Anthranilic acid

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Anthranilic acid
Names
IUPAC name
2-Aminobenzoic acid
Preferred IUPAC name
2-Aminobenzoic acid
Systematic IUPAC name
2-Aminobenzenecarboxylic acid
Other names
o-Aminobenzoic acid
Anthranilic acid
Vitamin L1
Properties
C7H7NO2
C6H4(NH2)(COOH)
Molar mass 137.138 g/mol
Appearance White solid
Density 1.412 g/cm3 (20 °C)
Melting point 146–148 °C (295–298 °F; 419–421 K)
Boiling point 200 °C (392 °F; 473 K) (sublimes)
0.450 g/100 ml (20 °C)
0.572 g/100 ml (25 °C)
Solubility Very soluble in chloroform, dichloromethane, pyridine
Soluble in diethyl ether, ethanol, methanol
Slightly soluble in benzene, trifluoroacetic acid
Vapor pressure 0.1 Pa (52.6 °C)
Acidity (pKa) 2.17 (carboxyl; H2O)
4.85 (amino; H2O)
Thermochemistry
-380.4 KJ/mol
Hazards
Safety data sheet Sigma-Aldrich
Lethal dose or concentration (LD, LC):
4,549 mg/kg mg/kg (rat, oral)
Related compounds
Related compounds
Salicylic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Anthranilic acid (o-aminobenzoic acid, 2-aminobenzoic acid, 2-AA, 2AA, AA) is an aromatic acid with the formula C6H4(NH2)(COOH). As a result of containing both acidic and basic functional groups, the compound is amphoteric.

Properties

Chemical

Decarboxylation of anthranillic acid yields aniline.[1]

Physical

Anthranilic acid is a white solid, soluble in organic solvents. It has a sweetish taste.

Availability

Anthranilic acid is sold by chemical suppliers.

Anthranilic acid is DEA List I Chemical because of its use in making the now-widely outlawed euphoric sedative drug methaqualone (Quaalude, Mandrax).

Preparation

Anthranilic acid can be produced by aminating phthalic anhydride in the presence of NaOH. The resulting sodium salt of phthalamic acid is decarbonylated via a Hofmann rearrangement of the amide group, induced by hypochlorite to anthranilic acid.

Can also be produced from phthalimide and sodium hypochloride/hypobromite.[2][3]

Projects

  • Make azo dyes
  • Make saccharin
  • Make methyl anthranilate
  • Make anthranilate-based insect repellents

Handling

Safety

Anthranilic acid chas low toxicity.

Storage

In closed bottles.

Disposal

Can be diluted and poured down the drain.

References

  1. https://www.nrcresearchpress.com/doi/pdf/10.1139/v52-065
  2. https://www.prepchem.com/synthesis-of-anthranilic-acid/
  3. https://www.erowid.org/archive/rhodium/chemistry/anthranilic.html

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