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57-66-9

Basic Information
CAS No.: 57-66-9
Name: Benzoic acid,4-[(dipropylamino)sulfonyl]-
Article Data: 23
Cas Database
Molecular Structure:
Molecular Structure of 57-66-9 (Benzoic acid,4-[(dipropylamino)sulfonyl]-)
Formula: C13H19NO4S
Molecular Weight: 285.364
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: N/A
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%
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Consensus Reports

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.