3516-87-8

Basic information

• Product Name: Ethyl (pentafluorobenzoyl)acetate
• Synonyms: 3-OXO-3-PENTAFLUOROPHENYL-PROPIONIC ACID ETHYL ESTER;ETHYL (PENTAFLUOROBENZOYL)ACETATE;Ethyl (pentafluorobenzoyl)acetate 98%;Ethyl(pentafluorobenzoyl)acetate98%;ethyl ester 2,3,4,5,6-pentafluoro-oxo-Benzenepropanoic acid;Ethyl (pentafluorobenzoyl)acetate, Ethyl 3-oxo-3-(pentafluorophenyl)propionate;Ethyl 3-oxo-3-(pentafluorophenyl)propanoate 98%;Ethyl 3-oxo-3-(perfluorophenyl)propanoate
• CAS NO: 3516-87-8
• Molecular Formula: C₁₁H₇F₅O₃
• Molecular Weight: 282.16
• EINECS: 1592732-453-0
• Product Categories: Fluorobenzene;Benzenes;C10 to C11;Carbonyl Compounds;Esters
• Mol File: 3516-87-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 103-104 °C4 mm Hg(lit.)
• Flash Point: 105 °F
• Appearance: /
• Density: 1.43 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00149mmHg at 25°C
• Refractive Index: n20/D 1.464(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: Ethyl (pentafluorobenzoyl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl (pentafluorobenzoyl)acetate(3516-87-8)
• EPA Substance Registry System: Ethyl (pentafluorobenzoyl)acetate(3516-87-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3516-87-8(Hazardous Substances Data)

Usage

General Description

Ethyl (pentafluorobenzoyl)acetate is a chemical compound with the formula C11H7F5O3. It is a derivative of acetic acid and is often used as a building block in organic synthesis. Ethyl (pentafluorobenzoyl)acetate is often utilized in the production of pharmaceuticals, agrochemicals, and fragrance ingredients. It is known for its high reactivity and is commonly used in the creation of novel compounds in the research and development of new materials. Ethyl (pentafluorobenzoyl)acetate is also used as a solvent and a reagent in numerous chemical reactions due to its versatile nature and potential for the formation of complex molecular structures.

InChI:InChI=1/C11H7F5O3/c1-2-5(18)19-3-4(17)6-7(12)9(14)11(16)10(15)8(6)13/h2-3H2,1H3

Synthetic route

pentafluorobenzoylchloride (2251-50-5) + ethyl potassium malonate (6148-64-7) → ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8)

Conditions	Yield
With triethylamine; magnesium chloride	97%
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) → ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8)

Conditions	Yield
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) + pentafluorobenzoylchloride (2251-50-5) → ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8)

Conditions	Yield
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) + orthoformic acid triethyl ester (122-51-0) → (Z)-ethyl 3-ethoxy-2-(2,3,4,5,6-pentafluorobenzoyl)acrylate (516479-35-9)

Conditions	Yield
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) + ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → N-(4,6-dimethyl-pyridin-2-yl)-3-hydroxy-3-pentafluorophenyl-acrylamide

Conditions	Yield
2-hydroxypyridin In toluene for 6h; Heating;	83%

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + orthoformic acid triethyl ester (122-51-0) → ethyl 2-ethoxymethylene-3-oxo-3-pentafluorophenylpropionate (114226-95-8)

Conditions	Yield
for 5h; Heating;	81%
With acetic anhydride
at 145℃; for 2.5h; Inert atmosphere;

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + acetic anhydride (108-24-7) + orthoformic acid triethyl ester (122-51-0) + Cyclopropylamine (765-30-0) → ethyl 2-(pentafluorobenzoyl)-3-cyclopropylaminoacrylate

Conditions	Yield
In ethanol; cyclohexane; Petroleum ether	72%

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + benzaldehyde (100-52-7) → 3,5-diethoxycarbonyl-2-pentafluorophenyl-4-phenyl-7,8,9,10-tetrafluoro-4,5-dihydrobenzo[b]oxacin-6-one

Conditions	Yield
With potassium fluoride In ethanol for 8h; Heating;	38%

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → 1-oxo-3-pentafluorophenyl-1H-pyrano<4,3-b>-6,7,8,9-tetrafluorochromone

Conditions	Yield
for 0.833333h; Heating;	37%

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → 3-pentafluorophenyl-2H-isoxazol-5-one (29107-99-1)

Conditions	Yield
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 + ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → 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;

