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Probenecid
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57-66-9 Usage

Fire Hazard

Flash point data for Probenecid are not available. Probenecid is probably combustible.

Brand name

Benemid (Merck); Probalan (Lannett).

General Description

Probenecid (Benemid) is the most widely used uricosuricagent in the United States. It is selectively excreted into therenal tubules by OATS. It is extensively metabolized via Ndealkylationor ω-oxidation, followed by phase II conjugationinto the active metabolite, p-sulfamyl hippurate, whichexhibits a high affinity, similar to p-aminohippurate, forbinding to OATS, thereby preventing uric acid reabsorptionfrom the renal proximal tubules.

Anti-gout drug

Probenecid is a chemically synthetic sulfa anti-gout drug, also known as oxybenzone sulfonamides, which has dual role of both promoting the excretion of uric acid excretion and inhibiting the excretion of penicillin. Clinically it is used for treating chronic gout and suppressing excretion of penicillin-type drugs in order to increase their clinical plasma concentration as an adjuvant drug of penicillin therapy. Its mechanism of action is inhibiting the re-absorption of renal tubular on uric acid, thus increasing uric acid excretion and further lowering plasma uric acid concentration for reducing the deposition of urate in tissues and prevent the crystallization of urate. This product can also promote the dissolution of the pre-formed urate, thereby reducing its damage on the joint. In addition, the product can also competitively inhibit the secretion of a weak organic acid (such as penicillin, cephalosporins) in the renal tubules, which can increase blood concentrations of these antibiotics and prolong their duration of action. This product is easy for oral administration with a plasma protein binding rate of 85% to 90%. Adults take 1 g orally each time with the plasma concentration reaches peak after 2~4 hour and with a half-life of being 6 to 12 hours. Probenecid is rapidly metabolized in the liver with the major metabolite being probenecid acetyl glucuronic acid. The main metabolite is excreted through the urine. This product has no anti-inflammatory and analgesic effect, and thus being invalid for treating acute gout. Acute toxicity test results: orally: LD50 of rats being 1600mg/kg. After the oral administration, the major adverse reactions are gastrointestinal reactions with others adverse reactions including dizziness, headache, facial flushing, urinary frequency, gingival swelling and pain, skin rash; there are also occasional allergic reactions. It is not suitable for being applied to patients of acute gout and with history of uric acid crystal deposition in kidney and ureter. Patients of peptic ulcer or blood abnormalities and pregnant women should take with caution. Patients of renal dysfunction are not allowed for using it.

Mechanism of action

Probenecid is rapidly absorbed after oral administration, with peak plasma levels usually reached in 2 to 4 hours. Its half-life is somewhat variable (6–12 hours) because of both its extensive plasma protein binding and its active proximal tubular secretion. Since tubular backdiffusion is decreased at alkaline urinary pH ranges, probenecid excretion increases with increasing urinary pH. Probenecid is rapidly metabolized, with less than 5% of an administered dose being eliminated in 24 hours.The major metabolite is an acyl monoglucuronide.

Indications

1. For treating hyperuricemia with chronic gouty arthritis and tophi, take 2 times per day for adults with the dose of each time being 25 mg, increase the dose to 2 times per day after 1 week with 500 mg each time. Upon the administration, maintain the daily intake of water being at 2500mL to prevent the formation of kidney stones, simultaneously take alkaline urine drug if necessary. But make sure that: 1, the filtration rate of glomerular should be greater than 50~60mL/min; 2, no kidney stones or history of kidney stones; 3, non-acidic urine; 4, patients of non-taking salicylates; 5, have regular tests of blood and urine pH value, liver and kidney function as well as the uric acid levels in blood and urine; 6, adjust the dose according to the clinical and uric acid level and maintain for a long time with the minimum effective amount. 2. As an adjunct drug for antibiotic treatment; it can be combined together with different antibiotics such as penicillin, ampicillin, oxacillin, amoxicillin ortho chlorine, and nafcillin; Probenecid can be used for inhibiting the discharge of these antibiotics, increase their blood concentration and can maintain for a relative long time. The above information is edited by the Chemicalbook of Dai Xiongfeng.

Veterinary Drugs and Treatments

Although there has been very limited clinical use or research on probenecid in veterinary medicine, it can be useful in treating gout (hyperuricemia), particularly in reptiles. Probenecid’s effect in inhibiting renal tubular secretion of certain beta-lactam antibiotics and other weak organic acids is of interest for increasing serum concentrations, or reducing doses and dosing frequency of these drugs. This may allow greater efficacy (but also toxic effects) and reduce the cost or dosing frequency of expensive human drugs. Probenecid has a significantly long elimination halflife in dogs (about 18 hours), which may make it particularly useful in this species; however, at present there is little research supporting this use of probenecid in veterinary patients.

Uses

Uricosuric drug.

