Product Name

  • Name

    Phenylbutazone

  • EINECS 200-029-0
  • CAS No. 50-33-9
  • Article Data30
  • CAS DataBase
  • Density 1.173 g/cm3
  • Solubility water: <0.1 g/100 mL at 23.5 °C
  • Melting Point 104-107 °C
  • Formula C19H20N2O2
  • Boiling Point 424.9 °C at 760 mmHg
  • Molecular Weight 308.38
  • Flash Point 174.3 °C
  • Transport Information
  • Appearance off-white powder
  • Safety 36/37/39-26-45-22-53
  • Risk Codes 36/37/38-20/21/22-42/43-45
  • Molecular Structure Molecular Structure of 50-33-9 (Phenylbutazone)
  • Hazard Symbols HarmfulXn,ToxicT
  • Synonyms 1,2-Diphenyl-3,5-dioxo-4-butylpyrazolidine;1,2-Diphenyl-3,5-dioxo-4-n-butylpyrazolidine;1,2-Diphenyl-4-butyl-3,5-pyrazolidinedione;3,5-Dioxo-1,2-diphenyl-4-n-butylpyrazolidine;
  • PSA 40.62000
  • LogP 3.91780

Synthetic route

1-bromo-butane
109-65-9

1-bromo-butane

1,2-diphenylpyrazolidine-3,5-dione
2652-77-9

1,2-diphenylpyrazolidine-3,5-dione

A

Phenylbutazone
50-33-9

Phenylbutazone

B

4,4-dibutyl-1,2-diphenylpyrazolidine-3,5-dione
102886-57-7

4,4-dibutyl-1,2-diphenylpyrazolidine-3,5-dione

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In hexane; acetonitrile at 55℃; for 18h; Inert atmosphere; Cooling with ice;A 85%
B 15%
...Expand
1-bromo-butane
109-65-9

1-bromo-butane

1,2-diphenylpyrazolidine-3,5-dione
2652-77-9

1,2-diphenylpyrazolidine-3,5-dione

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In hexane; acetonitrile at 55℃; for 22h; Inert atmosphere; Cooling with ice;78%
With sodium hydroxide
diethyl butylmalonate
133-08-4

diethyl butylmalonate

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
Stage #1: diethyl butylmalonate With sodium ethanolate In ethanol at 20℃; Inert atmosphere; Schlenk technique;
Stage #2: diphenyl hydrazine In ethanol for 24h; Reflux; Inert atmosphere; Schlenk technique;		75%
With sodium ethanolate
With sodium ethanolate
1,2-diphenylpyrazolidine-3,5-dione
2652-77-9

1,2-diphenylpyrazolidine-3,5-dione

butan-1-ol
71-36-3

butan-1-ol

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
With nickel; benzene
diethyl butylmalonate
133-08-4

diethyl butylmalonate

1-acetyl-1,2-diphenylhydrazine
22293-38-5

1-acetyl-1,2-diphenylhydrazine

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
With sodium ethanolate
bromo-butyl-malonyl chloride

bromo-butyl-malonyl chloride

diphenyl hydrazine
122-66-7

diphenyl hydrazine

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
With diethyl ether; diethylamine
diphenyl hydrazine
122-66-7

diphenyl hydrazine

2-n-butylmalonyl dichloride
17999-54-1

2-n-butylmalonyl dichloride

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
With pyridine; ethanol
hexanoic acid <N'-ethoxycarbonyl-N,N'-diphenyl-hydrazide

hexanoic acid <N'-ethoxycarbonyl-N,N'-diphenyl-hydrazide

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
With sodium hydride; benzene
n-butylmalonic acid
534-59-8

n-butylmalonic acid

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether; bromine / Behandeln einer Loesung des Reaktionsprodukts in Aether mit Phosphor(V)-chlorid
2: diethyl ether; diethylamine
View Scheme
C20H23N2O6P
1229645-19-5

C20H23N2O6P

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / ethanol; water
2: human placental alkaline phosphatase; magnesium chloride; zinc(II) chloride / 37 °C / pH 7.4 / aq. buffer; Enzymatic reaction
View Scheme
disodium (4-butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)methyl phosphate

disodium (4-butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)methyl phosphate

