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3-Nitrobenzaldehyde

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(Redirected from 3-nitrobenzaldehyde)
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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.520 Edit this at Wikidata
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 diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)

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

3-Nitrobenzaldehyde is the primary product obtained via the mono-nitration of benzaldehyde with nitric acid.[3]

C6H5CHO + HNO3 → O2NC6H4CHO + H2O

Product distribution is about 19% for the ortho-, 72% for the meta- and 9% for the para isomers.

Uses

[edit]

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.[4]

References

[edit]
  1. ↑ 3-Nitrobenzaldehyde
  2. ↑ "3-Nitrobenzaldehyde MSDS". Retrieved 2009-07-18.{{cite web}}: CS1 maint: deprecated archival service (link)
  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. ↑ Johannes S. Buck and Walter S. Ide (1933). "m-Chlorobenzaldehyde". Organic Syntheses. 13: 28. doi:10.15227/orgsyn.013.0028.
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