Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
2-phenylaminobenzonitrile
2-(phenylamino)benzoic acid
Conditions | Yield |
---|---|
With water at 25℃; for 1.5h; Reflux; | 92.2% |
Methyl N-phenylanthranilate
2-(phenylamino)benzoic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
aniline
diethylene glycol
2-bromobenzoic-acid
A
2-(phenylamino)benzoic acid
Conditions | Yield |
---|---|
With copper(II) acetate monohydrate; potassium carbonate at 110℃; for 8h; Inert atmosphere; | A 68% B 13% |
methyl 2-(methylamino)-2-oxoacetate
N-phenyl isatoic anhydride
2-(phenylamino)benzoic acid
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide for 0.5h; | 65% |
Conditions | Yield |
---|---|
With sodium nitrite In chloroform for 5h; Heating; | 1.5% |
methyl 2-(N-phenylbenzamido)benzoate
2-(phenylamino)benzoic acid
Conditions | Yield |
---|---|
With alkaline solution |
N-Nitrozo-N-phenyl-anthranilic acid
2-(phenylamino)benzoic acid
Conditions | Yield |
---|---|
With acetic acid; zinc |
Conditions | Yield |
---|---|
With copper; potassium carbonate; nitrobenzene | |
With copper chloride; i-Amyl alcohol | |
With copper(l) iodide; i-Amyl alcohol | |
With copper(l) iodide; copper; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere; |
Conditions | Yield |
---|---|
With copper; benzene |
n-butyllithium
diethyl ether
diphenylamine
2-(phenylamino)benzoic acid
Conditions | Yield |
---|---|
anschliessenden Behandeln mit festem Kohlendioxid; |
Conditions | Yield |
---|---|
Erhitzen der Alkalisalze in waessr. Loesung mit Anilin in Gegenwart von Kupferpulver oder Kupfersalzen; |
N-phenyl-anthranilic acid-anhydride
2-(phenylamino)benzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide |
2-<(1,2-dioxo-2-(methylamino)ethyl)phenylamino>benzoic acid methyl ester
A
2-(phenylamino)benzoic acid
B
3-phenylimino-2-indolinone
C
Methyl N-methylanthranilate
Conditions | Yield |
---|---|
With PPA at 80 - 90℃; for 2h; | A 70.0 mg B 0.380 g C 0.180 g |
With PPA at 80 - 90℃; for 2h; | A 70.0 mg B 0.380 g C 180.0 mg |
Diphenyliodonium-2-carboxylate
aniline
A
2-(phenylamino)benzoic acid
B
diphenylamine
Conditions | Yield |
---|---|
copper diacetate In isopropyl alcohol at 80℃; for 1h; | A 66 % Spectr. B 2.2 % Spectr. |
Conditions | Yield |
---|---|
With N-ethylmorpholine;; copper diacetate In N,N-dimethyl-formamide at 145℃; for 3h; |
Conditions | Yield |
---|---|
With tetrahydrofuran; isopentyl nitrite |
iodobenzene
nitrobenzene
1H,1H'-2,2'-Biindolylidene-3,3'-dione
A
2-(phenylamino)benzoic acid
sodium carbonate
aniline
ortho-chlorobenzoic acid
2-(phenylamino)benzoic acid
bromobenzene
i-Amyl alcohol
anthranilic acid
2-(phenylamino)benzoic acid
bromobenzene
i-Amyl alcohol
anthranilic acid
2-(phenylamino)benzoic acid
bromobenzene
anthranilic acid
nitrobenzene
2-(phenylamino)benzoic acid
Conditions | Yield |
---|---|
at 160℃; im Druckrohr; |
2-Iodobenzoic acid
N-Phenylhydroxylamine
benzene
A
2-(phenylamino)benzoic acid
B
Azobenzene
Conditions | Yield |
---|---|
With polyphosphoric acid at 120℃; for 3.5h; | 99% |
With boron trifluoride diethyl etherate In neat (no solvent) at 150℃; for 0.0166667h; Solvent; Temperature; Friedel-Crafts Acylation; Microwave irradiation; | 98% |
With polyphosphoric acid at 120℃; under 760.051 Torr; for 4h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With trichlorophosphate at 100℃; for 0.025h; Microwave irradiation; | 98% |
With trichlorophosphate at 135 - 140℃; for 2h; Inert atmosphere; | 96% |
With sulfuric acid; trichlorophosphate for 12h; Heating; | 84% |
Conditions | Yield |
---|---|
With H2O2 In diethyl ether; water byproducts: H2O; 2-phenylaminobenzoic acid and 37% aq. soln. of H2O2 added to soln. of BiPh3 in ether; mixt. was kept at 20°C for 18 h; solvent removed; residue washed (hexane); dried; | 97% |
2-(phenylamino)benzoic acid
trichloromethyl chloroformate
N-phenyl isatoic anhydride
Conditions | Yield |
---|---|
In 1,4-dioxane at 20 - 110℃; for 5h; | 96% |
Conditions | Yield |
---|---|
In not given recrystn. from CH2Cl2; | 95% |
2-(phenylamino)benzoic acid
5,5-dibenzyl-2,3,4,5-tetrahydropyridine
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In toluene at 90℃; for 20h; | 95% |
2-(phenylamino)benzoic acid
methylmagnesium chloride
α,α-Dimethyl-2-(phenylamino)benzolmethanol
Conditions | Yield |
---|---|
In tetrahydrofuran for 4h; Time; Reflux; Inert atmosphere; Large scale; | 95% |
