Chemistry:3-Nitrobenzaldehyde

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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
EC Number
  • 202-772-6
UNII
Hazards
Main hazards Harmful,Potentially mutagenic
GHS pictograms GHS07: HarmfulGHS09: Environmental hazard
GHS Signal word Warning
H302, H315, H319, H335, H411
P261, P264, P270, P271, P273, P280, P301+312, P302+352, P304+340, P305+351+338, P312, P321, P330, P332+313, P337+313, P362, P391, P403+233, P405, P501
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
2
0
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
Tracking categories (test):

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.

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". http://www.21cnlab.com/chemdict/MSDS/62565.html. 
  3. ↑ Structure of Benzene, California State University Dominguez Hills
  4. ↑ Brühne, Friedrich; Wright, Elaine (2011). "Ullmann's Encyclopedia of Industrial Chemistry". 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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