2-Nitrocinnamaldehyde
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IUPAC name
(E)-3-(2-Nitrophenyl)prop-2-enal
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3D model (JSmol)
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Properties | |
C9H7O3N | |
Appearance | Pale yellow crystalline powder |
Melting point | 124 to 126 °C (255 to 259 °F; 397 to 399 K) |
Slightly soluble | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Nitrocinnamaldehyde, ortho-nitrocinnamaldehyde or o-nitrocinnamaldehyde is an organic aromatic compound containing a nitro group ortho- to the 1-position of cinnamaldehyde.
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.
References
- ^ http://www.21cnlab.com/chemdict/MSDS/62967.html 2-Nitrocinnamaldehyde MSDS
- ^ http://www.orgsyn.org/orgsyn/prep.asp?rxntypeid=181&prep=CV4P0722