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
With human placental alkaline phosphatase; magnesium chloride; zinc(II) chloride at 37℃; pH=7.4; Kinetics; pH-value; Temperature; Reagent/catalyst; aq. buffer; Enzymatic reaction;
4-butyl-4-((methylthiomethoxy)methyl)-1,2-diphenylpyrazolidine-3,5-dione
1229521-07-6

4-butyl-4-((methylthiomethoxy)methyl)-1,2-diphenylpyrazolidine-3,5-dione

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-iodo-succinimide / tetrahydrofuran / 12 h / 20 °C
2: palladium 10% on activated carbon; hydrogen / ethanol / 6 h / 20 °C
3: sodium hydroxide / ethanol; water
4: human placental alkaline phosphatase; magnesium chloride; zinc(II) chloride / 37 °C / pH 7.4 / aq. buffer; Enzymatic reaction
View Scheme
dibenzyl ((4-butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)methoxy)methyl phosphate
1229521-08-7

dibenzyl ((4-butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)methoxy)methyl phosphate

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: palladium 10% on activated carbon; hydrogen / ethanol / 6 h / 20 °C
2: sodium hydroxide / ethanol; water
3: human placental alkaline phosphatase; magnesium chloride; zinc(II) chloride / 37 °C / pH 7.4 / aq. buffer; Enzymatic reaction
View Scheme
C21H25N2O7P
1229645-20-8

C21H25N2O7P

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / ethanol; water
2: human placental alkaline phosphatase; magnesium chloride; zinc(II) chloride / 37 °C / pH 7.4 / aq. buffer; Enzymatic reaction
View Scheme
disodium ((4-butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)methoxy)methyl phosphate

disodium ((4-butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)methoxy)methyl phosphate

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
With human placental alkaline phosphatase; magnesium chloride; zinc(II) chloride at 37℃; pH=7.4; Kinetics; pH-value; Reagent/catalyst; Temperature; aq. buffer; Enzymatic reaction;
4-n-Butyl-4-hydroxymethyl-1,2-diphenyl-3,5-dioxopyrazolidin
23111-33-3

4-n-Butyl-4-hydroxymethyl-1,2-diphenyl-3,5-dioxopyrazolidin

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: acetic anhydride; acetic acid / 24 h / 20 °C / Inert atmosphere
2: N-iodo-succinimide / tetrahydrofuran / 12 h / 20 °C
3: palladium 10% on activated carbon; hydrogen / ethanol / 6 h / 20 °C
4: sodium hydroxide / ethanol; water
5: human placental alkaline phosphatase; magnesium chloride; zinc(II) chloride / 37 °C / pH 7.4 / aq. buffer; Enzymatic reaction
View Scheme
Multi-step reaction with 3 steps
1.1: pyridine / dichloromethane / 0.5 h / Cooling with ice; Inert atmosphere
1.2: 2 h / 20 °C / Inert atmosphere
2.1: sodium hydroxide / ethanol; water
3.1: human placental alkaline phosphatase; magnesium chloride; zinc(II) chloride / 37 °C / pH 7.4 / aq. buffer; Enzymatic reaction
View Scheme
diphenyl hydrazine
122-66-7

diphenyl hydrazine

Phenylbutazone
50-33-9

Phenylbutazone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydride / chlorobenzene; mineral oil / 5 h / 0 °C / Reflux
2: potassium carbonate; sodium iodide / acetonitrile; hexane / 22 h / 55 °C / Inert atmosphere; Cooling with ice
View Scheme
Phenylbutazone
50-33-9

Phenylbutazone

4-Butyl-4-hydroxy-1,2-diphenyl-1H-pyrazol-3,5(2H,4H)-dion
16860-43-8

4-Butyl-4-hydroxy-1,2-diphenyl-1H-pyrazol-3,5(2H,4H)-dion

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydrogencarbonate In water; acetonitrile100%
With 1H-imidazole; Mn(TDCPP)Cl; dihydrogen peroxide In dichloromethane; acetonitrile at 20℃; for 4h;90%
With 3-chloro-benzenecarboperoxoic acid In ethanol for 12h; Heating;74%
Phenylbutazone
50-33-9

