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(+/-)-Sulfinpyrazone
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Name

(+/-)-Sulfinpyrazone

 EINECS 200-357-4
CAS No. 57-96-5 Density 1.39 g/cm3
PSA 76.90000 LogP 4.79120
Solubility 2.601g/L(22 oC) Melting Point >300°C(lit.)
Formula C23H20N2O3S Boiling Point 590.8 °C at 760 mmHg
Molecular Weight 404.489 Flash Point 311.1 °C
Transport Information N/A Appearance N/A
Safety 36 Risk Codes 22
Molecular Structure Molecular Structure of 57-96-5 ((+/-)-Sulfinpyrazone) Hazard Symbols HarmfulXn
Synonyms

1,2-Diphenyl-4-(2'-phenylsulfinethyl)-3,5-pyrazolidinedione;1,2-Diphenyl-4-[2-(phenylsulfinyl)ethyl]-3,5-pyrazolidinedione;4-(Phenylsulfoxyethyl)-1,2-diphenyl-3,5-pyrazolidinedione;Anturan;Anturane;Anturanil;Anturen;Anturidin;Diphenylpyrazone;Enturan;Enturen;G 28315;NSC75925;Sulfinpyrazon;Sulfinpyrazone;Sulfoxyphenylpyrazolidine;Sulphinpyrazone;

Article Data 6

(+/-)-Sulfinpyrazone Synthetic route

7722-86-3

caro's acid

3736-92-3

4-[2-(phenylthio)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione

57-96-5

4-[2-(phenylsulfinyl)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione

Conditions
ConditionsYield
With sodium hydrogencarbonate; sodium hydrogensulfite In water; acetic acid; ethyl acetate; toluene60%
57-96-5

4-[2-(phenylsulfinyl)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione

3736-92-3

4-[2-(phenylthio)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione

Conditions
ConditionsYield
With Lawessons reagent In benzene at 20℃; for 0.5h;95%
57-96-5

4-[2-(phenylsulfinyl)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione

141293-07-4

1,2-diphenyl-4-fluoro-4-<(2-phenylsulfinyl)ethyl>pyrazolidine-3,5-dione

Conditions
ConditionsYield
With N-fluorobis<(trifluoromethyl)sulfonyl>imide In chloroform Ambient temperature;90%
57-96-5

4-[2-(phenylsulfinyl)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione

74-88-4

methyl iodide

86636-32-0

4-(2-phenylthienylethyl)-4-methyl-1,2-diphenyl-3,5-pyrazolidinedione

Conditions
ConditionsYield
With triethylamine In benzene for 0.7h; Ambient temperature;70%
57-96-5

4-[2-(phenylsulfinyl)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione

3,5-Dioxo-1,2-diphenyl-4-(2-phenylsulfinylethyl)pyrazolidin-4-ylnitrat

Conditions
ConditionsYield
With sodium nitrite In acetic acid for 16h; Ambient temperature;10%
57-96-5

4-[2-(phenylsulfinyl)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione

A

94344-86-2

Ethyltartronic dianilide

B

94344-85-1

2-(Phenylthio)ethyltartronic dianilide

C

94344-87-3

2-(Phenylsulfinyl)ethyltartronic dianilide

D

1227476-15-4

Azobenzene

Conditions
ConditionsYield
In methanol for 18h; Product distribution; Mechanism; Irradiation; other solvent;A 4%
B 3%
C 1%
D n/a
57-96-5

4-[2-(phenylsulfinyl)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione

86636-31-9

4-(2-phenylthioethyl)-4-methyl-1,2-diphenyl-3,5-pyrazolidinedione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / 2,4-bi-(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide ( LR ) / benzene / 0.5 h / 20 °C
2: 74 percent / Et3N / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme
57-96-5