Uses

It is a kind of anti-gout drug. The product is organic acid, strongly fat-soluble, self-discharge from tubular secretion, very easily to be absorbed back. Therefore, in the presence of probenecid, the transfer of some organic acids in the tubular body will be inhibited, reducing the excretion of other organic acids. Thereby, it is used to treat chronic gout with being safe and effective. It has no effects on acute gout pain and inflammation and can’t be applied to acute gout. It is used for the treatment of gout, rheumatoid arthritis and other chronic diseases.

Reactivity Profile

Probenecid may be light sensitive .

clinical pharmacology

Probenecid is a uricosuric and renal tubular blocking agent. It inhibits the tubular reabsorption of urate, thus increasing the urinary excretion of uric acid and decreasing serum urate levels. Effective uricosuria reduces the miscible urate pool, retards urate deposition, and promotes resorption of urate deposits. Probenecid inhibits the tubular secretion of penicillin and usually increases penicillin plasma levels by any route the antibiotic is given. A 2-fold to 4-fold elevation has been demonstrated for various penicillins. Probenecid also has been reported to inhibit the renal transport of many other compounds including aminohippuric acid (PAH), aminosalicylic acid (PAS), indomethacin, sodium iodomethamate and related iodinated organic acids, 17 –ketosteroids, pantothenic acid, phenolsulfonphthalein (PSP), sulfonamides, and sulfonylureas. See also Drug Interactions. Probenecid decreases both hepatic and renal excretion of sulfobromophtalein (BSP). The tubular reabsorption of phosphorus is inhibited in hypoparathyroid but not in euparathyroid individuals. Probenecid does not influence plasma concentrations of salicylates, nor the excretion of streptomycin, chloramphenicol, chlortetracycline, oxytetracycline, or neomycin.

Clinical Use

Probenecid is an effective and relatively safe agent for controlling hyperuricemia and preventing tophi deposition in tissues. Chronic administration will decrease the incidence of acute gouty attacks as well as diminish the complications usually associated with hyperuricemia, such as renal damage and tophi deposition. Probenecid is still used by some physicians to maintain high blood levels of penicillin, cephalosporin, acyclovir, and cyclosporine. It is not useful in treating acute attacks of gouty arthritis. If the total amount of uric acid excreted is greater than 800 mg/day, the urine should be alkalinized to prevent kidney stone formation and promote uric acid.

Chemical Properties

White crystalline powder. Its melting point is 194-196 °C. It is soluble in acetone, and slightly soluble in ethanol or chloroform, but almost insoluble in water. It is also soluble in dilute sodium hydroxide solution, but almost insoluble in dilute acid. It is odorless with a slightly bitter taste.

Description

Probenecid is insoluble in water and acidic solutions but is soluble in alkaline solutions buffered to pH 7.4. Probenecid initially was synthesized as a result of studies in the 1940s on sulfonamides that indicated the sulfonamides decreased the renal clearance of penicillin, extending the half-life of penicillin as supplies diminished. Probenecid thus was initially used—and is still indicated—for that purpose. Probenecid promotes the excretion of uric acid by inhibiting the urate anion exchange transporter (URAT 1), decreasing the reabsorption of uric acid in the proximal tubules. The overall effect is to decrease plasma uric acid concentrations, thereby decreasing the rate and extent of urate crystal deposition in joints and synovial fluids. Within the series of N-dialkylsulfamyl benzoates from which probenecid is derived, renal clearance of these compounds is decreased as the length of the N-alkyl substituents is increased. Uricosuric activity increases with increasing size of the alkyl group in the series methyl, ethyl, and propyl.

Uses

An inhibitor of several ABC-transporters of the subfamily ABCC or MRP.

Uses

For the reduction of serum uric acid concentrations in chronic gouty arthritis and tophaceous gout in patients with frequent disabling gout attacks. Has also been effectively used to promote uric acid excretion in hyperuricemia secondary to the administra

