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91-40-7

Basic Information
CAS No.: 91-40-7
Name: N-Phenylanthranilic acid
Article Data: 142
Molecular Structure:
Molecular Structure of 91-40-7 (N-Phenylanthranilic acid)
Formula: C13H11NO2
Molecular Weight: 213.236
Synonyms: Anthranilicacid, N-phenyl- (6CI,7CI,8CI);2-(Phenylamino)benzoic acid;2-Anilinobenzoicacid;2-Carboxydiphenylamine;Diphenylamine-2-carboxylic acid;Fenamic acid;N-Phenyl-2-aminobenzoic acid;N-Phenyl-o-aminobenzoic acid;NSC 215211;NSC 4273;o-(Phenylamino)benzoic acid;o-Anilinobenzoic acid;o-Carboxydiphenylamine;N-Phenylanthranilic acid;
EINECS: 202-066-8
Density: 1.269 g/cm3
Melting Point: 182-185 °C(lit.)
Boiling Point: 385.2 °C at 760 mmHg
Flash Point: 186.7 °C
Solubility: insoluble in water
Appearance: Light grey-green to yellow-green fine powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-24/25
PSA: 49.33000
LogP: 3.20140
Synthetic route
88-67-5

2-Iodobenzoic acid

62-53-3

aniline

91-40-7

2-(phenylamino)benzoic acid

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 1h; Microwave irradiation;100%
With potassium hydroxide; copper In water for 9h; Heating;97%
With sodium acetate; copper (I) acetate In water for 0.5h; Heating;97%
62-53-3

aniline

118-91-2

ortho-chlorobenzoic acid

91-40-7

2-(phenylamino)benzoic acid

Conditions
ConditionsYield
With copper(I) sulfate; potassium carbonate; copper(II) sulfate In water for 0.0833333h; Ullmann condensation; microwave irradiation;98%
With potassium carbonate; copper(II) sulfate for 0.025h; Ullmann condensation; microwave irradiation;98%
With sodium acetate; copper (I) acetate In water for 4h; Heating;91%
62-53-3

aniline

88-65-3

2-bromobenzoic-acid

91-40-7

2-(phenylamino)benzoic acid

Conditions
ConditionsYield
With sodium acetate; copper (I) acetate In water for 2.5h; Heating;94%
With D-myo-inositol; copper; caesium carbonate In water at 100℃; for 24h;93%
With potassium carbonate; copper(I) oxide; copper In 2-ethoxy-ethanol at 130℃; for 24h;86%
17583-00-5

2-phenylaminobenzonitrile

91-40-7

2-(phenylamino)benzoic acid

Conditions
ConditionsYield
With water at 25℃; for 1.5h; Reflux;92.2%
35708-19-1

Methyl N-phenylanthranilate

91-40-7

2-(phenylamino)benzoic acid

Conditions
ConditionsYield
With lithium hydroxide; water In tetrahydrofuran; methanol at 20℃; for 12h;82%
Stage #1: Methyl N-phenylanthranilate With potassium hydroxide In ethanol; water for 3h; Inert atmosphere; Reflux;
Stage #2: With hydrogenchloride In ethanol; water pH=2; Inert atmosphere;
76%
With water; potassium hydroxide In ethanol at 100℃; Inert atmosphere;57%
Stage #1: Methyl N-phenylanthranilate With potassium hydroxide In ethanol; water at 20 - 100℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 0℃; pH=2; Inert atmosphere;
57%
118-92-3

anthranilic acid

108-90-7

chlorobenzene

91-40-7

2-(phenylamino)benzoic acid

Conditions
ConditionsYield
With di-tert-butyl{2′-isopropoxy-[1,1′-binaphthalen]-2-yl}phosphane; potassium hydroxide; bis(dibenzylideneacetone)-palladium(0) In tert-butyl alcohol at 90℃; for 20h; Inert atmosphere;81%
62-53-3

aniline

111-46-6

diethylene glycol

88-65-3

2-bromobenzoic-acid

A

91-40-7

2-(phenylamino)benzoic acid

B

C11H14O5

Conditions
ConditionsYield
With copper(II) acetate monohydrate; potassium carbonate at 110℃; for 8h; Inert atmosphere;A 68%
B 13%
54154-11-9

methyl 2-(methylamino)-2-oxoacetate

20877-86-5

N-phenyl isatoic anhydride

91-40-7

2-(phenylamino)benzoic acid

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 0.5h;65%
118-92-3

anthranilic acid

91-40-7

2-(phenylamino)benzoic acid

Conditions
ConditionsYield
With sodium nitrite In chloroform for 5h; Heating;1.5%
409111-58-6

methyl 2-(N-phenylbenzamido)benzoate

91-40-7

2-(phenylamino)benzoic acid

Conditions
ConditionsYield
With alkaline solution
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

N-Phenylanthranilic Acid, with the CAS NO.91-40-7, is a molecule which serves as a parent structure for several non-steroidal anti-inflammatory drugs, including mefenamic acid, tolfenamic acid, flufenamic acid, and meclofenamic acid. It is also named as LABOTEST-BB LT00053431; FENAMIC ACID; DIPHENYLAMINE-2-CARBOXYLIC ACID; 2-ANILINOBENZOIC ACID; 2-(PHENYLAMINO)BENZOIC ACID; 2,2'-IMINODIBENZOIC ACID; AKOS AU36-M185. The molecular formula of N-Phenylanthranilic acid is C13H11NO2 and its formula weight is C13H11NO2.

Physical properties about N-Phenylanthranilic Acid are: (1)ACD/LogP: 4.384; (2)ACD/LogD (pH 5.5): 2.66; (3)ACD/LogD (pH 7.4): 1.36; (4)ACD/BCF (pH 5.5): 23.88; (5)ACD/BCF (pH 7.4): 1.19; (6)ACD/KOC (pH 5.5): 109.18; (7)ACD/KOC (pH 7.4): 5.44; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.667; (12)Molar Refractivity: 62.557 cm3; (13)Molar Volume: 168.004 cm3; (14)Polarizability: 24.8 10-24cm3; (15)Surface Tension: 57.556999206543 dyne/cm; (16)Density: 1.269 g/cm3; (17)Flash Point: 186.735 °C; (18)Enthalpy of Vaporization: 66.865 kJ/mol; (19)Boiling Point: 385.155 °C at 760 mmHg

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing;
3. Avoid contact with skin and eyes;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C13H11NO2/c15-13(16)11-8-4-5-9-12(11)14-10-6-2-1-3-7-10/h1-9,14H,(H,15,16);
(2)InChIKey=ZWJINEZUASEZBH-UHFFFAOYSA-N;
(3)Smilesc1(c(cccc1)C(O)=O)Nc1ccccc1

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 235mg/kg (235mg/kg)   Russian Pharmacology and Toxicology Vol. 37, Pg. 105, 1974.
mouse LD50 intravenous 160mg/kg (160mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 89, Pg. 1392, 1969.