N-Acetylanthranilic acid - Wikipedia, the free encyclopedia

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N-Acetylanthranilic acid
From Wikipedia, the free encyclopedia

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

N-Acetylanthranilic acid

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.

Names
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
(http://www.commonchemistry.org/ChemicalDetail.aspx?
ref=89-52-1)

In the United States, it is a Drug

Enforcement Administration-controlled

ChEBI

Table I illicit drug precursor,[4] because

it has been used in the synthesis of
methaqualone.

ChemSpider 6705 (http://www.chemspider.com/Chemical-

See also

chebiId=36555)
Structure.6705.html)
Jmol 3D
image

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

Interactive graph
(http://chemapps.stolaf.edu/jmol/jmol.php?model=CC%
28%3DO%29NC1%3DCC%3DCC%3DC1C%28%
3DO%29O)

Acedoben

References

CHEBI:36555 (https://www.ebi.ac.uk/chebi/searchId.do?

PubChem

6971 (https://pubchem.ncbi.nlm.nih.gov/compound/6971)

InChI
SMILES

Properties
Chemical
formula

C9H9NO3

Molar mass 179.18 gmol1

Density

1.36 g/mL
184 to 186 C (363 to 367 F; 457 to 459 K)

https://en.wikipedia.org/wiki/N-Acetylanthranilic_acid

4/16/2016

N-Acetylanthranilic acid - Wikipedia, the free encyclopedia

Seyler 371 (10): 10051008.

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Melting
point
Boiling

399 C (750 F; 672 K)

point
Except where otherwise noted, data are given for materials in their
standard state (at 25 C [77 F], 100 kPa).
verify (what is

?)

Infobox references

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): 491500. 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): 46144617. doi:10.1021/jo00335a075.
4. Title 21 Code of Federal Regulations (http://www.deadiversion.usdoj.gov/21cfr/cfr/1310/1310_02.htm)

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Categories: Anthranilic acids Acetanilides
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https://en.wikipedia.org/wiki/N-Acetylanthranilic_acid

4/16/2016