Drug Interactions

When probenecid is used to elevate plasma concentrations of penicillin or other beta-lactams, or when such drugs are given to patients taking probenecid therapeutically, high plasma concentrations of the other drug may increase the incidence of adverse reactions associated with that drug. In the case of penicillin or other beta-lactams, psychic disturbances have been reported. The use of salicylates antagonizes the uricosuric action of probenecid (see WARNINGS). The uricosuric action of probenecid is also antagonized by pyrazinamide. Probenecid produces an insignificant increase in free sulfonamide plasma concentrations, but a significant increase in total sulfonamide plasma levels. Since probenecid decreases the renal excretion of conjugated sulfonamides, plasma concentrations of the latter should be determined from time to time when sulfonamide and probenecid are coadministered for prolonged periods. Probenecid may prolong or enhance the action of oral sulfonylureas and thereby increase the risk of hypoglycemia. It has been reported that patients receiving probenecid require significantly less thiopental for induction of anesthesia. In addition, ketamine and thiopental anesthesia were significantly prolonged in rats receiving probenecid. The concomitant administration of probenecid increases the mean plasma elimination half-life of a number of drugs which can lead to increased plasma concentrations. These include agents such as indomethacin, acetaminophen, naproxen, ketoprofen, meclofenamate, lorazepam, and rifampin. Although the clinical significance of this observation has not been established, a lower dosage of the drug may be required to produce a therapeutic effect, and increases a dosage of the drug in question should be made cautiously and in small increments when probenecid is being coadministered. Although specific instances of toxicity due to this potential interaction have not been observed to date, physicians should be alert to this possibility. Probenecid given concomitantly with sulindac had only a slight effect on plasma sulfide levels, while plasma levels of sulindac and sulfone were increased. Sulindac was shown to produce a modest reduction in the uricosuric action of probenecid, which probably is not significant under most circumstances. In animals and in humans, probenecid has been reported to increase plasma concentrations of methotrexate (see WARNINGS). Falsely high readings for theophylline have been reported in an in vitro study, using the Schack and Waxler technique, when therapeutic concentrations of theophylline and probenecid were added to human plasma.

Production methods

Toluene sulfonamide is oxidized by sodium dichromate to generate carboxylic benzenesulfonamide; then use bromopropane for alkylation, the resulting sodium probenecid is further acidified by acetate to obtain probenecid.

Air & Water Reactions

Insoluble in water.

General Description

Odorless white or almost white crystalline powder. Slightly bitter taste; pleasant aftertaste.

References

Probenecid is used to treat chronic gout and gouty arthritis. It is used to prevent attacks related to gout, not treat them once they occur. It acts on the kidneys to help the body eliminate uric acid. Probenecid is also used to make certain antibiotics more effective by preventing the body from passing them in the urine. https://medlineplus.gov/druginfo/meds/a682395.html https://go.drugbank.com/drugs/DB01032

Uses

pharmaceutical intermediate

Indications

When probenecid (ColBENEMID) is given in sufficient amounts, it will block the active reabsorption of uric acid in the proximal tubules following its glomerular filtration, thereby increasing the amount of urate eliminated. In contrast, low dosages of probenecid appear to compete preferentially with plasma uric acid for the proximal tubule anionic transport system and thereby block its access to this active secretory system. The uricosuric action of probenecid, however, is accounted for by the drug’s ability to inhibit the active reabsorption of filtered urate.

Pharmacokinetics

Probenecid is essentially completely absorbed from the GI tract on oral administration, with peak plasma levels observed within 2 to 4 hours. Like most acidic compounds, probenecid (pKa = 3.4) is extensively plasma protein bound (93–99%). The primary route of elimination of probenecid and its metabolites is the urine. It is extensively metabolized in humans, with only 5 to 10% being excreted as unchanged drug. The major metabolites detected result from glucuronide conjugation of the carboxylic acid, ω-oxidation of the n-propyl side chain and subsequent oxidation of the resulting alcohol to the carboxylic acid derivative, ω1-oxidation of the n-propyl group, and N-dealkylation.

Side effects

The major side effect is GI distress (e.g., nausea, vomiting, and anorexia), but these occur in only 2% of patients at low doses. Other effects include headache, dizziness, urinary frequency, hypersensitivity reactions, sore gums, and anemia.

Side effects

1. Gastrointestinal reactions: main reactions are that a small number of patients have loss of appetite, nausea, vomiting, and abdominal discomfort. 2. Central nervous system reactions and allergic reactions: occasional headache, facial flushing, fever and some allergic reactions such as itchy skin, dermatitis. 3. Other serious toxicities: for very few patients, they have got bleeding, neutropenia, aplastic anemia, nephrotic syndrome, and liver necrosis. Probenecid belongs to sulfa drugs, so patients with hypersensitivity to sulfa drugs are not allowed for using. Pregnant women, patients of peptic ulcer, liver and kidney dysfunction should use with caution. In addition, patients should drink lots of water for the medication should drink lots of water and add appropriate amount of sodium carbonate for preventing urinary stones. During the medication, people should pay attention to checking the blood.

Definition

ChEBI: A sulfonamide in which the nitrogen of 4-sulfamoylbenzoic acid is substituted with two propyl groups.

