4-Nitrobenzaldehyde is an organic compound with the formula O2NC6H4CHO. It is one of three isomers of nitrobenzaldehyde. It contains a nitro group para-substituted to an aldehyde.

4-Nitrobenzaldehyde
Skeletal formula of 4-nitrobenzaldehyde
Ball-and-stick model of the 4-nitrobenzaldehyde molecule
Names
Preferred IUPAC name
4-Nitrobenzaldehyde
Other names
p-Nitrobenzaldehyde
Properties
C7H5NO3
Molar mass 151.121 g·mol−1
Appearance slightly yellowish crystalline powder
Density 1.546 g/cm3[1]
Melting point 103 to 106 °C (217 to 223 °F; 376 to 379 K)[2]
Boiling point 300 °C (572 °F; 573 K)[1]
-66.57·10−6 cm3/mol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.259 Edit this at Wikidata
UNII
  • InChI=1S/C7H5NO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5H checkY
    Key: BXRFQSNOROATLV-UHFFFAOYSA-N checkY
  • InChI=1/C7H5NO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5H
    Key: BXRFQSNOROATLV-UHFFFAOYAO
  • O=[N+]([O-])c1ccc(C=O)cc1
Hazards
GHS labelling:
GHS07: Exclamation mark[2]
H317, H319
P280, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

4-Nitrobenzaldehyde is obtained by air-oxidation of 4-nitrotoluene according the following idealized equation:[3]

O2NC6H4CH3 + O2 → O2NC6H4CHO + H2O

In the laboratory, this oxidation can be achieved with chromium(VI) oxide in acetic anhydride, which affords nitrobenzyldiacetate.[4]

References

edit
  1. ^ a b 4-Nitrobenzaldehyde(555-16-8) (Date Accessed 17 April 2013)
  2. ^ a b Sigma-Aldrich Co., 4-Nitrobenzaldehyde. Retrieved on 4 May 2011.
  3. ^ Brühne, Friedrich; Wright, Elaine (2011). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a03_463.pub2. ISBN 978-3-527-30385-4.
  4. ^ Lieberman, S. V.; Connor, Ralph (1938). "p-Nitrobenzaldehyde". Organic Syntheses. 18: 61. doi:10.15227/orgsyn.018.0061.