4-Diethylaminobenzaldehyde Chemical Properties

Melting point:

37-41 °C(lit.)

Boiling point:

174 °C7 mm Hg(lit.)

Density 

1.03 g/cm3

refractive index 

1.5302 (estimate)

Flash point:

>230 °F

storage temp. 

Store below +30°C.

solubility 

2.5g/l

pka

3.36±0.32(Predicted)

form 

Coarse Crystals, Chunks or Crystalline Solid

color 

Brown to green to black

Water Solubility 

insoluble

Sensitive 

Air Sensitive

BRN 

511102

CAS DataBase Reference

120-21-8(CAS DataBase Reference)

NIST Chemistry Reference

Benzaldehyde, 4-(diethylamino)-(120-21-8)

EPA Substance Registry System

Benzaldehyde, 4-(diethylamino)- (120-21-8)

Safety Information

Hazard Codes 

Xi,N,Xn

Risk Statements 

36/37/38-50/53-21/22

Safety Statements 

26-36-61-60-36/37

WGK Germany 

2

RTECS 

CU5612850

TSCA 

Yes

HS Code 

29223990

Toxicity

mouse,LD50,intraperitoneal,700mg/kg (700mg/kg),National Technical Information Service. Vol. OTS0534444,

MSDS

• Language:English Provider:4-Diethylaminobenzaldehyde
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Diethylaminobenzaldehyde Usage And Synthesis

Chemical Properties

dark brown to green coarse crystals or

Uses

4-Diethylaminobenzaldehyde is used in the preparation of 5-(4-diethylamino-benzylidene)-selenazolidine-2,4-dione by using aqueous methylamine as a reagent.

Definition

ChEBI: A member of the class of benzaldehydes carrying a diethylamino substituent at position 4.

Synthesis

GENERAL STEPS: 4-Fluorobenzaldehyde (2.5 g, 20 mmol), diethylamine (5.12 g, 70 mmol), potassium carbonate (4.15 g), dimethylsulfoxide (25.0 mL), and Aliquat-336 (0.05 mL) were added to a 100 mL single-necked flask equipped with a stirrer and condenser. The reaction mixture was stirred at 95°C for 72 hours and subsequently cooled to room temperature. Upon addition of ice water, a yellow precipitate precipitated. The crude product was washed 2-3 times with cold water and recrystallized by ethanol to give N,N-diethyl-4-aminobenzaldehyde as a yellow solid. Yield: 92%. Elemental analysis calculated values (C11H15NO): C, 74.54; H, 8.53; N, 7.90; measured values: C, 74.67; H, 8.58; N, 7.85. 1H NMR (500 MHz, CDCl3, ppm) δ 9.71 (s, 1H), 7.72 (q, 2H), 6.69 (d, J = 8.8 Hz, 2H) , 3.46 (q, 4H), 1.24 (t, 6H). Step 2: Potassium metal (0.78 g, 20 mmol) was added to tert-butanol (11.3 mL, 120 mmol) in a 50 mL single-neck flask equipped with a condenser. After the potassium was fully reacted, 4-methylpyridine (0.975 mL, 10 mmol) and N,N-diethyl-4-aminobenzaldehyde (1.77 g, 10 mmol) were added. The mixture was heated with stirring at 80°C for 2 hours. After evaporation to remove the tert-butanol, 200 mL of dichloromethane was added and washed once with 200 mL of ice water. The aqueous phase was extracted three times with dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, the solvent was evaporated and the crude product was recrystallized from toluene. Yield: 86%.1H NMR (500 MHz, DMSO, ppm) δ 8.43 (d, J = 5.2 Hz, 2H), 7.42 (t, J = 8.8 Hz, 2H), 7.23 (d, J = 5.4 Hz, 2H), 7.04 (d, J = 8.7 Hz, 2H), 6.27-6.66 (m, 2H), 3.39 (m, 4H), 1.13 (m, 4H). 4H), 1.13 (t, 6H).13C NMR (500 MHz, CDCl3, ppm) δ 148.56-146.96 (m, py), 134.57 (s, py), 128.86 (s, benzene), 120.51-119.95 (d, benzene), 111.56 (s, CH=CH), 44.47 (s, CH2), 12.62 (d, J = 8.7 Hz, 2H), 6.27-6.66 (m, 2H), 3.39 (m, 2H), 3.39 (m, 6H). CH2), 12.62 (s, CH3). Calculated elemental analysis (C17H20N2, EI-MS: 253.3): C, 80.91; H, 7.99; N, 11.10; measured: C, 80.76; H, 7.91; N, 11.01. IR (KBr, cm-1): 3026 w, 2974 m, 1581 s, 1520 vs, 1408 m, 1355 m. 1329 w, 1272 m, 1185 m, 1158 m, 1074 w, 972 w, 818 m, 795 m, 518 w. Melting Point: 258°C.

References

[1] Dyes and Pigments, 2015, vol. 120, p. 175 - 183
[2] Journal of Molecular Structure, 2007, vol. 829, # 1-3, p. 202 - 207
[3] Journal of Materials Chemistry, 2012, vol. 22, # 33, p. 16927 - 16932
[4] Journal of Medicinal Chemistry, 2012, vol. 55, # 19, p. 8483 - 8492,10
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 19, p. 8483 - 8492

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