Phenylbutazone

phenylbutazone hydroperoxide
33053-06-4

phenylbutazone hydroperoxide

Conditions
ConditionsYield
With air; manganese triacetate In acetic acid at 23℃; for 2h;99%
With oxygen; manganese triacetate; acetic acid at 23℃; for 2h;88%
With air; di-tert-butyl peroxide In benzene for 336h; Ambient temperature;50%
sodium tetrafluoroborate
13755-29-8

sodium tetrafluoroborate

Phenylbutazone
50-33-9

Phenylbutazone

4-butyl-3,5-dichloro-1,2-diphenylpyrazolium tetrafluoroborate

4-butyl-3,5-dichloro-1,2-diphenylpyrazolium tetrafluoroborate

Conditions
ConditionsYield
Stage #1: Phenylbutazone With trichlorophosphate In toluene for 4h; Reflux;
Stage #2: sodium tetrafluoroborate In water		99%
Phenylbutazone
50-33-9

Phenylbutazone

C18H14N2O

C18H14N2O

C37H34N4O3

C37H34N4O3

Conditions
ConditionsYield
Stage #1: C18H14N2O With C38H38N4O2Rh(1+)*F6P(1-) In 1,2-dichloro-ethane at 23℃; for 0.0833333h; Michael Addition; Schlenk technique;
Stage #2: Phenylbutazone In 1,2-dichloro-ethane at 23℃; for 6h; Michael Addition; Inert atmosphere; enantioselective reaction;		98%
3-(4-bromophenyl)-1-(1-methyl-1H-imidazol-2-yl)prop-2-en-1-one

3-(4-bromophenyl)-1-(1-methyl-1H-imidazol-2-yl)prop-2-en-1-one

Phenylbutazone
50-33-9

Phenylbutazone

C32H31BrN4O3

C32H31BrN4O3

Conditions
ConditionsYield
Stage #1: 3-(4-bromophenyl)-1-(1-methyl-1H-imidazol-2-yl)prop-2-en-1-one With C38H38N4O2Rh(1+)*F6P(1-) In 1,2-dichloro-ethane at 23℃; for 0.0833333h; Michael Addition; Schlenk technique;
Stage #2: Phenylbutazone In 1,2-dichloro-ethane at 23℃; for 8h; Michael Addition; Inert atmosphere; enantioselective reaction;		98%
Phenylbutazone
50-33-9

Phenylbutazone

2-cinnamoyl-1-methyl-1H-imidazole
99802-91-2

2-cinnamoyl-1-methyl-1H-imidazole

C32H32N4O3

C32H32N4O3

Conditions
ConditionsYield
Stage #1: 2-cinnamoyl-1-methyl-1H-imidazole With C38H38N4O2Rh(1+)*F6P(1-) In 1,2-dichloro-ethane at 23℃; for 0.0833333h; Michael Addition; Schlenk technique;
Stage #2: Phenylbutazone In 1,2-dichloro-ethane at 23℃; for 6h; Reagent/catalyst; Michael Addition; Inert atmosphere; enantioselective reaction;		97%
C15H16N2O

C15H16N2O

Phenylbutazone
50-33-9

Phenylbutazone

C34H36N4O3

C34H36N4O3

Conditions
ConditionsYield
Stage #1: C15H16N2O With C38H38N4O2Rh(1+)*F6P(1-) In 1,2-dichloro-ethane at 23℃; for 0.0833333h; Michael Addition; Schlenk technique;
Stage #2: Phenylbutazone In 1,2-dichloro-ethane at 23℃; for 5.5h; Michael Addition; Inert atmosphere; enantioselective reaction;		96%
C14H14N2O2

