boron trifluoride diethyl etherate
anthranilic acid
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
at 120℃; for 4h; | 98% |
Conditions | Yield |
---|---|
With hydrogen; nickel In ethyl acetate at 30 - 35℃; under 760.051 Torr; for 10h; | 96% |
With 6H(1+)*SiW12O40(6-)=H6[SiW12O40] In water at 20℃; for 18h; Inert atmosphere; | 96% |
With 1,3-DIOXOLANE; water; zinc at 70℃; for 10h; Green chemistry; chemoselective reaction; | 87% |
Conditions | Yield |
---|---|
With sodium hydride In mineral oil for 2h; Reflux; Inert atmosphere; | 89% |
With sodium hydroxide at 65℃; | 72% |
With sodium Heating; | 50.2% |
With hydrogenchloride |
Conditions | Yield |
---|---|
With dihydrogen peroxide for 3h; Irradiation; | 82% |
Conditions | Yield |
---|---|
With sulfuric acid Reflux; | 78.97% |
Stage #1: ethanol; anthranilic acid With sulfuric acid In water for 20h; Heating / reflux; Stage #2: With sodium hydroxide; water | 78% |
With thionyl chloride at 80℃; for 12h; Heating / reflux; | 61% |
Conditions | Yield |
---|---|
With potassium acetate; copper diacetate; palladium diacetate; potassium iodide In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 24h; | 78% |
Conditions | Yield |
---|---|
With copper (II)-fluoride; trimethylsilylazide; ethanolamine In N,N-dimethyl acetamide at 95℃; for 24h; Inert atmosphere; | 76% |
With trimethylsilylazide; copper; ethanolamine In N,N-dimethyl acetamide at 95℃; for 24h; Inert atmosphere; | 55% |
Conditions | Yield |
---|---|
With sodium hypochlorite In water at -10 - -8℃; for 0.666667h; Inert atmosphere; | 72.4% |
Conditions | Yield |
---|---|
With dmap; ethyl 2-cyanoacetate at 20℃; for 4.5h; chemoselective reaction; | 72% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; caesium carbonate at 20 - 30℃; for 4h; Sealed tube; | 72% |
ethanol
4-Octyne
carbon monoxide
N-ethoxycarbonyl-2-iodoaniline
A
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
Stage #1: 4-Octyne; carbon monoxide; N-ethoxycarbonyl-2-iodoaniline With pyridine; palladium diacetate; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 100℃; under 760 Torr; for 12h; Stage #2: ethanol With sodium hydroxide at 20℃; for 0.5h; | A n/a B 71% |
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 5h; Irradiation; | A 56% B 11% C n/a |
ethanol
carbon monoxide
(3,3-dimethyl-but-1-ynyl)benzene
N-ethoxycarbonyl-2-iodoaniline
A
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
Stage #1: carbon monoxide; (3,3-dimethyl-but-1-ynyl)benzene; N-ethoxycarbonyl-2-iodoaniline With pyridine; palladium diacetate; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 100℃; under 760 Torr; for 12h; Stage #2: ethanol With sodium hydroxide at 20℃; for 0.5h; | A 39% B 14% |
ethanol
4,4-dimethyl-2-pentyne
carbon monoxide
N-ethoxycarbonyl-2-iodoaniline
A
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
Stage #1: 4,4-dimethyl-2-pentyne; carbon monoxide; N-ethoxycarbonyl-2-iodoaniline With pyridine; palladium diacetate; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 100℃; under 760 Torr; for 12h; Stage #2: ethanol With sodium hydroxide at 20℃; for 0.5h; | A 30% B 18% |
(2,2-diethoxyvinylidene)triphenylphosphorane
anthranilic acid
A
ethyl (triphenylphosphoranylidene)acetate
B
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
In tetrahydrofuran for 3h; Ambient temperature; | A n/a B 26% |
phthalimide
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
With sodium hypochlorite; alkaline alcohol |
isatoic anhydride
ethanol
A
