3-Nitrobenzoic acid

3-Nitrobenzoic acid

Names
IUPAC name 3-nitrobenzoic acid
Other names m-nitrobenzoic acid
Identifiers
CAS Number	121-92-6
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL274839
ChemSpider	8183
ECHA InfoCard	100.004.099
PubChem	8497
InChI InChI=1S/C7H5NO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10) Key: AFPHTEQTJZKQAQ-UHFFFAOYSA-N InChI=1/C7H5NO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10) Key: AFPHTEQTJZKQAQ-UHFFFAOYAS
SMILES O=[N+]([O-])c1cc(C(=O)O)ccc1
Properties
Chemical formula	C7H5NO4
Molar mass	167.12 g/mol
Appearance	cream-colored solid
Density	1.494 g/cm^3
Melting point	139 to 141 °C (282 to 286 °F; 412 to 414 K)
Solubility in water	0.24 g/100 mL (15 °C)
Acidity (pKa)	3.47 (in water)[1]
Related compounds
Related compounds	Benzoic acid Nitrobenzene Anthranilic acid 3,5-Dinitrobenzoic acid 2-Nitrobenzoic acid 4-Nitrobenzoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

3-Nitrobenzoic acid is an organic compound with the formula C₆H₄(NO₂)CO₂H. It is an off-white solid. It is a precursor to 3-aminobenzoic acid, which is used to prepare some dyes.^[2] With a pK_a of 3.47,^[1]

Preparation

It is prepared by nitration of benzoic acid. 2-Nitrobenzoic acid is a major side product. A less efficient but cleaner route involves nitration of methyl benzoate, followed by hydrolysis.^[3]

3-nitrobenzoic acid is about 10x more acidic than benzoic acid.

Safety

The compound is likely of modest toxicity, with LD₅₀ (i.v. mouse) of 640 mg/kg.

References

1. "Dissociation Constants Of Organic Acids And Bases". Retrieved 11 April 2010.
2. Takao Maki, Kazuo Takeda "Benzoic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_555.
3. Oliver Kamm and J. B. Segur "m-Nitrobenzoic Acid" Org. Synth. 1923, volume 3, 73.doi:10.15227/orgsyn.003.0073