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Ethyl (pentafluorobenzoyl)acetate

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Name

Ethyl (pentafluorobenzoyl)acetate

EINECS 621-882-9
CAS No. 3516-87-8 Density 1.447 g/cm3
PSA 43.37000 LogP 2.51800
Solubility N/A Melting Point N/A
Formula C11H7F5O3 Boiling Point 277.8 °C at 760 mmHg
Molecular Weight 282.167 Flash Point 118.1 °C
Transport Information UN 3272 3/PG 3 Appearance N/A
Safety 26-36 Risk Codes 20/21/22-36/37/38
Molecular Structure Molecular Structure of 3516-87-8 (Ethyl (pentafluorobenzoyl)acetate) Hazard Symbols IrritantXi,HarmfulXn
Synonyms

Aceticacid, (pentafluorobenzoyl)-, ethyl ester (8CI);Ethyl 2,3,4,5,6-pentafluorobenzoylacetate;Ethyl2-(2,3,4,5,6-pentafluorobenzoyl)acetate;

Article Data 13

Ethyl (pentafluorobenzoyl)acetate Synthetic route

2251-50-5

pentafluorobenzoylchloride

6148-64-7

ethyl potassium malonate

3516-87-8

ethyl 2,3,4,5,6-pentafluorobenzoylacetate

Conditions
ConditionsYield
With triethylamine; magnesium chloride97%
With triethylamine; magnesium chloride 1.) MeCN, 20 to 25 deg C, 2.5 h, 2.) 20 to 25 deg C, 12 h; Yield given. Multistep reaction;
In acetonitrile at -5℃; Inert atmosphere;
602-94-8

Pentafluorobenzoic acid

3516-87-8

ethyl 2,3,4,5,6-pentafluorobenzoylacetate

Conditions
ConditionsYield
With hydrogenchloride; n-butyllithium In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide
Multi-step reaction with 2 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 0 - 30 °C
2.1: n-butyllithium / tetrahydrofuran / 1 h / -10 - 20 °C / Inert atmosphere
2.2: 1 h / 20 °C / Inert atmosphere
View Scheme
1071-46-1

hydrogen ethyl malonate

2251-50-5

pentafluorobenzoylchloride

3516-87-8

ethyl 2,3,4,5,6-pentafluorobenzoylacetate

Conditions
ConditionsYield
Stage #1: hydrogen ethyl malonate With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere;
Stage #2: pentafluorobenzoylchloride In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;
Stage #1: hydrogen ethyl malonate With n-butyllithium In tetrahydrofuran; hexanes at -78 - -20℃;
Stage #2: pentafluorobenzoylchloride In tetrahydrofuran; hehanes at -78 - 20℃;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexanes; water for 1h;
Stage #1: hydrogen ethyl malonate With n-butyllithium In tetrahydrofuran at -10 - 20℃; for 1h; Inert atmosphere;
Stage #2: pentafluorobenzoylchloride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
10 g
3516-87-8

ethyl 2,3,4,5,6-pentafluorobenzoylacetate

122-51-0

orthoformic acid triethyl ester

516479-35-9

(Z)-ethyl 3-ethoxy-2-(2,3,4,5,6-pentafluorobenzoyl)acrylate

Conditions
ConditionsYield
With acetic anhydride at 120 - 130℃; for 1.5 - 4.5h; Product distribution / selectivity; Heating / reflux;100%
With acetic anhydride at 140℃; for 5h; Inert atmosphere;
5407-87-4

