4'-DIETHYLAMINOPHENYL ACETYLENE Chemical Properties

Melting point:

23-24 °C

Boiling point:

84-85 °C(Press: 0.5 Torr)

Density 

0.96±0.1 g/cm3(Predicted)

Flash point:

104 °C

storage temp. 

2-8°C

pka

4.86±0.32(Predicted)

CAS DataBase Reference

41876-70-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-36

Safety Statements 

26-36/37/39

HS Code 

2921490090

4'-DIETHYLAMINOPHENYL ACETYLENE Usage And Synthesis

Synthesis

General procedure for the synthesis of 4'-diethylaminophenylacetylene from N,N-diethyl-4-((trimethylsilyl)ethynyl)aniline: a mixture of N,N-diethyl-4-((trimethylsilyl)ethynyl)aniline (500 mg, 2.03 mmol), potassium carbonate (K2CO3, 1.5 g, 10.8 mmol), and methanol (30 mL) was reacted at 65 C for 30 hours with stirring. After completion of the reaction, the reaction mixture was cooled, poured into water and extracted with ethyl acetate (50 mL × 3). The organic extracts were combined and dried with anhydrous magnesium sulfate (MgSO4). Subsequently, the solvent was removed under reduced pressure to give the crude product. The crude product was chromatographed on a short silica gel column and further purified using a gradient elution of hexane/ethyl acetate (0-5%), and the final product was isolated as a semi-solid. Yield: 250 mg (72.2%). The product characterization data were as follows: IR (pure) 2971, 2098, 1607, 1551 cm-1; 1H NMR (400 MHz, CDCl3) δ 7.36 (d, J = 8.4 Hz, 2H), 6.59 (d, J = 8.4 Hz, 2H), 3.36 (q, J = 6.8 Hz, 4H), 1.16 (t, J = 6.8 Hz. 6H); 13C NMR (100 MHz, CDCl3) δ 147.68, 133.31, 110.90, 107.46, 84.96, 74.38, 44.19, 12.41.

References

[1] European Journal of Organic Chemistry, 2012, # 14, p. 2756 - 2765
[2] Chemical Communications, 2003, # 17, p. 2146 - 2147
[3] Organic Letters, 2003, vol. 5, # 11, p. 1841 - 1844
[4] Patent: US2010/29952, 2010, A1. Location in patent: Page/Page column 38
[5] Journal of the American Chemical Society, 2003, vol. 125, # 24, p. 7156 - 7157

4'-DIETHYLAMINOPHENYL ACETYLENE(41876-70-4)Related Product Information

• Phenylacetylene
• N,N-Diethylaniline
• 4'-N-PIPERIDINOPHENYL ACETYLENE
• 5-DIETHYLAMINO-2-ETHYNYL-PHENOL
• 4'-DIETHYLAMINOPHENYL ACETYLENE
• 4'-DIMETHYLAMINOPHENYL ACETYLENE
• 2-[(4-ETHYNYL-PHENYL)-(2-HYDROXY-ETHYL)-AMINO]-ETHANOL
• 4-ETHYNYLANILINE