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Basic Information
CAS No.: 5413-05-8
Name: ETHYL 2-PHENYLACETOACETATE
Article Data: 53
Molecular Structure:
Molecular Structure of 5413-05-8 (ETHYL 2-PHENYLACETOACETATE)
Formula: C12H14O3
Molecular Weight: 206.241
Synonyms: 2-Phenylacetoacetic acid ethyl ester;
EINECS: 226-500-0
Density: 1.087 g/cm3
Melting Point: 140-144 °C
Boiling Point: 281.6 °C at 760 mmHg
Flash Point: 119.2 °C
Safety: 24/25
PSA: 43.37000
LogP: 1.92230
Synthetic route
687981-26-6

3-Oxo-2-phenyl-butyrimidic acid ethyl ester

5413-05-8

ethyl 2-phenylacetoacetate

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 40℃; for 1.5h;97%
With sulfuric acid; water In ethyl acetate at 20 - 50℃; for 4.5h;
591-50-4

iodobenzene

141-97-9

ethyl acetoacetate

A

5413-05-8

ethyl 2-phenylacetoacetate

B

101-97-3

Ethyl 2-phenylethanoate

Conditions
ConditionsYield
With potassium carbonate; copper(l) iodide In dimethyl sulfoxide at 80℃; for 20h;A 9%
B 89%
With potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 80℃; for 20h;A 26%
B 20%
591-50-4

iodobenzene

141-97-9

ethyl acetoacetate

5413-05-8

ethyl 2-phenylacetoacetate

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate In 1,4-dioxane at 70℃; for 25h;78%
27262-63-1

ethyl 2-diazo-3-hydroxy-3-phenylbutanoate

5413-05-8

ethyl 2-phenylacetoacetate

Conditions
ConditionsYield
dirhodium tetraacetate In dichloromethane for 1h; Ambient temperature;75%
With tris-(dibenzylideneacetone)dipalladium(0); para-iodoanisole; diisopropylamine; XPhos In toluene at 100℃; for 48h; Inert atmosphere;57%
108-24-7

acetic anhydride

101-97-3

Ethyl 2-phenylethanoate

5413-05-8

ethyl 2-phenylacetoacetate

Conditions
ConditionsYield
Stage #1: Ethyl 2-phenylethanoate With sodium hydride In tetrahydrofuran at 60℃; for 0.5h; Cooling with ice;
Stage #2: acetic anhydride In tetrahydrofuran at 0 - 20℃; for 1h;
61%
Stage #1: Ethyl 2-phenylethanoate With sodium hydride In tetrahydrofuran at 60℃; for 0.5h;
Stage #2: acetic anhydride In tetrahydrofuran at 20℃; for 1h;
51%
Stage #1: Ethyl 2-phenylethanoate With sodium hydride In tetrahydrofuran at 60℃; for 0.5h;
Stage #2: acetic anhydride In tetrahydrofuran at 20℃; for 1h; Further stages.;
51%
Stage #1: Ethyl 2-phenylethanoate With sodium hydride In tetrahydrofuran at 60℃; for 0.5h; Inert atmosphere;
Stage #2: acetic anhydride In tetrahydrofuran at 0℃;
141-97-9

ethyl acetoacetate

58109-40-3

diphenyliodonium hexafluorophosphate

5413-05-8

ethyl 2-phenylacetoacetate

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;60%
141-97-9

ethyl acetoacetate

47252-14-2

triphenylbismuth carbonate

5413-05-8

ethyl 2-phenylacetoacetate

Conditions
ConditionsYield
In dichloromethane at 40℃; for 20h;59%
59%

diphenyliodonium tetrafluoroborate

141-97-9

ethyl acetoacetate

5413-05-8

ethyl 2-phenylacetoacetate

Conditions
ConditionsYield
Stage #1: ethyl acetoacetate With potassium tert-butylate In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere;
Stage #2: diphenyliodonium tetrafluoroborate In N,N-dimethyl-formamide at 0 - 20℃; for 18h; Reagent/catalyst; Inert atmosphere;
53%

(6-chloropyridin-3-yl)(phenyl)iodonium trifluoromethanesulfonate

141-97-9

ethyl acetoacetate

A

5413-05-8

ethyl 2-phenylacetoacetate

B

ethyl 2-(6-chloropyridin-3-yl)-3-oxobutanoate

Conditions
ConditionsYield
Stage #1: ethyl acetoacetate With potassium tert-butylate In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere;
Stage #2: (6-chloropyridin-3-yl)(phenyl)iodonium trifluoromethanesulfonate In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; chemoselective reaction;
A 12%
B 50%
66003-76-7

Diphenyliodonium triflate

141-97-9

ethyl acetoacetate

5413-05-8

ethyl 2-phenylacetoacetate

Conditions
ConditionsYield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;45%
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Specification

The Benzeneacetic acid, a-acetyl-, ethyl ester, with the CAS registry number 5413-05-8, is also known as 2-Phenylacetoacetic acid ethyl ester and Ethyl acetylphenylacetate. It belongs to the product category of Aromatics Compounds. Its EINECS registry number is 226-500-0. This chemical's molecular formula is C12H14O3 and molecular weight is 206.24. What's more, both its IUPAC name and systematic name are the same which is called Ethyl 3-oxo-2-phenylbutanoate. When you are dealing with this chemical, you should avoid contacting with skin and eyes.

Physical properties about this chemical are: (1)ACD/LogP: 2.53; (2)#of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.53; (4)ACD/LogD (pH 7.4): 2.53; (5)ACD/BCF (pH 5.5): 48.94; (6)ACD/BCF (pH 7.4): 48.92; (7)ACD/KOC (pH 5.5): 563.75; (8)ACD/KOC (pH 7.4): 563.46; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 43.37Å2; (13)Index of Refraction: 1.503; (14)Molar Refractivity: 56.14 cm3; (15)Molar Volume: 189.6 cm3; (16)Surface Tension: 38.2 dyne/cm; (17)Density: 1.087 g/cm3; (18)Flash Point: 119.2 °C; (19)Enthalpy of Vaporization: 52.04 kJ/mol; (20)Boiling Point: 281.6 °C at 760 mmHg; (21)Vapour Pressure: 0.00354 mmHg at 25 °C; (22)Melting Point: 140-144 °C.

Preparation of Benzeneacetic acid, a-acetyl-, ethyl ester: this chemical can be prepared by 3-Oxo-2-phenyl-butyrimidic acid ethyl ester.

This reaction needs reagent Conc. HCl and solvent Ethanol at temperature of 40 °C. The reaction time is 1.5 hours. The yield is 97%.

Uses of Benzeneacetic acid, a-acetyl-: it is used to produce other chemicals. For example, it is used to produce Diazo-phenyl-acetic acid ethyl ester.

The reaction occurs with reagents NaH, TsN3 and other condition of heating for 45 min. The yield is 43%.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(OCC)C(C(=O)C)c1ccccc1
(2) InChI: InChI=1/C12H14O3/c1-3-15-12(14)11(9(2)13)10-7-5-4-6-8-10/h4-8,11H,3H2,1-2H3
(3) InChIKey: PWRUKIPYVGHRFL-UHFFFAOYAT

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