Product Name

  • Name

    l-(4-Methylphenyl)-4,4,4-trifluorobutane-1,3-dione

  • EINECS 615-712-2
  • CAS No. 720-94-5
  • Article Data71
  • CAS DataBase
  • Density 1.253 g/cm3
  • Solubility 526.4mg/L at 20℃
  • Melting Point 44-46 °C
  • Formula C11H9F3O2
  • Boiling Point 269.893 °C at 760 mmHg
  • Molecular Weight 230.186
  • Flash Point 94.098 °C
  • Transport Information
  • Appearance Pale yellow solid
  • Safety 26-36/37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 720-94-5 (l-(4-Methylphenyl)-4,4,4-trifluorobutane-1,3-dione)
  • Hazard Symbols Xi
  • Synonyms 1,3-Butanedione,4,4,4-trifluoro-1-p-tolyl- (6CI,8CI);(4-Methylbenzoyl)trifluoroacetone;1,1,1-Trifluoro-4-(4-methylphenyl)-2,4-butanedione;1-(4-Methylphenyl)-4,4,4-trifluorobutane-1,3-dione;4,4,4-Trifluoro-1-(4-methylphenyl)-1,3 butanedione;4-(4-Methylphenyl)-1,1,1-trifluorobutane-2,4-dione;4-Methyl-1-(4,4,4-trifluoro-3-oxobutanoyl)benzene;
  • PSA 34.14000
  • LogP 2.69920

Synthetic route

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

para-methylacetophenone
122-00-9

para-methylacetophenone

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

Conditions
ConditionsYield
With sodium In ethanol at 20℃; for 3.2h; Temperature;100%
With potassium carbonate In isopropyl alcohol; acetonitrile at 40℃; for 24h; Temperature; Solvent;99.08%
With tert-butyl methyl ether; sodium ethanolate In ethanol at 25℃; for 24h; Claisen Condensation; Inert atmosphere;99.8%
para-methylacetophenone
122-00-9

para-methylacetophenone

trifluoroacetic acid
76-05-1

trifluoroacetic acid

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

Conditions
ConditionsYield
Stage #1: para-methylacetophenone With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere;
Stage #2: trifluoroacetic acid In tetrahydrofuran; mineral oil at 20℃; for 5h; Inert atmosphere;		100%
With sodium In methanol at 20 - 80℃; for 10h;95%
1,1,1-trifluoro-2-propanone
421-50-1

1,1,1-trifluoro-2-propanone

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

Conditions
ConditionsYield
Stage #1: 1,1,1-trifluoro-2-propanone With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h;
Stage #2: 4-methyl-benzoyl chloride In tetrahydrofuran; mineral oil at 40℃; for 2h; Reagent/catalyst;		96.1%
trifluoracetyl chloride
354-32-5

trifluoracetyl chloride

para-methylacetophenone
122-00-9

para-methylacetophenone

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

Conditions
ConditionsYield
Stage #1: para-methylacetophenone With sodium methylate In di-isopropyl ether at 50℃; for 6h;
Stage #2: trifluoracetyl chloride In toluene at 40℃; for 2h; Reagent/catalyst; Concentration; Temperature; Solvent;		93%
trifluoroacetyl fluoride
354-34-7

trifluoroacetyl fluoride

para-methylacetophenone
122-00-9

para-methylacetophenone

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

Conditions
ConditionsYield
Stage #1: para-methylacetophenone With sodium methylate In di-isopropyl ether at 30℃; for 6h;
Stage #2: trifluoroacetyl fluoride at 40℃; for 2h;		92.2%
trifluoroacetyl bromide
354-31-4

trifluoroacetyl bromide

para-methylacetophenone
122-00-9

para-methylacetophenone

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

Conditions
ConditionsYield
Stage #1: para-methylacetophenone With sodium ethanolate In diethyl ether at 40℃; for 6h;
Stage #2: trifluoroacetyl bromide In acetonitrile at 50℃; for 3h;		91.2%
4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

