Anthranilic acid
- 2- aminobenzoic acid
- O-aminobenzoic acid
- 2- carboxyaniline
- Benzene carboxylic acid -2-amine
- Benzolamincarboxol (old name)
Colorless to yellowish, sweet - tasting leaves
Fixed
1.41 g · cm -3
146-148 ° C
Decomposition above 200 ° C.
0.1 Pa ( 52.6 ° C)
2.05
Poorly in water ( 5.72 g · l-1 at 25 ° C)
1.578 (144 ° C)
Attention
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Anthranilic acid (2- aminobenzoic acid, o- aminobenzoic acid ) is an aromatic, colorless to pale yellow, blue fluorescent carboxylic acid, which is used as an intermediate for dyes, pharmaceuticals, cosmetics, photographic chemicals and fine chemicals, lubricant additives and corrosion inhibitors. It was in 1841 by Carl Julius Fritzsche ( 1808-1871 ) discovered the alkaline degradation of indigo.
In addition to the two positional isomers anthranilic forms exist: the 3 -aminobenzoic acid (m- aminobenzoic acid ) and 4-aminobenzoic acid (p- aminobenzoic acid ).
Production and representation
A technical production of anthranilic acid is carried out by a Hofmann rearrangement of phthalimide in the presence of sodium hydroxide and sodium hypochlorite.
In another manufacturing process 2 -nitrotoluene an intramolecular redox reaction is subjected.
Use
Anthranilic acid is used as starting material for the synthesis of anthranilic acid derivatives, which are used as non-opioid analgesics because of their similarity to salicylic acid. Anthranilic acid itself does not have this effect. The export of the substance from Germany partially subject to authorization (see Precursors Monitoring Act), as they can serve as starting material for addictive substances.
Anthranilic acid plays today as the starting material for the synthesis of anthranilic significant as fragrances and Indigo as well as drugs and pesticides ( acaricides ) play an important role. Anthranilic acid can be used for the determination and detection of Ag, Cd, Ce, Co, Cu, Hg, Mn, Ni, Pb, Pd, U and Zn are used.
Anthranilic acid is the starting material for the production of methyl red, an azo dye, the sodium salt is used as an acid - base indicator. To the amino group of the anthranilic acid is diazotized with sodium nitrite and hydrochloric acid, and then carried out a azo coupling with N, N- dimethylaniline.