N-Acetylanthranilic acid

N-Acetylanthranilic acid

N-acetylanthranilic Acid Ball-and-stick model of N-Acetylanthranilic acid
Names
Preferred 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  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:36555  Y
ChemSpider	6705  Y
ECHA InfoCard	100.001.741
PubChem CID	6971
UNII	P1IE9J75C2  Y
CompTox Dashboard (EPA)	DTXSID9058991
InChI InChI=1S/C9H9NO3/c1-6(11)10-8-5-3-2-4-7(8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13) Y Key: QSACCXVHEVWNMX-UHFFFAOYSA-N Y InChI=1/C9H9NO3/c1-6(11)10-8-5-3-2-4-7(8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13) Key: QSACCXVHEVWNMX-UHFFFAOYAX
SMILES CC(=O)NC1=CC=CC=C1C(=O)O
Properties
Chemical formula	C9H9NO3
Molar mass	179.175 g·mol−1
Appearance	Slightly beige solid
Density	1.36 g/mL
Melting point	184 to 186 °C (363 to 367 °F; 457 to 459 K)
Boiling point	399 °C (750 °F; 672 K)
Hazards
GHS labelling:
Pictograms
Lethal dose or concentration (LD, LC):
LD50 (median dose)	Oral, mouse = 1114 mg/kg
Safety data sheet (SDS)	-
Legal status	BR: Class D1 (Drug precursors) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) 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. ^{[2] [3]}

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. ^[4] In the laboratory, it can be easily synthesized from anthranilic acid and acetic anhydride.

N-Acetylanthranilic acid exhibits triboluminescence when crushed. ^[5] 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.

In the United States, it is a Drug Enforcement Administration-controlled List I chemical, ^[6] because it has been used in the synthesis of methaqualone.

See also

• Acedoben

References

1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
2. 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.
3. 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.
4. 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.
5. Erikson J (Oct 1972). "N-acetylanthranilic acid. A highly triboluminescent material". J Chem Educ. 49 (10): 688. doi:10.1021/ed049p688.
6. "PART 1310 - Section 1310.02 Substances covered". www.deadiversion.usdoj.gov. Archived from the original on 2014-12-15. Retrieved 2015-09-08.