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| | 4-Diethylaminobenzaldehyde Basic information |
| | 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) | | Fp | >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 | | InChI | 1S/C11H15NO/c1-3-12(4-2)11-7-5-10(9-13)6-8-11/h5-9H,3-4H2,1-2H3 | | InChIKey | MNFZZNNFORDXSV-UHFFFAOYSA-N | | SMILES | [H]C(=O)c1ccc(cc1)N(CC)CC | | 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) |
| 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 | TSCA listed | | HS Code | 29223990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Dermal
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 | | Toxicity | mouse,LD50,intraperitoneal,700mg/kg (700mg/kg),National Technical Information Service. Vol. OTS0534444, |
| | 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 |
| | 4-Diethylaminobenzaldehyde Preparation Products And Raw materials |
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