4-N-PROPOXYBENZALDEHYDE Chemical Properties

Melting point:

268 °C

Boiling point:

129-130 °C/10 mmHg (lit.)

Density 

1.039 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.546(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light orange to Yellow

Specific Gravity

1.06

Sensitive 

Air Sensitive

BRN 

743408

InChI

InChI=1S/C10H12O2/c1-2-7-12-10-5-3-9(8-11)4-6-10/h3-6,8H,2,7H2,1H3

InChIKey

FGXZWMCBNMMYPL-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(OCCC)C=C1

CAS DataBase Reference

5736-85-6(CAS DataBase Reference)

EPA Substance Registry System

Benzaldehyde, 4-propoxy- (5736-85-6)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-27-36/37/39

WGK Germany 

3

RTECS 

CU7700000

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29124990

MSDS

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

4-N-PROPOXYBENZALDEHYDE Usage And Synthesis

Chemical Properties

White liquid

Uses

4-Propoxybenzaldehyde was used in the preparation of (2S,4S,5R)-(±)-2-(4-propoxyphenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidine via condensation with 1-ephedrine.

General Description

Kinetic constants for the inhibition of the diphenolase activity of mushroom tyrosinase by 4-propoxybenzaldehyde was evaluated.

Synthesis

Step C: Synthesis of 3-chloro-4-propoxybenzaldehyde: A mixture of 4-hydroxybenzaldehyde (0.5 g, 4.1 mmol), 1-bromopropane (0.3 ml), and K2CO3 (0.69 g, 5 mmol) in anhydrous DMF (5 ml) was stirred and refluxed for 1 hour. After completion of the reaction, it was diluted to 100 ml with EtOAc and washed with H2O. The organic layer was separated, dried with MgSO4 and filtered. The filtrate was evaporated to dryness to give 4-propoxybenzaldehyde (0.55 g, 82.3%) as a yellow oil.1H-NMR (CDCl3) δ: 1.0 (t, 3H, J=7.41Hz); 1.7-2.0 (m, 2H); 3.95 (t, 2H, J=6.57Hz); 6.95 (d, 2H, J=8.73Hz); 8.00 (d, 2H, J=8.76Hz). To a stirred solution of 4-propoxybenzaldehyde (0.5 g, 3.07 mmol) in anhydrous DMF (3 ml) was added N-chlorosuccinimide (NCS, 0.5 g, 3.73 mmol) and the mixture was stirred at room temperature overnight. After completion of the reaction, it was diluted to 100 ml with EtOAc and washed with NaHCO3 solution (100 ml). The organic layer was separated, dried with MgSO4 and filtered. The filtrate was evaporated to dryness to give the crude product 3-chloro-4-propoxybenzaldehyde (0.59 g; 97%) as a light yellow oil.1H-NMR (CDCl3) δ: 9.81 (s, 1H); 7.87 (d, 1H, J=2.01 Hz); 7.71 (dd, 1H, J=2.02-8.47Hz); 6.98 (d, 1H, J= 8.47 Hz); 1.82-1.91 (m, 2H); 4.1 (t, 2H, J=6.3 Hz); 1.1 (t, 3H, J=7.4 Hz).

References

[1] Chemical Communications, 2013, vol. 49, # 54, p. 6042 - 6044
[2] Macromolecules, 2012, vol. 45, # 17, p. 6840 - 6849,10
[3] Patent: WO2010/42998, 2010, A1. Location in patent: Page/Page column 117; 118
[4] Patent: WO2014/63199, 2014, A1. Location in patent: Page/Page column 69
[5] Molecular Crystals and Liquid Crystals (1969-1991), 1988, vol. 154, p. 267 - 276

4-N-PROPOXYBENZALDEHYDE(5736-85-6)Related Product Information

• Diosmin
• 4-Pentyloxybenzoic acid
• 4-[3-(Dimethylamino)propoxy]benzaldehyde
• 4-N-BUTOXYBENZOIC ACID
• 4-N-BUTOXYBENZOYL CHLORIDE
• 4-N-BUTOXYBENZALDEHYDE
• 4-Hexyloxybenzoic acid
• 4-N-HEPTYLOXYBENZOIC ACID
• 4-N-HEXYLOXYBENZOYL CHLORIDE
• 4-n-Octyloxybenzoic acid
• STERIGMATOCYSTIN
• Hesperidin methylchalcone
• Rotenone
• 4-Dodecyloxybenzoic acid
• 4-N-HEPTYLOXYBENZOYL CHLORIDE
• 4-N-PENTYLOXYBENZALDEHYDE
• 2,4,5-Trifluorobenzoic acid
• 4-HEXADECYLOXYBENZOIC ACID