3-Nitrobenzaldehyde

3-Nitrobenzaldehyde is an organic aromatic compound containing a nitro group meta-substituted to an aldehyde. 3-Nitrobenzaldehyde is the primary product obtained via the mono-nitration of benzaldehyde with nitric acid.

3-Nitrobenzaldehyde[1][2]
Skeletal formula of 3-nitrobenzaldehyde
Ball-and-stick model of the 3-nitrobenzaldehyde molecule
Names
Preferred IUPAC name
3-Nitrobenzaldehyde
Other names
m-Nitrobenzaldehyde, meta-nitrobenzaldehyde
Properties
C7H5NO3
Molar mass 151.121 g·mol−1
Appearance Yellowish to brownish crystalline powder or granulate
Melting point 58.5 °C (137.3 °F; 331.6 K)
Boiling point 164 °C (327 °F; 437 K) at 23 mmHg
16.3 mg/mL
-68.55·10−6 cm3/mol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.520
EC Number
  • 202-772-6
UNII
  • InChI=1S/C7H5NO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-5H checkY
    Key: ZETIVVHRRQLWFW-UHFFFAOYSA-N checkY
  • InChI=1/C7H5NO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-5H
    Key: ZETIVVHRRQLWFW-UHFFFAOYAC
  • O=[N+]([O-])c1cc(C=O)ccc1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Harmful,Potentially mutagenic
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H315, H319, H335, H411
P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
2
1
0
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 ?)
Infobox references

Synthesis

The synthesis of 3-nitrobenzaldehyde is accomplished via nitration of benzaldehyde, which yields mostly the meta-isomer. Product distribution is about 19% for the ortho-, 72% for the meta- and 9% for the para isomers.[3][4]

Uses

3-Nitrobenzaldehyde is a precursor to the drug Tipranavir. It is a mainstay in the synthesis of Dihydropyridine calcium channel blockers. Via selective reduction of the nitro group, it is a precursor to the diazonium salt.[5]

References
  1. 3-Nitrobenzaldehyde
  2. "3-Nitrobenzaldehyde MSDS". Archived from the original on 2011-07-07. Retrieved 2009-07-18.
  3. Structure of Benzene, California State University Dominguez Hills
  4. Brühne, Friedrich; Wright, Elaine (2011). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_463.pub2.
  5. Johannes S. Buck and Walter S. Ide (1933). "m-Chlorobenzaldehyde". Organic Syntheses. 13: 28. doi:10.15227/orgsyn.013.0028.
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