3-Nitrobenzaldehyde

Last updated
3-Nitrobenzaldehyde [1] [2]
3-nitrobenzaldehyde.svg
3-Nitrobenzaldehyde-3D-balls.png
Names
Preferred IUPAC name
3-Nitrobenzaldehyde
Other names
m-Nitrobenzaldehyde, meta-nitrobenzaldehyde
Properties
C7H5NO3
Molar mass 151.121 g·mol−1
AppearanceYellowish 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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-772-6
PubChem CID
UNII
  • InChI=1S/C7H5NO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-5H Yes check.svgY
    Key: ZETIVVHRRQLWFW-UHFFFAOYSA-N Yes check.svgY
  • 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:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
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.svgHealth 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 mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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

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]

Related Research Articles

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In organic chemistry, xylene or xylol are any of three organic compounds with the formula (CH3)2C6H4. They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are substituted determines which of three structural isomers results. It is a colorless, flammable, slightly greasy liquid of great industrial value.

<span class="mw-page-title-main">Nitration</span> Chemical reaction which adds a nitro (–NO₂) group onto a molecule

In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid. The difference between the resulting molecular structures of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, whereas in nitrate esters, the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom.

Benzonitrile is the chemical compound with the formula C6H5(CN), abbreviated PhCN. This aromatic organic compound is a colorless liquid with a sweet bitter almond odour. It is mainly used as a precursor to the resin benzoguanamine.

<span class="mw-page-title-main">Cinnamic acid</span> Chemical compound

Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.

Arene substitution patterns are part of organic chemistry IUPAC nomenclature and pinpoint the position of substituents other than hydrogen in relation to each other on an aromatic hydrocarbon.

<span class="mw-page-title-main">Povarov reaction</span> Chemical reaction

The Povarov reaction is an organic reaction described as a formal cycloaddition between an aromatic imine and an alkene. The imine in this organic reaction is a condensation reaction product from an aniline type compound and a benzaldehyde type compound. The alkene must be electron rich which means that functional groups attached to the alkene must be able to donate electrons. Such alkenes are enol ethers and enamines. The reaction product in the original Povarov reaction is a quinoline. Because the reactions can be carried out with the three components premixed in one reactor it is an example of a multi-component reaction.

Chlorotoluenes are aryl chlorides based on toluene in which at least one aromatic hydrogen atom is replaced with a chlorine atom. They have the general formula C7H8–nCln, where n = 1–5 is the number of chlorine atoms.

<span class="mw-page-title-main">1,2-Dichlorobenzene</span> Chemical compound

1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. This colourless liquid is poorly soluble in water but miscible with most organic solvents. It is a derivative of benzene, consisting of two adjacent chlorine atoms.

3-Nitrobenzoic acid is an organic compound with the formula C6H4(NO2)CO2H. It is an aromatic compound and under standard conditions, it is an off-white solid. The two substituents are in a meta position with respect to each other, giving the alternative name of m-nitrobenzoic acid. This compound can be useful as it is a precursor to 3-aminobenzoic acid, which is used to prepare some dyes.

<span class="mw-page-title-main">2-Nitroaniline</span> Chemical compound

2-Nitroaniline is an organic compound with the formula H2NC6H4NO2. It is a derivative of aniline, carrying a nitro functional group in position 2. It is mainly used as a precursor to o-phenylenediamine.

<span class="mw-page-title-main">4-Nitroaniline</span> Chemical compound

4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. A yellow solid, it is one of three isomers of nitroaniline. It is an intermediate in the production of dyes, antioxidants, pharmaceuticals, gasoline, gum inhibitors, poultry medicines, and as a corrosion inhibitor.

Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and one of the most industrially useful.

<span class="mw-page-title-main">2-Nitrobenzaldehyde</span> Chemical compound

2-Nitrobenzaldehyde is an organic compound with the formula O2NC6H4CHO. It is one of three isomers of nitrobenzaldehyde. It contains a nitro group adjacent to the formyl group.

α-Phenylcinnamic acid Chemical compound

α-Phenylcinnamic acid is a phenylpropanoid, or, more specifically, a derivative of cinnamic acid. It has the formula C15H12O2 and appears as an off-white crystalline solid.

<span class="mw-page-title-main">4-Nitrobenzaldehyde</span> Chemical compound

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.

3-Nitrotoluene or meta-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is one of three isomers of nitrotoluene. A yellow liquid, it is used in the manufacture of meta-toluidine, which is an intermediate in the production of various dyes.

<span class="mw-page-title-main">1,3-Dinitrobenzene</span> Chemical compound

1,3-Dinitrobenzene is one of three isomers of dinitrobenzene, with the formula C6H4(NO2)2. It is one of three isomers of dinitrobenzene. The compound is a yellow solid that is soluble in organic solvents.

<span class="mw-page-title-main">2-Nitrochlorobenzene</span> Chemical compound

2-Nitrochlorobenzene is an organic compound with the formula ClC6H4NO2. It is one of three isomeric nitrochlorobenzenes. It is a yellow crystalline solid that is important as a precursor to other compounds due to its two functional groups.

<span class="mw-page-title-main">3-Nitrochlorobenzene</span> Chemical compound

3-Nitrochlorobenzene is an organic compound with the formula C6H4ClNO2. It is a yellow crystalline solid that is important as a precursor to other compounds due to the two reactive sites present on the molecule.

β-Nitrostyrene Chemical compound

β-Nitrostyrene is an aromatic compound and a nitroalkene used in the synthesis of indigo dye and the slimicide bromo-nitrostyrene.

References

  1. ↑ 3-Nitrobenzaldehyde
  2. ↑ "3-Nitrobenzaldehyde MSDS". Archived from the original on 2011-07-07. Retrieved 2009-07-18.
  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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