2-Nitrocinnamaldehyde

changed 477214896 http://www.21cnlab.com/chemdict/MSDS/62967.html https://web.archive.org/web/20110707061740/http://www.21cnlab.com/chemdict/MSDS/62967.html 2011-07-07 2-Nitrocinnamaldehyde MSDS 2-nitrocinnamaldehyde.svg 160px (2E)-3-(2-Nitrophenyl)prop-2-enal 1466-88-2 correct CAS 66894-06-2 correct CAS (E) correct FDA 72Y4RH8QTA correct EBI 53723 correct chemspider 4518729 215-988-0 5367122 1/C9H7NO3/c11-7-3-5-8-4-1-2-6-9(8)10(12)13/h1-7H/b5-3+ correct chemspider 1S/C9H7NO3/c11-7-3-5-8-4-1-2-6-9(8)10(12)13/h1-7H/b5-3+ O=[N+]([O-])c1ccccc1\C=C\C=O VMSMELHEXDVEDE-HWKANZROBN correct chemspider VMSMELHEXDVEDE-HWKANZROSA-N C9H7O3N Pale yellow crystalline powder 124 to 126 Slightly soluble 07 Warning 315 319 335 261 264 271 280 302+352 304+340 305+351+338 312 321 332+313 337+313 362 403+233 405 501 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.http://www.orgsyn.org/orgsyn/prep.asp?rxntypeid=181&prep=CV4P0722 Organic Syntheses 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 Category:Aldehydes Category:2-Nitrophenyl compounds