4-hydrazinobenzene-1-sulfonamide hydrochloride
17852-52-7, 27918-19-0

4-hydrazinobenzene-1-sulfonamide hydrochloride

4-[5-(4-(methyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide
169590-42-5

4-[5-(4-(methyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide

Conditions
ConditionsYield
at 90℃; Temperature;99%
In ethanol Reflux;90%
In methanol; water at 120℃; under 24002.4 Torr; for 0.221667h; Temperature; Pressure; Time; Solvent; Flow reactor;85%
4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

diethyl 4-(4-methylbenzoyl)-3-(trifluoromethyl)cyclobut-2-ene-1,2-dicarboxylate

diethyl 4-(4-methylbenzoyl)-3-(trifluoromethyl)cyclobut-2-ene-1,2-dicarboxylate

Conditions
ConditionsYield
With Bis(p-nitrophenyl) phosphate; phenylsilane; C28H21P*C19H22NO4PS In toluene at 40℃; for 40h; Inert atmosphere; enantioselective reaction;99%
4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

4-(aminosulfonyl)phenylhydrazine hydrochloride

4-(aminosulfonyl)phenylhydrazine hydrochloride

4-[5-(4-(methyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide
169590-42-5

4-[5-(4-(methyl)phenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulphonamide

Conditions
ConditionsYield
In ethanol for 24h; Solvent; Inert atmosphere; Reflux;98.8%
Stage #1: 4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione; 4-hydrazinobenzene-1-sulfonamide hydrochloride With hydrogenchloride In water at 100℃; for 2h;
Stage #2: In methanol; water; toluene at 70℃; for 1h;		93.3%
4-hydrazinobenzenesulfonic acid hydrochloride

4-hydrazinobenzenesulfonic acid hydrochloride

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

4-(5-p-methylphenyl-3-trifluoromethyl-pyrazol-1-yl)-benzenesulfonic acid
921617-76-7

4-(5-p-methylphenyl-3-trifluoromethyl-pyrazol-1-yl)-benzenesulfonic acid

Conditions
ConditionsYield
With trifluoroacetic acid In isopropyl alcohol at 55 - 65℃; Temperature;98%
4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

4-bromophenylhydrazine hydrochloride
622-88-8

4-bromophenylhydrazine hydrochloride

1-(4-bromophenyl)-5-(p-tolyl)-3- (trifluoromethyl)-1H-pyrazole

1-(4-bromophenyl)-5-(p-tolyl)-3- (trifluoromethyl)-1H-pyrazole

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 8h; Reflux; Inert atmosphere;92%
With hydrogenchloride In ethanol for 12h; Reflux;92%
In ethanol at 80℃; for 24h;74%
In ethanol at 90℃; for 15h; Inert atmosphere;72%
In ethanol at 90℃; for 15h; Inert atmosphere;72%
4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

(4-iodophenyl)hydrazine hydrochloride
62830-55-1

(4-iodophenyl)hydrazine hydrochloride

1-(4-iodophenyl)-5-(p-tolyl)-3-(trifluoromethyl)-1H-pyrazole

1-(4-iodophenyl)-5-(p-tolyl)-3-(trifluoromethyl)-1H-pyrazole

Conditions
ConditionsYield
In acetic acid at 80℃; for 15h; Schlenk technique; Inert atmosphere;92%
4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

1-(4-methoxyphenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one
107165-84-4

1-(4-methoxyphenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

(6-hydroxy-7-(4-methylbenzoyl)-6-(trifluoromethyl)-2,3,4,6-tetrahydro-1H-pyrido[1,2-a]pyrimidin-9-yl)(4-methoxyphenyl)methanone

(6-hydroxy-7-(4-methylbenzoyl)-6-(trifluoromethyl)-2,3,4,6-tetrahydro-1H-pyrido[1,2-a]pyrimidin-9-yl)(4-methoxyphenyl)methanone

