3-Nitrobenzoic acid

3-Nitrobenzoic acid
IUPAC name 3-nitrobenzoic acid
Other names m-nitrobenzoic acid
Identifiers
CAS number	121-92-6 Y
PubChem	8497
ChemSpider	8183 Y
ChEMBL	CHEMBL274839 Y
Jmol-3D images	{{#if:O=[N+]([O-])c1cc(C(=O)O)ccc1|Image 1
SMILES O=[N+]([O-])c1cc(C(=O)O)ccc1
InChI InChI=1S/C7H5NO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10) Y Key: AFPHTEQTJZKQAQ-UHFFFAOYSA-N Y InChI=1/C7H5NO4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10) Key: AFPHTEQTJZKQAQ-UHFFFAOYAS
Properties
Molecular formula	C7H5NO4
Molar mass	167.12 g/mol
Density	1.494
Melting point	139-141 °C
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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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

Preparation and properties

It is prepared by nitration of benzoic acid, together with significant amounts of 2-nitrobenzoic acid. With a pK_a of 3.47,^[1] 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. ↑ 1.0 1.1 "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.