3-Nitrobenzaldehyde

3-Nitrobenzaldehyde^[1]^[2]
Names
	Preferred IUPAC name 3-Nitrobenzaldehyde
	Other names m-Nitrobenzaldehyde, meta-nitrobenzaldehyde
Properties
Chemical formula	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
Solubility in water	16.3 mg/mL
Magnetic susceptibility (χ)	-68.55·10−6 cm3/mol
Identifiers
CAS Number	99-61-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:231487;
ChEMBL	ChEMBL238132 ;
ChemSpider	7169 ;
ECHA InfoCard	100.002.520
EC Number	202-772-6;
PubChem CID	7449;
UNII	G4O92KO71Z ;
CompTox Dashboard (EPA)	DTXSID8049383 ;
	InChI InChI=1S/C7H5NO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-5H Key: ZETIVVHRRQLWFW-UHFFFAOYSA-N ; InChI=1/C7H5NO3/c9-5-6-2-1-3-7(4-6)8(10)11/h1-5H Key: ZETIVVHRRQLWFW-UHFFFAOYAC;
	SMILES O=[N+]([O-])c1cc(C=O)ccc1;
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Harmful,Potentially mutagenic
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335, H411
Precautionary statements	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). verify (what is ?) Infobox references

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]

O₂NC₆H₄CH₃ + O₂ → 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]

References

^ 3-Nitrobenzaldehyde
^ "3-Nitrobenzaldehyde MSDS". Archived from the original on 2011-07-07. Retrieved 2009-07-18.
^ 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.
^ Johannes S. Buck and Walter S. Ide (1933). "m-Chlorobenzaldehyde". Organic Syntheses. 13: 28. doi:10.15227/orgsyn.013.0028.

[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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