Nitrobenzoic acids are derivatives of

benzoic acid Benzoic acid is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, wh ...

. Two are commercially important. They are about ten times more acidic than the parent benzoic acid.Takao Maki, Kazuo Takeda "Benzoic Acid and Derivatives" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2002, Wiley-VCH, Weinheim. Nitrobenzoic acid can be prepared through the oxidation of

styrene Styrene () is an organic compound with the chemical formula C6H5CH=CH2. This derivative of benzene is a colorless oily liquid, although aged samples can appear yellowish. The compound evaporates easily and has a sweet smell, although high concen ...

in boiling nitric acid. The

salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively cha ...

and

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

s of nitrobenzoic acids are known as nitrobenzoates.

Isomers

The three isomers of nitrobenzoic acid are: *

2-Nitrobenzoic acid 2-Nitrobenzoic acid or ''o''-nitrobenzoic acid is an organic compound with the formula C6H4(NO2)CO2H. It is prepared by oxidation of 2-nitrotoluene with nitric acid.Takao Maki, Kazuo Takeda "Benzoic Acid and Derivatives" in Ullmann's Encycloped ...

is prepared by oxidation of 2-nitrotoluene. *

3-Nitrobenzoic acid 3-Nitrobenzoic acid is an organic compound with the formula C6H4(NO2)CO2H. It is an aromatic compound and under standard conditions, it is an off-white solid. The two substituents are in a meta position with respect to each other, giving the alte ...

is a precursor to

3-aminobenzoic acid 3-Aminobenzoic acid (also known as ''meta''-aminobenzoic acid or MABA) is an organic compound with the molecular formula H2NC6H4CO2H. MABA is a white solid, although commercial samples are often colored. It is only slightly soluble in water. It i ...

, which in turn is used to prepare some dyes. It can be prepared by

nitration In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and ...

of benzoic acid. It also can be prepared by treating

benzaldehyde Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful. It is a colorless liquid with a characteristic almond-like odor. ...

under nitration conditions, a process that initially converts the aldehyde to the acid. *

4-Nitrobenzoic acid 4-Nitrobenzoic acid is an organic compound with the formula C6H4(NO2)CO2H. It is a pale yellow solid. It is a precursor to 4-nitrobenzoyl chloride, the precursor to the anesthetic procaine and folic acid. It is also a precursor to 4-aminobenzoic ...

is a precursor to

4-aminobenzoic acid 4-Aminobenzoic acid (also known as ''para''-aminobenzoic acid or PABA because the two functional groups are attached to the benzene ring across from one another in the ''para'' position) is an organic compound with the formula H2NC6H4CO2H. PABA i ...

, which is in turn used to prepare the anesthetic

procaine Procaine is a local anesthetic drug of the amino ester group. It is most commonly used in dental procedures to numb the area around a tooth and is also used to reduce the pain of intramuscular injection of penicillin. Owing to the ubiquity ...

. 4-Nitrobenzoic acid is prepared by oxidation of

4-nitrotoluene 4-Nitrotoluene or ''para''-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene. Synthesis and reactions Together with other isomers, 4-nitrotoluene is prepared by ...

References

{{chemistry index Benzoic acids Nitrobenzenes