4-[2-(phenylsulfinyl)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione

86636-23-9

3,3'-dithiobis (4-(2-phenylthio)ethyl-1,2-diphenyl-3-pyrazoline-5-thione)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / 2,4-bi-(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide ( LR ) / benzene / 0.5 h / 20 °C
2: 74 percent / 2,4-bi-(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide ( LR ) / toluene / 0.5 h / Heating
View Scheme
50-00-0

formaldehyd

57-96-5

4-[2-(phenylsulfinyl)ethyl]-1,2-diphenyl-3,5-pyrazolidinedione

1,2-diphenyl-4-[2-(phenylsulfinyl)-ethyl]-4-hydroxymethyl-pyrazolidine-3,5-dione

Conditions
ConditionsYield
In methanol

(+/-)-Sulfinpyrazone Chemical Properties

IUPAC Name: 4-[2-(Benzenesulfinyl)ethyl]-1,2-diphenylpyrazolidine-3,5-dione
The MF of (+/-)-Sulfinpyrazone (CAS NO.57-96-5) is C23H20N2O3S.

(+/-)-Sulfinpyrazone Specification

The Sulfinpyrazone, also known as 1,2-diphenyl-4-[2-(phenylsulfinyl)ethyl]pyrazolidine-3,5-dione, is a uricosuric medication with the formula C23H20N2O3S. Its EINECS registry number is 200-357-4. With the CAS registry number 57-96-5, its IUPAC name is 4-[2-(benzenesulfinyl)ethyl]-1,2-diphenylpyrazolidine-3,5-dione. This chemical's classification codes are Antirheumatic Agents; Drug / Therapeutic Agent; Gout Suppressants Human Data; Mutation Data; Renal Agents; Uricosuric; Uricosuric Agents.

Physical properties of Sulfinpyrazone: (1)ACD/LogP: 2.30; (2)ACD/LogD (pH 5.5): 1.97; (3)ACD/LogD (pH 7.4): 0.45; (4)ACD/BCF (pH 5.5): 15.47; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 199.34; (7)ACD/KOC (pH 7.4): 5.97; (8)#H bond acceptors: 5; (9)#Freely Rotating Bonds: 6; (10)Index of Refraction: 1.716; (11)Molar Refractivity: 114.13 cm3; (12)Molar Volume: 290 cm3; (13)Surface Tension: 75.9 dyne/cm; (14)Density: 1.39 g/cm3; (15)Flash Point: 311.1 °C; (16)Enthalpy of Vaporization: 88.14 kJ/mol; (17)Boiling Point: 590.8 °C at 760 mmHg; (18)Vapour Pressure: 6.2E-14 mmHg at 25°C.

Preparation: this chemical can be prepared as the following reaction equation:

Sulfinpyrazone can be prepared as the following reaction equation

Uses of Sulfinpyrazone: it can be used to used to treat gout. It also sometimes is used to reduce platelet aggregation by inhibiting degranulation of platelets which reduces the release of ADP and thromboxane. This chemical must not be used in persons with renal impairment or a high rate of excretion of uric acid (hyperuricosuria).

When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health. It is harmful if swallowed. In addition, it is irritating to eyes.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)N2C(=O)C(C(=O)N2C3=CC=CC=C3)CCS(=O)C4=CC=CC=C4
(2)InChI: InChI=1S/C23H20N2O3S/c26-22-21(16-17-29(28)20-14-8-3-9-15-20)23(27)25(19-12-6-2-7-13-19)24(22)18-10-4-1-5-11-18/h1-15,21H,16-17H2
(3)InChIKey: MBGGBVCUIVRRBF-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 29mg/kg (29mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA New England Journal of Medicine. Vol. 303, Pg. 702, 1980.
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   National Technical Information Service. Vol. AD414-344,
mouse LD50 intravenous 240mg/kg (240mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: EXCITEMENT		 Annals of the New York Academy of Sciences. Vol. 86, Pg. 263, 1960.
mouse LD50 oral 298mg/kg (298mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: EXCITEMENT		 Annals of the New York Academy of Sciences. Vol. 86, Pg. 263, 1960.
rabbit LD50 intravenous 195mg/kg (195mg/kg)   Medicinal Chemistry: A Series of Monographs. Vol. 5, Pg. 391, 1965.
rat LD50 intravenous 154mg/kg (154mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 Annals of the New York Academy of Sciences. Vol. 86, Pg. 263, 1960.
rat LD50 oral 358mg/kg (358mg/kg)   Drugs in Japan Vol. 6, Pg. 393, 1982.

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