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.

2-Nitrocinnamaldehyde[1]

Names
IUPAC name (E)-3-(2-Nitrophenyl)prop-2-enal
Identifiers
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL53723
ChemSpider	4518729
PubChem CID	5367122
InChI InChI=1S/C9H7NO3/c11-7-3-5-8-4-1-2-6-9(8)10(12)13/h1-7H/b5-3+ Key: VMSMELHEXDVEDE-HWKANZROSA-N InChI=1/C9H7NO3/c11-7-3-5-8-4-1-2-6-9(8)10(12)13/h1-7H/b5-3+ Key: VMSMELHEXDVEDE-HWKANZROBN
SMILES O=[N+]([O-])c1ccccc1\C=C\C=O
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
Hazards
S-phrases (outdated)	S24 S25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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Infobox references

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

1. http://www.21cnlab.com/chemdict/MSDS/62967.html 2-Nitrocinnamaldehyde MSDS
2. http://www.orgsyn.org/orgsyn/prep.asp?rxntypeid=181&prep=CV4P0722