Chemical Properties

White to Off-White Solid
InChI:InChI=1/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)/p-1

57-66-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (B20010)  Probenecid, 98%    57-66-9 2.5g 534.0CNY Detail
Alfa Aesar (B20010)  Probenecid, 98%    57-66-9 10g 1807.0CNY Detail
Sigma-Aldrich (P3000000)  Probenecid  European Pharmacopoeia (EP) Reference Standard 57-66-9 P3000000 1,880.19CNY Detail
Sigma (P8761)  Probenecid   57-66-9 P8761-25G 926.64CNY Detail
Sigma (P8761)  Probenecid   57-66-9 P8761-100G 3,099.33CNY Detail
USP (1563003)  Probenecid  United States Pharmacopeia (USP) Reference Standard 57-66-9 1563003-200MG 4,662.45CNY Detail

57-66-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name probenecid

1.2 Other means of identification

Product number -
Other names Proben

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:57-66-9 SDS

57-66-9Synthetic route

p-carboxyphenylsulfonyl chloride
10130-89-9

p-carboxyphenylsulfonyl chloride

di-n-propylamine
142-84-7

di-n-propylamine

4-[(dipropylamino)sulfonyl]benzoic acid
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%
4-(hydroxymethyl)-N,N-dipropylbenzenesulfonamide
15148-72-8

4-(hydroxymethyl)-N,N-dipropylbenzenesulfonamide

4-[(dipropylamino)sulfonyl]benzoic acid
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%
4-(aminosulfonyl)-benzoic acid
138-41-0

4-(aminosulfonyl)-benzoic acid

propyl bromide
106-94-5

propyl bromide

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

Conditions
ConditionsYield
With potassium hydroxide
4-dipropylsulfamoyl-benzoic acid (benzoyl-ethoxycarbonylmethyl-amino)-methyl ester

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

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

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

Probenecid glucuronide

A

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

B

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

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

C

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

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

D

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

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;
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

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

dipropylamine-N-carbonitrile

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

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

4-carboxybenzenesulfonyl fluoride

di-n-propylamine
142-84-7

di-n-propylamine

4-[(dipropylamino)sulfonyl]benzoic acid
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

C15H23NO4S

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

Conditions
ConditionsYield
With methanol; potassium carbonate177 mg
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

methylamine
74-89-5

methylamine

methyl 4-(N,N-dipropylsulfamoyl)benzoate
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%
3,4,5-trimethoxybenzylamine
18638-99-8

3,4,5-trimethoxybenzylamine

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

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

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%
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

phenol
108-95-2

phenol

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

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%
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

4-bromopiperidine hydrobromide
54288-70-9

4-bromopiperidine hydrobromide

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

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%
benzoxazole
273-53-0

benzoxazole

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

C19H22N2O3S

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%
2-methyl-1-buten-4-ol
763-32-6

2-methyl-1-buten-4-ol

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

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

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;
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

N,N-dipropylbenzenesulfonamide
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%
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

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

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

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

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%
trifluoroethylamine
753-90-2

trifluoroethylamine

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

acetonitrile
75-05-8

acetonitrile

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

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%
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

4-(N,N-dipropylsulfamoyl)benzamide

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%
piperidine-2,6-dione
1121-89-7

piperidine-2,6-dione

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

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

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%
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

4-(dipropylsulfamoyl)-benzoyl chloride
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;
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

carbonic acid 1,1-dimethyl-3-phenyl-prop-2-ynyl ester methyl ester
371256-80-3

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

C24H29NO4S

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%
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

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

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%
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

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

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%
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

4-(hydroxymethyl)-N,N-dipropylbenzenesulfonamide
15148-72-8

4-(hydroxymethyl)-N,N-dipropylbenzenesulfonamide

Conditions
ConditionsYield
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;90%
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

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

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%
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

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

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%
4,4’-difluorobenzophenone oxime
363-02-0

4,4’-difluorobenzophenone oxime

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

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

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%
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

2-methoxy-6-octylaniline

2-methoxy-6-octylaniline

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

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%
homoalylic alcohol
627-27-0

homoalylic alcohol

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

C17H25NO4S

C17H25NO4S

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

N-hydroxyphthalimide

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

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

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%
4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

2-methoxy-6-pentadecylaniline

2-methoxy-6-pentadecylaniline

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

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%
methanol
67-56-1

methanol

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

methyl 4-(N,N-dipropylsulfamoyl)benzoate
53212-75-2

methyl 4-(N,N-dipropylsulfamoyl)benzoate

Conditions
ConditionsYield
With sulfuric acid Heating;85%
With sulfuric acid Reflux;84%
2,2,2-trifluorodiazoethane
371-67-5

2,2,2-trifluorodiazoethane

2-naphthaleneacetonitrile
7498-57-9

2-naphthaleneacetonitrile

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

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

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%
Phenylpropargyl aldehyde
2579-22-8

Phenylpropargyl aldehyde

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

C22H25NO5S

C22H25NO5S

Conditions
ConditionsYield
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
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

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

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%
pent-1-yn-5-ol
5390-04-5

pent-1-yn-5-ol

4-[(dipropylamino)sulfonyl]benzoic acid
57-66-9

4-[(dipropylamino)sulfonyl]benzoic acid

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

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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