N-Acetylanthranilic acid

N-Acetylanthranilic acid
IUPAC name

2-acetamidobenzoic acid
Other names

2-acetamidobenzoic acid, 2-Carboxyacetanilide, o-Acetoaminobenozic acid, Acetylanthranilic acid, 2-(Acetylamino)benzoic acid
Identifiers
CAS number 89-52-1 N
PubChem 6971
ChemSpider 6705 Y
ChEBI CHEBI:36555 Y
Jmol-3D images Image 1
Properties
Molecular formula C9H9NO3
Molar mass 179.17 g mol−1
Melting point

184-186 °C
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

N-Acetylanthranilic acid is an organic compound with the molecular formula C9H9NO3. It is an intermediate product in catabolism of quinaldine in Arthrobacter sp., and is further metabolized to anthranilic acid.[1][2]

N-Acetylanthranilic acid can be synthesized from 2-bromoacetanilide via palladium-catalyzed carbonylation in tri-n-butylamine-water at 110-130 °C, under 3 atm of carbon monoxide.[3]

N-Acetylanthranilic acid exhibits triboluminescence when crushed. The fractured crystals have large electrical potentials between areas of high and low charge. When the electrons suddenly migrate to neutralize these potentials, flashes of deep blue light are created.

See also

References

  1. ^ Hund HK, de Beyer A, Lingens F. (1990). "Microbial metabolism of quinoline and related compounds. VI. Degradation of quinaldine by Arthrobacter sp". Biol Chem Hoppe Seyler 371 (10): 1005–1008. doi:10.1515/bchm3.1990.371.2.1005. PMID 2076195. 
  2. ^ Overhage J et al. (2005). "Identification of large linear plasmids in Arthrobacter spp. encoding the degradation of quinaldine to anthranilate". Microbiology 151 (2): 491–500. doi:10.1099/mic.0.27521-0. PMID 15699198. 
  3. ^ Donald Valentine, Jefferson W. Tilley, Ronald A. LeMahieu (1981). "Practical, catalytic synthesis of anthranilic acids". Journal of Organic Chemistry 46 (22): 4614–4617. doi:10.1021/jo00335a075.