Product Name

  • Name

    Ethyl (pentafluorobenzoyl)acetate

  • EINECS 621-882-9
  • CAS No. 3516-87-8
  • Article Data13
  • CAS DataBase
  • Density 1.447 g/cm3
  • Solubility
  • Melting Point
  • 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
  • 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;
  • PSA 43.37000
  • LogP 2.51800

Synthetic route

pentafluorobenzoylchloride
2251-50-5

pentafluorobenzoylchloride

ethyl potassium malonate
6148-64-7

ethyl potassium malonate

ethyl 2,3,4,5,6-pentafluorobenzoylacetate
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;
Pentafluorobenzoic acid
602-94-8

Pentafluorobenzoic acid

ethyl 2,3,4,5,6-pentafluorobenzoylacetate
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
hydrogen ethyl malonate
1071-46-1

hydrogen ethyl malonate

pentafluorobenzoylchloride
2251-50-5

pentafluorobenzoylchloride

ethyl 2,3,4,5,6-pentafluorobenzoylacetate
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
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

(Z)-ethyl 3-ethoxy-2-(2,3,4,5,6-pentafluorobenzoyl)acrylate
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;
2-Amino-4,6-dimethylpyridine
5407-87-4

2-Amino-4,6-dimethylpyridine

ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

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

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

Conditions
ConditionsYield
2-hydroxypyridin In toluene for 6h; Heating;83%
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

ethyl 2-ethoxymethylene-3-oxo-3-pentafluorophenylpropionate
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;
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

acetic anhydride
108-24-7

acetic anhydride

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

Cyclopropylamine
765-30-0

Cyclopropylamine

ethyl 2-(pentafluorobenzoyl)-3-cyclopropylaminoacrylate

ethyl 2-(pentafluorobenzoyl)-3-cyclopropylaminoacrylate

Conditions
ConditionsYield
In ethanol; cyclohexane; Petroleum ether72%
...Expand
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

benzaldehyde
100-52-7

benzaldehyde

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

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%
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

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

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

Conditions
ConditionsYield
for 0.833333h; Heating;37%
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

3-pentafluorophenyl-2H-isoxazol-5-one
29107-99-1

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

Conditions
ConditionsYield
With hydroxylamine hydrochloride In ethanol
1-amino-4-ethoxycarbonyl-7-methoxy-3-phenyl-4a,5,6,7-tetrahydro-2H-pyrrolo[1,2-c]pyrimidin-8-ylium; trifluoro-acetate

1-amino-4-ethoxycarbonyl-7-methoxy-3-phenyl-4a,5,6,7-tetrahydro-2H-pyrrolo[1,2-c]pyrimidin-8-ylium; trifluoro-acetate

ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

Trifluoro-acetate(2aR,8aR)-3,8-bis-ethoxycarbonyl-4-pentafluorophenyl-7-phenyl-1,2,2a,5,6,8a-hexahydro-5,6,8b-triaza-acenaphthylen-8b-ylium;

Trifluoro-acetate(2aR,8aR)-3,8-bis-ethoxycarbonyl-4-pentafluorophenyl-7-phenyl-1,2,2a,5,6,8a-hexahydro-5,6,8b-triaza-acenaphthylen-8b-ylium;

Trifluoro-acetate(2aR,8aS)-3,8-bis-ethoxycarbonyl-4-pentafluorophenyl-7-phenyl-1,2,2a,5,6,8a-hexahydro-5,6,8b-triaza-acenaphthylen-8b-ylium;

Trifluoro-acetate(2aR,8aS)-3,8-bis-ethoxycarbonyl-4-pentafluorophenyl-7-phenyl-1,2,2a,5,6,8a-hexahydro-5,6,8b-triaza-acenaphthylen-8b-ylium;

Conditions
ConditionsYield
With morpholinium acetate; sodium sulfate In 2,2,2-trifluoroethanol at 70℃; for 72h;A 325 mg
B 325 mg
...Expand
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

5,6,7,8-tetrafluorochromone
22697-40-1

5,6,7,8-tetrafluorochromone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 81 percent / 5 h / Heating
2: 62 percent / H2O / 0.33 h / Heating
3: 73 percent / AcOH, conc. HCl / 6 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 81 percent / 5 h / Heating
2: 62 percent / H2O / 0.33 h / Heating
3: 69 percent / AcOH, conc. HCl / 20 h / 40 - 50 °C
4: 79 percent / 190 - 200 °C
View Scheme
Multi-step reaction with 3 steps
1: 81 percent / 5 h / Heating
2: 62 percent / H2O / 0.33 h / Heating
3: 1.) conc. HCl / 1.) CH3COOH, reflux, 6 h, 2.) 200 deg C
View Scheme
Multi-step reaction with 4 steps
1: 81 percent / 5 h / Heating
2: 62 percent / H2O / 0.33 h / Heating
3: 69 percent / HCl / acetic acid / 20 h / 40 - 45 °C
4: 79 percent / 190 - 200 °C
View Scheme
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