C14H14N2O2

Phenylbutazone
50-33-9

Phenylbutazone

C33H34N4O4

C33H34N4O4

Conditions
ConditionsYield
Stage #1: C14H14N2O2 With C38H38N4O2Rh(1+)*F6P(1-) In 1,2-dichloro-ethane at 23℃; for 0.0833333h; Michael Addition; Schlenk technique;
Stage #2: Phenylbutazone In 1,2-dichloro-ethane at 23℃; for 5h; Michael Addition; Inert atmosphere; enantioselective reaction;		96%
Phenylbutazone
50-33-9

Phenylbutazone

C11H10N2OS

C11H10N2OS

C30H30N4O3S

C30H30N4O3S

Conditions
ConditionsYield
Stage #1: C11H10N2OS With C38H38N4O2Rh(1+)*F6P(1-) In 1,2-dichloro-ethane at 23℃; for 0.0833333h; Michael Addition; Schlenk technique;
Stage #2: Phenylbutazone In 1,2-dichloro-ethane at 23℃; for 12h; Michael Addition; Inert atmosphere; enantioselective reaction;		96%
Phenylbutazone
50-33-9

Phenylbutazone

4-methoxy-aniline
104-94-9

4-methoxy-aniline

2-(N,N'-Diphenyl-hydrazinocarbonyl)-hexanoic acid (4-methoxy-phenyl)-amide
76383-80-7

2-(N,N'-Diphenyl-hydrazinocarbonyl)-hexanoic acid (4-methoxy-phenyl)-amide

Conditions
ConditionsYield
at 150℃; for 5h;95%
Phenylbutazone
50-33-9

Phenylbutazone

1,2-diphenyl-4-n-butyl-4-fluoropyrazolidine-3,5-dione
141293-06-3

1,2-diphenyl-4-n-butyl-4-fluoropyrazolidine-3,5-dione

Conditions
ConditionsYield
With N-fluorobis<(trifluoromethyl)sulfonyl>imide In acetic acid for 0.5h; Ambient temperature;95%
Phenylbutazone
50-33-9

Phenylbutazone

C14H14N2O

C14H14N2O

C33H34N4O3

C33H34N4O3

Conditions
ConditionsYield
Stage #1: C14H14N2O With C38H38N4O2Rh(1+)*F6P(1-) In 1,2-dichloro-ethane at 23℃; for 0.0833333h; Michael Addition; Schlenk technique;
Stage #2: Phenylbutazone In 1,2-dichloro-ethane at 23℃; for 7h; Michael Addition; Inert atmosphere; enantioselective reaction;		95%
Phenylbutazone
50-33-9

Phenylbutazone

C13H9F3N2O

C13H9F3N2O

C32H29F3N4O3

C32H29F3N4O3

Conditions
ConditionsYield
Stage #1: C13H9F3N2O With C38H38N4O2Rh(1+)*F6P(1-) In 1,2-dichloro-ethane at 23℃; for 0.0833333h; Michael Addition; Schlenk technique;
Stage #2: Phenylbutazone In 1,2-dichloro-ethane at 23℃; for 5h; Michael Addition; Inert atmosphere; enantioselective reaction;		95%
Phenylbutazone
50-33-9

Phenylbutazone

C15H14N2O

C15H14N2O

C34H34N4O3

C34H34N4O3

Conditions
ConditionsYield
Stage #1: C15H14N2O With C38H38N4O2Rh(1+)*F6P(1-) In 1,2-dichloro-ethane at 23℃; for 0.0833333h; Michael Addition; Schlenk technique;
Stage #2: Phenylbutazone In 1,2-dichloro-ethane at 23℃; for 16h; Michael Addition; Inert atmosphere; enantioselective reaction;		95%
9-hydroxyxanthene
90-46-0

9-hydroxyxanthene

Phenylbutazone
50-33-9

Phenylbutazone

1,2-Diphenyl-4-n-butyl-4-xanthen-9-yl-pyrazolidin-3,5-dion
103325-80-0

1,2-Diphenyl-4-n-butyl-4-xanthen-9-yl-pyrazolidin-3,5-dion

Conditions
ConditionsYield
With hydrogenchloride In methanol for 0.333333h; Ambient temperature;93%
Phenylbutazone
50-33-9