Conditions | Yield |
---|---|
With sulfuric acid for 8h; Reflux; | 94% |
With hydrogenchloride |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 2h; Reflux; | 94% |
With potassium carbonate In acetone at 60℃; for 3h; Inert atmosphere; | 94% |
With potassium carbonate In acetone for 2h; Reflux; | 92% |
With potassium hydroxide |
2-(phenylamino)benzoic acid
methyl iodide
2-(N-Methyl-N-phenylamino)-benzoic acid
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane; water | 93% |
With sodium hydroxide |
1,10-Phenanthroline
2-(phenylamino)benzoic acid
water
sodium hydroxide
Conditions | Yield |
---|---|
In methanol at 70℃; for 1h; pH=5; | 93% |
Conditions | Yield |
---|---|
Stage #1: methanol; 2-(phenylamino)benzoic acid for 0.166667h; Cooling with ice; Stage #2: With thionyl chloride at 0 - 90℃; for 12h; | 92% |
With thionyl chloride at 0 - 90℃; for 12h; Reflux; | 92% |
With thionyl chloride at 0 - 90℃; for 12h; | 92% |
2-(phenylamino)benzoic acid
N-benzyl(but-3-en-2-yl)amine
N-benzyl-N-(but-3-en-2-yl)-2-(phenylamino)benzamide
Conditions | Yield |
---|---|
Stage #1: 2-(phenylamino)benzoic acid; N-benzyl(but-3-en-2-yl)amine With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.0333333h; Inert atmosphere; Stage #2: With diisopropyl-carbodiimide In dichloromethane for 22h; Inert atmosphere; | 92% |
2-(phenylamino)benzoic acid
dimethyl sulfate
1-(2-anilinophenyl)ethan-1-one
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 2h; Reflux; | 92% |
Conditions | Yield |
---|---|
In methanol at 70℃; for 1h; pH=6-6.5; | 92% |
2-(phenylamino)benzoic acid
para-bromotoluene
4-methyl-2'-(N-phenylamino)biphenyl
Conditions | Yield |
---|---|
Stage #1: 2-(phenylamino)benzoic acid With potassium carbonate In various solvent(s) at 120℃; for 0.5h; Stage #2: para-bromotoluene With [2,2]bipyridinyl; copper(l) iodide In various solvent(s) at 160℃; for 24h; Further stages.; | 91% |
With potassium carbonate; copper(l) iodide; dipyridyl; bis(acetylacetonato)palladium(II) In 1-methyl-pyrrolidin-2-one at 160℃; for 24h; Product distribution / selectivity; Molecular sieve; | 91 %Chromat. |
2-(phenylamino)benzoic acid
4,4'-dimethoxydiphenylacetylene
8-(N-phenylamino)-3,4-bis(4-methoxyphenyl)isocoumarin
Conditions | Yield |
---|---|
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In o-xylene at 120℃; for 2h; | 91% |
2-(phenylamino)benzoic acid
N-allyl-N-octylamine
N-allyl-N-octyl-2-(phenylamino)benzamide
Conditions | Yield |
---|---|
Stage #1: 2-(phenylamino)benzoic acid; N-allyloctan-1-amine With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.0333333h; Inert atmosphere; Stage #2: With diisopropyl-carbodiimide In dichloromethane for 24h; Inert atmosphere; | 91% |
2-(phenylamino)benzoic acid
2-Methyl-5-phenyl-isoxazolium-methosulfat
N-Methyl-N-(3-oxo-3-phenyl-propionyl)-2-phenylamino-benzamide
Conditions | Yield |
---|---|
With potassium hydroxide In water at -5℃; pH=<9; | 90% |
Conditions | Yield |
---|---|
In methanol at 70℃; for 1h; pH=6-6.5; | 90% |
1,10-Phenanthroline
2-(phenylamino)benzoic acid
water
sodium hydroxide
Conditions | Yield |
---|---|
In methanol at 70℃; for 1h; pH=5; | 90% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 5h; | 90% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 8h; | 75% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 10h; Inert atmosphere; |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 5h; | 90% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 8h; | 90% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 10h; Inert atmosphere; |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 5h; | 90% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 8h; | 75% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 8h; | 75% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 10h; Inert atmosphere; |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 5h; | 90% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 8h; | 75% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 10h; Inert atmosphere; |
2-(phenylamino)benzoic acid
1,2-bis(4-methylphenyl)acetylene
8-(N-phenylamino)-3,4-bis(4-methylphenyl)isocoumarin
Conditions | Yield |
---|---|
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In o-xylene at 120℃; for 2h; | 89% |
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. |
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