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57-66-9

Basic Information
CAS No.: 57-66-9
Name: Benzoic acid,4-[(dipropylamino)sulfonyl]-
Molecular Structure:
Molecular Structure of 57-66-9 (Benzoic acid,4-[(dipropylamino)sulfonyl]-)
Formula: C13H19NO4S
Molecular Weight: 285.39
Synonyms: Benzoicacid, p-(dipropylsulfamoyl)- (8CI);4-(Dipropylaminosulfonyl)benzoic acid;4-(Dipropylsulfamoyl)benzoic acid;4-(N,N-Dipropylaminosulfonyl)benzoic acid;Apurina;Benecid;Benemid;Benuryl;NSC 18786;Probecid;Proben;Probenecid acid;Prolongine;Synergid R;Tubophan;Uricosid;p-(Dipropylsulfamoyl)benzoic acid;
EINECS: 200-344-3
Density: 1.221 g/cm3
Melting Point: 194-196 °C
Boiling Point: 438 °C at 760 mmHg
Flash Point: 218.7 °C
Solubility: Soluble in water
Appearance: white crystalline power
Hazard Symbols: HarmfulXn
Risk Codes: 22-40
Safety: 36/37
Transport Information:
PSA: 83.06000
LogP: 3.27630
Synthetic route
10130-89-9

p-carboxyphenylsulfonyl chloride

142-84-7

di-n-propylamine

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 18h;99%
With sodium hydrogencarbonate In water; acetone at 25℃; Schotten-Baumann Reaction; Flow reactor;78%
15148-72-8

4-(hydroxymethyl)-N,N-dipropylbenzenesulfonamide

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

Conditions
ConditionsYield
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In dichloromethane at 20℃; for 24h;92%
138-41-0

4-(aminosulfonyl)-benzoic acid

106-94-5

propyl bromide

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

Conditions
ConditionsYield
With potassium hydroxide

4-dipropylsulfamoyl-benzoic acid (benzoyl-ethoxycarbonylmethyl-amino)-methyl ester

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

Conditions
ConditionsYield
With NADPH-generating system; rat liver homogenate at 37℃; Enzyme kinetics; Hydrolysis; Enzymatic reaction;
34017-15-7

Probenecid glucuronide

A

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

B

3-O-[p-(dipropylsulfamoyl)benzoyl]-D-glucopyranuronic acid

C

2-O-[p-(dipropylsulfamoyl)benzoyl]-D-glucopyranuronic acid

D

4-O-[p-(dipropylsulfamoyl)benzoyl]-D-glucopyranuronic acid

Conditions
ConditionsYield
With sodium phosphate buffer In water; acetonitrile at 37℃; pH=7.4; Product distribution; Kinetics; Further Variations:; Reagents; pH-values;
70-55-3

toluene-4-sulfonamide

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KMnO4
2: aqueous KOH
View Scheme
1531-36-8

dipropylamine-N-carbonitrile

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous sulfuric acid; hydrogen
View Scheme
455-26-5

4-carboxybenzenesulfonyl fluoride

142-84-7

di-n-propylamine

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

Conditions
ConditionsYield
With 1,1,3,3-Tetramethyldisiloxane; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 25℃; for 24h; Reagent/catalyst;

C15H23NO4S

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

Conditions
ConditionsYield
With methanol; potassium carbonate177 mg
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

74-89-5

methylamine

53212-75-2

methyl 4-(N,N-dipropylsulfamoyl)benzoate

Conditions
ConditionsYield
With propane-1,3-diyl dinitrite In tetrahydrofuran at 90℃; under 12929 Torr; for 0.333333h; Flow reactor;100%
18638-99-8

3,4,5-trimethoxybenzylamine

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

3,4,5-trimethoxybenzyl 4-(N,N-dipropylsulfamoyl)benzoate

Conditions
ConditionsYield
With propane-1,3-diyl dinitrite In 2-methyltetrahydrofuran at 90℃; under 12929 Torr; for 0.333333h; Flow reactor;100%
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

108-95-2

phenol

phenyl 4-(N,N-dipropylsulfamoyl)-benzoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 7h; Inert atmosphere;98%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 50℃; Inert atmosphere;70%
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

54288-70-9

4-bromopiperidine hydrobromide

4-(4-bromopiperidine-1-carbonyl)-N, N-di-propylbenzenesulfonamide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h; Inert atmosphere;98%
273-53-0

benzoxazole

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

C19H22N2O3S

Conditions
ConditionsYield
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction;98%
763-32-6

2-methyl-1-buten-4-ol

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

3-methylbut-3-en-1-yl 4-(N, N-dipropylsulfamoyl)benzoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;97%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;86%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere;
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

28859-91-8

N,N-dipropylbenzenesulfonamide

Conditions
ConditionsYield
With triethylsilane; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In toluene at 160℃; for 15h; chemoselective reaction;97%
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