Phenylbutazone

p-toluidine
106-49-0

p-toluidine

2-(N,N'-Diphenyl-hydrazinocarbonyl)-hexanoic acid p-tolylamide
76383-78-3

2-(N,N'-Diphenyl-hydrazinocarbonyl)-hexanoic acid p-tolylamide

Conditions
ConditionsYield
at 150℃; for 5h;93%
C13H11ClN2O
128204-32-0

C13H11ClN2O

Phenylbutazone
50-33-9

Phenylbutazone

C32H31ClN4O3

C32H31ClN4O3

Conditions
ConditionsYield
Stage #1: C13H11ClN2O With C38H38N4O2Rh(1+)*F6P(1-) In 1,2-dichloro-ethane at 23℃; for 0.0833333h; Michael Addition; Schlenk technique;
Stage #2: Phenylbutazone In 1,2-dichloro-ethane at 23℃; for 8h; Michael Addition; Inert atmosphere; enantioselective reaction;		93%
Phenylbutazone
50-33-9

Phenylbutazone

2-methyl-N-(quinolin-8-yl)but‐3‐enamide

2-methyl-N-(quinolin-8-yl)but‐3‐enamide

4-(4-butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)-2-methyl-N-(quinolin-8-yl)butanamide

4-(4-butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)-2-methyl-N-(quinolin-8-yl)butanamide

Conditions
ConditionsYield
With palladium diacetate; acetic acid In acetonitrile at 120℃; for 4h;92%
Phenylbutazone
50-33-9

Phenylbutazone

C14H14N2O

C14H14N2O

C33H34N4O3

C33H34N4O3

Conditions
ConditionsYield
Stage #1: C14H14N2O With C38H38N4O2Rh(1+)*F6P(1-) In 1,2-dichloro-ethane at 23℃; for 0.0833333h; Michael Addition; Schlenk technique;
Stage #2: Phenylbutazone In 1,2-dichloro-ethane at 23℃; for 6h; Michael Addition; Inert atmosphere; enantioselective reaction;		92%
Phenylbutazone
50-33-9

Phenylbutazone

benzylamine
100-46-9

benzylamine

2-(N,N'-Diphenyl-hydrazinocarbonyl)-hexanoic acid benzylamide
76383-73-8

2-(N,N'-Diphenyl-hydrazinocarbonyl)-hexanoic acid benzylamide

Conditions
ConditionsYield
for 5h; Heating;90%
Phenylbutazone
50-33-9

Phenylbutazone

2-<3-(4-methylphenyl)acryloyl>-1-methyl-1H-imidazole
118416-05-0

2-<3-(4-methylphenyl)acryloyl>-1-methyl-1H-imidazole

C33H34N4O3

C33H34N4O3

Conditions
ConditionsYield
Stage #1: 2-<3-(4-methylphenyl)acryloyl>-1-methyl-1H-imidazole With C38H38N4O2Rh(1+)*F6P(1-) In 1,2-dichloro-ethane at 23℃; for 0.0833333h; Michael Addition; Schlenk technique;
Stage #2: Phenylbutazone In 1,2-dichloro-ethane at 23℃; for 5h; Michael Addition; Inert atmosphere; enantioselective reaction;		90%
Phenylbutazone
50-33-9

Phenylbutazone

3,3'-dithio-bis(4-butyl-1,2-diphenyl-5-thioxo-3-pyrazoline)
79202-01-0

3,3'-dithio-bis(4-butyl-1,2-diphenyl-5-thioxo-3-pyrazoline)

Conditions
ConditionsYield
With Lawessons reagent In toluene for 1.5h; Heating;89%
With 2,4-bis(4-methoxyphenyl)-1,3,4,2-dithiadiphosphetane In benzene at 80℃; for 3h;85%
Phenylbutazone
50-33-9

