3-Nitroaniline

3-Nitroaniline
Names
	Preferred IUPAC name 3-Nitroaniline
	Systematic IUPAC name 3-Nitrobenzenamine
	Other names meta-Nitroaniline; m-Nitroaniline
Identifiers
CAS Number	99-09-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL14068 ;
ChemSpider	7145 ;
ECHA InfoCard	100.002.481
EC Number	202-729-1;
PubChem CID	7423;
RTECS number	BY6825000;
UNII	CM50SM561T;
UN number	1661
CompTox Dashboard (EPA)	DTXSID6025725;
	InChI InChI=1S/C6H6N2O2/c7-5-2-1-3-6(4-5)8(9)10/h1-4H,7H2 Key: XJCVRTZCHMZPBD-UHFFFAOYSA-N ; InChI=1/C6H6N2O2/c7-5-2-1-3-6(4-5)8(9)10/h1-4H,7H2 Key: XJCVRTZCHMZPBD-UHFFFAOYAY;
	SMILES O=[N+]([O-])c1cccc(N)c1;
Properties
Chemical formula	C6H6N2O2
Molar mass	138.126 g·mol−1
Appearance	Yellow solid
Density	0.9011
Melting point	114 °C (237 °F; 387 K)
Boiling point	306 °C (583 °F; 579 K)
Solubility in water	0.1 g/100 ml (20 °C)
Acidity (pKa)	2.47
Magnetic susceptibility (χ)	-70.09·10−6 cm3/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H331, H373, H412
Precautionary statements	P260, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P314, P321, P322, P330, P361, P363, P403+P233, P405, P501
Related compounds
Related compounds	2-Nitroaniline, 4-Nitroaniline
	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-Nitroaniline is an organic compound with the formula H₂NC₆H₄NO₂. A yellow solid, it is a derivative of aniline, carrying a nitro functional group in position 3. It is an isomer of 2-nitroaniline and 4-nitroaniline. It is used as a precursor to dyes.^[1]

Synthesis and applications

Structure of disperse yellow 5, a disperse dye derived from 3-nitroaniline.

3-Nitroaniline is produced on a commercial scale by reduction of 1,3-dinitrobenzene with hydrogen sulfide:^[1]

In principle it can also be prepared by nitration of benzamide followed by the Hofmann rearrangement of the resulting 3-nitrobenzamide. The reaction involves treating the 3-nitrobenzamide with sodium hypobromite or sodium hypochlorite to transform the amide group into an amine.

It is used as a chemical intermediate for azo coupling component 17 and the dyes disperse yellow 5 and acid blue 29. The chemical is changed to other substances (dyestuffs and m-nitrophenol) during the dyeing process.

References

1 2 Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.

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[Booth-1] 1 2 Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.

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