2-((ethoxycarbonyl)amino)benzoic acid
B
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
at 130 - 140℃; im Druckrohr; |
2-amino-cyclohex-3-enecarboxylic acid ethyl ester
2-ethoxycarbonylaniline
ethyl bromide
potassium anthranilate
A
ethyl 2-(ethylamino)benzoate
B
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
With tetrabutylammomium bromide at 60℃; for 8h; | A 10 % Chromat. B 74 % Chromat. |
With tetrabutylammomium bromide at 60℃; for 8h; | A 20 % Chromat. B 45 % Chromat. |
diethyl sulfate
potassium anthranilate
A
ethyl 2-(ethylamino)benzoate
B
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
With tetrabutylammomium bromide at 60℃; for 2h; | A 24 % Chromat. B 63 % Chromat. |
With tetrabutylammomium bromide at 60℃; for 2h; | A 44 % Chromat. B 46 % Chromat. |
benzoic acid ethyl ester
A
3-aminobenzoic acid ethyl ester
B
p-aminoethylbenzoate
C
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
With hydroxylamine-O-sulfonic acid; iron(II) sulfate In water; acetic acid at 40℃; for 2h; Yield given. Yields of byproduct given; | |
With hydroxylamine-O-sulfonic acid; iron(II) sulfate In water; acetic acid at 40℃; for 2h; Product distribution; Mechanism; k(C6H5COOEt)/k(C6H6); |
N-carboethoxyaniline
A
aniline
B
p-aminoethylbenzoate
C
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
In cyclohexane Quantum yield; Mechanism; Irradiation; |
phthalimide
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
With toluene |
Conditions | Yield |
---|---|
Kinetics; Hydrogenation; |
ethyl 2-nitrobenzoate
B
ethyl 2-(hydroxyamino)benzoate
C
2-ethoxycarbonylaniline
2-nitrobenzyl chloride
2-ethoxycarbonylaniline
ethyl 2-(2-nitrobenzoylamino)-benzoate
Conditions | Yield |
---|---|
With pyridine In 1,2-dichloro-ethane at 20℃; for 0.75h; Inert atmosphere; | 100% |
With sodium hydroxide | |
With benzene | |
With pyridine In 1,2-dichloro-ethane at 20℃; Inert atmosphere; | |
With pyridine In 1,2-dichloro-ethane at 20℃; for 0.75h; Inert atmosphere; | 2.24 g |
Conditions | Yield |
---|---|
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 80℃; for 17h; Buchwald-Hartwig Coupling; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In 1,4-dioxane at 100℃; for 24h; | 99% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 30℃; for 19h; | 98.6% |
phthalic anhydride
2-ethoxycarbonylaniline
2-(2-ethoxycarbonylphenyl)phthalimide
Conditions | Yield |
---|---|
With triethylamine In toluene for 24h; Heating; | 98% |
chloroformic acid ethyl ester
4-quinolinic acid
2-ethoxycarbonylaniline
ethyl (2-ethoxycarbonyl)phenylcarbamate
Conditions | Yield |
---|---|
With potassium carbonate In water; acetone | 98% |
2,5-hexanedione
2-ethoxycarbonylaniline
ethyl 2-(2,5-dimethyl-1-pyrrol-1-yl)benzoate
Conditions | Yield |
---|---|
In acetic acid for 1h; Paal-Knorr pyrrole synthesis; Inert atmosphere; Reflux; | 98% |
2-Chloroanisole
2-ethoxycarbonylaniline
ethyl 2-((2-methoxyphenyl)amino)benzoate
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); biphenyl; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; tetrabutylammomium bromide; potassium hydroxide In water; ethyl acetate; toluene Inert atmosphere; | 98% |
1,3-Diphenylcarbodiimide
2-ethoxycarbonylaniline
2-(phenylamino)-3-(phenyl)-4(3H)-quinazolinone
Conditions | Yield |
---|---|
With tris(bis(trimethylsilyl)amido)lanthanum(III) In neat (no solvent) at 100℃; for 24h; Schlenk technique; Inert atmosphere; | 98% |
With zinc trifluoromethanesulfonate In benzene at 80℃; for 8h; | 85% |
