Ethyl 3-(4-fluorophenyl)-3-oxopropanoate

Bezeichnung:Ethyl 3-(4-fluorophenyl)-3-oxopropanoate

CAS-Nr1999-00-4

Englisch Name:Ethyl 3-(4-fluorophenyl)-3-oxopropanoate

CBNumberCB2480433

SummenformelC11H11FO3

Molgewicht210.2

MOL-Datei1999-00-4.mol

Ethyl 3-(4-fluorophenyl)-3-oxopropanoate physikalisch-chemischer Eigenschaften

Schmelzpunkt	117-120℃
Siedepunkt	117-120 °C(lit.)
Dichte	1.174 g/mL at 25 °C(lit.)
Brechungsindex	n20/D 1.5040(lit.)
Flammpunkt	>230 °F
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
pka	9.82±0.25(Predicted)
Aggregatzustand	clear liquid
Farbe	Colorless to Almost colorless
Wichte	1.19
InChI	InChI=1S/C11H11FO3/c1-2-15-11(14)7-10(13)8-3-5-9(12)6-4-8/h3-6H,2,7H2,1H3
InChIKey	SJUXLKYJKQBZLM-UHFFFAOYSA-N
SMILES	C1(=CC=C(F)C=C1)C(=O)CC(=O)OCC
CAS Datenbank	1999-00-4(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
S-Sätze:	24/25
WGK Germany	3
Hazard Note	Irritant
HS Code	29183000
Speicherklasse	10 - Combustible liquids

Gefahreninformationscode (GHS)

Ethyl 3-(4-fluorophenyl)-3-oxopropanoate Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Colorless liquid
Verwenden
Reactant used as a precursor in:
- Condensation reactions with diamines via C-C bond cleavage for synthesis of benzimidazoles and perimidines for possible use as antimalarial treatments
- Base-promoted domino Michael addition / cyclization / elimination reactions for synthesis of hydroxybenzophenones
- Oxidative cross-coupling with indoles via dioxygen activation
- Cyclization of keto esters for synthesis of pyrones
- Lewis base catalyzed hydrosilylation for synthesis of α-acetoxy β-amino acid derivatives
- Conia-ene reactions for synthesis of methylenecyclopentane derivatives
Allgemeine Beschreibung
Ethyl (4-fluorobenzoyl)acetate on condensation with benzofurazan oxide yields 2-(carboethoxy)-3-(4′-fluoro)phenylquinoxaline1,4-dioxide.
Synthese

403-42-9

105-58-8

1999-00-4

(Step 1) Diethyl carbonate (47.4 mL, 391 mmol) and sodium hydride (55 wt% paraffin oil dispersion, 23.7 g, 543 mmol) were sequentially added to a suspension of tetrahydrofuran (THF) at 60 °C, followed by slow addition of 4'-fluoroacetophenone (26.4 mL, 271 mmol). The reaction mixture was heated to reflux for 1 h. After cooling to room temperature, it was slowly poured into a mixture of acetic acid (33.6 mL, 586 mmol) and ice water (1 L). The reaction mixture was extracted with ether (2×500 mL), and the organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine sequentially, dried over anhydrous sodium sulfate, and then the solvent was concentrated under reduced pressure to afford ethyl 3-(4-fluorophenyl)-3-oxopropanoate as a yellow oil (45.7 g, 100% yield, ketone formula: enol formula = 5:1). The product was characterized by 1H-NMR (400 MHz, CDCl3): keto formula: δ 1.26 (3H, t, J=7.2 Hz), 3.97 (3H, s), 4.22 (2H, q, J=7.2 Hz), 7.13-7.19 (2H, m), 7.96-8.01 (2H, m); enol formula: δ 1.34 (0.6H, t, J =7.2 Hz), 4.27 (0.4H, q, J=7.2 Hz), 5.61 (0.2H, s), 7.08-7.12 (0.4H, m), 7.76-7.80 (0.4H, m), 12.62 (0.2H, s).
Einzelnachweise
[1] Molecules, 2004, vol. 9, # 3, p. 135 - 157
[2] Patent: EP2738170, 2014, A1. Location in patent: Paragraph 0465
[3] Tetrahedron Letters, 2014, vol. 55, # 14, p. 2212 - 2216
[4] Patent: US2014/213571, 2014, A1. Location in patent: Paragraph 0780
[5] Patent: EP1362846, 2003, A1. Location in patent: Page/Page column 41

Ethyl 3-(4-fluorophenyl)-3-oxopropanoate Upstream-Materialien And Downstream Produkte

Ethyl 3-(4-fluorophenyl)-3-oxopropanoate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

1999-00-4, Ethyl 3-(4-fluorophenyl)-3-oxopropanoate Verwandte Suche:

Send Inquriy