2-Amino-4,6-dimethylpyridine

3516-87-8

ethyl 2,3,4,5,6-pentafluorobenzoylacetate

N-(4,6-dimethyl-pyridin-2-yl)-3-hydroxy-3-pentafluorophenyl-acrylamide

Conditions
ConditionsYield
2-hydroxypyridin In toluene for 6h; Heating;83%
3516-87-8

ethyl 2,3,4,5,6-pentafluorobenzoylacetate

122-51-0

orthoformic acid triethyl ester

114226-95-8

ethyl 2-ethoxymethylene-3-oxo-3-pentafluorophenylpropionate

Conditions
ConditionsYield
for 5h; Heating;81%
With acetic anhydride
at 145℃; for 2.5h; Inert atmosphere;
3516-87-8

ethyl 2,3,4,5,6-pentafluorobenzoylacetate

108-24-7

acetic anhydride

122-51-0

orthoformic acid triethyl ester

765-30-0

Cyclopropylamine

ethyl 2-(pentafluorobenzoyl)-3-cyclopropylaminoacrylate

Conditions
ConditionsYield
In ethanol; cyclohexane; Petroleum ether72%
3516-87-8

ethyl 2,3,4,5,6-pentafluorobenzoylacetate

100-52-7

benzaldehyde

3,5-diethoxycarbonyl-2-pentafluorophenyl-4-phenyl-7,8,9,10-tetrafluoro-4,5-dihydrobenzo[b]oxacin-6-one

Conditions
ConditionsYield
With potassium fluoride In ethanol for 8h; Heating;38%
3516-87-8

ethyl 2,3,4,5,6-pentafluorobenzoylacetate

1-oxo-3-pentafluorophenyl-1H-pyrano<4,3-b>-6,7,8,9-tetrafluorochromone

Conditions
ConditionsYield
for 0.833333h; Heating;37%
3516-87-8

ethyl 2,3,4,5,6-pentafluorobenzoylacetate

29107-99-1

3-pentafluorophenyl-2H-isoxazol-5-one

Conditions
ConditionsYield
With hydroxylamine hydrochloride In ethanol

Ethyl (pentafluorobenzoyl)acetate Specification

This chemical is called Ethyl (pentafluorobenzoyl)acetate, and its CAS registry number is 3516-87-8. With the molecular formula of C11H7F5O3, its product categories are Fluorobenzene; Benzenes; C10 to C11; Carbonyl Compounds; Esters. In addition, this chemical should be sealed in the cool and dry place, away from oxides.  

Other characteristics of the Ethyl (pentafluorobenzoyl)acetate can be summarised as followings: (1)ACD/LogP: 1.31; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.31; (4)ACD/LogD (pH 7.4): 1.31; (5)ACD/BCF (pH 5.5): 5.87; (6)ACD/BCF (pH 7.4): 5.87; (7)ACD/KOC (pH 5.5): 123.54; (8)ACD/KOC (pH 7.4): 123.48; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 43.37 Å2; (13)Index of Refraction: 1.445; (14)Molar Refractivity: 51.92 cm3; (15)Molar Volume: 195 cm3; (16)Polarizability: 20.58×10-24cm3; (17)Surface Tension: 34.3 dyne/cm; (18)Density: 1.446 g/cm3; (19)Flash Point: 118.1 °C; (20)Enthalpy of Vaporization: 51.64 kJ/mol; (21)Boiling Point: 277.8 °C at 760 mmHg; (22)Vapour Pressure: 0.00442 mmHg at 25°C.

Uses of this chemical: The 6,7,8,9-tetrafluoro-3-(2,3,4,5,6-pentafluoro-phenyl)-pyrano[4,3-b]chromene-1,10-dione could be obtained by the reactant of Ethyl (pentafluorobenzoyl)acetate. This reaction needs to be taken for 50 minutes with the heating . The yield is 37%.

When you are using this chemical, please be cautious about it as the following: This chemical is irritating / harmful to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure: 
1.SMILES: Fc1c(c(F)c(F)c(F)c1F)C(=O)CC(=O)OCC
2.InChI: InChI=1/C11H7F5O3/c1-2-19-5(18)3-4(17)6-7(12)9(14)11(16)10(15)8(6)13/h2-3H2,1H3
3.InChIKey: SFYYMUUQGSQVFT-UHFFFAOYAF

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