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1-(4-Nitrophenyl)-1-octyne

Department of Chemistry, Southeast Missouri State University, MS 6400, One University Plaza, Cape Girardeau, Missouri, 63701, USA
*
Author to whom correspondence should be addressed.
Molecules 2000, 5(7), M171; https://doi.org/10.3390/M171
Submission received: 27 June 2000 / Accepted: 17 July 2000 / Published: 30 July 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 05 m171 i001
Following the procedure of Takahashi, et al (1), to a mixture of 1-iodo-4-nitrobenzene (7.76 mmol, 1.90g) and 1-octyne (9.3 mmol, 1.023g) in diethylamine (40 mL) are added bis[triphenylphosphine]palladium dichloride (0.2mmol, 0.14g) and copper(I) iodide (0.1mmol, 0.01g). The reaction is stirred at room temperature under a nitrogen atmosphere for 24 hours. The solvent is then removed by rotary evaporation. The remaining solution is suspended in petroleum ether. The resulting suspension is filtered, and the solvent removed. The crude oily product is purified by means of column chromatography using a 19:1 petroleum ether: diethyl ether as the eluent. Yield: 1.17g (65.6%)
IR (NaCl plates, cm-1): 3080, 2931, 2858, 2227, 1594, 1518, 1342, 1108, 854, 750, 734, 688.
1H-NMR (300 MHz, CDCl3): 0.83 (3H, t, J=6.87 Hz), 1.25 (4H, m), 1.38 (2H, m), 1.53 (2H, q, J=7.38 Hz), 7.43 (2H, d, J=8.94), 8.07 (2H, d, J=8.94).
13C-NMR (75.5 MHz, CDCl3): 146.88, 132.52, 131.56, 123.73, 97.08, 79.62, 31.69, 28.99, 28.76, 22.91, 19.88, 14.34.
GC-MS (ion trap, m/e, in order of decreasing peak size): 128, 142, 232 (M + 1), 202, 115, 116, 156, 215, 102, 188.

Supplementary Materials

Reference

  1. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627–630. [CrossRef]
Sample Availability: Available from the authors.

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MDPI and ACS Style

Hathaway, B.A.; Blanner, S.W. 1-(4-Nitrophenyl)-1-octyne. Molecules 2000, 5, M171. https://doi.org/10.3390/M171

AMA Style

Hathaway BA, Blanner SW. 1-(4-Nitrophenyl)-1-octyne. Molecules. 2000; 5(7):M171. https://doi.org/10.3390/M171

Chicago/Turabian Style

Hathaway, Bruce A., and Steven W. Blanner. 2000. "1-(4-Nitrophenyl)-1-octyne" Molecules 5, no. 7: M171. https://doi.org/10.3390/M171

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