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
In acetic acid at 110℃; for 6h; Temperature; Concentration; | 98% |
1,1,1,3,3,3-hexamethyl-disilazane
2-ethoxycarbonylaniline
ethyl N-(trimethylsilyl)anthranilate
Conditions | Yield |
---|---|
With sulfuric acid for 0.5h; Heating; | 97% |
1-chloro-3-methoxy-benzene
2-ethoxycarbonylaniline
ethyl 2-(3-methoxyphenylamino)benzoate
Conditions | Yield |
---|---|
With potassium carbonate; XPhos palladium(II) phenethylamine chloride In tert-butyl alcohol at 110℃; for 0.5h; | 97% |
diethyl malonate
2-ethoxycarbonylaniline
ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate
Conditions | Yield |
---|---|
With sodium In ethanol at 145℃; for 19h; | 96% |
diethyl malonate
2-ethoxycarbonylaniline
N,N'-di-2-carboethoxyanilide of malonic acid
Conditions | Yield |
---|---|
at 200 - 220℃; for 2h; | 96% |
1-bromo-2-chloro-4-fluorobenzene
2-ethoxycarbonylaniline
ethyl 2-((2-chloro-4-fluorophenyl)amino)benzoate
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; potassium carbonate In tert-butyl alcohol at 100℃; for 5h; Inert atmosphere; | 96% |
cyanoacetic acid
2-ethoxycarbonylaniline
ethyl 2-(2-cyanoacetamido)benzoate
Conditions | Yield |
---|---|
Stage #1: cyanoacetic acid With phosphorus pentachloride In dichloromethane for 0.5h; Reflux; Stage #2: 2-ethoxycarbonylaniline In dichloromethane for 2h; Reflux; | 96% |
diisopropyl-carbodiimide
2-ethoxycarbonylaniline
3-isopropyl-2-(isopropylamino)quinazolin-4(3H)-one
Conditions | Yield |
---|---|
With tris(bis(trimethylsilyl)amido)lanthanum(III) In neat (no solvent) at 100℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Schlenk technique; Inert atmosphere; | 96% |
With [(ImMesN)2Ti(NMe2)2] In neat (no solvent) at 60℃; for 12h; Mechanism; Solvent; Temperature; Reagent/catalyst; Glovebox; Schlenk technique; | 92% |
With zinc trifluoromethanesulfonate In benzene at 80℃; for 8h; | 91% |
3-iodobenzo[b]thiophene
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
With copper; potassium carbonate In dibutyl ether for 24h; Reflux; Inert atmosphere; | 96% |
succinic acid anhydride
2-ethoxycarbonylaniline
4-[(2-ethoxycarbonylphenyl)amino]-4-oxobutanoic acid
Conditions | Yield |
---|---|
In 1,4-dioxane; diethyl ether; benzene Ambient temperature; | 95% |
In toluene at 20 - 115℃; |
3-iodobenzonitrile
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate In toluene for 17h; Heating; | 95% |
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 17h; Heating; | 95% |
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane; tert-butyl alcohol at 100℃; | 91% |
di-p-tolylcarbodiimide
2-ethoxycarbonylaniline
2-(p-tolyl)amino-3-(p-tolyl)-4(3H)-quinazolinone
Conditions | Yield |
---|---|
With tris(bis(trimethylsilyl)amido)lanthanum(III) In neat (no solvent) at 100℃; for 24h; Schlenk technique; Inert atmosphere; | 95% |
With zinc trifluoromethanesulfonate In benzene at 80℃; for 8h; | 89% |
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 70℃; | 95% |
Conditions | Yield |
---|---|
With [(ImMesN)2Ti(NMe2)2] In neat (no solvent) at 20℃; for 12h; Glovebox; Schlenk technique; | 95% |
ethyl chlorocarbonylacetate
2-ethoxycarbonylaniline
2-carboethoxymalonanilic acid ethyl ester
Conditions | Yield |
---|---|
With pyridine In acetone for 5h; Ambient temperature; | 94% |
With triethylamine In acetone Ambient temperature; | 94% |
2,6-dimethylphenylisocyanate
2-ethoxycarbonylaniline
methyl 2-(3-(2,6-dimethylphenyl)ureido)benzoate
Conditions | Yield |
---|---|
