2-Nitrocinnamaldehyde
2-Nitrocinnamaldehyde, ortho-nitrocinnamaldehyde or o-nitrocinnamaldehyde is an organic aromatic compound containing a nitro group ortho- to the 1-position of cinnamaldehyde.
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| IUPAC name
(E)-3-(2-Nitrophenyl)prop-2-enal | |
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| Properties | |
Chemical formula |
C9H7O3N |
| Appearance | Pale yellow crystalline powder |
| Melting point | 124 to 126 °C (255 to 259 °F; 397 to 399 K) |
Solubility in water |
Slightly soluble |
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| S-phrases (outdated) | S24 S25 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Synthesis
2-Nitrocinnamaldehyde can be synthesized by dissolving cinnamaldehyde to a solution of acetic anhydride in acetic acid, and adding a stoichiometric amount of concentrated nitric acid at 0–5 °C. Yields are around 36-46% of theoretical.
Nitration of cinnamaldehyde via acidification of a nitrate salt with H2SO4 also yields the ortho-nitro compound, however it also yields some of the para-nitro compound, which is generally undesired.
2-Nitrocinnamaldehyde can also be prepared by reacting 2-nitrobenzaldehyde with acetaldehyde in a condensation reaction.[2]
Uses
2-Nitrocinnamaldehyde can be oxidized to 2-nitrocinnamic acid which can be used in the Baeyer-Emmerling indole synthesis to produce indole and substituted indoles.