Conditions
ConditionsYield
In neat (no solvent) for 2h; Reflux; Green chemistry;91%
...Expand
trimethylsilyl trifluoromethanesulfonate
27607-77-8

trimethylsilyl trifluoromethanesulfonate

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

C14H17F3O2Si

C14H17F3O2Si

Conditions
ConditionsYield
With triethylamine In diethyl ether at 0 - 20℃; for 72.5h; Inert atmosphere;90%
2-(4-hydrazinylphenyl)-N-methylethane-1-sulfonamide hydrochloride
42381-27-1

2-(4-hydrazinylphenyl)-N-methylethane-1-sulfonamide hydrochloride

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

C20H20F3N3O2S
1363256-89-6

C20H20F3N3O2S

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80 - 85℃; for 3h;90%
4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

2-(tetrahydropyrimidin-2(1H)-ylidene)-1-(p-tolyl)ethan-1-one
115859-76-2

2-(tetrahydropyrimidin-2(1H)-ylidene)-1-(p-tolyl)ethan-1-one

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

(6-hydroxy-6-(trifluoromethyl)-2,3,4,6-tetrahydro-1H-pyrido[1,2-a]pyrimidine-7,9-diyl)bis(p-tolylmethanone)

(6-hydroxy-6-(trifluoromethyl)-2,3,4,6-tetrahydro-1H-pyrido[1,2-a]pyrimidine-7,9-diyl)bis(p-tolylmethanone)

Conditions
ConditionsYield
In neat (no solvent) for 2h; Reflux; Green chemistry;90%
...Expand
4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

C13H13F3N2O

C13H13F3N2O

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

(6-hydroxy-6-(trifluoromethyl)-9-(4-(trifluoromethyl)benzoyl)-2,3,4,6-tetrahydro-1H-pyrido[1,2-a]pyrimidin-7-yl)(p-tolyl)methanone

(6-hydroxy-6-(trifluoromethyl)-9-(4-(trifluoromethyl)benzoyl)-2,3,4,6-tetrahydro-1H-pyrido[1,2-a]pyrimidin-7-yl)(p-tolyl)methanone

Conditions
ConditionsYield
In neat (no solvent) for 2h; Reflux; Green chemistry;90%
...Expand
methyl coumalate
6018-41-3

methyl coumalate

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

methyl 3-(4-methylbenzoyl)-4-(trifluoromethyl)benzoate

methyl 3-(4-methylbenzoyl)-4-(trifluoromethyl)benzoate

Conditions
ConditionsYield
With potassium tert-butylate In neat (no solvent) at 80℃; for 2h; Green chemistry;90%
4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

4-(methylsulfonyl)phenylhydrazine
877-66-7

4-(methylsulfonyl)phenylhydrazine

1-(4-(methylsulfonyl)phenyl)-5-(4-methylphenyl)-3-(trifluoromethyl)-1Hpyrazole
675605-72-8

1-(4-(methylsulfonyl)phenyl)-5-(4-methylphenyl)-3-(trifluoromethyl)-1Hpyrazole

Conditions
ConditionsYield
In ethanol for 8h; Reflux;90%
4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

4-phenyl-1H-pyrazol-3-ylamine
5591-70-8

4-phenyl-1H-pyrazol-3-ylamine

5-(4''-methylphenyl)-3-phenyl-7-trifluoromethylpyrazolo[1,5-a]pyrimidine

5-(4''-methylphenyl)-3-phenyl-7-trifluoromethylpyrazolo[1,5-a]pyrimidine

Conditions
ConditionsYield
In ethanol for 6h; Reflux; regioselective reaction;89%
4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

1-(4-fluorophenyl)-2-(imidazolidin-2-ylidene)ethan-1-one
251940-06-4

1-(4-fluorophenyl)-2-(imidazolidin-2-ylidene)ethan-1-one

(8-(4-fluorobenzoyl)-5-hydroxy-5-(trifluoromethyl)-1,2,3,5-tetrahydroimidazo[1,2-a]pyridin-6-yl)(p-tolyl)methanone

(8-(4-fluorobenzoyl)-5-hydroxy-5-(trifluoromethyl)-1,2,3,5-tetrahydroimidazo[1,2-a]pyridin-6-yl)(p-tolyl)methanone

