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Ethyl anthranilate
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Name

Ethyl anthranilate

 EINECS 201-735-1
CAS No. 87-25-2 Density 1.13 g/cm3
PSA 52.32000 LogP 2.02670
Solubility N/A Melting Point 13-15 °C(lit.)
Formula C9H11NO2 Boiling Point 264.7 °C at 760 mmHg
Molecular Weight 165.192 Flash Point 126.5 °C
Transport Information N/A Appearance colourless liquid
Safety 26-36 Risk Codes 36/38
Molecular Structure Molecular Structure of 87-25-2 (ETHYL ANTHRANILATE) Hazard Symbols IrritantXi
Synonyms

Anthranilicacid, ethyl ester (6CI,7CI,8CI);(2-(Ethoxycarbonyl)phenyl)amine;2-(Ethoxycarbonyl)aniline;2-Aminobenzoic acid ethyl ester;2-Carboethoxyaniline;Ethyl 2-aminobenzoate;Ethylo-aminobenzoate;NSC 4146;o-(Ethoxycarbonyl)aniline;

Article Data 72

Ethyl anthranilate Synthetic route

109-63-7

boron trifluoride diethyl etherate

118-92-3

anthranilic acid

87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
at 120℃; for 4h;98%
610-34-4

ethyl 2-nitrobenzoate

87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
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%
118-48-9

isatoic anhydride

64-17-5

ethanol

87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
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
5344-90-1

2-Aminobenzyl alcohol

64-17-5

ethanol

87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With dihydrogen peroxide for 3h; Irradiation;82%
64-17-5

ethanol

118-92-3

anthranilic acid

87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
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%
64-17-5

ethanol

201230-82-2

carbon monoxide

62-53-3

aniline

87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With potassium acetate; copper diacetate; palladium diacetate; potassium iodide In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 24h;78%
6091-64-1

2-bromobenzoic acid ethyl ester

87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
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%
64-17-5

ethanol

C8H6NO3(1-)*Na(1+)

87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With sodium hypochlorite In water at -10 - -8℃; for 0.666667h; Inert atmosphere;72.4%
64-17-5

ethanol

552-89-6

2-nitro-benzaldehyde

87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With dmap; ethyl 2-cyanoacetate at 20℃; for 4.5h; chemoselective reaction;72%
64-17-5

ethanol

91-56-5

indole-2,3-dione

87-25-2

2-ethoxycarbonylaniline

Conditions
ConditionsYield
With tert.-butylhydroperoxide; caesium carbonate at 20 - 30℃; for 4h; Sealed tube;72%

Ethyl anthranilate Consensus Reports

Reported in EPA TSCA Inventory.

Ethyl anthranilate Specification

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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