3-Carboxy-5,6,7,8-tetrafluorochromone
154679-02-4

3-Carboxy-5,6,7,8-tetrafluorochromone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 81 percent / 5 h / Heating
2: 62 percent / H2O / 0.33 h / Heating
3: 69 percent / AcOH, conc. HCl / 20 h / 40 - 50 °C
View Scheme
Multi-step reaction with 3 steps
1: 81 percent / 5 h / Heating
2: 62 percent / H2O / 0.33 h / Heating
3: 69 percent / HCl / acetic acid / 20 h / 40 - 45 °C
View Scheme
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

3-ethoxycarbonyl-5,6,7,8-tetrafluorochromone
154679-00-2

3-ethoxycarbonyl-5,6,7,8-tetrafluorochromone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 81 percent / 5 h / Heating
2: 62 percent / H2O / 0.33 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 81 percent / 5 h / Heating
2: 62 percent / H2O / 0.33 h / Heating
View Scheme
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

2-pentafluorobenzoylmethyl-5,6,7,8-tetrafluorochromone

2-pentafluorobenzoylmethyl-5,6,7,8-tetrafluorochromone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 37 percent / 0.83 h / Heating
2: 43 percent / conc. HCl / acetic acid / 20 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 37 percent / 0.83 h / Heating
2: 43 percent / CH3COOH, conc. HCl / 20 h / Heating
View Scheme
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

C11H9F5O3

C11H9F5O3

Conditions
ConditionsYield
With hydrogen; [Ru(R)-SYNPHOSBr2] In ethanol at 80℃; under 7500.75 Torr; for 3h; Conversion of starting material;n/a
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

3-oxetanamine
21635-88-1

3-oxetanamine

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

ethyl 1-(oxetan-3-yl)-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate
132918-24-2

ethyl 1-(oxetan-3-yl)-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Conditions
ConditionsYield
With acetic anhydride; potassium carbonate In N-methyl-acetamide; hexane; chloroform; benzene
...Expand
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

3-acetylaminopyrrolidine
79286-74-1

3-acetylaminopyrrolidine

ethyl 4-(3-acetamidopyrrolidin-1-yl)-2,3,5,6-tetrafluorobenzoylacetate
155035-70-4

ethyl 4-(3-acetamidopyrrolidin-1-yl)-2,3,5,6-tetrafluorobenzoylacetate

Conditions
ConditionsYield
With triethylamine In pyridine; chloroform
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

1-phenyl-3-(pentafluorophenyl)-5-hydroxypyrazole

1-phenyl-3-(pentafluorophenyl)-5-hydroxypyrazole

Conditions
ConditionsYield
With hydrogenchloride; phenylhydrazine In methanol1.76 g (54%)
piperidine
110-89-4

piperidine

ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

3,5-Difluoro-2,4-dihydroxybenzaldehyde
209541-27-5

3,5-Difluoro-2,4-dihydroxybenzaldehyde

6,8-difluoro-7-hydroxy-3-pentafluorobenzoylcoumarin

6,8-difluoro-7-hydroxy-3-pentafluorobenzoylcoumarin

Conditions
ConditionsYield
In methanol; chloroform
...Expand
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

recorcinol
108-46-3

recorcinol

7-hydroxy-4-pentafluorophenylcoumarin

7-hydroxy-4-pentafluorophenylcoumarin

Conditions
ConditionsYield
In methane sulfonic acid; water
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

Cyclopropylamine
765-30-0

Cyclopropylamine

1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester
107564-02-3

1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester

Conditions
ConditionsYield
With acetic anhydride In N-methyl-acetamide; ethanol
...Expand
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

Cyclopropylamine
765-30-0

Cyclopropylamine

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

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

Conditions
ConditionsYield
With acetic anhydride In isopropyl alcohol; pentane
...Expand
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

Phenyl N-cyclopropyliminochlorothioformate
130878-55-6

Phenyl N-cyclopropyliminochlorothioformate

ethyl 1-cyclopropyl-2-phenylthio-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate
193283-44-2

ethyl 1-cyclopropyl-2-phenylthio-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Conditions
ConditionsYield
Stage #1: ethyl 2,3,4,5,6-pentafluorobenzoylacetate With sodium hydride In toluene for 0.5h;
Stage #2: Phenyl N-cyclopropyliminochlorothioformate In toluene at 50℃; for 24h; Heating / reflux;
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

C15H14F5NO4

C15H14F5NO4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic anhydride
2: dichloromethane / 0 °C
View Scheme
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

C15H14F5NO4

C15H14F5NO4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic anhydride
2: dichloromethane / 0 °C
View Scheme
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

C17H18F5NO4
1337541-25-9

C17H18F5NO4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic anhydride
2: dichloromethane / 0 °C
View Scheme
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

C17H18F5NO4

C17H18F5NO4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic anhydride
2: dichloromethane / 0 °C
View Scheme
ethyl 2,3,4,5,6-pentafluorobenzoylacetate
3516-87-8

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

C16H16F5NO4

C16H16F5NO4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic anhydride
2: dichloromethane / 0 °C
View Scheme

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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