Phenylbutazone

C17H14N2O

C17H14N2O

C36H34N4O3

C36H34N4O3

Conditions
ConditionsYield
Stage #1: C17H14N2O With C38H38N4O2Rh(1+)*F6P(1-) In 1,2-dichloro-ethane at 23℃; for 0.0833333h; Michael Addition; Schlenk technique;
Stage #2: Phenylbutazone In 1,2-dichloro-ethane at 23℃; for 10h; Michael Addition; Inert atmosphere; enantioselective reaction;		89%
formaldehyd
50-00-0

formaldehyd

Phenylbutazone
50-33-9

Phenylbutazone

4-n-Butyl-4-hydroxymethyl-1,2-diphenyl-3,5-dioxopyrazolidin
23111-33-3

4-n-Butyl-4-hydroxymethyl-1,2-diphenyl-3,5-dioxopyrazolidin

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 20℃; for 24h;86%
Phenylbutazone
50-33-9

Phenylbutazone

3-nitrophenyldiazonium chloride
2028-76-4

3-nitrophenyldiazonium chloride

4-Butyl-4-(3-nitro-phenylazo)-1,2-diphenyl-pyrazolidine-3,5-dione
76383-48-7

4-Butyl-4-(3-nitro-phenylazo)-1,2-diphenyl-pyrazolidine-3,5-dione

Conditions
ConditionsYield
With sodium hydroxide In water for 2h;86%
2,4,6-tri-tert-butylphenoxyl
3315-32-0, 2525-39-5

2,4,6-tri-tert-butylphenoxyl

Phenylbutazone
50-33-9

Phenylbutazone

4-n-Butyl-4-(1,3,5-tri-tert-butyl-4-oxo-cyclohexa-2,5-dien-1-yl)-1,2-diphenyl-pyrazolidin-3,5-dion
156304-69-7

4-n-Butyl-4-(1,3,5-tri-tert-butyl-4-oxo-cyclohexa-2,5-dien-1-yl)-1,2-diphenyl-pyrazolidin-3,5-dion

Conditions
ConditionsYield
In benzene at 25℃; for 6h;85%
Phenylbutazone
50-33-9

Phenylbutazone

thiophenol
108-98-5

thiophenol

4-butyl-1,2-diphenyl-4-(phenylthio)pyrazolidine-3,5-dione

4-butyl-1,2-diphenyl-4-(phenylthio)pyrazolidine-3,5-dione

Conditions
ConditionsYield
With oxygen; potassium iodide; sodium hydroxide In acetonitrile at 80℃; under 760.051 Torr; for 24h; Green chemistry;83%
Phenylbutazone
50-33-9

Phenylbutazone

2-Methylpiperidin
109-05-7, 3000-79-1

2-Methylpiperidin

2-(2-Methyl-piperidine-1-carbonyl)-hexanoic acid N,N'-diphenyl-hydrazide
76383-74-9

2-(2-Methyl-piperidine-1-carbonyl)-hexanoic acid N,N'-diphenyl-hydrazide

Conditions
ConditionsYield
at 150℃; for 5h;81%
Phenylbutazone
50-33-9

Phenylbutazone

[bromo(difluoro)methyl](trimethyl)silane
115262-01-6

[bromo(difluoro)methyl](trimethyl)silane

A

C20H20F2N2O2

C20H20F2N2O2

B

4-butyl-4-(difluoromethyl)-1,2-diphenylpyrazolidine-3,5-dione

4-butyl-4-(difluoromethyl)-1,2-diphenylpyrazolidine-3,5-dione

Conditions
ConditionsYield
Stage #1: Phenylbutazone With lithium iodide; sodium t-butanolate In dichloromethane at 20℃; for 0.166667h; Schlenk technique; Glovebox; Inert atmosphere;
Stage #2: [bromo(difluoro)methyl]-trimethyl-silane In dichloromethane at 20℃; for 0.5h; Temperature; Schlenk technique; Glovebox; Inert atmosphere; regioselective reaction;		A n/a
B 81%
...Expand

Phenylbutazone Chemical Properties

IUPAC Name: 4-butyl-1,2-diphenylpyrazolidine-3,5-dione 
Empirical Formula: C19H20N2O2
Molecular Weight: 308.3743g/mol
EINECS: 200-029-0 
Structure of 4-Butyl-1,2-diphenyl-3,5-dioxopyrazolidine (CAS NO.50-33-9):

