p-carboxyphenylsulfonyl chloride
di-n-propylamine
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; for 18h; | 99% |
With sodium hydrogencarbonate In water; acetone at 25℃; Schotten-Baumann Reaction; Flow reactor; | 78% |
4-(hydroxymethyl)-N,N-dipropylbenzenesulfonamide
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In dichloromethane at 20℃; for 24h; | 92% |
4-(aminosulfonyl)-benzoic acid
propyl bromide
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
With potassium hydroxide |
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
With NADPH-generating system; rat liver homogenate at 37℃; Enzyme kinetics; Hydrolysis; Enzymatic reaction; |
Probenecid glucuronide
A
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
With sodium phosphate buffer In water; acetonitrile at 37℃; pH=7.4; Product distribution; Kinetics; Further Variations:; Reagents; pH-values; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: KMnO4 2: aqueous KOH View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous sulfuric acid; hydrogen View Scheme |
4-carboxybenzenesulfonyl fluoride
di-n-propylamine
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
With 1,1,3,3-Tetramethyldisiloxane; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 25℃; for 24h; Reagent/catalyst; |
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
With methanol; potassium carbonate | 177 mg |
4-[(dipropylamino)sulfonyl]benzoic acid
methylamine
methyl 4-(N,N-dipropylsulfamoyl)benzoate
Conditions | Yield |
---|---|
With propane-1,3-diyl dinitrite In tetrahydrofuran at 90℃; under 12929 Torr; for 0.333333h; Flow reactor; | 100% |
3,4,5-trimethoxybenzylamine
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
With propane-1,3-diyl dinitrite In 2-methyltetrahydrofuran at 90℃; under 12929 Torr; for 0.333333h; Flow reactor; | 100% |
Conditions | Yield |
---|---|
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% |
4-[(dipropylamino)sulfonyl]benzoic acid
4-bromopiperidine hydrobromide
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
4-[(dipropylamino)sulfonyl]benzoic acid
N,N-dipropylbenzenesulfonamide
Conditions | Yield |
---|---|
With triethylsilane; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In toluene at 160℃; for 15h; chemoselective reaction; | 97% |
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; | 97% |
Conditions | Yield |
---|---|
With copper(l) iodide; tert.-butylnitrite at 25℃; for 12h; | 96% |
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
Stage #1: 4-[(dipropylamino)sulfonyl]benzoic acid With oxalyl dichloride In dichloromethane Stage #2: piperidine-2,6-dione With triethylamine In dichloromethane | 94% |
4-[(dipropylamino)sulfonyl]benzoic acid
4-(dipropylsulfamoyl)-benzoyl chloride
Conditions | Yield |
---|---|
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; |
4-[(dipropylamino)sulfonyl]benzoic acid
carbonic acid 1,1-dimethyl-3-phenyl-prop-2-ynyl ester methyl ester
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
4-[(dipropylamino)sulfonyl]benzoic acid
bis(pinacol)diborane
Conditions | Yield |
---|---|
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% |
4-[(dipropylamino)sulfonyl]benzoic acid
4-(hydroxymethyl)-N,N-dipropylbenzenesulfonamide
Conditions | Yield |
---|---|
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
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% |
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; Schlenk technique; | 89% |
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 17h; | 88% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; for 2h; Schlenk technique; Inert atmosphere; | 87% |
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
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% |
methanol
4-[(dipropylamino)sulfonyl]benzoic acid
methyl 4-(N,N-dipropylsulfamoyl)benzoate
Conditions | Yield |
---|---|
With sulfuric acid Heating; | 85% |
With sulfuric acid Reflux; | 84% |
2,2,2-trifluorodiazoethane
2-naphthaleneacetonitrile
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
With copper(l) iodide In toluene at 40℃; for 12h; | 85% |
Conditions | Yield |
---|---|
With (S)-α-α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanol trimethylsilyl ether In dichloromethane at 0℃; stereoselective reaction; | 84% |
4-[(dipropylamino)sulfonyl]benzoic acid
Conditions | Yield |
---|---|
With potassium fluoride; formic acid; tetramethylammonium fluoride; N,N`-sulfuryldiimidazole In N,N-dimethyl-formamide at 25℃; for 4h; Reagent/catalyst; Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
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% |
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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