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 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

^ 3-Nitrobenzaldehyde
^ "3-Nitrobenzaldehyde MSDS". Archived from the original on 2011-07-07. Retrieved 2009-07-18.
^ Structure of Benzene, California State University Dominguez Hills
^ Brühne, Friedrich; Wright, Elaine (2011). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_463.pub2. ISBN 978-3527306732.
^ 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] Structure of Benzene, California State University Dominguez Hills

[4] Brühne, Friedrich; Wright, Elaine (2011). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_463.pub2. ISBN 978-3527306732.

[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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