Index of Refraction: 1.59
Molar Refractivity: 88.7 cm3
Molar Volume: 262.7 cm3
Polarizability: 35.16×10-24cm3
Surface Tension: 47.3 dyne/cm
Density: 1.173 g/cm3
Flash Point: 174.3 °C
Enthalpy of Vaporization: 67.94 kJ/mol 
Melting Point: 104-107 °C
Boiling Point: 424.9 °C at 760 mmHg
Vapour Pressure: 2E-07 mmHg at 25°C 
Water Solubility: <0.1 g/100 mL at 23.5 ºC 
Stability: Stable. Incompatible with strong oxidizing agents, strong acids, strong bases. 
Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals  
Canonical SMILES: CCCCC1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3
InChI: InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3
InChIKey: VYMDGNCVAMGZFE-UHFFFAOYSA-N

Phenylbutazone Uses

 4-Butyl-1,2-diphenyl-3,5-dioxopyrazolidine (50-33-9) is a non-steroidal anti-inflammatory compound. An inhibitor of cyclooxygenase that is also a substrate for peroxidation by cyclooxygenase.

Phenylbutazone Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intravenous 100mg/kg (100mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 36, 1969.
dog LD50 intravenous 121mg/kg (121mg/kg) BEHAVIORAL: ANALGESIA Archives Internationales de Pharmacodynamie et de Therapie. Vol. 149, Pg. 571, 1964.
dog LD50 oral 332mg/kg (332mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 265, 1980.
guinea pig LD50 oral 250mg/kg (250mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1207, 1969.
hamster LD50 oral 1260mg/kg (1260mg/kg)   Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
mammal (species unspecified) LD50 intraperitoneal 300mg/kg (300mg/kg) BEHAVIORAL: ANALGESIA European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 21, Pg. 277, 1986.
mammal (species unspecified) LD50 oral 700mg/kg (700mg/kg) BEHAVIORAL: ANALGESIA European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 21, Pg. 277, 1986.
man TDLo oral 17500ug/kg/3W (17.5mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED		 Annals of Internal Medicine. Vol. 41, Pg. 1075, 1954.
man TDLo oral 2426mg/kg/24H (2426mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Annals of Emergency Medicine. Vol. 20, Pg. 204, 1991.
man TDLo unreported 200mg/kg/5W-I (200mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED

KIDNEY, URETER, AND BLADDER: HEMATURIA		 British Medical Journal. Vol. 282, Pg. 950, 1981.
mouse LD50 intramuscular 430mg/kg (430mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Oyo Yakuri. Pharmacometrics. Vol. 13, Pg. 97, 1977.
mouse LD50 intraperitoneal 128mg/kg (128mg/kg)   Pharmaceutical Chemistry Journal Vol. 19, Pg. 33, 1985.
mouse LD50 intravenous 90mg/kg (90mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 36, 1969.
mouse LD50 oral 238mg/kg (238mg/kg)   Pharmacological Research Communications. Vol. 18, Pg. 241, 1986.
mouse LD50 subcutaneous 230mg/kg (230mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 7, Pg. 1022, 1955.
mouse LD50 unreported 128mg/kg (128mg/kg)   Farmatsevtichnii Zhurnal Vol. (5), Pg. 26, 1983.
rabbit LD50 intravenous 146mg/kg (146mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 129, 1960.
rabbit LD50 oral 781mg/kg (781mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)		 Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 265, 1980.
rat LD50 intramuscular 220mg/kg (220mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 665, 1960.
rat LD50 intraperitoneal 142mg/kg (142mg/kg)   Farmaco, Edizione Scientifica. Vol. 14, Pg. 347, 1959.
rat LD50 intravenous 100mg/kg (100mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 665, 1960.
rat LD50 oral 245mg/kg (245mg/kg) BEHAVIORAL: ANALGESIA Archives Internationales de Pharmacodynamie et de Therapie. Vol. 123, Pg. 48, 1959.
rat LD50 subcutaneous 230mg/kg (230mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR		 Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1285, 1972.
women TDLo oral 168mg/kg/4W-I (168mg/kg) VASCULAR: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: CHANGES PRIMARILY IN GLOMERULI		 Archives of Internal Medicine. Vol. 145, Pg. 685, 1985.
women TDLo unreported 40mg/kg/4D-I (40mg/kg) BLOOD: LEUKOPENIA

BLOOD: AGRANULOCYTOSIS		 Problemy Gematologii i Perelivaniia Krovi. Problems of Hematology and Blood Transfusion. Vol. 4(5), Pg. 48, 1959.