N-tert-butoxycarbonyl-O-diethylcarbamoyl-N-bromopropylhydroxylamine

3-((tert-butoxycarbonyl)((diethylcarbamoyl)oxy)amino)propyl 4-(N,N-dipropylsulfamoyl)benzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;97%
753-90-2

trifluoroethylamine

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

75-05-8

acetonitrile

N-acetyl-4-(N,N-dipropylsulfamoyl)-N-(2,2,2-trifluoroethyl)benzamide

Conditions
ConditionsYield
With copper(l) iodide; tert.-butylnitrite at 25℃; for 12h;96%
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

4-(N,N-dipropylsulfamoyl)benzamide

Conditions
ConditionsYield
Stage #1: 4-[(dipropylamino)sulfonyl]benzoic acid With oxalyl dichloride In dichloromethane at 30℃; for 2h;
Stage #2: With ammonia at 25℃; for 8h;
95%
1121-89-7

piperidine-2,6-dione

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

4-(2,6-dioxopiperidine-1-carbonyl)-N,N-dipropylbenzenesulfonamide

Conditions
ConditionsYield
Stage #1: 4-[(dipropylamino)sulfonyl]benzoic acid With oxalyl dichloride In dichloromethane
Stage #2: piperidine-2,6-dione With triethylamine In dichloromethane
94%
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

29171-72-0

4-(dipropylsulfamoyl)-benzoyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;93%
With thionyl chloride; N,N-dimethyl-formamide In toluene at 60 - 70℃; for 0.5h;
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

371256-80-3

carbonic acid 1,1-dimethyl-3-phenyl-prop-2-ynyl ester methyl ester

C24H29NO4S

Conditions
ConditionsYield
With potassium phosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In N,N-dimethyl acetamide at 110℃; regiospecific reaction;93%
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

762-04-9

phosphonic acid diethyl ester

diethyl (4-(N,N-dipropylsulfamoyl)phenyl)phosphonate

Conditions
ConditionsYield
With palladium diacetate; 2,2-dimethylpropanoic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Inert atmosphere; Schlenk technique;93%
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

73183-34-3

bis(pinacol)diborane

N,N-dipropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide

Conditions
ConditionsYield
With palladium diacetate; 2,2-dimethylpropanoic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h;91%
With palladium diacetate; 2,2-dimethylpropanoic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h;91%
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

15148-72-8

4-(hydroxymethyl)-N,N-dipropylbenzenesulfonamide

Conditions
ConditionsYield
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;90%
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

123-08-0

4-hydroxy-benzaldehyde

4-formylphenyl 4-(N,N-dipropylsulfamoyl)benzoate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃;89%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 23℃; for 24h;69%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 23℃; for 24h; Inert atmosphere;50%
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

4-(N,N-di-n-propylsulfamoyl)benzoyl fluoride

Conditions
ConditionsYield
With dmap; trifluoromethyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Schlenk technique;89%
With triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate at 20℃;82%
With (3,3-difluorocycloprop-1-ene-1,2-diyl)dibenzene In dichloromethane at 50℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;82%
363-02-0

4,4’-difluorobenzophenone oxime

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

4-((((bis(4-fluorophenyl)methylene)amino)oxy)carbonyl)-N,N-dipropylbenzenesulfonamide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;89%
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

2-methoxy-6-octylaniline

4-(N,N-dipropylsulfamoyl)-N-(2-methoxy-6-octylphenyl)benzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;88%
627-27-0

homoalylic alcohol

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

C17H25NO4S

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 17h;88%
524-38-9

N-hydroxyphthalimide

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

1,3-dioxoisoindolin-2-yl 4-(N,N-dipropylsulfamoyl)benzoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; for 2h; Schlenk technique; Inert atmosphere;87%
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

2-methoxy-6-pentadecylaniline

4-(N,N-dipropylsulfamoyl)-N-(2-methoxy-6-pentadecylphenyl)benzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;86%
67-56-1

methanol

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

53212-75-2

methyl 4-(N,N-dipropylsulfamoyl)benzoate

Conditions
ConditionsYield
With sulfuric acid Heating;85%
With sulfuric acid Reflux;84%
371-67-5

2,2,2-trifluorodiazoethane

7498-57-9

2-naphthaleneacetonitrile

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

4-(N,N-dipropylsulfamoyl)-N-[2-(naphthalen-2-yl)acetyl]-N-(2,2,2-trifluoroethyl)benzamide

Conditions
ConditionsYield
With copper(l) iodide In toluene at 40℃; for 12h;85%
2579-22-8

Phenylpropargyl aldehyde

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

C22H25NO5S

Conditions
ConditionsYield
With (S)-α-α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether In dichloromethane at 0℃; stereoselective reaction;84%
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

