4,4,4-Trifluoro-1-(p-tolyl)-1,3-butanedione Chemical Properties

Melting point:

44-46°C

Boiling point:

269.9±35.0 °C(Predicted)

Density 

1.252±0.06 g/cm3(Predicted)

vapor pressure 

0.633Pa at 20℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Sparingly), Methanol (Slightly)

pka

5.91±0.25(Predicted)

form 

Solid

color 

Off-White to Light Beige

Water Solubility 

526.4mg/L at 20℃

InChI

InChI=1S/C11H9F3O2/c1-7-2-4-8(5-3-7)9(15)6-10(16)11(12,13)14/h2-5H,6H2,1H3

InChIKey

WRZMHTIRFOFFPY-UHFFFAOYSA-N

SMILES

C(C1=CC=C(C)C=C1)(=O)CC(=O)C(F)(F)F

LogP

1.95 at 20℃

CAS DataBase Reference

720-94-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2914790090

4,4,4-Trifluoro-1-(p-tolyl)-1,3-butanedione Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

A Celecoxib (Celebrex) intermediate.

Flammability and Explosibility

Non flammable

Synthesis

To a 500 mL single-necked flask was added 200 mL of a solvent mixture of acetonitrile-isopropanol (1:1, v/v), 200 mmol (26.8 mL) of 4'-methylacetophenone (I) and 600 mmol (72 mL) of trifluoroacetic acid ethyl ester (II) were added sequentially, followed by the addition of 360 mmol of potassium carbonate with a particle size of 600 nm. The reaction mixture was stirred at 40°C for 24 hours. Upon completion of the reaction, the potassium carbonate was recovered by filtration along with the by-product potassium bicarbonate, which could be regenerated and used after high temperature treatment. The filtrate was distilled under reduced pressure to recover the solvent and unreacted raw materials for subsequent use. To the distillation residue, an equal volume of water was added and the pH was adjusted to 6 with 10% hydrochloric acid solution, followed by extraction with ethyl acetate (70 mL each time) for four times. The organic phases were combined, concentrated and freeze-crystallized to give a light yellow solid product, 4,4,4-trifluoro-1-(4-methylphenyl)-1,3-butanedione (III) 45.6 g in 99.08% yield.

References

[1] Patent: CN103951549, 2016, B. Location in patent: Paragraph 0008; 0027-0028
[2] Patent: CN107759519, 2018, A. Location in patent: Paragraph 0033-0035
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 18, p. 4444 - 4452
[4] Journal of Medicinal Chemistry, 1997, vol. 40, # 9, p. 1347 - 1365
[5] Patent: WO2005/49014, 2005, A1. Location in patent: Page/Page column 137

4,4,4-Trifluoro-1-(p-tolyl)-1,3-butanedione(720-94-5)Related Product Information

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