N Acetylanthranilic Acid
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N-Acetylanthranilic acid 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) ChEBI CHEBI:36555 (https://www.ebi.ac.uk/chebi/searchId.do? chebiId=36555) ChemSpider 6705 (http://www.chemspider.com/Chemical- Structure.6705.html) Jmol 3D image Interactive graph (http://chemapps.stolaf.edu/jmol/jmol.php?model=CC% 28%3DO%29NC1%3DCC%3DCC%3DC1C%28% 3DO%29O) PubChem 6971 (https://pubchem.ncbi.nlm.nih.gov/compound/6971) Properties Chemical formula C 9 H 9 NO 3 Molar mass 179.18 g·mol −1 Density 1.36 g/mL 184 to 186 °C (363 to 367 °F; 457 to 459 K) N-Acetylanthranilic acid From Wikipedia, the free encyclopedia N-Acetylanthranilic acid is an organic compound with the molecular formula C 9 H 9 NO 3 . 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. In the United States, it is a Drug Enforcement Administration-controlled Table I illicit drug precursor, [4] because it has been used in the synthesis of methaqualone. See also ◾ Acedoben 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 InChI SMILES Page 1 of 2 N-Acetylanthranilic acid - Wikipedia, the free encyclopedia 4/16/2016 https://en.wikipedia.org/wiki/N-Acetylanthranilic_acid
description
Physical Constants of N-Acetylanthranilic Acid
Transcript of N Acetylanthranilic Acid
N-Acetylanthranilic acid
Names
IUPAC name 2-Acetamidobenzoic acid
Other names 2-Acetamidobenzoic acid; 2-Carboxyacetanilide; o-Acetoaminobenozic acid; Acetylanthranilic acid; 2-(Acetylamino)benzoic acid
IdentifiersCAS Number
89-52-1 (http://www.commonchemistry.org/ChemicalDetail.aspx?
ref=89-52-1)
ChEBI CHEBI:36555 (https://www.ebi.ac.uk/chebi/searchId.do?
chebiId=36555)
ChemSpider 6705 (http://www.chemspider.com/Chemical-
Structure.6705.html)
Jmol 3D image
Interactive graph (http://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28%3DO%29NC1%3DCC%3DCC%3DC1C%28%3DO%29O)
PubChem 6971 (https://pubchem.ncbi.nlm.nih.gov/compound/6971)
PropertiesChemical formula
C9H9NO3
Molar mass 179.18 g·mol−1
Density 1.36 g/mL
184 to 186 °C (363 to 367 °F; 457 to 459 K)
N-Acetylanthranilic acidFrom 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 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.
In the United States, it is a Drug Enforcement Administration-controlled Table I illicit drug precursor,[4] because it has been used in the synthesis of methaqualone.
See also
◾ Acedoben
References1. 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
InChI
SMILES
Page 1 of 2N-Acetylanthranilic acid - Wikipedia, the free encyclopedia
4/16/2016https://en.wikipedia.org/wiki/N-Acetylanthranilic_acid
Melting point
Boiling point
399 °C (750 °F; 672 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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.
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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