1-[(dipropylamino)sulfonyl]-4-(difluoromethyl)benzene

Conditions
ConditionsYield
With potassium fluoride; formic acid; tetramethylammonium fluoride; N,N`-sulfuryldiimidazole In N,N-dimethyl-formamide at 25℃; for 4h; Reagent/catalyst; Inert atmosphere;84%
5390-04-5

pent-1-yn-5-ol

57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

pent-4-yn-1-yl 4-(N,N-dipropylsulfamoyl)benzoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃;83%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 12h;79%
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    CAS No.:57-66-9 Other Names:4-[(dipropylamino)sulfonyl]-benzoicaci acid MF:C13H19NO4S EINECS No.:200-344-3 Place of Origin:Anhui, China (Mainland) Type:Antineoplastic Agents, Auxiliaries and Other Medici

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    Product Name: Probenecid Synonyms: Apurina; benacen; Benemid; benemide CAS: 57-66-9 MF: C13H19NO4S MW: 285.36 EINECS: 200-344-3 Purity:99% Appearance:White to Off-White powder Appearance:White crystal powder Storage: Store in cool and dry

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Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

The p-(Dipropylsulfamoyl)benzoic acid, with the CAS registry number 57-66-9, has the IUPAC name of 4-(dipropylsulfamoyl)benzoic acid. For being a kind of white crystalline powder, it is soluble in acetone, slightly soluble in ethanol or chloroform while insoluble in water. Besides, it is stable chemically but may be sensitive to light, and then incompatible with strong oxidizing agents. In addition, it is usually applied in the pharmaceutics, such as being the gout suppressant to cure gout, chronic rheumatic arthritis and so on, and then it has the product categories which are including Miscellaneous; API; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds; API's; Vanilloid/TRPV channel.

The characteristics of this chemical are as below: (1)ACD/LogP: 3.30; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.5; (4)ACD/LogD (pH 7.4): 0.26; (5)ACD/BCF (pH 5.5): 3.03; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 23.74; (8)ACD/KOC (pH 7.4): 1.34; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 72.06; (13)Index of Refraction: 1.542; (14)Molar Refractivity: 73.5 cm3; (15)Molar Volume: 233.5 cm3; (16)Polarizability: 29.14×10-24 cm3; (17)Surface Tension: 46.7 dyne/cm; (18)Density: 1.221 g/cm3; (19)Flash Point: 218.7 °C; (20)Enthalpy of Vaporization: 73.22 kJ/mol; (21)Boiling Point: 438 °C at 760 mmHg; (22)Vapour Pressure: 1.91E-08 mmHg at 25°C; (23)Exact Mass: 285.103479; (24)MonoIsotopic Mass: 285.103479; (25)Topological Polar Surface Area: 83.1; (26)Heavy Atom Count: 19; (27)Complexity: 374.

Use of this chemical: p-(Dipropylsulfamoyl)benzoic acid could react to produce C13H17D2NO4S. This reaction could happen in the presence of the reagent of RhCl3*3H2O, D2O and the solvent of dimethylformamide and it needs the reaction temperature of 108 ℃.

The production method of this chemical is below: Oxidatize the toluenesulfonamide with sodium dichromate to produce p-carboxyphenylsulfonylamine; Next to have the alkylation with bromopropane to get probenecid sodium; Lastly have the acidification with acetic acid to obtain this chemical.

When you are dealing with this chemical, you should be more cautious. For being a kind of harmful chemical, it may cause damage to health. This chemical is harmful if swallowed, and it has limited evidence of a carcinogenic effect. Therefore, you should wear suitable protective clothing and gloves.

In adddition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(=O)O
(2)InChI: InChI=1S/C13H19NO4S/c1-3-9-14(10-4-2)19(17,18)12-7-5-11(6-8-12)13(15)16/h5-8H,3-4,9-10H2,1-2H3,(H,15,16)
(3)InChIKey: DBABZHXKTCFAPX-UHFFFAOYSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 230mg/kg (230mg/kg)   Compilation of LD50 Values of New Drugs.
man TDLo oral 50mg/kg/1W-I (50mg/kg) BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA Journal of Rheumatology. Vol. 13, Pg. 208, 1986.
 
mouse LD50 oral 1666mg/kg (1666mg/kg)   Drugs in Japan Vol. 6, Pg. 735, 1982.
mouse LDLo intraperitoneal 1gm/kg (1000mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 16, Pg. 1655, 1968.
 
mouse LDLo intravenous 458mg/kg (458mg/kg)   Compilation of LD50 Values of New Drugs.
mouse LDLo subcutaneous 1156mg/kg (1156mg/kg)   Compilation of LD50 Values of New Drugs.
rabbit LD50 intravenous 304mg/kg (304mg/kg)   Drugs in Japan Vol. -, Pg. 1045, 1990.
rat LD50 oral 1600mg/kg (1600mg/kg)   "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989Vol. 11, Pg. 1230, 1989.
rat LDLo intraperitoneal 394mg/kg (394mg/kg)   Compilation of LD50 Values of New Drugs.
rat LDLo subcutaneous 611mg/kg (611mg/kg)   Compilation of LD50 Values of New Drugs.

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