4-(Diethylamino)salicylaldehyde Chemical Properties

Melting point:

60-62 °C (lit.)

Boiling point:

329.46°C (rough estimate)

Density 

1.0945 (rough estimate)

refractive index 

1.5041 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

8.29±0.10(Predicted)

form 

Powder or Crystalline Powder

color 

Pale brown to pink to purple

Water Solubility 

Insoluble in water.

Sensitive 

Air Sensitive

BRN 

2212234

InChIKey

XFVZSRRZZNLWBW-UHFFFAOYSA-N

CAS DataBase Reference

17754-90-4(CAS DataBase Reference)

EPA Substance Registry System

Benzaldehyde, 4-(diethylamino)-2-hydroxy- (17754-90-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

2

RTECS 

CU5615150

TSCA 

Yes

HS Code 

29225090

MSDS

• Language:English Provider:4-Diethylamino-2-hydroxybenzaldehyde

4-(Diethylamino)salicylaldehyde Usage And Synthesis

Chemical Properties

4-(Diethylamino)salicylaldehyde is beige to purple crystalline powder

Uses

4-(Diethylamino)salicylaldehyde was used in the synthesis of Schiff-base ligand by monocondensation with diaminomaleonitrile.

Uses

4-(Diethylamino)salicylaldehyde is usually used in the synthesis of Schiff-base ligand by monocondensation with diaminomaleonitrile.

Definition

ChEBI: 4-(Diethylamino)salicylaldehyde is a hydroxybenzaldehyde.

Synthesis

The temperature of the reaction system was maintained at 5-10 °C under continuous stirring and phosphorus oxychloride (POCl3, 2.75 mL, 0.03 mol) was slowly added dropwise to N,N-dimethylformamide (DMF, 3.65 mL, 0.05 mol). Subsequently, 3-(N,N-diethylamino)phenol (0.01 mmol) dissolved in DMF (6 mL) was slowly added to the above cooled mixture at the same temperature. The reaction mixture was stirred at a constant temperature at 75 °C for 4 hours. After the reaction was completed, the mixture was cooled to room temperature and slowly poured into 60 mL of ice water. The reaction mixture was neutralized with sodium carbonate solution and a brown solid precipitated. The solid product was collected by filtration, washed with cold water, dried and recrystallized from ethanol to give the pure 4-(diethylamino)salicylaldehyde in 80% yield with a melting point of 62 °C (literature value: 62 °C).

References

[1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 12, p. 2575 - 2584
[2] Journal of Fluorescence, 2015, vol. 25, # 6, p. 1615 - 1628
[3] Chemical Communications, 2016, vol. 52, # 60, p. 9434 - 9437
[4] Chemistry Letters, 2011, vol. 40, # 3, p. 279 - 281
[5] Patent: US2789125, 1953,

4-(Diethylamino)salicylaldehyde(17754-90-4)Related Product Information

• 2,4-Dihydroxybenzaldehyde
• 4-Aminobenzaldehyde
• 4-Aminoacetophenone
• 4-Dimethylaminobenzaldehyde
• 3-Hydroxybenzaldehyde
• 2-Aminoacetophenone
• 4-Diethylaminobenzaldehyde
• 1-Hydroxyethylidene-1,1-diphosphonic acid
• Acetaminophen
• Taurine
• 4-Hydroxybenzaldehyde
• Salicylaldehyde
• Diethylaminoethanol
• ACETAMINOPHENOL BP/USP
• Dimethylaminobenzaldehyde
• 4-(Diethylamino)salicylaldehyde
• 4-(N,N-DIETHYLAMINO)SALICYLALDEHYDE