Conditions	Yield
With morpholinium acetate; sodium sulfate In 2,2,2-trifluoroethanol at 70℃; for 72h;	A 325 mg B 325 mg

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → 5,6,7,8-tetrafluorochromone (22697-40-1)

Conditions	Yield
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) → 3-Carboxy-5,6,7,8-tetrafluorochromone (154679-02-4)

Conditions	Yield
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) → 3-ethoxycarbonyl-5,6,7,8-tetrafluorochromone (154679-00-2)

Conditions	Yield
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) → 2-pentafluorobenzoylmethyl-5,6,7,8-tetrafluorochromone

Conditions	Yield
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) → C11H9F5O3

Conditions	Yield
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) + 3-oxetanamine (21635-88-1) + orthoformic acid triethyl ester (122-51-0) → ethyl 1-(oxetan-3-yl)-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (132918-24-2)

Conditions	Yield
With acetic anhydride; potassium carbonate In N-methyl-acetamide; hexane; chloroform; benzene

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + 3-acetylaminopyrrolidine (79286-74-1) → ethyl 4-(3-acetamidopyrrolidin-1-yl)-2,3,5,6-tetrafluorobenzoylacetate (155035-70-4)

Conditions	Yield
With triethylamine In pyridine; chloroform

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) → 1-phenyl-3-(pentafluorophenyl)-5-hydroxypyrazole

Conditions	Yield
With hydrogenchloride; phenylhydrazine In methanol	1.76 g (54%)

piperidine (110-89-4) + ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + 3,5-Difluoro-2,4-dihydroxybenzaldehyde (209541-27-5) → 6,8-difluoro-7-hydroxy-3-pentafluorobenzoylcoumarin

Conditions	Yield
In methanol; chloroform

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + recorcinol (108-46-3) → 7-hydroxy-4-pentafluorophenylcoumarin

Conditions	Yield
In methane sulfonic acid; water

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + orthoformic acid triethyl ester (122-51-0) + Cyclopropylamine (765-30-0) → 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid,ethyl ester (107564-02-3)

Conditions	Yield
With acetic anhydride In N-methyl-acetamide; ethanol

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + orthoformic acid triethyl ester (122-51-0) + Cyclopropylamine (765-30-0) → ethyl 3-cyclopropylamino-2-(2,3,4,5,6-pentafluorobenzoyl)-acrylate

Conditions	Yield
With acetic anhydride In isopropyl alcohol; pentane

ethyl 2,3,4,5,6-pentafluorobenzoylacetate (3516-87-8) + Phenyl N-cyclopropyliminochlorothioformate (130878-55-6) → ethyl 1-cyclopropyl-2-phenylthio-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (193283-44-2)

Conditions	Yield
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) → C15H14F5NO4

Conditions	Yield
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) → C15H14F5NO4

Conditions	Yield
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) → C17H18F5NO4 (1337541-25-9)

Conditions	Yield
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) → C17H18F5NO4

Conditions	Yield
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) → C16H16F5NO4

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

Upstream product

• 1071-46-1 hydrogen ethyl malonate 
• 2251-50-5 pentafluorobenzoylchloride 
• 602-94-8 Pentafluorobenzoic acid 
• 6148-64-7 ethyl potassium malonate 

Downstream Products

• 114226-95-8 ethyl-2-ethoxymethylene-3-oxo-3-pentafluorophenylpropionate 
• 155035-70-4 ethyl 4-(3-acetamidopyrrolidin-1-yl)-2,3,5,6-tetrafluorobenzoylacetate 
• 193283-44-2 ethyl 1-cyclopropyl-2-phenylthio-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate 
• 103772-14-1 5-Amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 
• 103772-13-0 ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate 
• 1352946-32-7 C₂₅H₂₄F₂N₂O₄ 
• 1352946-31-6 C₂₄H₂₂F₂N₂O₄ 
• 1352946-30-5 C₂₄H₂₄F₂N₂O₄ 
• 1352946-29-2 C₂₃H₂₂F₂N₂O₄ 
• 1352946-28-1 C₂₃H₂₂F₂N₂O₄ 
• 1352946-27-0 C₂₄H₂₄F₂N₂O₄ 
• 1337541-27-1 C₂₄H₂₄F₂N₂O₄ 
• 1352946-26-9 C₂₂H₂₀F₂N₂O₄ 
• 1352946-25-8 C₂₂H₂₀F₂N₂O₄ 

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