Conditions
ConditionsYield
In neat (no solvent) for 2h; Reflux; Green chemistry;89%
...Expand
4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

3-amino-5-methyl-4-phenyl-1Н-pyrazole
31924-81-9

3-amino-5-methyl-4-phenyl-1Н-pyrazole

2-methyl-5-(4''-methylphenyl)-3-phenyl-7-trifluoromethylpyrazolo[1,5-a]pyrimidine

2-methyl-5-(4''-methylphenyl)-3-phenyl-7-trifluoromethylpyrazolo[1,5-a]pyrimidine

Conditions
ConditionsYield
In ethanol for 6h; Reflux; regioselective reaction;88.4%
4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

4-hydrazinobenzonitrile hydrochloride
2863-98-1

4-hydrazinobenzonitrile hydrochloride

4-[5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile

4-[5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile

Conditions
ConditionsYield
In ethanol for 7h; Reflux;87%
In ethanol for 20h; Heating;50%
4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione
720-94-5

4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione

guanidine salt

guanidine salt

2-amino-4-(4-methylphenyl)-6-(trifluoromethyl)pyrimidine
26974-12-9

2-amino-4-(4-methylphenyl)-6-(trifluoromethyl)pyrimidine

Conditions
ConditionsYield
With sodium methylate In methanol for 6h; Reflux;87%

l-(4-Methylphenyl)-4,4,4-trifluorobutane-1,3-dione Specification

The IUPAC name of l-(4-Methylphenyl)-4,4,4-trifluorobutane-1,3-dione is 4,4,4-trifluoro-1-(4-methylphenyl)butane-1,3-dione. With the CAS registry number 720-94-5, it is also named as 3-(4-methylbenzoyl)-1,1,1-trifluoroacetone; AKOS MSC-0332. The product's categories are API intermediates, aromatics compounds, osteoarthritis and rheumatoid arthritis, aromatics, intermediates & fine chemicals and pharmaceuticals. It is pale yellow solid which can be used as Celecoxib (Celebrex) intermediate.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.64; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.493; (4)ACD/LogD (pH 7.4): 2.173; (5)ACD/BCF (pH 5.5): 245.995; (6)ACD/BCF (pH 7.4): 11.777; (7)ACD/KOC (pH 5.5): 1632.265; (8)ACD/KOC (pH 7.4): 78.148; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.466; (13)Molar Refractivity: 50.858 cm3; (14)Molar Volume: 183.764 cm3; (15)Polarizability: 20.162×10-24 cm3; (16)Surface Tension: 32.378 dyne/cm; (17)Enthalpy of Vaporization: 50.805 kJ/mol; (18)Vapour Pressure: 0.007 mmHg at 25°C; (19)Rotatable Bond Count: 3; (20)Tautomer Count: 11; (21)Exact Mass: 230.055464; (22)MonoIsotopic Mass: 230.055464; (23)Topological Polar Surface Area: 34.1; (24)Heavy Atom Count: 16

Preparation of l-(4-Methylphenyl)-4,4,4-trifluorobutane-1,3-dione: It can be obtained by 1-p-tolyl-ethanone andtrifluoroacetic acid ethyl ester. This reaction needs reagent NaOMe and solvent methanol by heating. The reaction time is 24 hours. The yield is 94%.

Uses of l-(4-Methylphenyl)-4,4,4-trifluorobutane-1,3-dione: It can react with 4-hydrazino-benzenesulfonic acid amide; hydrochloride to get 4-(5-p-tolyl-3-trifluoromethyl-pyrazol-1-yl)-benzenesulfonamide. This reaction needs solvent ethanol by heating. The reaction time is 20 hours. The yield is 46%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES: Cc1ccc(cc1)C(=O)CC(=O)C(F)(F)F;
2. InChI: InChI=1/C11H9F3O2/c1-7-2-4-8(5-3-7)9(15)6-10(16)11(12,13)14/h2-5H,6H2,1H3.

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