Anthranilate

Anthranilic acid

Names
IUPAC name 2-Aminobenzoic acid
Other names o-Aminobenzoic acid; 2-Aminobenzoic acid; Vitamin L1; Anthranilate
Identifiers
CAS Number	118-92-3 Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:30754 Y
ChemSpider	222 Y
DrugBank	DB04166 N
ECHA InfoCard	100.003.898
EC Number	204-287-5
KEGG	C00108 Y
PubChem CID	227
RTECS number	CB2450000
InChI InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10) Y Key: RWZYAGGXGHYGMB-UHFFFAOYSA-N Y InChI=1/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10) Key: RWZYAGGXGHYGMB-UHFFFAOYAS
SMILES O=C(O)c1ccccc1N c1ccc(c(c1)C(=O)O)N
Properties
Chemical formula	C7H7NO2
Molar mass	137.14 g·mol−1
Appearance	white or yellow solid
Odor	odorless
Density	1.412 g/cm3
Melting point	146 to 148 °C (295 to 298 °F; 419 to 421 K)
Boiling point	200 °C (392 °F; 473 K) (sublimes)
Solubility in water	0.572 g/100 mL (25 °C)
Solubility	very soluble in chloroform, pyridine soluble in ethanol, ether, ethyl ether slightly soluble in trifluoroacetic acid, benzene
log P	1.21
Vapor pressure	0.1 Pa (52.6 °C)
Acidity (pKa)	2.14
Magnetic susceptibility (χ)	-77.18·10−6 cm3/mol
Refractive index (nD)	1.578 (144 °C)
Thermochemistry
Std enthalpy of formation (ΔfHo298)	-380.4 KJ/mol
Hazards
Safety data sheet	External MSDS
R-phrases (outdated)	R36 R37
S-phrases (outdated)	S26 S39
NFPA 704	1 2 0
Flash point	> 150 °C (302 °F; 423 K)
Autoignition temperature	> 530 °C (986 °F; 803 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	1400 mg/kg (oral, rat)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Anthranilic acid (o-amino-benzoic acid, 2-aminobenzoic acid, 2-AA, 2AA, AA) is an aromatic acid with the formula C₆H₄(NH₂)(CO₂H). The molecule consists of a substituted benzene ring, hence is classed as aromatic, with two adjacent, or "ortho-" functional groups, a carboxylic acid and an amine. The compound is consequently amphoteric. In appearance, anthranilic acid is a white solid when pure, although commercial samples may appear yellow. It is sometimes referred to as vitamin L₁ and has a sweetish taste. The anion [C₆H₄(NH₂)(CO₂)]⁻, obtained by the deprotonation of anthranilic acid, is called anthranilate.

Although not usually referred to as such, it is an amino acid. Solid anthranilic acid consists of both the amino-carboxylic acid and the zwitterionic ammonium carboxylate forms.

Many routes to anthranilic acid have been described. Industrially it is produced from phthalic anhydride, beginning with amination:

The resulting sodium salt of phthalamic acid is decarbonylated via a Hofmann rearrangement of the amide group, induced by hypochlorite:

A related method involves treating phthalimide with sodium hypobromite in aqueous sodium hydroxide, followed by neutralization. In the era when indigo dye was obtained from plants, it was degraded to give anthranilic acid.

Anthranilic acid was first obtained by base-induced degradation of indigo.

Anthranilic acid is biosynthesized from chorismic acid. It is the precursor to the amino acid tryptophan via the attachment of phosphoribosyl pyrophosphate to the amine group.