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Names | |||
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Preferred IUPAC name
2-Acetamidobenzoic acid | |||
Other names
2-Acetamidobenzoic acid; 2-Carboxyacetanilide; o-Acetoaminobenozic acid; Acetylanthranilic acid; 2-(Acetylamino)benzoic acid
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Identifiers | |||
3D model (
JSmol)
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ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.001.741 | ||
PubChem
CID
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UNII | |||
CompTox Dashboard (
EPA)
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Properties | |||
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: | |||
![]() | |||
Lethal dose or concentration (LD, LC): | |||
LD50 (
median dose)
|
Oral, mouse = 1114 mg/kg | ||
Safety data sheet (SDS) | - | ||
Legal status | |||
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
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.
| |||
Names | |||
---|---|---|---|
Preferred IUPAC name
2-Acetamidobenzoic acid | |||
Other names
2-Acetamidobenzoic acid; 2-Carboxyacetanilide; o-Acetoaminobenozic acid; Acetylanthranilic acid; 2-(Acetylamino)benzoic acid
| |||
Identifiers | |||
3D model (
JSmol)
|
|||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.001.741 | ||
PubChem
CID
|
|||
UNII | |||
CompTox Dashboard (
EPA)
|
|||
| |||
| |||
Properties | |||
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: | |||
![]() | |||
Lethal dose or concentration (LD, LC): | |||
LD50 (
median dose)
|
Oral, mouse = 1114 mg/kg | ||
Safety data sheet (SDS) | - | ||
Legal status | |||
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
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.