(1H)-thione
• 16-(p-butoxybenzylidene)androsta-1,4-diene-3,17-dione via condensation reaction with androsta-1,4-diene-3,17-dione

Synthesis Reference(s)

The Journal of Organic Chemistry, 66, p. 2966, 2001 DOI: 10.1021/jo0056848

General Description

Kinetic constant for the inhibition of the diphenolase activity of mushroom tyrosinase by 4-butoxybenzaldehyde has been evaluated.

Synthesis

In a 100 mL round-bottomed flask equipped with a reflux condenser tube and a magnetic stirrer, p-hydroxybenzaldehyde (35 g, 287 mmol) and 1-bromobutane (30.92 mL, 287 mmol) were dissolved in N,N-dimethylformamide (DMF, 750 mL). The reaction mixture was stirred for 20 min under nitrogen protection. Subsequently, anhydrous potassium carbonate (118.83 g, 860 mmol) was added and the reaction was continued to be stirred at 70 °C for 20 hours. After completion of the reaction, the mixture was cooled to room temperature. The reaction was quenched with excess water and extracted with ethyl acetate. The organic phases were combined, washed several times with water, dried over anhydrous sodium sulfate and filtered. The crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 20:1) to afford the brown oily target product 4-butoxybenzaldehyde. Yield: 95%; 1H NMR (500 MHz, CDCl3) δH (ppm): 9.89 (s, 1H), 7.84 (d, J = 8.8 Hz, 2H), 7.00 (d, J = 8.6 Hz, 2H), 4.06 (t, J = 6.3 Hz, 2H), 1.79-1.85 (m, 2H), 1.49-1.57 (m. 2H), 1.01 (t, J = 7.3 Hz, 3H); 13C NMR (125 MHz, CDCl3) δC (ppm): 190.7, 164.2, 131.9, 129.8, 114.7, 68.1, 31.0, 19.1, 13.7; ESI-MS: m/z 179.2 ([M + H]+). The following alkoxybenzaldehyde derivatives 4b-h were synthesized by a similar method.

References

[1] Journal of the American Chemical Society, 2014, vol. 136, # 46, p. 16399 - 16410
[2] Journal of the American Chemical Society, 2010, vol. 132, # 39, p. 13675 - 13683
[3] European Journal of Medicinal Chemistry, 2017, vol. 130, p. 286 - 307
[4] Synthetic Communications, 2001, vol. 31, # 21, p. 3323 - 3328
[5] Patent: CN107556333, 2018, A. Location in patent: Paragraph 0076-0079

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