In tetrahydrofuran for 24h; Ambient temperature; | 94% |
pyridinium paratoluene sulfonic acid
2-ethoxycarbonylaniline
Conditions | Yield |
---|---|
Stage #1: pyridinium paratoluene sulfonic acid With trifluoromethanesulfonic acid anhydride; Triphenylphosphine oxide In dichloromethane Stage #2: 2-ethoxycarbonylaniline With triethylamine In dichloromethane at 0 - 20℃; | 94% |
chloroacetonitrile
2-ethoxycarbonylaniline
2-(chloromethyl)quinazolin-4(3H)-one
Conditions | Yield |
---|---|
With hydrogenchloride In water for 0.5h; Microwave irradiation; | 94% |
Stage #1: chloroacetonitrile; 2-ethoxycarbonylaniline With hydrogenchloride In 1,4-dioxane at 25℃; for 10.5h; Stage #2: With ammonia In 1,4-dioxane; water at 0℃; pH=7; | 81% |
With hydrogenchloride In 1,4-dioxane for 6h; Cooling; | |
Stage #1: chloroacetonitrile; 2-ethoxycarbonylaniline With hydrogenchloride In 1,4-dioxane at 20℃; for 15h; Stage #2: With sodium carbonate In 1,4-dioxane; water |
Conditions | Yield |
---|---|
Stage #1: benzonitrile; 2-ethoxycarbonylaniline at 25℃; for 0.166667h; Stage #2: With hydrogenchloride at 25 - 80℃; for 4h; | 94% |
Reported in EPA TSCA Inventory.
The IUPAC name of Ethyl anthranilate is ethyl 2-aminobenzoate. With the CAS registry number 87-25-2, it is also named as 2-Aminobenzoic acid ethyl ester. The product's category is Aromatic Esters. Besides, it is colorless liquid with a fruity odor, which should be sealed in dark and dry place. In addition, this chemical is insoluble in water, and incompatible with acids, bases, oxidizing agents. It is stable and combustible.
The other characteristics of this product can be summarized as: (1)EINECS: 201-735-1; (2)ACD/LogP: 2.57; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 2.57; (5)ACD/LogD (pH 7.4): 2.57; (6)ACD/BCF (pH 5.5): 52.84; (7)ACD/BCF (pH 7.4): 52.87; (8)ACD/KOC (pH 5.5): 595.48; (9)ACD/KOC (pH 7.4): 595.77; (10)H bond acceptors: 3; (11)H bond donors: 2; (12)Freely Rotating Bonds: 4; (13)Index of Refraction: 1.554; (14)Molar Refractivity: 46.89 cm3; (15)Molar Volume: 146.1 cm3; (16)Surface Tension: 44.6 dyne/cm; (17)Density: 1.13 g/cm3; (18)Flash Point: 126.5 °C; (19)Melting point: 13-15 °C; (20)Enthalpy of Vaporization: 50.26 kJ/mol; (21)Boiling Point: 264.7 °C at 760 mmHg; (22)Vapour Pressure: 0.00954 mmHg at 25 °C.
Preparation of Ethyl anthranilate: this chemical can be prepared by 1H-Benzo[d][1,3]oxazine-2,4-dione and Ethanol.
This reaction needs Na by heating. The yield is 50.2 %.
Uses of Ethyl anthranilate: it can be used as perfuming agents in cosmetics. It is also used in the creation and manufacturing of fragrance and flavor concentrates of all types. Furthermore, it can react with Chloroacetyl chloride to get N-Chloroacetyl-anthranilic acid ethyl ester.
This reaction needs triethylamine and CH2Cl2 for 2 hours. The yield is 90 %.
When you are using this chemical, please be cautious about it as the following: it is irritating to skin and eyes. You should wear suitable protective clothing when use it. Moreover, in case of contact with eyes, please rinse immediately with plenty of water and seek medical advice.
People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: CCOC(=O)C1=CC=CC=C1N
(2)InChI: InChI=1S/C9H11NO2/c1-2-12-9(11)7-5-3-4-6-8(7)10/h3-6H,2,10H2,1H3
(3)InChIKey: TWLLPUMZVVGILS-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | oral | 3750mg/kg (3750mg/kg) | Food and Cosmetics Toxicology. Vol. 14, Pg. 759, 1976. |
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