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N-Acetylanthranilic acid

N-Acetylanthranilic acid Basic information
Product Name:N-Acetylanthranilic acid
Synonyms:2-(acetylamino)-benzoicaci;2-carboxyacetanilide;acetylanthranilicacid;Lappaconiticacid;n-acetylaminobenzoicacid;n-acetyl-anthranilicaci;N-Acetylanthranilic acid~2-Carboxyacetanilide;N-Acetylanthranilic acid;2-Acetamidobenzoic acid
CAS:89-52-1
MF:C9H9NO3
MW:179.17
EINECS:201-914-4
Product Categories:Pharmaceutical Intermediate;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;API intermediates
Mol File:89-52-1.mol
N-Acetylanthranilic acid Structure
N-Acetylanthranilic acid Chemical Properties
Melting point 184-187 °C(lit.)
Boiling point 311.69°C (rough estimate)
density 1.2822 (rough estimate)
refractive index 1.5600 (estimate)
solubility DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml; PBS (pH 7.2): 0.5 mg/ml
form A crystalline solid
pkapK1: 3.63 (25°C)
Water Solubility slightly soluble
BRN 880371
Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
CAS DataBase Reference89-52-1(CAS DataBase Reference)
EPA Substance Registry SystemBenzoic acid, 2-(acetylamino)- (89-52-1)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38
Safety Statements 36-37/39-26
WGK Germany 3
RTECS CB2455000
Hazard Note Irritant
TSCA Yes
HS Code 29242300
ToxicityLD50 orl-mus: 1114 mg/kg FRPSAX 38,847,83
MSDS Information
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N-Acetylanthranilic acid English
SigmaAldrich English
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N-Acetylanthranilic acid Usage And Synthesis
Chemical Propertiessolid
DefinitionChEBI: An amidobenzoic acid consisting of anthranilic acid carrying an N-acetyl group.
Synthesis Reference(s)The Journal of Organic Chemistry, 46, p. 4614, 1981 DOI: 10.1021/jo00335a075
Tetrahedron Letters, 23, p. 4473, 1982 DOI: 10.1016/S0040-4039(00)85631-2
Safety ProfileModerately toxic by ingestion.When heated to decomposition it emits toxic vapors ofNOx.
Purification MethodsWash the acid with distilled H2O and recrystallise it from aqueous AcOH, dry it and recrystallise again from EtOAc. Also recrystallise it from water or EtOH. UV: max 221, 252 and 305nm (EtOH). The amide crystallises from aqueous EtOH and has m 186-187o and max 218, 252 and 301nm. [Chattaway J Chem Soc 2495 1931, Walker J Am Chem Soc 77 6698 1955, Beilstein 14 H 337, 14 I 540, 14 II 219, 14 III 922.]
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