| Identification | More | [Name]
4'-DIETHYLAMINOPHENYL ACETYLENE | [CAS]
41876-70-4 | [Synonyms]
4-Ethynyl-N,N-diethylaniline
N,N-Diethyl-4-ethynylaniline
4'-DIETHYLAMINOPHENYL ACETYLENE
N,N-DIETHYL-4-ETHYNYLBENEZEAMINE
N,N-DIETHYL-4-ETHYNYLBENZENAMINE
DIETHYL-(4-ETHYNYL-PHENYL)-AMINE
Benzenamine, N,N-diethyl-4-ethynyl- | [Molecular Formula]
C12H15N | [MDL Number]
MFCD00168817 | [Molecular Weight]
173.25 | [MOL File]
41876-70-4.mol |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H319 | [Precautionary statements ]
P264-P280-P305+P351+P338-P337+P313P | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [HS Code ]
2921490090 |
| Hazard Information | Back Directory | [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 |
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