5,6-Difluoroindanone Chemical Properties

Boiling point:

251.3±40.0 °C(Predicted)

Density 

1.362±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

color 

White to light yellow

InChI

InChI=1S/C9H6F2O/c10-7-3-5-1-2-9(12)6(5)4-8(7)11/h3-4H,1-2H2

InChIKey

OSJRTWXVMCRBKZ-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=C(F)C(F)=C2)CC1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

TSCA 

No

HS Code 

2914790090

5,6-Difluoroindanone Usage And Synthesis

Uses

5,6-Difluoro-1-indanone is a ketone organic compound that can be used as an organic reagent.

Synthesis

Step 2: To a carbon disulfide solution (300 mL) containing AlCl3 (76.4 g, 572.6 mmol) was added 3-(3,4-difluorophenyl)propionyl chloride (33.4 g, 163.6 mmol) to a carbon disulfide solution (120 mL) dropwise over 10 minutes at 0°C. The reaction mixture was stirred at 0°C for 30 minutes and then heated to reflux for 4 hours. After the reaction was completed, it was cooled to room temperature and the reaction solution was carefully poured onto crushed ice. The carbon disulfide layer was separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, dried with MgSO4 and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent: 5-10% ethyl acetate/hexane) to afford 5,6-difluoro-2,3-dihydro-1H-inden-1-one 19.3 g (114.9 mmol, 70% yield) as a white solid.1H NMR (400 MHz, CDCl3) δ ppm: 7.50 (t, 1H, J=8.0 Hz),. 7.24 (t, 1H, J=6.6Hz), 3.09 (t, 2H, J=5.5Hz), 2.72-2.69 (m, 2H).

References

[1] Patent: US2009/54431, 2009, A1. Location in patent: Page/Page column 40
[2] Patent: US2006/223830, 2006, A1. Location in patent: Page/Page column 40
[3] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 5, p. 602 - 606
[4] Patent: WO2015/88564, 2015, A1. Location in patent: Paragraph 00254
[5] Patent: CN102516115, 2016, B. Location in patent: Paragraph 0283; 0284

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