3-Nitrobenzaldehyde

3-Nitrobenzaldehyde, meta-nitrobenzaldehyde or m-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]
Names
Preferred IUPAC name
3-Nitrobenzaldehyde
Other names
m-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 Y
    Key: ZETIVVHRRQLWFW-UHFFFAOYSA-N Y
  • 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:
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)
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 YN ?)
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]

Uses

A known use of 3-Nitrobenzaldehyde is in the synthesis of Tipranavir.

3-Nitrobenzaldehyde is a mainstay in the synthesis of Dihydropyridine calcium channel blockers.

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
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