Phenylbutazone Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 316.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 13 (1977),p. 183.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Phenylbutazone Safety Profile

Hazard Codes: HarmfulXn,ToxicT
Risk Statements: 36/37/38-20/21/22-42/43-45
R36/37/38:Irritating to eyes, respiratory system and skin. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R42/43:May cause sensitization by inhalation and skin contact. 
R45:May cause cancer.
Safety Statements: 36/37/39-26-45-22-53
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S22:Do not breathe dust. 
S53:Avoid exposure - obtain special instructions before use.
RIDADR: 3249
RTECS: UQ8225000
HazardClass: 6.1(b)
PackingGroup: III
Hazardous Substances Data: 50-33-9(Hazardous Substances Data)
Suspected human carcinogen producing leukemia. A human poison by parenteral route. An experimental poison by ingestion, intraperitoneal, subcutaneous, intravenous, and intramuscular routes. Human systemic effects by ingestion and possibly other routes: fever, blood pressure increase, other unspecified vascular effects, damage to kidney tubules and glomeruli, decreased urine volume, blood in the urine, reduction in the number of white blood cells, and agranulocytosis. Experimental teratogenic and reproductive effects. Human mutation data reported. An eye irritant. An anti-inflammatory agent. When heated to decomposition it emits toxic fumes of NOx.

Phenylbutazone Specification

  4-Butyl-1,2-diphenyl-3,5-dioxopyrazolidine , its cas register number is 50-33-9. It also can be called 'Esteve' ; 1,2-Diphenyl-3,5-dioxo-4-butylpyrazolidine ; 3,5-Dioxe-4 buty-1, diphenyl-pyrazolidine ; 5-24-05-00400 (Beilstein Handbook Reference) ; Alindor ; Alkabutazona ; Alqoverin ; Anerval ; Anpuzone ; Antadol ; Anuspiramin ; Arthrizon ; Artrizin ; 
 Artrizone ; Artropan ; Azobutyl ; Azolid ; Benzone ; Betazed ; Bizolin ; Bizolin 200 ; Bunetzone ; Busone ; Buta phen ;
 Butacompren ; Butacote ; Butadion ; Butadiona ; Butadione ; Butadionum ; Butagesic ; Butalgina ; Butalidon ; Butaluy ;
 Butaphen ; Butapirazol ; Butapirazole ; Butapyrazole ; Butarecbon ; Butartril ; Butartrina ; Butazina ; Butazolidin ; 
 Butazolidine ; Butazona ; Bute ; Butidiona ; Butiwas-simple ; Butone ; Butoz ; Butylpyrin ; Buvetzone ; Buzon ;
 Chembutazone ; Digibutina ; Diossidone ; Diozol ; Diphebuzol ; Diphenylbutazone ; Ecobutazone ; Elmedal ; Equi bute ;
 Equipalazone ; Eributazone ; Exrheudon N ; Febuzina ; Fenartil ; Fenibutal ; Fenibutasan ; Fenibutazona ; Fenibutol ;
 Fenilbutazona ; Fenilbutazone ; Fenilbutina ; Fenilbutine ; Fenilidina ; Fenotone ; Fenylbutazon ; Intalbut ; Intrabutazone ;
 Mephabutazon ; Phebuzin ; Phebuzine ; Phen-Buta-Vet ; Phenbutazol ; Phenopyrine ; Phenyl-mobuzon ; Pyrazolidin ;
 Scanbutazone ; Schemergen ; UNII-GN5P7K3T8S . 4-Butyl-1,2-diphenyl-3,5-dioxopyrazolidine (CAS NO.50-33-9) is a off-whtie Solid.

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